#------------------------------------------------------------------------------
#$Date: 2019-10-08 10:00:35 +0300 (Tue, 08 Oct 2019) $
#$Revision: 219153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234450.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_7234450
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 * c3 f2 i1'
_chemical_formula_sum            'C26 H21 F2 I N3 O2'
_chemical_formula_weight         572.36
_chemical_name_common            'XB co-crystal'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.669(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1722(4)
_cell_length_b                   11.5170(11)
_cell_length_c                   38.904(3)
_cell_measurement_reflns_used    2053
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5430
_cell_measurement_theta_min      3.1630
_cell_volume                     2312.7(3)
_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 92)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1340
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142  -99.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   10.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142  -99.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00    7.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142  -99.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00   45.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142   38.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00    3.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642  -57.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega    2.00   84.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   57.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   60.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642  -99.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   -1.00   87.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   57.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
  9 omega   30.00   92.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   19.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega  -24.00    7.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   19.0000   90.0000 31

;
_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  0.1732
_diffrn_reflns_av_sigmaI/netI    0.2175
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            25307
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    1.430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45366
_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            'pale yellow'
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.2418
_refine_ls_R_factor_gt           0.0836
_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)+(0.0131P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2291
_reflns_number_total             6047
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-9425.cif
_cod_data_source_block           '[(2)2(I2F4)]'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7234450
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.6306(13) 0.0863(5) 0.76028(18) 0.0442(19) Uani 1 1 d . . .
H1 H 0.5121 0.0353 0.7690 0.053 Uiso 1 1 calc R . .
C2 C 0.7791(12) 0.1548(5) 0.78234(18) 0.0363(17) Uani 1 1 d . . .
C3 C 0.9692(13) 0.2280(5) 0.76931(18) 0.0386(18) Uani 1 1 d . . .
C4 C 1.1311(13) 0.2960(5) 0.79177(19) 0.0412(18) Uani 1 1 d . . .
C5 C 1.3239(13) 0.3635(6) 0.7791(2) 0.055(2) Uani 1 1 d . . .
H5 H 1.4271 0.4102 0.7939 0.066 Uiso 1 1 calc R . .
C6 C 1.3628(13) 0.3612(6) 0.7440(2) 0.055(2) Uani 1 1 d . . .
H6 H 1.4980 0.4038 0.7357 0.067 Uiso 1 1 calc R . .
C7 C 1.2052(12) 0.2974(6) 0.72175(19) 0.051(2) Uani 1 1 d . . .
H7 H 1.2338 0.2976 0.6984 0.061 Uiso 1 1 calc R . .
C8 C 1.0010(12) 0.2315(5) 0.73362(19) 0.0387(18) Uani 1 1 d . . .
C9 C 0.8306(13) 0.1649(6) 0.71079(19) 0.0435(18) Uani 1 1 d . . .
C10 C 0.6541(13) 0.0918(5) 0.72462(18) 0.0453(19) Uani 1 1 d . . .
H10 H 0.5487 0.0453 0.7101 0.054 Uiso 1 1 calc R . .
C11 C 0.7289(14) 0.1581(6) 0.8187(2) 0.047(2) Uani 1 1 d . . .
C12 C 1.0894(14) 0.3001(6) 0.8287(2) 0.048(2) Uani 1 1 d . . .
C13 C 0.8137(14) 0.2487(6) 0.87560(18) 0.058(2) Uani 1 1 d . . .
H13A H 0.6274 0.2587 0.8754 0.070 Uiso 1 1 calc R . .
H13B H 0.8929 0.3196 0.8847 0.070 Uiso 1 1 calc R . .
C14 C 0.8890(13) 0.1522(5) 0.89957(19) 0.0432(19) Uani 1 1 d . . .
C15 C 1.0908(13) 0.0757(6) 0.89495(19) 0.054(2) Uani 1 1 d . . .
H15 H 1.1849 0.0803 0.8754 0.064 Uiso 1 1 calc R . .
C16 C 1.1493(14) -0.0061(6) 0.9194(2) 0.060(2) Uani 1 1 d . . .
H16 H 1.2846 -0.0579 0.9167 0.073 Uiso 1 1 calc R . .
C17 C 1.0091(17) -0.0121(7) 0.9479(2) 0.074(3) Uani 1 1 d . . .
H17 H 1.0434 -0.0681 0.9648 0.089 Uiso 1 1 calc R . .
C18 C 0.8149(15) 0.0683(7) 0.9505(2) 0.069(3) Uani 1 1 d . . .
H18 H 0.7201 0.0654 0.9700 0.083 Uiso 1 1 calc R . .
C19 C 0.7838(13) 0.2936(6) 0.66102(18) 0.054(2) Uani 1 1 d . . .
H19A H 0.8524 0.3528 0.6768 0.065 Uiso 1 1 calc R . .
H19B H 0.5970 0.3028 0.6586 0.065 Uiso 1 1 calc R . .
C20 C 0.8941(14) 0.3105(7) 0.62656(19) 0.067(2) Uani 1 1 d . . .
H20A H 1.0817 0.3064 0.6291 0.080 Uiso 1 1 calc R . .
H20B H 0.8461 0.3865 0.6175 0.080 Uiso 1 1 calc R . .
C21 C 0.7916(17) 0.2172(8) 0.6016(2) 0.089(3) Uani 1 1 d . . .
H21A H 0.6071 0.2281 0.5966 0.107 Uiso 1 1 calc R . .
H21B H 0.8764 0.2238 0.5802 0.107 Uiso 1 1 calc R . .
C22 C 0.8408(16) 0.0977(7) 0.6169(2) 0.086(3) Uani 1 1 d . . .
H22A H 1.0256 0.0825 0.6188 0.104 Uiso 1 1 calc R . .
H22B H 0.7590 0.0396 0.6018 0.104 Uiso 1 1 calc R . .
C23 C 0.7336(16) 0.0884(6) 0.6527(2) 0.075(3) Uani 1 1 d . . .
H23A H 0.5466 0.0969 0.6507 0.090 Uiso 1 1 calc R . .
H23B H 0.7739 0.0125 0.6624 0.090 Uiso 1 1 calc R . .
C24 C 0.0239(15) 0.3872(6) 1.0084(2) 0.054(2) Uani 1 1 d . . .
C25 C 0.1629(13) 0.4260(7) 0.98200(19) 0.051(2) Uani 1 1 d . . .
C26 C 0.1323(13) 0.5413(7) 0.97454(18) 0.054(2) Uani 1 1 d . . .
N1 N 0.7530(11) 0.1493(5) 0.92737(17) 0.0591(18) Uani 1 1 d . . .
N2 N 0.8838(12) 0.2346(5) 0.84014(15) 0.0486(16) Uani 1 1 d . . .
N3 N 0.8467(11) 0.1784(5) 0.67538(15) 0.0559(16) Uani 1 1 d . . .
O1 O 0.5628(9) 0.1006(4) 0.83190(13) 0.0659(16) Uani 1 1 d . . .
O2 O 1.2184(10) 0.3599(4) 0.84894(14) 0.0705(16) Uani 1 1 d . . .
F1 F 0.0454(9) 0.2747(4) 1.01731(12) 0.0916(16) Uani 1 1 d . . .
F2 F 0.2662(9) 0.5882(4) 0.94865(12) 0.0922(16) Uani 1 1 d . . .
I001 I 0.40430(10) 0.31777(5) 0.955356(14) 0.0653(2) 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
C2 C1 C10 121.0(6) . .
C1 C2 C3 119.7(6) . .
C1 C2 C11 119.9(7) . .
C3 C2 C11 120.3(7) . .
C4 C3 C8 119.5(6) . .
C4 C3 C2 120.6(7) . .
C8 C3 C2 119.9(7) . .
C5 C4 C3 120.4(7) . .
C5 C4 C12 119.1(7) . .
C3 C4 C12 120.4(7) . .
C4 C5 C6 119.5(7) . .
C7 C6 C5 121.0(7) . .
C6 C7 C8 120.9(7) . .
C7 C8 C3 118.6(7) . .
C7 C8 C9 122.1(7) . .
C3 C8 C9 119.3(6) . .
C10 C9 N3 122.5(7) . .
C10 C9 C8 118.8(7) . .
N3 C9 C8 118.6(6) . .
C9 C10 C1 121.1(7) . .
O1 C11 N2 118.2(7) . .
O1 C11 C2 124.6(7) . .
N2 C11 C2 117.2(7) . .
O2 C12 N2 119.8(7) . .
O2 C12 C4 123.0(7) . .
N2 C12 C4 117.2(7) . .
N2 C13 C14 116.1(6) . .
N1 C14 C15 122.1(7) . .
N1 C14 C13 113.5(6) . .
C15 C14 C13 124.3(7) . .
C16 C15 C14 119.1(7) . .
C15 C16 C17 119.8(7) . .
C16 C17 C18 117.1(8) . .
N1 C18 C17 124.8(8) . .
N3 C19 C20 111.6(6) . .
C19 C20 C21 109.9(6) . .
C22 C21 C20 110.4(7) . .
C21 C22 C23 111.0(6) . .
N3 C23 C22 110.2(6) . .
F1 C24 C26 120.1(8) . 3_567
F1 C24 C25 118.1(8) . .
C26 C24 C25 121.8(7) 3_567 .
C26 C25 C24 114.7(7) . .
C26 C25 I001 122.7(6) . .
C24 C25 I001 122.6(6) . .
C24 C26 C25 123.4(7) 3_567 .
C24 C26 F2 117.7(8) 3_567 .
C25 C26 F2 118.9(7) . .
C18 N1 C14 117.1(6) . .
C12 N2 C11 123.9(6) . .
C12 N2 C13 118.8(6) . .
C11 N2 C13 117.3(6) . .
C9 N3 C23 118.1(6) . .
C9 N3 C19 116.8(6) . .
C23 N3 C19 109.9(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.365(8) .
C1 C10 1.402(8) .
C2 C3 1.413(8) .
C2 C11 1.455(9) .
C3 C4 1.409(8) .
C3 C8 1.409(8) .
C4 C5 1.380(8) .
C4 C12 1.466(9) .
C5 C6 1.391(9) .
C6 C7 1.366(9) .
C7 C8 1.403(8) .
C8 C9 1.434(8) .
C9 C10 1.376(8) .
C9 N3 1.394(8) .
C11 O1 1.223(7) .
C11 N2 1.424(8) .
C12 O2 1.213(7) .
C12 N2 1.400(8) .
C13 N2 1.458(7) .
C13 C14 1.486(8) .
C14 N1 1.328(8) .
C14 C15 1.387(8) .
C15 C16 1.359(9) .
C16 C17 1.364(9) .
C17 C18 1.375(9) .
C18 N1 1.322(9) .
C19 N3 1.469(7) .
C19 C20 1.503(8) .
C20 C21 1.520(9) .
C21 C22 1.514(9) .
C22 C23 1.534(9) .
C23 N3 1.460(8) .
C24 F1 1.344(7) .
C24 C26 1.357(9) 3_567
C24 C25 1.367(9) .
C25 C26 1.366(9) .
C25 I001 2.087(7) .
C26 C24 1.357(9) 3_567
C26 F2 1.370(7) .
