A Guanidium Salt as a Chaotropic Agent for Aqueous Battery Electrolytes
Brown, John; Forero-Saboya, Juan David; Baptiste, Benoît; Karlsmo, Martin; Rousse, Gwenaëlle; Grimaud, Alexis; Chemical Communications  (2023) –; doi:10.1039/D3CC03769J

data_7132144
_publ_section_title
;
 A Guanidium Salt as a Chaotropic Agent for Aqueous Battery Electrolytes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03769J
_journal_year                    2023
_chemical_formula_moiety         'C2 H F6 N O4 S2, C H6 N3'
_chemical_formula_sum            'C3 H6 F6 N4 O4 S2'
_chemical_formula_weight         340.24
_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
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                89.960(3)
_cell_angle_beta                 85.636(3)
_cell_angle_gamma                87.428(4)
_cell_formula_units_Z            24
_cell_length_a                   15.9721(9)
_cell_length_b                   18.6173(9)
_cell_length_c                   25.1641(5)
_cell_measurement_reflns_used    11184
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.3610
_cell_measurement_theta_min      1.6190
_cell_volume                     7453.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 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      293
_diffrn_detector                 'Rigaku Raxis4++ flat IP area detector'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -90.00  90.00   1.00  120.00   0.00   0.00   0.00    --   180
;
_diffrn_measurement_device       'Newport rotation stage'
_diffrn_measurement_device_type
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0136702000
_diffrn_orient_matrix_UB_12      -0.0342176000
_diffrn_orient_matrix_UB_13      -0.0070096000
_diffrn_orient_matrix_UB_21      -0.0422700000
_diffrn_orient_matrix_UB_22      0.0118110000
_diffrn_orient_matrix_UB_23      0.0068838000
_diffrn_orient_matrix_UB_31      -0.0037426000
_diffrn_orient_matrix_UB_32      0.0120054000
_diffrn_orient_matrix_UB_33      -0.0265069000
_diffrn_radiation_monochromator  'multilayer Osmic confocal optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            40087
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        23.256
_diffrn_reflns_theta_max         23.256
_diffrn_reflns_theta_min         1.647
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MM007HF rotating anode'
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_description       plate
_exptl_crystal_F_000             4080
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2443
_refine_ls_number_reflns         20251
_refine_ls_number_restraints     269
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.1027
_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^)+(0.1304P)^2^+19.3566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2681
_refine_ls_wR_factor_ref         0.2976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12552
_reflns_number_total             20251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03769j2.cif
_cod_data_source_block           gua_
_cod_database_code               7132144
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 72.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.27
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2. Restrained distances
 S1-O2A
 1.416 with sigma of 0.02
 O27A-S16
 1.416 with sigma of 0.02
 S15-O26A
 1.416 with sigma of 0.02
 O1A-S1
 1.416 with sigma of 0.02
 S16-O28A
 1.416 with sigma of 0.02
 O25A-S15
 1.416 with sigma of 0.02
 O4A-S2
 1.416 with sigma of 0.02
 S2-O3A
 1.416 with sigma of 0.02
 O2-S1
 1.416 with sigma of 0.02
 O26-S15
 1.416 with sigma of 0.02
 S16-O27
 1.416 with sigma of 0.02
 S1-O1
 1.416 with sigma of 0.02
 O3-S2
 1.416 with sigma of 0.02
 S15-O25
 1.416 with sigma of 0.02
 S2-O4
 1.416 with sigma of 0.02
 O28-S16
 1.416 with sigma of 0.02
 O26-O25
 2.44 with sigma of 0.02
 O37-S21
 1.416 with sigma of 0.02
 O38-S21
 1.416 with sigma of 0.02
 O3A-O4A
 2.44 with sigma of 0.02
 O38-O37
 2.44 with sigma of 0.02
 O10-S5
 1.416 with sigma of 0.02
 O37A-S21
 1.416 with sigma of 0.02
 O40A-O39A
 2.44 with sigma of 0.02
 O38A-O37A
 2.44 with sigma of 0.02
 O9-S5
 1.416 with sigma of 0.02
 O10A-S5
 1.416 with sigma of 0.02
 O40-O39
 2.44 with sigma of 0.02
 O11-O12
 2.44 with sigma of 0.02
 O2-O1
 2.44 with sigma of 0.02
 O28-O27
 2.44 with sigma of 0.02
 O38A-S21
 1.416 with sigma of 0.02
 O9A-S5
 1.416 with sigma of 0.02
 O3-O4
 2.44 with sigma of 0.02
 O11-S6
 1.416 with sigma of 0.02
 O2A-O1A
 2.44 with sigma of 0.02
 O11A-S6
 1.416 with sigma of 0.02
 O28A-O27A
 2.44 with sigma of 0.02
 O12-S6
 1.416 with sigma of 0.02
 O26A-O25A
 2.44 with sigma of 0.02
 O12A-S6
 1.416 with sigma of 0.02
 O10-O9
 2.44 with sigma of 0.02
 O40A-S22
 1.416 with sigma of 0.02
 O10A-O9A
 2.44 with sigma of 0.02
 O40-S22
 1.416 with sigma of 0.02
 O11A-O12A
 2.44 with sigma of 0.02
 O39A-S22
 1.416 with sigma of 0.02
 S22-O39
 1.416 with sigma of 0.02
 F6A-F4A
 2.122 with sigma of 0.02
 F1A-F2A
 2.122 with sigma of 0.02
 C1-F3A
 1.305 with sigma of 0.02
 F34-F35 = C1-F2A
 1.305 with sigma of 0.02
 F2A-F3A
 2.122 with sigma of 0.02
 F5-F6
 2.122 with sigma of 0.02
 F3A-F1A
 2.122 with sigma of 0.02
 F4A-F5A
 2.122 with sigma of 0.02
 C1-F1A
 1.305 with sigma of 0.02
 F6-F4
 2.122 with sigma of 0.02
 F5A-F6A
 2.122 with sigma of 0.02
 C1-F2
 1.305 with sigma of 0.02
 F5-F4
 2.122 with sigma of 0.02
 F62A-F61A
 2.122 with sigma of 0.02
 F44-F43
 2.122 with sigma of 0.02
 F18A-F16A
 2.122 with sigma of 0.02
 F17-C6
 1.305 with sigma of 0.02
 C2-F4
 1.305 with sigma of 0.02
 F17A-F16A
 2.122 with sigma of 0.02
 F15A-F13A
 2.122 with sigma of 0.02
 F13A-C5
 1.305 with sigma of 0.02
 F15-F14
 2.122 with sigma of 0.02
 F66A-F65A
 2.122 with sigma of 0.02
 F15-F13
 2.122 with sigma of 0.02
 F2-C1
 1.305 with sigma of 0.02
 F63-F61
 2.122 with sigma of 0.02
 C2-F6
 1.305 with sigma of 0.02
 F62-F63
 2.122 with sigma of 0.02
 F15A-C5
 1.305 with sigma of 0.02
 C15-F43A
 1.305 with sigma of 0.02
 F18-F16
 2.122 with sigma of 0.02
 C15-F44A
 1.305 with sigma of 0.02
 F65A-F64A
 2.122 with sigma of 0.02
 C16-F46A
 1.305 with sigma of 0.02
 F1-C1
 1.305 with sigma of 0.02
 C16-F47A
 1.305 with sigma of 0.02
 S1-C1
 1.305 with sigma of 0.02
 C16-F48A
 1.305 with sigma of 0.02
 F65A-F66A
 2.122 with sigma of 0.02
 F48A-F46A
 2.122 with sigma of 0.02
 F46A-F47A
 2.122 with sigma of 0.02
 F14A-C5
 1.305 with sigma of 0.02
 F47A-F48A
 2.122 with sigma of 0.02
 F16A-C6
 1.305 with sigma of 0.02
 F45A-F43A
 2.122 with sigma of 0.02
 F18A-C6
 1.305 with sigma of 0.02
 F43A-F44A
 2.122 with sigma of 0.02
 F17-F18
 2.122 with sigma of 0.02
 F44A-F45A
 2.122 with sigma of 0.02
 F63A-F61A
 2.122 with sigma of 0.02
 F63-F62
 2.122 with sigma of 0.02
 F62A-F63A
 2.122 with sigma of 0.02
 F1A-C1
 1.305 with sigma of 0.02
 F64-F65
 2.122 with sigma of 0.02
 F2A-C1
 1.305 with sigma of 0.02
 F65-F66
 2.122 with sigma of 0.02
 F66-F64
 2.122 with sigma of 0.02
 F66A-F64A
 2.122 with sigma of 0.02
 C22-F66
 1.305 with sigma of 0.02
 C2-F5A
 1.305 with sigma of 0.02
 C22-F64
 1.305 with sigma of 0.02
 C2-F6A
 1.305 with sigma of 0.02
 C22-F65
 1.305 with sigma of 0.02
 F13-C5
 1.305 with sigma of 0.02
 C21-F61
 1.305 with sigma of 0.02
 F14-C5
 1.305 with sigma of 0.02
 C21-F62
 1.305 with sigma of 0.02
 F15-C5
 1.305 with sigma of 0.02
 C21-F63
 1.305 with sigma of 0.02
 C21-F61A
 1.305 with sigma of 0.02
 F16-C6
 1.305 with sigma of 0.02
 C21-F62A
 1.305 with sigma of 0.02
 F17A-C6
 1.305 with sigma of 0.02
 C21-F63A
 1.305 with sigma of 0.02
 F18-C6
 1.305 with sigma of 0.02
 C22-F66A
 1.305 with sigma of 0.02
 F16-F17
 2.122 with sigma of 0.02
 C22-F64A
 1.305 with sigma of 0.02
 F61A-F62A
 2.122 with sigma of 0.02
 C22-F65A
 1.305 with sigma of 0.02
 F14-F13
 2.122 with sigma of 0.02
 F48-F46
 2.122 with sigma of 0.02
 F62-F61
 2.122 with sigma of 0.02
 F46-F47
 2.122 with sigma of 0.02
 F65-F64
 2.122 with sigma of 0.02
 F47-F48
 2.122 with sigma of 0.02
 F64-F66
 2.122 with sigma of 0.02
 F45-F43
 2.122 with sigma of 0.02
 F64A-F65A
 2.122 with sigma of 0.02
 F43-F44
 2.122 with sigma of 0.02
 F61A-F63A
 2.122 with sigma of 0.02
 F44-F45
 2.122 with sigma of 0.02
 F63A-F62A
 2.122 with sigma of 0.02
 C15-F45
 1.305 with sigma of 0.02
 F18A-F17A
 2.122 with sigma of 0.02
 C15-F43
 1.305 with sigma of 0.02
 F15A-F14A
 2.122 with sigma of 0.02
 C15-F44
 1.305 with sigma of 0.02
 F14A-F13A
 2.122 with sigma of 0.02
 F3A-C1
 1.305 with sigma of 0.02
 C16-F48
 1.305 with sigma of 0.02
 C2-F4A
 1.305 with sigma of 0.02
 C16-F46
 1.305 with sigma of 0.02
 C2-F5
 1.305 with sigma of 0.02
 C16-F47
 1.305 with sigma of 0.02
 F45A-C15
 1.305 with sigma of 0.02
 F3-F2
 2.122 with sigma of 0.02
 F1-F2
 1.305 with sigma of 0.02
 C1-F3
 1.305 with sigma of 0.02
 C1-F1
 1.305 with sigma of 0.02
 F3-F1
 2.122 with sigma of 0.02
 F2-F3
 2.122 with sigma of 0.02
 F2-F1
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O26) = Uanis(S15)
4. Rigid body (RIGU) restrains
 O3, O4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O3, S2, O4, O4A, O3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N8A, O28, O28A, S16, O27, O27A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2, O2A, S1, O1, O1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O37, O37A, O38, O38A, S21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S22, O39, O39A, O40, O40A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3A, C1, F1A, F2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, F2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, F1, F2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O25, O26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S15, O26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F62A(0.5) F1(0.5) F14(0.5) F13(0.5) F44A(0.5) F16A(0.5) F66A(0.5)
 F18A(0.5) F5(0.5) O37A(0.5) F6(0.5) F2(0.5) F47A(0.5) F65A(0.5) F64A(0.5)
 F63A(0.5) F48A(0.5) F4(0.5) F43A(0.5) F15(0.5) F46A(0.5) F45A(0.5) O26A(0.5)
 F61A(0.5) O39A(0.5) F17A(0.5) O9(0.5) O28A(0.5) O27A(0.5) O2(0.5) N1(0.5)
 H1(0.5) O4(0.5) O1(0.5) O3A(0.5) O10(0.5) O12A(0.5) N3A(0.5) H3A(0.5)
 O11A(0.5) O40A(0.5) O25A(0.5) N11(0.5) H11(0.5) O38A(0.5) N8A(0.5) H8A(0.5)
 N8(0.5) H8(0.5) N1A(0.5) H1A(0.5) N3(0.5) H3(0.5) N11A(0.5) H11A(0.5) O3(0.5)
 O2A(0.5) O1A(0.5) O4A(0.5) O26(0.5) O28(0.5) O27(0.5) O25(0.5) O37(0.5)
 O38(0.5) O39(0.5) O9A(0.5) O40(0.5) O12(0.5) O10A(0.5) O11(0.5) F4A(0.5)
 F5A(0.5) F3A(0.5) F1A(0.5) F6A(0.5) F2A(0.5) F65(0.5) F64(0.5) F14A(0.5)
 F15A(0.5) F66(0.5) F62(0.5) F17(0.5) F16(0.5) F13A(0.5) F43(0.5) F44(0.5)
 F63(0.5) F61(0.5) F48(0.5) F47(0.5) F46(0.5) F45(0.5) F18(0.5) F3(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N6(H6), N4(H4), N10(H10), N9(H9), N7(H7), N12(H12), N5(H5), N2(H2), N1(H1),
 N3A(H3A), N11(H11), N8A(H8A), N8(H8), N1A(H1A), N3(H3), N11A(H11A)
6.b X=CH2 refined with riding coordinates:
 N01J(H01A,H01B), N21(H21A,H21B), N28(H28A,H28B), N39(H39A,H39B), N29(H29A,
 H29B), N023(H02A,H02B), N42(H42A,H42B), N20(H20A,H20B), N19(H19A,H19B),
 N36(H36A,H36B), N02H(H02C,H02D), N30(H30A,H30B), N27(H27A,H27B), N17(H17A,
 H17B), N24(H24A,H24B), N44(H44A,H44B), N26(H26A,H26B), N16(H16A,H16B),
 N37(H37A,H37B), N35(H35A,H35B), N18(H18A,H18B), N33(H33A,H33B), N31(H31A,H31B),
  N25(H25A,H25B), N34(H34A,H34B), N15(H15A,H15B), N45(H45A,H45B), N40(H40A,
 H40B), N32(H32A,H32B), N43(H43A,H43B), N13(H13A,H13B), N23(H23A,H23B),
 N22(H22A,H22B), N38(H38A,H38B), N14(H14A,H14B), N41(H41A,H41B)
;
_shelx_res_checksum              12333
_shelx_hkl_checksum              75183
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.332
_oxdiff_exptl_absorpt_empirical_full_min 0.235