Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids
O’Rourke, Brianna; Lauderback, Clare; Teodoro, Lara I.; Grimm, Morgan; Zeller, Matthias; Mirjafari, Arsalan; Guillet, Gary L.; Hillesheim, Patrick C.; ACS Omega 6 (2021) 32285–32296; doi:10.1021/acsomega.1c05241

data_4519184
_publ_section_title
;
 Developing Structural First Principles for Alkylated
 Triphenylphosphonium-Based Ionic Liquids
;
_journal_issue                   47
_journal_name_full               'ACS Omega'
_journal_page_first              32285
_journal_page_last               32296
_journal_paper_doi               10.1021/acsomega.1c05241
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C4 F10 N O4 S2, C22 H24 P'
_chemical_formula_sum            'C26 H24 F10 N O4 P S2'
_chemical_formula_weight         699.55
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                85.995(5)
_cell_angle_beta                 84.791(12)
_cell_angle_gamma                89.282(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4948(13)
_cell_length_b                   10.1971(10)
_cell_length_c                   15.5070(19)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    102.0
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.42
_cell_volume                     1491.5(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      102.0
_diffrn_detector                 'Bruker PhotonII CPAD'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
;
charge-integrating pixel array detector (CPAD)
;
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type
'Bruker AXS D8 Eco Quest diffractometer with PhotonII charge-integrating pixel'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1456
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51845
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.730
_diffrn_reflns_theta_min         2.627
_diffrn_source                   '1 kW fine focus sealed tube X-ray source'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0600 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.9025.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       Needles
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         7707
_refine_ls_number_restraints     581
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0402P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5156
_reflns_number_total             7707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05241_si_002.cif
_cod_data_source_block           fgcupch0018_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4519184
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11A) = Uanis(C13A)
Uanis(C12A) = Uanis(C14A)
Uanis(C11B) = Uanis(C13B)
Uanis(C12B) = Uanis(C14B)
Uanis(S1A) = Uanis(S2A)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{S1A, F1A, F2A, F3A, F5A, F4A, O1A, O2A, C11A, C12A} sigma for 1-2: 0.02, 1-3:
0.04
as in
{S2A, F6A, F7A, F8A, F9A, F10A, O3A, O4A, C13A, C14A}
{S1A, F1A, F2A, F3A, F5A, F4A, O1A, O2A, C11A, C12A} sigma for 1-2: 0.01, 1-3:
0.02
as in
{S1B, F6B, F7B, F8B, F9B, F10B, O1B, O2B, C13B, C14B}
{S1A, F1A, F2A, F3A, F5A, F4A, O1A, O2A, C11A, C12A} sigma for 1-2: 0.02, 1-3:
0.04
as in
{S2B, F1B, F2B, F3B, F4B, F5B, O3B, O4B, C11B, C12B}
5. Others
 Fixed Sof: S1A(0.5) F1A(0.5) F2A(0.5) F3A(0.5) F5A(0.5) F4A(0.5) O1A(0.5)
 O2A(0.5) C11A(0.5) C12A(0.5) S2A(0.5) F6A(0.5) F7A(0.5) F8A(0.5) F9A(0.5)
 F10A(0.5) O3A(0.5) O4A(0.5) C13A(0.5) C14A(0.5) N1A(0.5) S1B(0.5) F6B(0.5)
 F7B(0.5) F8B(0.5) F9B(0.5) F10B(0.5) O1B(0.5) O2B(0.5) C13B(0.5) C14B(0.5)
 S2B(0.5) F1B(0.5) F2B(0.5) F3B(0.5) F4B(0.5) F5B(0.5) O3B(0.5) O4B(0.5)
 C11B(0.5) C12B(0.5) N1B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
6.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C6B(H6B), C6C(H6C), C7A(H7A), C7B(H7B), C7C(H7C), C8A(H8A),
 C8B(H8B), C8C(H8C), C9A(H9A), C9B(H9B), C9C(H9C), C10A(H10A), C10B(H10B),
 C10C(H10C)
6.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              42755
_shelx_hkl_checksum              67813
_olex2_submission_special_instructions 'No special instructions were received'