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_7059505
_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         'C20 H30 Br2 N2 O2'
_chemical_formula_sum            'C20 H30 Br2 N2 O2'
_chemical_formula_weight         490.26
_chemical_name_systematic        AMC22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-12-23
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-26 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.868(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5709(14)
_cell_length_b                   17.1752(12)
_cell_length_c                   8.9783(10)
_cell_measurement_reflns_used    1684
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.7920
_cell_measurement_theta_min      4.3000
_cell_volume                     2181.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 16.1158
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
  1 omega  -11.00   78.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000 -120.0000 89

  2 omega   51.00   90.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000  120.0000 39

  3 omega   54.00   81.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000  -90.0000 27

  4 omega  -10.00   73.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000    0.0000 83

  5 omega   35.00   83.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583  178.0000   90.0000 48

  6 omega  -25.00   66.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583  -99.0000 -150.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0351402000
_diffrn_orient_matrix_UB_12      0.0154225000
_diffrn_orient_matrix_UB_13      -0.0343824000
_diffrn_orient_matrix_UB_21      -0.0356329000
_diffrn_orient_matrix_UB_22      0.0123743000
_diffrn_orient_matrix_UB_23      -0.0640856000
_diffrn_orient_matrix_UB_31      -0.0027944000
_diffrn_orient_matrix_UB_32      0.0362535000
_diffrn_orient_matrix_UB_33      0.0365263000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7402
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.310
_diffrn_reflns_theta_min         3.732
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.732
_exptl_absorpt_correction_T_max  0.689
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.493
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_preparation
'Slow evaporation of the solvent from acetone solution'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0187P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1664
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01440k2.cif
_cod_data_source_block           exp_3823
_cod_depositor_comments
;Adding full bibliography for 7059505--7059506.cif.

 Adding full bibliography for 7059505--7059506.cif.
;
_cod_database_code               7059505
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H30 N2 O2 Br2'
_chemical_oxdiff_usercomment     AMC22_acetona_3
_reflns_odcompleteness_completeness 99.65
_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:
 C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              10533
_olex2_submission_original_sample_id AMC22
_olex2_submission_special_instructions 'No special instructions were received'