#------------------------------------------------------------------------------
#$Date: 2022-05-13 01:17:29 +0300 (Fri, 13 May 2022) $
#$Revision: 275379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/69/1566961.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_1566961
loop_
_publ_author_name
'Valentini, Cataldo'
'Gowland, Duncan'
'Bezzu, C. Grazia'
'Romito, Deborah'
'Demitri, Nicola'
'Bonini, Nicola'
'Bonifazi, Davide'
_publ_section_title
;
 Customising excitation properties of polycyclic aromatic hydrocarbons by
 rational positional heteroatom doping: the peri-xanthenoxanthene (PXX)
 case
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01038K
_journal_year                    2022
_chemical_formula_sum            'C24 H8 F4 I2 N2 O2'
_chemical_formula_weight         686.12
_chemical_name_systematic        4,10-N,N-PXX:DITFB
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                92.097(5)
_cell_angle_beta                 90.002(5)
_cell_angle_gamma                99.199(5)
_cell_formula_units_Z            1
_cell_length_a                   4.1848(3)
_cell_length_b                   7.7399(5)
_cell_length_c                   16.2513(11)
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.6660
_cell_measurement_theta_min      4.5130
_cell_volume                     519.25(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4071
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.760
_diffrn_reflns_theta_min         3.730
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.091
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_type   gaussian
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_description       Prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0169P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2025
_reflns_number_total             2460
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01038k2.cif
_cod_data_source_block           shelx_CCDC2
_cod_database_code               1566961
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.379
_shelx_estimated_absorpt_t_max   0.790
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0891(9) 0.7093(6) 0.8463(3) 0.0288(11) Uani 1 1 d . . . . .
H1 H 0.045144 0.813948 0.823018 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0156(9) 0.6746(6) 0.9270(3) 0.0235(10) Uani 1 1 d . . . . .
C3 C 0.0479(9) 0.5238(6) 0.9593(3) 0.0238(10) Uani 1 1 d . . . . .
C4 C 0.2118(9) 0.4087(6) 0.9135(3) 0.0225(10) Uani 1 1 d . . . . .
C5 C 0.2776(9) 0.2520(6) 0.9475(3) 0.0273(10) Uani 1 1 d . . . . .
C6 C 0.4364(9) 0.1410(6) 0.9032(3) 0.0287(10) Uani 1 1 d . . . . .
H6 H 0.482999 0.036418 0.925979 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5310(9) 0.1853(6) 0.8218(3) 0.0298(11) Uani 1 1 d . . . . .
H7 H 0.640111 0.107714 0.789938 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4708(9) 0.3356(7) 0.7877(3) 0.0321(11) Uani 1 1 d . . . . .
H8 H 0.537601 0.360899 0.732938 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3104(9) 0.4524(7) 0.8334(3) 0.0287(11) Uani 1 1 d . . . . .
C10 C 0.9530(11) 1.0793(7) 0.5740(3) 0.0362(12) Uani 1 1 d . . . . .
C11 C 0.8140(9) 0.9056(6) 0.5607(3) 0.0267(10) Uani 1 1 d . . . . .
C12 C 0.8633(10) 0.8294(7) 0.4856(3) 0.0350(12) Uani 1 1 d . . . . .
N1 N 0.2432(8) 0.6064(5) 0.8013(2) 0.0295(9) Uani 1 1 d . . . . .
O1 O -0.1794(6) 0.7895(4) 0.97128(19) 0.0297(7) Uani 1 1 d . . . . .
F1 F 0.9149(8) 1.1610(4) 0.64672(19) 0.0686(10) Uani 1 1 d . . . . .
F2 F 0.7330(8) 0.6629(4) 0.4681(2) 0.0731(11) Uani 1 1 d . . . . .
I1 I 0.55564(6) 0.76565(4) 0.65355(2) 0.03188(12) 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
_geom_angle_publ_flag
N1 C1 C2 124.0(4) . . ?
C3 C2 O1 121.8(4) . . ?
C3 C2 C1 117.3(4) . . ?
O1 C2 C1 120.9(4) . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 C3 121.7(5) . 2_567 ?
C4 C3 C3 117.3(5) . 2_567 ?
C3 C4 C9 118.6(4) . . ?
C3 C4 C5 120.7(4) . . ?
C9 C4 C5 120.7(4) . . ?
C6 C5 O1 119.2(4) . 2_567 ?
C6 C5 C4 120.7(4) . . ?
O1 C5 C4 120.1(4) 2_567 . ?
C5 C6 C7 118.1(4) . . ?
C8 C7 C6 122.4(5) . . ?
C7 C8 C9 120.0(4) . . ?
N1 C9 C8 122.1(4) . . ?
N1 C9 C4 119.7(4) . . ?
C8 C9 C4 118.2(4) . . ?
F1 C10 C12 118.6(5) . 2_776 ?
F1 C10 C11 119.9(4) . . ?
C12 C10 C11 121.5(5) 2_776 . ?
C12 C11 C10 117.1(4) . . ?
C12 C11 I1 121.9(3) . . ?
C10 C11 I1 121.0(4) . . ?
F2 C12 C11 120.3(4) . . ?
F2 C12 C10 118.3(5) . 2_776 ?
C11 C12 C10 121.4(5) . 2_776 ?
C1 N1 C9 119.5(4) . . ?
C2 O1 C5 118.4(3) . 2_567 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.306(6) . ?
C1 C2 1.405(6) . ?
C2 C3 1.361(6) . ?
C2 O1 1.388(5) . ?
C3 C4 1.402(6) . ?
C3 C3 1.427(8) 2_567 ?
C4 C9 1.403(6) . ?
C4 C5 1.417(6) . ?
C5 C6 1.354(6) . ?
C5 O1 1.416(5) 2_567 ?
C6 C7 1.419(6) . ?
C7 C8 1.365(6) . ?
C8 C9 1.402(6) . ?
C9 N1 1.387(6) . ?
C10 F1 1.341(6) . ?
C10 C12 1.380(6) 2_776 ?
C10 C11 1.386(7) . ?
C11 C12 1.366(6) . ?
C11 I1 2.089(4) . ?
C12 F2 1.337(6) . ?
