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_1564989
_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(C4 H10 O), 9(C H4 O), 8[CH4O]'
_chemical_formula_sum            'C143 H224 O47'
_chemical_formula_weight         2695.21
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-30
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   30.9611(2)
_cell_length_b                   30.9611(2)
_cell_length_c                   13.12040(10)
_cell_measurement_reflns_used    94896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.2210
_cell_measurement_theta_min      1.8380
_cell_volume                     10892.07(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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    -48.00  77.00   0.50   20.00    --  -12.70  60.00   0.00  250
  2  \w    -56.00  77.00   0.50   20.00    --  -12.70  38.00-120.00  266
  3  \w   -102.00  23.00   0.50   20.00    --  -12.70 -60.00-120.00  250
  4  \w    -48.00  77.00   0.50   20.00    --  -12.70  57.00 -60.00  250
  5  \w    -48.00  77.00   0.50   20.00    --  -12.70  60.00 150.00  250
  6  \w   -102.00  23.00   0.50   20.00    --  -12.70 -60.00  90.00  250
  7  \w   -102.00  23.00   0.50   20.00    --  -12.70 -60.00  30.00  250
  8  \w    -54.00  77.00   0.50   20.00    --  -12.70  42.00  92.90  262
  9  \w    -48.00  77.00   0.50   20.00    --  -12.70  60.00  90.00  250
 10  \w    -48.00  77.00   0.50   20.00    --  -12.70  60.00-120.00  250
 11  \w   -102.00  23.00   0.50   20.00    --  -12.70 -60.00 120.00  250
 12  \w   -102.00  23.00   0.50   20.00    --  -12.70 -60.00 -60.00  250
 13  \w   -102.00  -2.00   0.50   20.00    --  -12.70  19.00-180.00  200
 14  \w   -102.00  31.00   0.50   20.00    --  -12.70 -38.00-180.00  266
;
_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      -0.0065696000
_diffrn_orient_matrix_UB_12      -0.0243212000
_diffrn_orient_matrix_UB_13      0.0166761000
_diffrn_orient_matrix_UB_21      -0.0187001000
_diffrn_orient_matrix_UB_22      -0.0004241000
_diffrn_orient_matrix_UB_23      0.0319672000
_diffrn_orient_matrix_UB_31      -0.0175191000
_diffrn_orient_matrix_UB_32      -0.0103871000
_diffrn_orient_matrix_UB_33      -0.0402813000
_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  0.0244
_diffrn_reflns_av_unetI/netI     0.0065
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            178473
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         2.172
_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    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       prism
_exptl_crystal_F_000             4374
_exptl_crystal_recrystallization_method
'The material was recrystallised from methanol'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6248
_refine_ls_number_restraints     591
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0631
_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^)+(0.1118P)^2^+16.7021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.1890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5748
_reflns_number_total             6248
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03367k2.cif
_cod_data_source_block           Noria
_cod_original_cell_volume        10892.06(16)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1564989
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C102 H96 O24'
_chemical_oxdiff_usercomment     FMA-1-159-Methanol
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_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, All O(H,H,H,H) groups
2. Restrained distances
 O51-C51
 1.42 with sigma of 0.02
 O41-C41
 1.42 with sigma of 0.02
 O31C-C31C = O31-C31 = O31B-C31B
 1.44 with sigma of 0.01
 C24B-O21B \\sim O21B-C22B
 with sigma of 0.04
 C24-C23 \\sim C21-C22
 with sigma of 0.02
 O21-C23 \\sim O21-C21
 with sigma of 0.02
 C24-O21 \\sim O21-C22
 with sigma of 0.04
 C24B-C23B \\sim C21B-C22B
 with sigma of 0.02
 O21B-C23B \\sim O21B-C21B
 with sigma of 0.02
 O31-C31 \\sim O31C-C31C \\sim C31B-O31B
 with sigma of 0.02
 O31B-O2 \\sim O2-O31 \\sim O31C-O2
 with sigma of 0.04
 H31H-O2 \\sim O2-H31 \\sim H31D-O2
 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
C41 \\sim O41 \\sim C51 \\sim O51: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
O31 \\sim C31 \\sim O31C \\sim C31C \\sim O31B \\sim C31B: within 2A with sigma
of 0.005 and sigma for terminal atoms of 0.01 within 2A
O21B \\sim C21B \\sim C23B \\sim C22B \\sim C24B \\sim O21 \\sim C21 \\sim C23
\\sim C22 \\sim C24: within 2A with sigma of 0.02 and sigma for terminal atoms
of 0.04 within 2A
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
 O31, C31, O31C, C31C, O31B, C31B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 1*[Sof(O31)+Sof(H31)+Sof(C31)+Sof(H31A)+Sof(H31B)+Sof(H31C)]+1*[Sof(O31C)+
 Sof(H31D)+Sof(C31C)+Sof(H31E)+Sof(H31F)+Sof(H31G)]+1*[Sof(O31B)+Sof(H31H)+
 Sof(C31B)+Sof(H31I)+Sof(H31J)+Sof(H31K)]=1 with esd of 0.000001
 Sof(O21B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=1-FVAR(1)
 Sof(O21)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
 Sof(O31)=Sof(H31)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(2)
 Sof(O31C)=Sof(H31D)=Sof(C31C)=Sof(H31E)=Sof(H31F)=Sof(H31G)=FVAR(3)
 Sof(O31B)=Sof(H31H)=Sof(C31B)=Sof(H31I)=Sof(H31J)=Sof(H31K)=FVAR(4)
 Fixed Sof: C41(0.16667) O41(0.16667) H41(0.16667) H41A(0.16667) H41B(0.16667)
 H41C(0.16667) C51(0.33333) O51(0.33333) H51(0.33333) H51A(0.33333)
 H51B(0.33333) H51C(0.33333)
6.a Free rotating group:
 C41(O41,H41,H41A,H41B,H41C,C51,O51,H51,H51A,H51B,H51C)
6.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
6.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C21(H21A,H21B), C23(H23A,
 H23B), C21B(H21C,H21D), C23B(H23C,H23D)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C6(H6), C10(H10), C13(H13)
6.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C), C22B(H22D,H22E,
 H22F), C24B(H24D,H24E,H24F), C31C(H31E,H31F,H31G), C31B(H31I,H31J,H31K)
6.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O31(H31), O31C(H31D), O31B(H31H)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              6782
_shelx_hkl_checksum              99909
_shelx_fab_checksum              68816
_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-1-159-Methanol
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.716
_oxdiff_exptl_absorpt_empirical_full_min 0.675