#------------------------------------------------------------------------------
#$Date: 2024-12-10 04:51:12 +0200 (Tue, 10 Dec 2024) $
#$Revision: 296811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312734.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_2312734
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          '0.5C6 H10 O4 2+, Sb2 F11 -'
_chemical_formula_moiety         '0.5(C6 H10 O4 2+), F11 Sb2 -'
_chemical_formula_sum            'C3 H5 F11 O2 Sb2'
_chemical_formula_weight         525.57
_chemical_name_systematic
;
Hemi{[1,4-dimethoxy-4-oxidaniumylidenebut-2-en-1-ylidene]oxidanium}
undecafluorodiarsenate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8461(6)
_cell_length_b                   15.1531(11)
_cell_length_c                   19.5536(17)
_cell_measurement_reflns_used    3099
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      31.4330
_cell_measurement_theta_min      3.0730
_cell_volume                     2324.8(3)
_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      101(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_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  0.0526
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13316
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.201
_diffrn_reflns_theta_min         2.883
_diffrn_source_current           40
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    3.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.049
_refine_diff_density_max         1.088
_refine_diff_density_min         -1.007
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0210P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0706
_reflns_number_gt                2878
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3025.cif
_cod_data_source_block           VII
_cod_database_code               2312734
_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   0.384
_shelx_estimated_absorpt_t_max   0.799
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb Sb1 0.53289(3) 0.11951(2) 0.58884(2) 0.01838(7) Uani d 1 . .
Sb Sb2 0.87980(3) 0.29435(2) 0.64518(2) 0.01906(8) Uani d 1 . .
F F6 0.6878(3) 0.20173(15) 0.64187(14) 0.0290(6) Uani d 1 . .
F F4 0.3807(3) 0.04618(14) 0.54353(14) 0.0254(6) Uani d 1 . .
F F11 1.0501(3) 0.37949(16) 0.64744(16) 0.0325(7) Uani d 1 . .
F F7 0.7631(3) 0.34255(15) 0.57101(14) 0.0267(6) Uani d 1 . .
F F1 0.4121(3) 0.22282(15) 0.56555(15) 0.0288(6) Uani d 1 . .
F F8 0.7357(3) 0.35628(15) 0.70374(15) 0.0313(6) Uani d 1 . .
F F2 0.4096(4) 0.11295(17) 0.66985(15) 0.0331(6) Uani d 1 . .
F F3 0.6723(3) 0.13957(15) 0.51323(14) 0.0278(6) Uani d 1 . .
O O2 0.4521(4) 0.52155(17) 0.62437(16) 0.0208(6) Uani d 1 . .
F F5 0.6789(3) 0.03114(16) 0.61891(17) 0.0360(7) Uani d 1 . .
F F10 0.9958(3) 0.21939(16) 0.58552(17) 0.0348(7) Uani d 1 . .
F F9 0.9623(4) 0.23004(17) 0.71862(17) 0.0414(8) Uani d 1 . .
O O1 0.4065(4) 0.37941(18) 0.61581(18) 0.0226(6) Uani d 1 . .
H H1 0.400397 0.339397 0.586174 0.034 Uiso calc 1 . .
C C1 0.4470(5) 0.4521(2) 0.5871(2) 0.0175(8) Uani d 1 . .
C C3 0.4204(6) 0.5136(3) 0.6992(3) 0.0283(10) Uani d 1 . .
H H4 0.312992 0.482094 0.706860 0.043 Uiso calc 1 . .
H H5 0.413086 0.572665 0.719463 0.043 Uiso calc 1 . .
H H3 0.514077 0.480919 0.720535 0.043 Uiso calc 1 . .
C C2 0.4888(5) 0.4604(3) 0.5143(2) 0.0189(9) Uani d 1 . .
H H2 0.498(5) 0.410(3) 0.488(2) 0.006(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
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'
Sb Sb -0.5866 1.5461 '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
F4 Sb1 F5 . . 96.68(11) ?
F4 Sb1 F2 . . 92.29(12) ?
F5 Sb1 F2 . . 90.73(14) ?
F4 Sb1 F3 . . 95.54(11) ?
F5 Sb1 F3 . . 90.38(13) ?
F2 Sb1 F3 . . 171.91(11) ?
F4 Sb1 F1 . . 93.34(11) ?
F5 Sb1 F1 . . 169.97(12) ?
F2 Sb1 F1 . . 89.34(12) ?
F3 Sb1 F1 . . 88.18(12) ?
F4 Sb1 F6 . . 176.70(11) ?
F5 Sb1 F6 . . 84.91(11) ?
F2 Sb1 F6 . . 84.78(11) ?
F3 Sb1 F6 . . 87.33(11) ?
F1 Sb1 F6 . . 85.11(11) ?
F9 Sb2 F11 . . 95.48(12) ?
F9 Sb2 F8 . . 90.04(14) ?
F11 Sb2 F8 . . 94.12(12) ?
F9 Sb2 F7 . . 168.79(11) ?
F11 Sb2 F7 . . 95.72(12) ?
F8 Sb2 F7 . . 89.00(12) ?
F9 Sb2 F10 . . 89.65(14) ?
F11 Sb2 F10 . . 94.98(12) ?
F8 Sb2 F10 . . 170.88(11) ?
F7 Sb2 F10 . . 89.53(13) ?
F9 Sb2 F6 . . 85.50(11) ?
F11 Sb2 F6 . . 178.88(11) ?
F8 Sb2 F6 . . 85.34(11) ?
F7 Sb2 F6 . . 83.29(11) ?
F10 Sb2 F6 . . 85.55(11) ?
Sb1 F6 Sb2 . . 150.90(15) ?
C1 O2 C3 . . 119.2(3) ?
O1 C1 O2 . . 117.7(4) ?
O1 C1 C2 . . 123.8(4) ?
O2 C1 C2 . . 118.4(4) ?
C2 C2 C1 5_666 . 120.8(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
Sb1 F4 . 1.856(2) ?
Sb1 F5 . 1.858(2) ?
Sb1 F2 . 1.859(3) ?
Sb1 F3 . 1.864(3) ?
Sb1 F1 . 1.886(2) ?
Sb1 F6 . 2.026(2) ?
Sb2 F9 . 1.852(3) ?
Sb2 F11 . 1.858(2) ?
Sb2 F8 . 1.863(3) ?
Sb2 F7 . 1.864(3) ?
Sb2 F10 . 1.865(3) ?
Sb2 F6 . 2.060(2) ?
O2 C1 . 1.281(5) ?
O2 C3 . 1.489(6) ?
O1 C1 . 1.277(5) ?
C1 C2 . 1.466(6) ?
C2 C2 5_666 1.334(8) ?
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
O1 H1 F1 . 0.84 1.81 2.569(4) 148.6 yes
C3 H5 F9 8_765 0.98 2.58 3.427(5) 145.1 yes
C3 H3 F8 . 0.98 2.59 3.437(5) 145.0 yes
C2 H2 F10 4_456 0.92(4) 2.43(4) 3.352(5) 175(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
C3 O2 C1 O1 . . . . 3.3(5) ?
C3 O2 C1 C2 . . . . -176.4(4) ?
O1 C1 C2 C2 . . . 5_666 172.3(5) ?
O2 C1 C2 C2 . . . 5_666 -8.1(7) ?
