#------------------------------------------------------------------------------
#$Date: 2022-05-13 01:17:29 +0300 (Fri, 13 May 2022) $
#$Revision: 275379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/69/1566959.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_1566959
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            1,7_N2PXX
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.073(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.3819(9)
_cell_length_b                   13.469(3)
_cell_length_c                   10.1801(18)
_cell_measurement_reflns_used    634
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.8590
_cell_measurement_theta_min      3.6240
_cell_volume                     596.3(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2815
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.488
_diffrn_reflns_theta_min         3.025
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       Needle
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0684
_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)+(0.1115P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                702
_reflns_number_total             1409
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01038k2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566959
_shelx_shelxl_version_number     2014/7
_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   0.977
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_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_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
O1 O 0.2696(4) 0.63134(11) 0.63406(17) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.0250(5) 0.54601(15) 0.7822(2) 0.0316(6) Uani 1 1 d . . . . .
C1 C 0.5399(5) 0.54711(15) 0.4760(2) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.2824(5) 0.45111(17) 0.6295(2) 0.0223(6) Uani 1 1 d . . . . .
C3 C 0.4462(6) 0.63329(17) 0.5299(2) 0.0239(6) Uani 1 1 d . . . . .
C4 C 0.1896(6) 0.54071(17) 0.6846(2) 0.0254(6) Uani 1 1 d . . . . .
C5 C 0.7033(5) 0.72829(18) 0.3758(2) 0.0281(7) Uani 1 1 d . . . . .
H5 H 0.7578 0.7909 0.3425 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8034(6) 0.64008(17) 0.3183(2) 0.0251(6) Uani 1 1 d . . . . .
C7 C -0.0587(6) 0.45637(19) 0.8322(3) 0.0329(7) Uani 1 1 d . . . . .
H7 H -0.1796 0.4582 0.9035 0.040 Uiso 1 1 calc R U . . .
C8 C 0.5279(6) 0.72478(17) 0.4794(2) 0.0279(6) Uani 1 1 d . . . . .
H8 H 0.4626 0.7847 0.5166 0.033 Uiso 1 1 calc R U . . .
C9 C 0.0169(6) 0.36604(19) 0.7883(3) 0.0301(7) Uani 1 1 d . . . . .
H9 H -0.0494 0.3074 0.8282 0.036 Uiso 1 1 calc R U . . .
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'
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 O1 C3 119.37(19) . . ?
C4 N1 C7 115.6(2) . . ?
C3 C1 C2 121.0(2) . 3_666 ?
C3 C1 C1 121.4(3) . 3_666 ?
C2 C1 C1 117.6(3) 3_666 3_666 ?
C1 C2 C6 120.2(2) 3_666 3_666 ?
C1 C2 C4 120.3(2) 3_666 . ?
C6 C2 C4 119.5(2) 3_666 . ?
C1 C3 O1 120.9(2) . . ?
C1 C3 C8 119.8(2) . . ?
O1 C3 C8 119.3(2) . . ?
N1 C4 O1 115.1(2) . . ?
N1 C4 C2 124.4(2) . . ?
O1 C4 C2 120.5(2) . . ?
C8 C5 C6 121.1(2) . . ?
C8 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C2 C6 C5 117.7(2) 3_666 . ?
C2 C6 C9 115.9(2) 3_666 3_666 ?
C5 C6 C9 126.4(2) . 3_666 ?
C9 C7 N1 125.4(2) . . ?
C9 C7 H7 117.3 . . ?
N1 C7 H7 117.3 . . ?
C5 C8 C3 120.2(2) . . ?
C5 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C7 C9 C6 119.1(2) . 3_666 ?
C7 C9 H9 120.4 . . ?
C6 C9 H9 120.4 3_666 . ?
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
O1 C4 1.386(3) . ?
O1 C3 1.388(3) . ?
N1 C4 1.300(3) . ?
N1 C7 1.377(3) . ?
C1 C3 1.368(3) . ?
C1 C2 1.402(4) 3_666 ?
C1 C1 1.419(4) 3_666 ?
C2 C1 1.402(4) 3_666 ?
C2 C6 1.408(3) 3_666 ?
C2 C4 1.412(3) . ?
C3 C8 1.398(3) . ?
C5 C8 1.380(3) . ?
C5 C6 1.418(3) . ?
C5 H5 0.9500 . ?
C6 C2 1.408(3) 3_666 ?
C6 C9 1.419(4) 3_666 ?
C7 C9 1.351(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C6 1.419(4) 3_666 ?
C9 H9 0.9500 . ?
