The effect of vicinal di-halo substituents on the organogelling properties of aromatic supramolecular gelators and their application as soft templates
Mac Cormack, Andrea S.; Busch, Verónica M.; Japas, M. Laura; Giovanetti, Lisandro; Di Salvo, Florencia; Di Chenna, Pablo H.; New Journal of Chemistry 44 (2020) 8198–8208; doi:10.1039/D0NJ01440K

data_7059506
_publ_section_title
;
 The effect of vicinal di-halo substituents on the organogelling
 properties of aromatic supramolecular gelators and their application as
 soft templates
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8198
_journal_page_last               8208
_journal_paper_doi               10.1039/D0NJ01440K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H27 Cl2 N O'
_chemical_formula_sum            'C18 H27 Cl2 N O'
_chemical_formula_weight         344.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-27 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.916(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.382(2)
_cell_length_b                   12.2314(14)
_cell_length_c                   9.8293(7)
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.8520
_cell_measurement_theta_min      4.0330
_cell_volume                     1919.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1158
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.877
_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    -54.00  96.00   1.00  175.76    --   20.98   0.00 -60.00  150
  2  \w    -51.00  54.00   1.00  175.76    --   20.98 -77.00 -60.00  105
  3  \w    -25.00  24.00   1.00  175.76    --  -21.29 -99.00  30.00   49
  4  \w   -103.00 -53.00   1.00  175.76    --  -21.29 178.00-120.00   50
  5  \w    -53.00 -28.00   1.00  175.76    --   20.98 -37.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0160717000
_diffrn_orient_matrix_UB_12      -0.0539878000
_diffrn_orient_matrix_UB_13      0.0080517000
_diffrn_orient_matrix_UB_21      0.0365360000
_diffrn_orient_matrix_UB_22      0.0178559000
_diffrn_orient_matrix_UB_23      -0.0209617000
_diffrn_orient_matrix_UB_31      0.0195017000
_diffrn_orient_matrix_UB_32      0.0113680000
_diffrn_orient_matrix_UB_33      0.0705646000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12878
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.939
_diffrn_reflns_theta_min         3.828
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0502P)^2^+0.1189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2310
_reflns_number_total             4456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01440k2.cif
_cod_data_source_block           exp_5006
_cod_depositor_comments
;Adding full bibliography for 7059505--7059506.cif.

 Adding full bibliography for 7059505--7059506.cif.
;
_cod_original_cell_volume        1919.8(4)
_cod_database_code               7059506
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C34 H58 Br2 N2 O2'
_chemical_oxdiff_usercomment     'aguja sin cortar'
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C15(H15A,H15B), C10(H10A,H10B), C13(H13A,
 H13B), C11(H11A,H11B), C9(H9A,H9B), C8(H8A,H8B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              25533
_olex2_exptl_crystal_mounting_method loop
_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.749