Original polymorphism in a naphthalene bisimide π-conjugated organogelator: a complex interplay between hydrogen bonding and heterocycle π-stacking
Diebold, Morgane; Christ, Elliot; Biniek, Laure; Karmazin, Lydia; Heinrich, Benoît; Contal, Christophe; Ghosh, Suhrit; Mesini, Philippe J.; Brinkmann, Martin; Journal of Materials Chemistry C 7 (2019) 13120–; doi:10.1039/C9TC04402G

data_7237992
_publ_section_title
;
 Original polymorphism in a naphthalene bisimide \p-conjugated
 organogelator: a complex interplay between hydrogen bonding and
 heterocycle \p-stacking
;
_journal_issue                   42
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              13120
_journal_paper_doi               10.1039/C9TC04402G
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C80 H120 N4 O12'
_chemical_formula_sum            'C80 H120 N4 O12'
_chemical_formula_weight         1329.79
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-09-12 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.135(6)
_cell_angle_gamma                90
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_cell_length_b                   16.1704(12)
_cell_length_c                   9.8778(7)
_cell_measurement_reflns_used    4353
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      65.62
_cell_measurement_theta_min      3.29
_cell_volume                     3849.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26423
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.018
_diffrn_reflns_theta_min         1.833
_diffrn_source                   'Cu-ImuS microfocus tube'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       needle
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.45
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_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00077(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         6626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0762
_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^)+(0.1085P)^2^+1.2861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1924
_refine_ls_wR_factor_ref         0.2371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3493
_reflns_number_total             6626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc04402g2.cif
_cod_data_source_block           cgmb160309
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7237992
_shelxl_version_number           2013-4
_shelx_res_checksum              73320