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_7234449
_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'
_chemical_formula_sum            'C23 H21 N3 O2'
_chemical_formula_weight         371.43
_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                90.00
_cell_angle_beta                 111.307(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4693(8)
_cell_length_b                   7.1860(3)
_cell_length_c                   17.5613(8)
_cell_measurement_reflns_used    2831
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.9550
_cell_measurement_theta_min      3.2120
_cell_volume                     1818.72(16)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 16.1340
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details
;
  1 omega  -22.00   11.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000  -90.0000 33

  2 omega  -13.00   19.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000  150.0000 32

  3 omega  -80.00  -47.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955 -179.0000   60.0000 33

  4 omega   -4.00   22.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000   30.0000 26

  5 omega  -46.00   39.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673  -57.0000  120.0000 85

  6 omega   -1.00   28.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673   57.0000   30.0000 29

  7 omega  -51.00   38.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673  -77.0000   30.0000 89

  8 omega  -39.00   36.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673  -57.0000 -120.0000 75

;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'w 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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14288
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.33
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97860
_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    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0169(17)
_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   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.2511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                2512
_reflns_number_total             4340
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-9425.cif
_cod_data_source_block           2
_cod_original_cell_volume        1818.72(15)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7234449