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#$Date: 2023-09-05 05:04:54 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286015 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/97/1569784.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1569784
loop_
_publ_author_name
'Uppu, Rao M.'
'Fronczek, Frank R.'
_publ_section_title
;
 1H-Benzo[g]pteridine-2,4-dione.
;
_journal_coeditor_code           HB4421
_journal_issue                   'Pt 1'
_journal_name_full               IUCrData
_journal_page_first              x221223
_journal_paper_doi               10.1107/S2414314622012238
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C10 H6 N4 O2'
_chemical_formula_moiety         'C10 H6 N4 O2'
_chemical_formula_sum            'C10 H6 N4 O2'
_chemical_formula_weight         214.19
_chemical_name_common            alloxazine
_chemical_name_systematic
;
1H-Benzo[g]pteridine-2,4-dione
;
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                70.483(2)
_cell_angle_beta                 84.150(2)
_cell_angle_gamma                84.208(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8027(2)
_cell_length_b                   7.5404(3)
_cell_length_c                   10.1345(4)
_cell_measurement_reflns_used    4433
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      69.08
_cell_measurement_theta_min      4.64
_cell_volume                     414.72(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6802
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.357
_diffrn_reflns_theta_min         4.641
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Bruker, 2001)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         6802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0484
_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)+(0.0713P)²+0.0047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                4832
_reflns_number_total             6802
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4421.cif
_cod_data_source_block           I
_cod_database_code               1569784
_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   0.892
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6141(4) 0.4107(3) 0.8404(2) 0.0215(6) Uani d 1 . .
O O2 -0.0946(3) 0.7091(3) 0.8834(2) 0.0213(6) Uani d 1 . .
N N1 0.2942(4) 0.8937(4) 0.4485(2) 0.0150(6) Uani d 1 . .
N N2 0.6687(4) 0.6283(4) 0.5564(2) 0.0160(6) Uani d 1 . .
N N3 0.2614(4) 0.5646(4) 0.8587(3) 0.0166(6) Uani d 1 . .
H H3N 0.231(5) 0.487(5) 0.949(4) 0.020 Uiso d 1 . .
N N4 0.1014(4) 0.7992(4) 0.6692(2) 0.0160(6) Uani d 1 . .
H H4N -0.018(6) 0.884(5) 0.638(3) 0.019 Uiso d 1 . .
C C1 0.4878(5) 0.8700(4) 0.3647(3) 0.0154(7) Uani d 1 . .
C C2 0.6759(5) 0.7382(4) 0.4193(3) 0.0154(7) Uani d 1 . .
C C3 0.8747(5) 0.7183(4) 0.3300(3) 0.0165(7) Uani d 1 . .
H H3 1.001181 0.631113 0.366387 0.020 Uiso calc 1 . .
C C4 0.8827(5) 0.8255(5) 0.1911(3) 0.0181(7) Uani d 1 . .
H H4 1.014200 0.811737 0.130392 0.022 Uiso calc 1 . .
C C5 0.6963(5) 0.9562(5) 0.1379(3) 0.0179(7) Uani d 1 . .
H H5 0.704994 1.030108 0.041346 0.022 Uiso calc 1 . .
C C6 0.5034(5) 0.9801(5) 0.2209(3) 0.0171(7) Uani d 1 . .
H H6 0.380553 1.069981 0.182484 0.020 Uiso calc 1 . .
C C7 0.2926(5) 0.7827(4) 0.5806(3) 0.0135(6) Uani d 1 . .
C C8 0.4803(5) 0.6503(4) 0.6354(3) 0.0147(7) Uani d 1 . .
C C9 0.4648(5) 0.5301(5) 0.7850(3) 0.0163(7) Uani d 1 . .
C C10 0.0784(5) 0.6913(5) 0.8079(3) 0.0164(7) Uani d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 115.5(3) ?
C8 N2 C2 . . 116.9(3) ?
C10 N3 C9 . . 127.3(3) ?
C10 N3 H3N . . 113(2) ?
C9 N3 H3N . . 119(2) ?
C10 N4 C7 . . 123.5(3) ?
C10 N4 H4N . . 116(2) ?
C7 N4 H4N . . 121(2) ?
N1 C1 C6 . . 119.7(3) ?
N1 C1 C2 . . 121.5(3) ?
C6 C1 C2 . . 118.8(3) ?
N2 C2 C3 . . 118.8(3) ?
N2 C2 C1 . . 121.1(3) ?
C3 C2 C1 . . 120.1(3) ?
C4 C3 C2 . . 119.5(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 122.0(3) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C1 . . 119.5(3) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N1 C7 N4 . . 118.0(3) ?
N1 C7 C8 . . 123.0(3) ?
N4 C7 C8 . . 119.0(3) ?
N2 C8 C7 . . 122.0(3) ?
N2 C8 C9 . . 118.3(3) ?
C7 C8 C9 . . 119.8(3) ?
O1 C9 N3 . . 121.7(3) ?
O1 C9 C8 . . 124.5(3) ?
N3 C9 C8 . . 113.8(3) ?
O2 C10 N4 . . 121.8(3) ?
O2 C10 N3 . . 121.6(3) ?
N4 C10 N3 . . 116.6(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 . 1.217(3) ?
O2 C10 . 1.224(4) ?
N1 C7 . 1.321(4) ?
N1 C1 . 1.372(4) ?
N2 C8 . 1.318(4) ?
N2 C2 . 1.358(4) ?
N3 C10 . 1.372(4) ?
N3 C9 . 1.381(4) ?
N3 H3N . 0.92(3) ?
N4 C10 . 1.369(4) ?
N4 C7 . 1.377(4) ?
N4 H4N . 0.90(3) ?
C1 C6 . 1.414(4) ?
C1 C2 . 1.422(4) ?
C2 C3 . 1.420(4) ?
C3 C4 . 1.368(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.407(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.364(4) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.423(4) ?
C8 C9 . 1.483(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3N O2 2_567 0.92(3) 2.00(4) 2.883(3) 162(3) yes
N4 H4N N1 2_576 0.90(3) 2.22(3) 3.114(3) 176(3) yes
C3 H3 N2 2_766 0.95 2.58 3.520(4) 173 yes
C6 H6 O2 2_576 0.95 2.21 3.158(4) 173 yes
