#------------------------------------------------------------------------------
#$Date: 2022-05-13 01:17:29 +0300 (Fri, 13 May 2022) $
#$Revision: 275379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/69/1566962.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_1566962
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            'C18 H8 N2 O2'
_chemical_formula_weight         284.26
_chemical_name_common            4,10_N2PXX
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.54(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.589(3)
_cell_length_b                   3.7599(12)
_cell_length_c                   14.384(3)
_cell_measurement_reflns_used    851
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.9570
_cell_measurement_theta_min      6.0960
_cell_volume                     578.9(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4883
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.679
_diffrn_reflns_theta_min         4.195
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       Plate
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0899
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1946P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2405
_refine_ls_wR_factor_ref         0.2993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                678
_reflns_number_total             1171
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01038k2.cif
_cod_data_source_block           shelx_CCDC3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1566962
_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   0.680
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_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_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 0.1266(3) 0.5456(10) -0.0471(2) 0.0334(9) Uani 1 1 d . . . . .
C2 C 0.0812(3) 0.6958(10) 0.1255(2) 0.0338(9) Uani 1 1 d . . . . .
C3 C 0.2196(3) 0.7042(10) 0.0375(2) 0.0345(9) Uani 1 1 d . . . . .
C4 C -0.1470(3) 0.5332(10) 0.1354(2) 0.0377(9) Uani 1 1 d . . . . .
C5 C -0.0092(3) 0.5424(10) 0.0451(2) 0.0343(9) Uani 1 1 d . . . . .
C6 C 0.3348(3) 0.7828(10) 0.0359(2) 0.0381(9) Uani 1 1 d . . . . .
H6 H 0.398910 0.885375 0.092738 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2655(3) 0.5524(10) -0.1361(2) 0.0399(9) Uani 1 1 d . . . . .
H7 H 0.283347 0.503794 -0.194011 0.048 Uiso 1 1 calc R U . . .
C8 C 0.0547(3) 0.7643(10) 0.2117(2) 0.0368(9) Uani 1 1 d . . . . .
H8 H 0.118041 0.869029 0.268590 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3546(3) 0.7056(10) -0.0530(2) 0.0383(9) Uani 1 1 d . . . . .
H9 H 0.433372 0.762562 -0.055277 0.046 Uiso 1 1 calc R U . . .
N1 N -0.0541(3) 0.6895(9) 0.21714(19) 0.0413(9) Uani 1 1 d . . . . .
O1 O 0.1972(2) 0.7848(7) 0.12438(15) 0.0376(8) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 C1 C5 117.7(3) 3_565 3_565 ?
C4 C1 C3 121.9(3) 3_565 . ?
C5 C1 C3 120.4(3) 3_565 . ?
C5 C2 O1 121.8(3) . . ?
C5 C2 C8 118.0(3) . . ?
O1 C2 C8 120.2(3) . . ?
C6 C3 O1 118.7(3) . . ?
C6 C3 C1 120.2(3) . . ?
O1 C3 C1 121.1(3) . . ?
N1 C4 C1 120.7(3) . 3_565 ?
N1 C4 C7 122.1(3) . 3_565 ?
C1 C4 C7 117.2(3) 3_565 3_565 ?
C2 C5 C1 121.2(3) . 3_565 ?
C2 C5 C5 122.2(4) . 3_565 ?
C1 C5 C5 116.5(4) 3_565 3_565 ?
C3 C6 C9 117.8(3) . . ?
C9 C7 C4 119.9(3) . 3_565 ?
N1 C8 C2 123.1(3) . . ?
C7 C9 C6 123.1(3) . . ?
C8 N1 C4 119.2(3) . . ?
C2 O1 C3 117.9(2) . . ?
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 C4 1.410(4) 3_565 ?
C1 C5 1.410(5) 3_565 ?
C1 C3 1.412(5) . ?
C2 C5 1.356(5) . ?
C2 O1 1.390(4) . ?
C2 C8 1.411(4) . ?
C3 C6 1.376(5) . ?
C3 O1 1.404(4) . ?
C4 N1 1.384(5) . ?
C4 C7 1.415(5) 3_565 ?
C5 C5 1.429(5) 3_565 ?
C6 C9 1.413(4) . ?
C7 C9 1.372(5) . ?
C8 N1 1.324(4) . ?
