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_4519187
_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         'C3 F6 N O4 S2, C22 H24 P'
_chemical_formula_sum            'C25 H24 F6 N O4 P S2'
_chemical_formula_weight         611.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-10-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6631(4)
_cell_length_b                   15.9667(4)
_cell_length_c                   19.1524(5)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.8223
_cell_measurement_theta_min      2.7665
_cell_volume                     5401.4(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2018), 
SHELXLE Rev1030 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24216
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.993
_diffrn_reflns_theta_min         2.767
_exptl_absorpt_coefficient_mu    3.030
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       block
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.049(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     915
_refine_ls_number_reflns         9967
_refine_ls_number_restraints     895
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0387
_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/[\s^2^(Fo^2^)+(0.0629P)^2^+0.5913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.818
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                9123
_reflns_number_total             9967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c05241_si_003.cif
_cod_data_source_block           butppcyctf2n_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               4519187
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.643
_shelx_estimated_absorpt_t_min   0.542
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.951(17)
 0.049(17)
2. 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
3. Uiso/Uaniso restraints and constraints
P2 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim
C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim
C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim P2B \\sim
C23B \\sim C24B \\sim C25B \\sim C26B \\sim C27B \\sim C28B \\sim C29B \\sim
C30B \\sim C31B \\sim C32B \\sim C33B \\sim C34B \\sim C35B \\sim C36B \\sim
C37B \\sim C38B \\sim C39B \\sim C40B \\sim C41B \\sim C42B \\sim C43B \\sim
C44B: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
4. Same fragment restrains
{P1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16,
C17, C18, C19, C20, C21, C22} sigma for 1-2: 0.02, 1-3: 0.04
as in
{P2, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37,
C38, C39, C40, C41, C42, C43, C44}
{P1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16,
C17, C18, C19, C20, C21, C22} sigma for 1-2: 0.02, 1-3: 0.04
as in
{P2B, C23B, C24B, C25B, C26B, C27B, C28B, C29B, C30B, C31B, C32B, C33B, C34B,
C35B, C36B, C37B, C38B, C39B, C40B, C41B, C42B, C43B, C44B}
5. Others
 Sof(P2B)=Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=
 Sof(C25B)=Sof(H25C)=Sof(H25D)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=
 Sof(C27B)=Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(H29B)=Sof(C30B)=Sof(H30B)=
 Sof(C31B)=Sof(H31B)=Sof(C32B)=Sof(H32B)=Sof(C33B)=Sof(C34B)=Sof(H34B)=
 Sof(C35B)=Sof(H35B)=Sof(C36B)=Sof(H36B)=Sof(C37B)=Sof(H37B)=Sof(C38B)=
 Sof(H38B)=Sof(C39B)=Sof(C40B)=Sof(H40B)=Sof(C41B)=Sof(H41B)=Sof(C42B)=
 Sof(H42B)=Sof(C43B)=Sof(H43B)=Sof(C44B)=Sof(H44B)=1-FVAR(1)
 Sof(P2)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=
 Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(C28)=
 Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=
 Sof(H32)=Sof(C33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=
 Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=Sof(C39)=Sof(C40)=Sof(H40)=Sof(C41)=
 Sof(H41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C23B(H23C,H23D), C24B(H24C,H24D), C25B(H25C,H25D)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
 C37(H37), C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44),
 C28B(H28B), C29B(H29B), C30B(H30B), C31B(H31B), C32B(H32B), C34B(H34B),
 C35B(H35B), C36B(H36B), C37B(H37B), C38B(H38B), C40B(H40B), C41B(H41B),
 C42B(H42B), C43B(H43B), C44B(H44B)
6.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C26(H26A,H26B,H26C), C26B(H26D,H26E,H26F)
;
_shelx_res_checksum              56699
_shelx_hkl_checksum              33912
_olex2_submission_special_instructions 'No special instructions were received'