Norbornene chaotropic salts as low molecular mass ionic organogelators (LMIOGs).
Engstrom, Jordan R.; Savyasachi, Aramballi J.; Parhizkar, Marzieh; Sutti, Alessandra; Hawes, Chris S.; White, Jonathan M.; Gunnlaugsson, Thorfinnur; Pfeffer, Frederick M.; Chemical science 9 (2018) 5233–5241; doi:10.1039/c8sc01798k

data_1549425
_publ_section_title
;
 Norbornene chaotropic salts as low molecular mass ionic organogelators
 (LMIOGs).
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              5233
_journal_page_last               5241
_journal_paper_doi               10.1039/c8sc01798k
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 N O4, 2(H2 O), C8 H20 N'
_chemical_formula_sum            'C26 H40 N2 O6'
_chemical_formula_weight         476.60
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-02-27 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                93.9720(10)
_cell_angle_beta                 99.6020(10)
_cell_angle_gamma                107.2150(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8976(3)
_cell_length_b                   9.7399(3)
_cell_length_c                   15.4155(5)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.79
_cell_volume                     1248.19(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33371
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.296
_diffrn_reflns_theta_min         2.931
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Dataset was created by merging two collections carried out 
on the same crystal after manual reorientation, in order to
collect satisfactory Friedel pair coverage. Each dataset was
scaled separately. SADABS-2016/2 (Bruker,2016/2) was used for 
absorption correction. 
The Ratio of minimum to maximum transmission is 0.8598
wR2(int) was 0.0643 before and 0.0504 after correction. 
The Ratio of minimum to maximum transmission is 0.9085. The 
\l/2 correction factor is Not present.'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 4397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         9072
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0600P)^2^+0.2530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                9004
_reflns_number_total             9072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01798k2.cif
_cod_data_source_block           9TEA_S
_cod_depositor_comments
'Adding full bibliography for 1549423--1549425.cif.'
_cod_original_cell_volume        1248.18(7)
_cod_database_code               1549425
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.806
_exptl_absorpt_special_details   'See Above'
_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 C(H,H,H,H,H,H,H,H,H,H,H) groups
2. Restrained distances
 O12-H12C = O12-H12D
 0.87 with sigma of 0.02
 O9-H9A = O9-H9B
 0.87 with sigma of 0.02
 O10-H10A = O10-H10B
 0.87 with sigma of 0.02
 O11-H11A = O11-H11B
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C7(H7), C10(H10), C19(H19), C22(H22), C24(H24),
 C25(H25), C28(H28)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B), C23(H23A,H23B), C30(H30A,H30B), C38(H38A,H38B),
 C39(H39A,H39B), C42(H42A,H42B), C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B),
  C50(H50A,H50B), C51(H51A,H51B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C21(H21), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
3.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C52(H52A,
 H52B,H52C)
;
_shelx_res_checksum              84057
_olex2_submission_special_instructions 'No special instructions were received'