Fluorescent supramolecular hierarchical self-assemblies from glycosylated 4-amino- and 4-bromo-1,8-naphthalimides.
Calatrava-Pérez, Elena; Acherman, Stefan; Stricker, Lucas; McManus, Gavin; Delente, Jason; Lynes, Amy D.; Henwood, Adam F.; Lovitt, June I.; Hawes, Chris S.; Byrne, Kevin; Schmitt, Wolfgang; Kotova, Oxana; Gunnlaugsson, Thorfinnur; Scanlan, Eoin M.; Organic & biomolecular chemistry 18 (2020) 3475–3480; doi:10.1039/d0ob00033g

data_7157471
_publ_section_title
;
 Fluorescent supramolecular hierarchical self-assemblies from glycosylated
 4-amino- and 4-bromo-1,8-naphthalimides.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3475
_journal_page_last               3480
_journal_paper_doi               10.1039/d0ob00033g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H22 Br N O2'
_chemical_formula_sum            'C20 H22 Br N O2'
_chemical_formula_weight         388.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-11-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                81.534(3)
_cell_angle_beta                 86.654(4)
_cell_angle_gamma                84.890(3)
_cell_formula_units_Z            2
_cell_length_a                   4.6972(2)
_cell_length_b                   11.9618(5)
_cell_length_c                   15.7954(7)
_cell_measurement_reflns_used    2912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.85
_cell_measurement_theta_min      3.75
_cell_volume                     873.41(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.978
_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  0.0449
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7358
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_min         3.748
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0825 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.6931. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.239
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1140P)^2^+0.9070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.1935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2664
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00033g2.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7157470--7157472.cif.'
_cod_database_code               7157471
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.655
_olex2_refinement_description
;
1. Others
 Fixed Sof: Br1(0.93) Br2(0.07) H13(0.07) H15(0.93)
 Fixed Uiso: H1A(0.081) H1B(0.081) H1C(0.081) H2A(0.055) H2B(0.055) H3A(0.05)
 H3B(0.05) H4A(0.048) H4B(0.048) H5A(0.046) H5B(0.046) H6A(0.045) H6B(0.045)
 H7A(0.041) H7B(0.041) H8A(0.036) H8B(0.036) H11(0.039) H12(0.042) H13(0.041)
 H15(0.04) H16(0.041) H17(0.038)
 Fixed X: H1A(1.0701) H1B(1.1872) H1C(0.8826) H2A(1.0007) H2B(0.6939)
 H3A(0.675) H3B(0.9841) H4A(0.4785) H4B(0.7882) H5A(0.8038) H5B(0.4899)
 H6A(0.5925) H6B(0.2869) H7A(0.4306) H7B(0.7026) H8A(0.3492) H8B(0.1175)
 H11(0.1265) H12(0.2409) H13(0.5477) H15(0.8681) H16(1.0587) H17(0.9447)
 Fixed Y: H1A(0.8801) H1B(0.8277) H1C(0.8992) H2A(0.6887) H2B(0.7582)
 H3A(0.724) H3B(0.6563) H4A(0.5818) H4B(0.5157) H5A(0.4825) H5B(0.5451)
 H6A(0.345) H6B(0.4011) H7A(0.2348) H7B(0.2945) H8A(0.4422) H8B(0.3522)
 H11(0.0201) H12(-0.0616) H13(0.0217) H15(0.1812) H16(0.3471) H17(0.4237)
 Fixed Z: H1A(-0.0491) H1B(0.0427) H1C(0.0363) H2A(-0.0276) H2B(-0.0252)
 H3A(0.127) H3B(0.1254) H4A(0.0652) H4B(0.0566) H5A(0.2096) H5B(0.2166)
 H6A(0.1376) H6B(0.1662) H7A(0.2627) H7B(0.2852) H8A(0.3337) H8B(0.3325)
 H11(0.5543) H12(0.6931) H13(0.7673) H15(0.7761) H16(0.7099) H17(0.5702)
;
_shelx_res_checksum              80325
_olex2_submission_special_instructions 'No special instructions were received'