A new family of urea-based low molecular-weight organogelators for environmental remediation: the influence of structure.
Peveler, William J.; Packman, Hollie; Alexander, Shirin; Chauhan, Raamanand R.; Hayes, Lilian M.; Macdonald, Thomas J.; Cockcroft, Jeremy K.; Rogers, Sarah; Aarts, Dirk G. A. L.; Carmalt, Claire J.; Parkin, Ivan P.; Bear, Joseph C.; Soft matter 14 (2018) 8821–8827; doi:10.1039/c8sm01682h

data_1550031
_publ_section_title
;
 A new family of urea-based low molecular-weight organogelators for
 environmental remediation: the influence of structure.
;
_journal_issue                   43
_journal_name_full               'Soft matter'
_journal_page_first              8821
_journal_page_last               8827
_journal_paper_doi               10.1039/c8sm01682h
_journal_volume                  14
_journal_year                    2018
_chemical_formula_moiety         'C14 H22 N2 O, 0.5(C6 H12)'
_chemical_formula_sum            'C17 H28 N2 O'
_chemical_formula_weight         276.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-05-29 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.82090(10)
_cell_length_b                   19.6496(2)
_cell_length_c                   20.23180(10)
_cell_measurement_reflns_used    25391
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.1280
_cell_measurement_theta_min      4.3400
_cell_volume                     3506.72(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_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    -67.00  32.00   1.00   14.16    --  -42.62  38.00 120.00   99
  2  \w    -67.00  32.00   1.00   14.16    --  -42.62  38.00  30.00   99
  3  \w      1.00  84.00   1.00   14.16    --   42.62 -99.00 -30.00   83
  4  \w     94.00 178.00   1.00   56.65    --  107.94 125.00 120.00   84
  5  \w     26.00 109.00   1.00   56.65    --  107.94 -95.00 150.00   83
  6  \w     26.00 161.00   1.00   56.65    --  107.94 -15.00 120.00  135
  7  \w   -116.00 -14.00   1.00   14.16    --  -42.62 -57.00-150.00  102
  8  \w   -119.00 -10.00   1.00   14.16    --  -42.62 -77.00   0.00  109
  9  \w   -116.00 -14.00   1.00   14.16    --  -42.62 -57.00  90.00  102
 10  \w     36.00 137.00   1.00   56.65    --  107.94 -61.00-150.00  101
 11  \w     75.00 178.00   1.00   56.65    --  107.94  77.00-180.00  103
 12  \w     80.00 178.00   1.00   56.65    --  107.94  30.00 -90.00   98
 13  \w   -119.00 -10.00   1.00   14.16    --  -42.62 -77.00-180.00  109
 14  \w   -116.00 -57.00   1.00   14.16    --  -42.62-150.00  88.00   59
 15  \w   -119.00 -10.00   1.00   14.16    --  -42.62 -77.00 -60.00  109
 16  \w     35.00 121.00   1.00   56.65    --  107.94-125.00 120.00   86
 17  \w     79.00 178.00   1.00   56.65    --  107.94  61.00 120.00   99
 18  \w     79.00 178.00   1.00   56.65    --  107.94  61.00 -30.00   99
 19  \w   -123.00  -2.00   1.00   14.16    --  -42.62 -19.00 -60.00  121
 20  \w   -119.00 -10.00   1.00   14.16    --  -42.62 -77.00  90.00  109
 21  \w     23.00  99.00   1.00   14.16    --   42.62-125.00-150.00   76
 22  \w     75.00 100.00   1.00   56.65    --  107.94  77.00  60.00   25
 23  \w     79.00 178.00   1.00   56.65    --  107.94  61.00 -60.00   99
 24  \w     79.00 178.00   1.00   56.65    --  107.94  61.00  30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0039778000
_diffrn_orient_matrix_UB_12      -0.0287276000
_diffrn_orient_matrix_UB_13      -0.0708346000
_diffrn_orient_matrix_UB_21      -0.0192192000
_diffrn_orient_matrix_UB_22      0.0725997000
_diffrn_orient_matrix_UB_23      -0.0275261000
_diffrn_orient_matrix_UB_31      0.1735121000
_diffrn_orient_matrix_UB_32      0.0073360000
_diffrn_orient_matrix_UB_33      -0.0047107000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            48013
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.212
_diffrn_reflns_theta_min         4.500
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.047
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1090P)^2^+0.5912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6571
_reflns_number_total             7051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sm01682h2.cif
_cod_data_source_block           xstr0751
_cod_depositor_comments
'Adding full bibliography for 1550029--1550031.cif.'
_cod_database_code               1550031
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C34 H56 N4 O2'
_chemical_oxdiff_usercomment     'Molecule 5'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C12A(H12A), C9B(H9B), C12B(H12B)
2.b Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C5C(H5CA,
 H5CB), C6C(H6CA,H6CB)
2.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A), C2B(H2B), C4B(H4B), C5B(H5B), C6B(H6B)
2.d Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C10A(H10D,H10E,H10F), C11A(H11D,H11E,H11F), C13A(H13D,
 H13E,H13F), C14A(H14D,H14E,H14F), C7B(H7BA,H7BB,H7BC), C10B(H10A,H10B,H10C),
 C11B(H11A,H11B,H11C), C13B(H13A,H13B,H13C), C14B(H14A,H14B,H14C)
;
_olex2_date_sample_data_collection 2017-05-19
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.812