#------------------------------------------------------------------------------
#$Date: 2019-10-08 10:00:35 +0300 (Tue, 08 Oct 2019) $
#$Revision: 219153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234455.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7234455
loop_
_publ_author_name
'F. Grepioni'
'S. d'Agostino'
'D. Braga'
'A. Bertocco'
'L. Catalano'
'B. Ventura'
_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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   24.00   49.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      -17.8298   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   70.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   79.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
  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/[σ²(Fo²)+(0.0193P)²+0.0000P] where P=(Fo²+2Fc²)/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     >2σ(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-9425.cif
_cod_data_source_block           '[(4)2(I2F4)]'
_cod_database_code               7234455
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0831(3) 0.0480(3) 0.1995(3) 0.0608(11) Uani 1 1 d . . .
H1 H -0.1357 0.0752 0.1574 0.073 Uiso 1 1 calc R . .
C2 C -0.0271(3) -0.0259(3) 0.1572(3) 0.0509(9) Uani 1 1 d . . .
H2 H -0.0419 -0.0472 0.0887 0.061 Uiso 1 1 calc R . .
C3 C 0.0510(2) -0.0683(3) 0.2169(3) 0.0470(9) Uani 1 1 d . . .
C4 C 0.0698(3) -0.0319(3) 0.3171(3) 0.0613(11) Uani 1 1 d . . .
H4 H 0.1227 -0.0571 0.3603 0.074 Uiso 1 1 calc R . .
C5 C 0.0085(3) 0.0426(3) 0.3522(3) 0.0616(11) Uani 1 1 d . . .
H5 H 0.0219 0.0657 0.4203 0.074 Uiso 1 1 calc R . .
C6 C 0.1108(2) -0.1531(3) 0.1749(3) 0.0565(10) Uani 1 1 d . . .
H6A H 0.0798 -0.2129 0.1987 0.068 Uiso 1 1 calc R . .
H6B H 0.1055 -0.1523 0.0984 0.068 Uiso 1 1 calc R . .
C7 C 0.2858(3) -0.0947(3) 0.1510(3) 0.0489(9) Uani 1 1 d . . .
C8 C 0.3963(2) -0.0981(2) 0.1830(3) 0.0388(8) Uani 1 1 d . . .
C9 C 0.4635(3) -0.0377(3) 0.1334(3) 0.0493(9) Uani 1 1 d . . .
H9 H 0.4387 0.0046 0.0812 0.059 Uiso 1 1 calc R . .
C10 C 0.5687(3) -0.0392(3) 0.1605(3) 0.0500(9) Uani 1 1 d . . .
H10 H 0.6134 0.0030 0.1276 0.060 Uiso 1 1 calc R . .
C11 C 0.6060(2) -0.1030(2) 0.2358(2) 0.0403(8) Uani 1 1 d . . .
H11 H 0.6762 -0.1040 0.2528 0.048 Uiso 1 1 calc R . .
C12 C 0.5398(2) -0.1672(2) 0.2881(2) 0.0361(7) Uani 1 1 d . . .
C13 C 0.5756(2) -0.2319(2) 0.3701(3) 0.0387(8) Uani 1 1 d . . .
C14 C 0.5039(3) -0.2787(2) 0.4299(3) 0.0460(9) Uani 1 1 d . . .
H14 H 0.5260 -0.3161 0.4874 0.055 Uiso 1 1 calc R . .
C15 C 0.3981(3) -0.2705(2) 0.4049(3) 0.0457(9) Uani 1 1 d . . .
H15 H 0.3513 -0.3038 0.4453 0.055 Uiso 1 1 calc R . .
C16 C 0.3625(2) -0.2144(2) 0.3223(3) 0.0380(8) Uani 1 1 d . . .
C17 C 0.4326(2) -0.1611(2) 0.2630(2) 0.0351(7) Uani 1 1 d . . .
C18 C 0.7435(2) -0.2815(3) 0.3054(2) 0.0492(9) Uani 1 1 d . . .
H18A H 0.7173 -0.2578 0.2374 0.059 Uiso 1 1 calc R . .
H18B H 0.7382 -0.3517 0.3055 0.059 Uiso 1 1 calc R . .
C19 C 0.8551(3) -0.2514(3) 0.3229(3) 0.0667(12) Uani 1 1 d . . .
H19A H 0.8960 -0.2788 0.2676 0.080 Uiso 1 1 calc R . .
H19B H 0.8603 -0.1813 0.3190 0.080 Uiso 1 1 calc R . .
C20 C 0.8966(3) -0.2855(3) 0.4287(3) 0.0754(13) Uani 1 1 d . . .
H20A H 0.9660 -0.2610 0.4410 0.090 Uiso 1 1 calc R . .
H20B H 0.8995 -0.3558 0.4296 0.090 Uiso 1 1 calc R . .
C21 C 0.8284(3) -0.2502(3) 0.5153(3) 0.0656(12) Uani 1 1 d . . .
H21A H 0.8333 -0.1801 0.5205 0.079 Uiso 1 1 calc R . .
H21B H 0.8524 -0.2775 0.5824 0.079 Uiso 1 1 calc R . .
C22 C 0.7167(3) -0.2789(3) 0.4937(3) 0.0527(10) Uani 1 1 d . . .
H22A H 0.7104 -0.3491 0.4938 0.063 Uiso 1 1 calc R . .
H22B H 0.6742 -0.2532 0.5486 0.063 Uiso 1 1 calc R . .
C23 C 0.4091(2) 0.0249(2) 0.4512(3) 0.0398(8) Uani 1 1 d . . .
C24 C 0.4068(2) -0.0388(2) 0.5340(3) 0.0381(8) Uani 1 1 d . . .
C25 C 0.5003(3) -0.0636(2) 0.5825(3) 0.0401(8) Uani 1 1 d . . .
C26 C 0.2506(3) -0.2084(2) 0.2976(3) 0.0473(9) Uani 1 1 d . . .
N1 N 0.2206(2) -0.1523(2) 0.2088(2) 0.0475(7) Uani 1 1 d . . .
N2 N 0.6820(2) -0.2404(2) 0.3910(2) 0.0419(7) Uani 1 1 d . . .
N3 N -0.0677(2) 0.0837(2) 0.2961(3) 0.0587(9) Uani 1 1 d . . .
O1 O 0.25171(19) -0.0458(2) 0.0773(2) 0.0675(8) Uani 1 1 d . . .
O2 O 0.18606(19) -0.24831(18) 0.3495(2) 0.0660(7) Uani 1 1 d . . .
F1 F 0.32048(14) 0.05151(15) 0.39942(16) 0.0602(6) Uani 1 1 d . . .
F2 F 0.50375(15) -0.12665(15) 0.66339(16) 0.0614(6) Uani 1 1 d . . .
I1 I 0.267327(17) -0.086803(17) 0.592317(18) 0.05051(10) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N3 C1 C2 124.8(4) . .
C1 C2 C3 119.5(4) . .
C2 C3 C4 117.0(3) . .
C2 C3 C6 121.0(3) . .
C4 C3 C6 122.0(3) . .
C3 C4 C5 118.8(4) . .
N3 C5 C4 124.9(4) . .
N1 C6 C3 113.4(3) . .
O1 C7 N1 120.5(3) . .
O1 C7 C8 123.3(3) . .
N1 C7 C8 116.2(3) . .
C9 C8 C17 120.1(3) . .
C9 C8 C7 118.8(3) . .
C17 C8 C7 121.0(3) . .
C8 C9 C10 120.7(3) . .
C11 C10 C9 119.9(3) . .
C10 C11 C12 121.4(3) . .
C11 C12 C17 117.7(3) . .
C11 C12 C13 122.8(3) . .
C17 C12 C13 119.3(3) . .
C14 C13 N2 122.4(3) . .
C14 C13 C12 118.7(3) . .
N2 C13 C12 118.7(3) . .
C13 C14 C15 120.8(3) . .
C16 C15 C14 121.4(3) . .
C15 C16 C17 119.6(3) . .
C15 C16 C26 119.8(3) . .
C17 C16 C26 120.5(3) . .
C8 C17 C16 120.1(3) . .
C8 C17 C12 120.0(3) . .
C16 C17 C12 119.8(3) . .
N2 C18 C19 109.0(3) . .
C20 C19 C18 110.8(3) . .
C19 C20 C21 110.1(3) . .
C20 C21 C22 111.4(3) . .
N2 C22 C21 109.2(3) . .
F1 C23 C24 120.2(3) . .
F1 C23 C25 117.8(3) . 3_656
C24 C23 C25 122.0(3) . 3_656
C23 C24 C25 117.1(3) . .
C23 C24 I1 121.1(2) . .
C25 C24 I1 121.5(2) . .
F2 C25 C23 118.9(3) . 3_656
F2 C25 C24 120.2(3) . .
C23 C25 C24 120.9(3) 3_656 .
O2 C26 N1 120.3(3) . .
O2 C26 C16 123.5(4) . .
N1 C26 C16 116.2(3) . .
C7 N1 C26 125.4(3) . .
C7 N1 C6 116.9(3) . .
C26 N1 C6 117.7(3) . .
C13 N2 C22 118.0(3) . .
C13 N2 C18 116.6(3) . .
C22 N2 C18 110.8(3) . .
C5 N3 C1 114.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N3 1.327(5) .
C1 C2 1.372(5) .
C2 C3 1.374(4) .
C3 C4 1.378(5) .
C3 C6 1.510(4) .
C4 C5 1.383(5) .
C5 N3 1.324(5) .
C6 N1 1.475(4) .
C7 O1 1.222(4) .
C7 N1 1.389(4) .
C7 C8 1.478(5) .
C8 C9 1.374(4) .
C8 C17 1.403(4) .
C9 C10 1.397(4) .
C10 C11 1.372(4) .
C11 C12 1.416(4) .
C12 C17 1.419(4) .
C12 C13 1.433(4) .
C13 C14 1.380(4) .
C13 N2 1.403(4) .
C14 C15 1.404(4) .
C15 C16 1.368(4) .
C16 C17 1.408(4) .
C16 C26 1.478(4) .
C18 N2 1.481(4) .
C18 C19 1.516(4) .
C19 C20 1.502(5) .
C20 C21 1.515(5) .
C21 C22 1.520(5) .
C22 N2 1.462(4) .
C23 F1 1.355(3) .
C23 C24 1.368(4) .
C23 C25 1.374(4) 3_656
C24 C25 1.384(4) .
C24 I1 2.089(3) .
C25 F2 1.342(3) .
C25 C23 1.374(4) 3_656
C26 O2 1.215(4) .
C26 N1 1.407(4) .
