Noria and its derivatives as hosts for chemically and thermally robust Type II Porous Liquids
Alexander, Francesca M.; Fonrouge, Sergio; Borioni, Jose Luis; Del Popolo, Mario G.; Horton, Peter; Coles, Simon; Hutchings, Benjamin; Crawford, Deborah E.; James, Stuart; Chemical Science  (2021) –; doi:10.1039/D1SC03367K

data_1564990
_publ_section_title
;
 Noria and its derivatives as hosts for chemically and thermally robust
 Type II Porous Liquids
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03367K
_journal_year                    2021
_chemical_formula_moiety         'C102 H96 O24, 6(C2 H6 O S)'
_chemical_formula_sum            'C114 H132 O30 S6'
_chemical_formula_weight         2174.55
_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
_audit_creation_date             2021-03-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-27 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                117.141(3)
_cell_angle_beta                 115.302(3)
_cell_angle_gamma                90.835(2)
_cell_formula_units_Z            2
_cell_length_a                   19.5728(5)
_cell_length_b                   22.2124(7)
_cell_length_c                   22.5739(6)
_cell_measurement_reflns_used    19226
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2660
_cell_measurement_theta_min      1.7900
_cell_volume                     7623.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -97.00  25.00   0.50  120.00    --   -7.30 -60.00-120.00  244
  2  \w    -97.00  82.00   0.50  120.00    --   -7.30   0.00-150.00  358
  3  \w    -97.00  25.00   0.50  120.00    --   -7.30 -60.00 -30.00  244
  4  \w    -40.00   3.00   0.50  120.00    --   -7.30  60.00 -90.00   86
  5  \w    -40.00  82.00   0.50  120.00    --   -7.30  58.00 -16.97  244
;
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208669000
_diffrn_orient_matrix_UB_12      0.0178762000
_diffrn_orient_matrix_UB_13      0.0187670000
_diffrn_orient_matrix_UB_21      0.0028744000
_diffrn_orient_matrix_UB_22      0.0260568000
_diffrn_orient_matrix_UB_23      -0.0093387000
_diffrn_orient_matrix_UB_31      -0.0357773000
_diffrn_orient_matrix_UB_32      -0.0195660000
_diffrn_orient_matrix_UB_33      -0.0345920000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            110888
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_min         1.778
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.947
_exptl_crystal_description       plate
_exptl_crystal_F_000             2304
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of THF and DMSO by vapour diffusion'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.924
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1515
_refine_ls_number_reflns         26905
_refine_ls_number_restraints     2596
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0894
_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/[\s^2^(Fo^2^)+(0.1344P)^2^+10.8738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2586
_refine_ls_wR_factor_ref         0.2796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17088
_reflns_number_total             26905
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03367k2.cif
_cod_data_source_block           R3
_cod_original_cell_volume        7623.2(4)
_cod_database_code               1564990
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C102 H96 O24 (C2H6SO)8'
_chemical_oxdiff_usercomment     'FMA-1-131 last try on Ros'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, All O(H) groups
2. Restrained distances
 O351-S351
 1.69 with sigma of 0.02
 O251-S251
 1.69 with sigma of 0.02
 S351-C351 = S351-C352
 1.89 with sigma of 0.02
 S251-C251 = S251-C252
 1.89 with sigma of 0.02
 O321-S321
 1.69 with sigma of 0.02
 S321-C321 = S321-C322
 1.89 with sigma of 0.02
 O231-S231
 1.69 with sigma of 0.02
 S231-C232 = S231-C231
 1.89 with sigma of 0.02
 S331-C331 = S331-C332
 1.89 with sigma of 0.02
 O331-S331
 1.69 with sigma of 0.02
 O211-S211
 1.69 with sigma of 0.02
 O341-S341
 1.69 with sigma of 0.02
 S341-C341 = S341-C342
 1.89 with sigma of 0.02
 S211-C211 = S211-C212
 1.89 with sigma of 0.02
 S201-C202 = S201-C201
 1.89 with sigma of 0.02
 O201-S201
 1.69 with sigma of 0.02
 O231-C232 = O231-C231
 2.79 with sigma of 0.04
 O221-C222 = O221-C221
 2.79 with sigma of 0.04
 O251-C251 = O251-C252
 2.79 with sigma of 0.04
 O351-C351 = O351-C352
 2.79 with sigma of 0.04
 O321-C321 = O321-C322
 2.79 with sigma of 0.04
 O331-C331 = O331-C332
 2.79 with sigma of 0.04
 O341-C341 = O341-C342
 2.79 with sigma of 0.04
 O241-C242 = O241-C241
 2.79 with sigma of 0.04
 O211-C211 = O211-C212
 2.79 with sigma of 0.04
 O201-C202 = O201-C201
 2.79 with sigma of 0.04
 S331-C331 \\sim S331-C332
 with sigma of 0.02
 C232-O231 \\sim C231-O231
 with sigma of 0.04
 C351-O351 \\sim C352-O351
 with sigma of 0.04
 C251-O251 \\sim C252-O251
 with sigma of 0.04
 S351-C351 \\sim S351-C352
 with sigma of 0.02
 S231-C232 \\sim S231-C231
 with sigma of 0.02
 S251-C251 \\sim S251-C252
 with sigma of 0.02
 C331-O331 \\sim C332-O331
 with sigma of 0.04
 C222-O221 \\sim C221-O221
 with sigma of 0.04
 S321-C321 \\sim S321-C322
 with sigma of 0.02
 C321-O321 \\sim C322-O321
 with sigma of 0.04
 C242-O241 \\sim C241-O241
 with sigma of 0.04
 S341-C341 \\sim S341-C342
 with sigma of 0.02
 C341-O341 \\sim C342-O341
 with sigma of 0.04
 S211-C211 \\sim S211-C212
 with sigma of 0.02
 C211-O211 \\sim C212-O211
 with sigma of 0.04
 S201-C202 \\sim S201-C201
 with sigma of 0.02
 C202-O201 \\sim C201-O201
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(O341) = Uanis(O241)
Uanis(C221) = Uanis(C321)
4. 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
5. Others
 Sof(S321)=Sof(O321)=Sof(C321)=Sof(H32E)=Sof(H32C)=Sof(H32D)=Sof(C322)=
 Sof(H32G)=Sof(H32F)=Sof(H32H)=1-FVAR(1)
 Sof(S221)=Sof(O221)=Sof(C221)=Sof(H22E)=Sof(H22F)=Sof(H22D)=Sof(C222)=
 Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
 Sof(S331)=Sof(O331)=Sof(C331)=Sof(H33C)=Sof(H33D)=Sof(H33E)=Sof(C332)=
 Sof(H33G)=Sof(H33H)=Sof(H33F)=1-FVAR(2)
 Sof(S231)=Sof(O231)=Sof(C231)=Sof(H23E)=Sof(H23D)=Sof(H23F)=Sof(C232)=
 Sof(H23B)=Sof(H23A)=Sof(H23C)=FVAR(2)
 Sof(S341)=Sof(O341)=Sof(C341)=Sof(H34E)=Sof(H34C)=Sof(H34D)=Sof(C342)=
 Sof(H34H)=Sof(H34G)=Sof(H34F)=1-FVAR(3)
 Sof(S241)=Sof(O241)=Sof(C241)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C242)=
 Sof(H24B)=Sof(H24A)=Sof(H24C)=FVAR(3)
 Sof(S351)=Sof(O351)=Sof(C351)=Sof(H35C)=Sof(H35A)=Sof(H35B)=Sof(C352)=
 Sof(H35E)=Sof(H35D)=Sof(H35F)=1-FVAR(4)
 Sof(S251)=Sof(O251)=Sof(C251)=Sof(H25A)=Sof(H25C)=Sof(H25B)=Sof(C252)=
 Sof(H25D)=Sof(H25F)=Sof(H25E)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28), C41(H41), C48(H48), C55(H55), C62(H62),
 C75(H75), C82(H82), C89(H89), C96(H96)
6.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,
 H33B), C34(H34A,H34B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B),
 C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B), C97(H97A,H97B), C98(H98A,H98B),
  C99(H99A,H99B), C100(H10C,H10D), C101(H10A,H10B), C102(H10E,H10F)
6.c Me refined with riding coordinates:
 C221(H22E,H22F,H22D), C222(H22A,H22B,H22C), C231(H23E,H23D,H23F), C232(H23B,
 H23A,H23C), C241(H24D,H24E,H24F), C242(H24B,H24A,H24C), C251(H25A,H25C,H25B),
 C252(H25D,H25F,H25E), C321(H32E,H32C,H32D), C322(H32G,H32F,H32H), C331(H33C,
 H33D,H33E), C332(H33G,H33H,H33F), C341(H34E,H34C,H34D), C342(H34H,H34G,H34F),
 C351(H35C,H35A,H35B), C352(H35E,H35D,H35F)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C10(H10), C13(H13), C17(H17), C20(H20), C24(H24), C27(H27),
 C37(H37), C40(H40), C44(H44), C47(H47), C51(H51), C54(H54), C58(H58), C61(H61),
  C71(H71), C74(H74), C78(H78), C81(H81), C85(H85), C88(H88), C92(H92), C95(H95)
6.e Idealised Me refined as rotating group:
 C201(H20D,H20E,H20F), C202(H20A,H20B,H20C), C211(H21C,H21B,H21A), C212(H21D,
 H21F,H21E)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O9(H9), O11(H11), O16(H16), O18(H18), O23(H23), O25(H25),
 O36(H36), O38(H38), O43(H43), O45(H45), O50(H50), O52(H52), O57(H57), O59(H59),
  O70(H70), O72(H72), O77(H77), O79(H79), O84(H84), O86(H86), O91(H91), O93(H93)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              80710
_shelx_hkl_checksum              7773
_shelx_fab_checksum              29939
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id FMA-1-131
_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 1.846
_oxdiff_exptl_absorpt_empirical_full_min 0.339