#------------------------------------------------------------------------------
#$Date: 2022-05-13 01:17:29 +0300 (Fri, 13 May 2022) $
#$Revision: 275379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/69/1566960.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_1566960
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 H12 N2 O4'
_chemical_formula_weight         320.30
_chemical_name_common            3,9_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   mixed
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.995(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5646(6)
_cell_length_b                   3.6755(3)
_cell_length_c                   23.933(2)
_cell_measurement_reflns_used    658
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.6870
_cell_measurement_theta_min      6.6150
_cell_volume                     661.79(9)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2160
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.052
_diffrn_reflns_theta_min         3.714
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
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    1.607
_exptl_crystal_description       Prism
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0758
_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)+(0.1530P)²+0.1868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1027
_reflns_number_total             1306
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01038k2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_cell_volume        661.78(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566960
_shelx_shelxl_version_number     2018/1
_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   0.870
_shelx_estimated_absorpt_t_max   0.945
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
C2 C 0.9359(3) 0.0370(6) 0.97678(9) 0.0234(6) Uani 1 1 d . . . . .
C3 C 0.9834(3) -0.0377(6) 0.92269(9) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.7711(3) 0.1776(6) 0.98405(9) 0.0251(6) Uani 1 1 d . . . . .
C5 C 1.1535(3) -0.1813(6) 0.91623(10) 0.0246(6) Uani 1 1 d . . . . .
C7 C 0.6480(3) 0.2461(6) 0.93729(11) 0.0291(6) Uani 1 1 d . . . . .
H7 H 0.534042 0.341851 0.942260 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6932(3) 0.1737(7) 0.88393(10) 0.0301(6) Uani 1 1 d . . . . .
H8 H 0.609293 0.222167 0.852458 0.036 Uiso 1 1 calc R U . . .
C9 C 1.1973(3) -0.2480(7) 0.86304(10) 0.0298(6) Uani 1 1 d . . . . .
H9 H 1.311319 -0.338584 0.856881 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8618(3) 0.0288(6) 0.87495(10) 0.0272(6) Uani 1 1 d . . . . .
C11 C 1.0664(3) -0.1770(7) 0.81759(10) 0.0321(6) Uani 1 1 d . . . . .
H11 H 1.096487 -0.229232 0.780869 0.038 Uiso 1 1 calc R U . . .
N1 N 0.9062(3) -0.0445(6) 0.82194(9) 0.0320(6) Uani 1 1 d . . . . .
O1 O 0.7251(2) 0.2532(5) 1.03776(7) 0.0280(5) Uani 1 1 d . . . . .
O2 O 0.3933(4) 0.3646(17) 0.76081(12) 0.1038(17) Uani 1 1 d D . . . .
H1 H 0.458(8) 0.179(16) 0.745(3) 0.125 Uiso 1 1 d D U . . .
H2 H 0.297(5) 0.386(19) 0.7321(18) 0.125 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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 C2 C3 120.7(2) . . ?
C4 C2 C2 121.7(3) . 3_757 ?
C3 C2 C2 117.5(2) . 3_757 ?
C2 C3 C10 120.3(2) . . ?
C2 C3 C5 119.8(2) . . ?
C10 C3 C5 120.0(2) . . ?
C2 C4 O1 120.5(2) . . ?
C2 C4 C7 120.1(2) . . ?
O1 C4 C7 119.42(19) . . ?
C9 C5 O1 120.0(2) . 3_757 ?
C9 C5 C3 118.7(2) . . ?
O1 C5 C3 121.3(2) 3_757 . ?
C8 C7 C4 119.7(2) . . ?
C7 C8 C10 121.7(2) . . ?
C5 C9 C11 117.6(2) . . ?
N1 C10 C3 120.8(2) . . ?
N1 C10 C8 121.6(2) . . ?
C3 C10 C8 117.5(2) . . ?
N1 C11 C9 125.5(2) . . ?
C11 N1 C10 117.4(2) . . ?
C5 O1 C4 119.12(17) 3_757 . ?
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
C2 C4 1.377(3) . ?
C2 C3 1.406(3) . ?
C2 C2 1.423(5) 3_757 ?
C3 C10 1.411(3) . ?
C3 C5 1.414(3) . ?
C4 O1 1.394(3) . ?
C4 C7 1.402(3) . ?
C5 C9 1.371(3) . ?
C5 O1 1.384(3) 3_757 ?
C7 C8 1.382(3) . ?
C8 C10 1.419(3) . ?
C9 C11 1.417(4) . ?
C10 N1 1.373(3) . ?
C11 N1 1.321(3) . ?
