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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/80/1558089.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_1558089
loop_
_publ_author_name
'Wang, Yunzhong'
'Tang, Saixing'
'Wen, Yating'
'Zheng, Shuyuan'
'Yang, Bing'
'Yuan, Wang Zhang'
_publ_section_title
;
 Nonconventional luminophores with unprecedented efficiencies and
 color-tunable afterglows
;
_journal_issue                   8
_journal_name_full               'Materials Horizons'
_journal_page_first              2105
_journal_page_last               2112
_journal_paper_doi               10.1039/D0MH00688B
_journal_volume                  7
_journal_year                    2020
_chemical_formula_moiety         'C8 H10 N4 O4'
_chemical_formula_sum            'C8 H10 N4 O4'
_chemical_formula_weight         226.20
_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-2018/3
_audit_update_record
;
2020-01-31 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.292(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8982(5)
_cell_length_b                   12.4995(11)
_cell_length_c                   14.3372(10)
_cell_measurement_reflns_used    6448
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.38
_cell_volume                     963.42(14)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6844
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        66.538
_diffrn_reflns_theta_max         66.538
_diffrn_reflns_theta_min         4.896
_exptl_absorpt_coefficient_mu    1.094
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.5606
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.115(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   2.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.107
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0811
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2448
_refine_ls_wR_factor_ref         0.2781
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1356
_reflns_number_total             1644
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0mh00688b3.cif
_cod_data_source_block           aa_a_CCDC1
_cod_depositor_comments
;Adding full bibliography for 1558087--1558090.cif.

 Adding full bibliography for 1558087--1558090.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1558089
_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   0.779
_shelx_estimated_absorpt_t_max   0.811
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 -0.6394(3) 0.5599(2) -0.63514(16) 0.0588(8) Uani 1 1 d . . . . .
O2 O -0.9463(5) 0.6291(2) -0.39641(17) 0.0701(9) Uani 1 1 d . . . . .
O3 O -0.9159(4) 0.60677(16) -0.90674(17) 0.0561(8) Uani 1 1 d . . . . .
O4 O -1.4674(5) 0.3473(2) -0.9121(2) 0.0772(9) Uani 1 1 d . . . . .
N1 N -0.9818(4) 0.65616(19) -0.64483(15) 0.0468(8) Uani 1 1 d . . . . .
N2 N -1.1574(4) 0.5878(2) -0.81541(16) 0.0459(8) Uani 1 1 d . . . . .
N3 N -0.7372(4) 0.5868(2) -0.49600(16) 0.0522(8) Uani 1 1 d . . . . .
H3 H -0.612183 0.554136 -0.450583 0.063 Uiso 1 1 d R U . . .
N4 N -1.1783(4) 0.46206(19) -0.92614(18) 0.0533(8) Uani 1 1 d . . . . .
H4 H -1.147076 0.427777 -0.971558 0.064 Uiso 1 1 d R U . . .
C1 C -0.7734(4) 0.5981(2) -0.5972(2) 0.0456(9) Uani 1 1 d . . . . .
C3 C -0.9228(5) 0.6325(2) -0.4771(2) 0.0519(9) Uani 1 1 d . . . . .
C4 C -1.0948(5) 0.6832(2) -0.57560(19) 0.0486(9) Uani 1 1 d . . . . .
H4A H -1.261201 0.653756 -0.598949 0.058 Uiso 1 1 calc R U . . .
H4B H -1.102522 0.760110 -0.568330 0.058 Uiso 1 1 calc R U . . .
C5 C -1.0754(4) 0.6835(2) -0.75283(18) 0.0457(9) Uani 1 1 d . . . . .
H5 H -0.938491 0.715227 -0.765348 0.055 Uiso 1 1 calc R U . . .
C6 C -1.2834(6) 0.7656(3) -0.7819(3) 0.0618(10) Uani 1 1 d . . . . .
H6A H -1.420232 0.736046 -0.770625 0.093 Uiso 1 1 calc R U . . .
H6B H -1.337901 0.784044 -0.852877 0.093 Uiso 1 1 calc R U . . .
H6C H -1.223595 0.828579 -0.740735 0.093 Uiso 1 1 calc R U . . .
C7 C -1.3323(5) 0.5093(2) -0.8087(2) 0.0507(9) Uani 1 1 d . . . . .
H7A H -1.494744 0.540809 -0.825572 0.061 Uiso 1 1 calc R U . . .
H7B H -1.272551 0.477877 -0.740893 0.061 Uiso 1 1 calc R U . . .
C8 C -1.3405(5) 0.4276(3) -0.8876(2) 0.0530(9) Uani 1 1 d . . . . .
C10 C -1.0685(5) 0.5585(2) -0.8840(2) 0.0458(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
C1 N1 C4 111.1(2) . . ?
C1 N1 C5 122.3(2) . . ?
C4 N1 C5 126.6(2) . . ?
C10 N2 C7 111.5(2) . . ?
C10 N2 C5 123.1(2) . . ?
C7 N2 C5 125.4(2) . . ?
C3 N3 C1 112.2(2) . . ?
C3 N3 H3 124.0 . . ?
C1 N3 H3 123.8 . . ?
C8 N4 C10 112.4(3) . . ?
C8 N4 H4 123.8 . . ?
C10 N4 H4 123.8 . . ?
O1 C1 N1 127.3(3) . . ?
O1 C1 N3 125.2(2) . . ?
N1 C1 N3 107.6(2) . . ?
O2 C3 N3 126.2(3) . . ?
O2 C3 C4 127.7(3) . . ?
N3 C3 C4 106.1(2) . . ?
N1 C4 C3 103.0(2) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 N2 110.3(2) . . ?
N1 C5 C6 111.2(2) . . ?
N2 C5 C6 111.1(2) . . ?
N1 C5 H5 108.0 . . ?
N2 C5 H5 108.0 . . ?
C6 C5 H5 108.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 102.2(2) . . ?
N2 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
N2 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
O4 C8 N4 126.8(3) . . ?
O4 C8 C7 127.0(3) . . ?
N4 C8 C7 106.3(2) . . ?
O3 C10 N2 127.5(3) . . ?
O3 C10 N4 124.9(3) . . ?
N2 C10 N4 107.7(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
O1 C1 1.226(3) . ?
O2 C3 1.221(4) . ?
O3 C10 1.234(3) . ?
O4 C8 1.214(4) . ?
N1 C1 1.347(3) . ?
N1 C4 1.445(3) . ?
N1 C5 1.455(3) . ?
N2 C10 1.341(3) . ?
N2 C7 1.455(3) . ?
N2 C5 1.454(4) . ?
N3 C3 1.358(4) . ?
N3 C1 1.384(4) . ?
N3 H3 0.8601 . ?
N4 C8 1.356(4) . ?
N4 C10 1.384(4) . ?
N4 H4 0.8605 . ?
C3 C4 1.499(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.520(4) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.510(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 O1 177.5(3) . . . . ?
C5 N1 C1 O1 -1.2(5) . . . . ?
C4 N1 C1 N3 -1.4(3) . . . . ?
C5 N1 C1 N3 179.9(2) . . . . ?
C3 N3 C1 O1 -176.4(3) . . . . ?
C3 N3 C1 N1 2.5(3) . . . . ?
C1 N3 C3 O2 175.3(3) . . . . ?
C1 N3 C3 C4 -2.5(3) . . . . ?
C1 N1 C4 C3 0.0(3) . . . . ?
C5 N1 C4 C3 178.6(3) . . . . ?
O2 C3 C4 N1 -176.3(3) . . . . ?
N3 C3 C4 N1 1.5(3) . . . . ?
C1 N1 C5 N2 66.7(3) . . . . ?
C4 N1 C5 N2 -111.8(3) . . . . ?
C1 N1 C5 C6 -169.6(3) . . . . ?
C4 N1 C5 C6 11.9(4) . . . . ?
C10 N2 C5 N1 -123.6(2) . . . . ?
C7 N2 C5 N1 52.9(3) . . . . ?
C10 N2 C5 C6 112.7(3) . . . . ?
C7 N2 C5 C6 -70.9(3) . . . . ?
C10 N2 C7 C8 -1.4(3) . . . . ?
C5 N2 C7 C8 -178.3(2) . . . . ?
C10 N4 C8 O4 178.1(3) . . . . ?
C10 N4 C8 C7 -1.6(3) . . . . ?
N2 C7 C8 O4 -178.0(3) . . . . ?
N2 C7 C8 N4 1.8(3) . . . . ?
C7 N2 C10 O3 -179.2(3) . . . . ?
C5 N2 C10 O3 -2.3(4) . . . . ?
C7 N2 C10 N4 0.6(3) . . . . ?
C5 N2 C10 N4 177.5(2) . . . . ?
C8 N4 C10 O3 -179.5(2) . . . . ?
C8 N4 C10 N2 0.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 85843700
