Fluorescent crystals and co-crystals of 1,8-naphthalimide derivatives: synthesis, structure determination and photophysical characterization
F. Grepioni; S. d'Agostino; D. Braga; A. Bertocco; L. Catalano; B. Ventura; Journal of Materials Chemistry C 3 (2015) 9425–9434; doi:10.1039/C5TC01518A

data_7234455
_publ_section_title
;
 Fluorescent crystals and co-crystals of 1,8-naphthalimide derivatives:
 synthesis, structure determination and photophysical characterization
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9425
_journal_page_last               9434
_journal_paper_doi               10.1039/C5TC01518A
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C23 H21 N3 O2, 0.5(C6 F4 I2)'
_chemical_formula_sum            'C26 H21 F2 I N3 O2'
_chemical_formula_weight         572.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000
_cell_angle_beta                 92.047(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   12.989(5)
_cell_length_b                   13.783(5)
_cell_length_c                   12.664(5)
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.9220
_cell_measurement_theta_min      3.1290
_cell_volume                     2265.8(15)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 92 (Altomare, Giacovazzo, 1994)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.1340
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details
;
  1 omega   24.00   49.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      -17.8298   77.0000    0.0000 25

  2 omega   -9.00   70.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000 -150.0000 79

  3 omega  -11.00   79.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000   90.0000 90

  4 omega   -8.00   20.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000  -30.0000 28

;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10219
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.36
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94763
_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            orange
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0193P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                3656
_reflns_number_total             5206
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-9425.cif
_cod_data_source_block           '[(4)2(I2F4)]'
_cod_database_code               7234455