#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/11/2001189.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_2001189
loop_
_publ_author_name
'Ertan, A.'
'Koziol, J.'
_publ_section_title
;
 Structure of 1,3,9-trimethylalloxazine
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2179
_journal_page_last               2181
_journal_paper_doi               10.1107/S0108270193005803
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C13 H12 N4 O2'
_chemical_formula_weight         256.3
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 93.420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0520(10)
_cell_length_b                   7.6160(10)
_cell_length_c                   22.429(3)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      10.7
_cell_volume                     1202.5(3)
_diffrn_measurement_device       'Siemens STOE/AED2'
_diffrn_measurement_method       'ω-2θ scan'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54183
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2600
_diffrn_reflns_theta_max         69.53
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  90
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.4155(3)
_exptl_crystal_description       clean_faces
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.07
_refine_diff_density_min         -0.08
_refine_ls_hydrogen_treatment    refU_riding_on_respective_mother_atoms
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1451
_refine_ls_R_factor_obs          0.048
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = [σ²(F) + 0.00024|F|²]⁻¹'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.069
_reflns_number_observed          1451
_reflns_number_total             1987
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ab1075.cif
_cod_data_source_block           ab1075_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '[\s^2^(F) + 0.00024|F|^2^]^-1^'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = [\s^2^(F) +
0.00024|F|^2^]^-1^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2001189
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) .1751(3) .1729(2) .61120(10) .0420(10)
C(11) .3587(4) .0963(4) .59780(10) .0540(10)
C(2) .1348(4) .1911(3) .67010(10) .0490(10)
O(2) .2417(3) .1397(3) .71070(10) .0740(10)
N(3) -.0365(3) .2725(3) .68200(10) .0500(10)
C(31) -.0762(6) .2949(5) .74530(10) .0770(10)
C(4) -.1685(3) .3387(3) .63980(10) .0440(10)
O(4) -.3120(2) .4122(3) .65400(10) .0580(10)
C(4a) -.1212(3) .3128(3) .57730(10) .0370(10)
N(5) -.2419(2) .3692(2) .53470(10) .0380(10)
C(5a) -.1946(3) .3455(3) .47750(10) .0370(10)
C(6) -.3181(3) .4101(3) .43040(10) .0430(10)
C(7) -.2697(4) .3888(3) .37300(10) .0480(10)
C(8) -.0994(4) .3024(3) .36040(10) .0480(10)
C(9) .0265(3) .2393(3) .40460(10) .0420(10)
C(91) .2108(4) .1550(4) .39110(10) .0560(10)
C(9a) -.0212(3) .2614(3) .46470(10) .0360(10)
N(10) .1018(2) .2026(2) .50970(10) .0390(10)
C(10a) .0529(3) .2290(3) .56410(10) .0360(10)
H(11A) .4191 .0645 .6364 ?
H(11B) .4353 .1826 .5747 ?
H(11C) .3477 -.0126 .5747 ?
H(31A) -.0955 .1831 .7649 ?
H(31B) .0356 .3428 .7643 ?
H(31C) -.1872 .3629 .7512 ?
H(6) -.4446 .4654 .4423 ?
H(7) -.3542 .4333 .3377 ?
H(8) -.0666 .2774 .3166 ?
H(91A) .2161 .1116 .3503 ?
H(91B) .3139 .2379 .3959 ?
H(91C) .2387 .0537 .4202 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) N(1) C(10a) 123.0(2) yes
C(11) N(1) C(10a) 118.7(2) yes
C(11) N(1) C(2) 118.2(2) yes
N(1) C(2) N(3) 117.3(2) yes
N(1) C(2) O(2) 122.4(2) yes
O(2) C(2) N(3) 120.3(2) yes
C(2) N(3) C(4) 125.8(2) yes
C(2) N(3) C(31) 116.9(2) yes
C(31) N(3) C(4) 117.3(2) yes
N(3) C(4) C(4a) 114.9(2) yes
N(3) C(4) O(4) 121.7(2) yes
O(4) C(4) C(4a) 123.4(2) yes
C(4) C(4a) C(10a) 120.1(2) yes
C(4) C(4a) N(5) 118.3(2) yes
N(5) C(4a) C(10a) 121.6(2) yes
C(4a) N(5) C(5a) 117.3(2) yes
N(5) C(5a) C(9a) 120.8(2) yes
N(5) C(5a) C(6) 118.9(2) yes
C(6) C(5a) C(9a) 120.2(2) yes
C(5a) C(6) C(7) 119.0(2) yes
C(6) C(7) C(8) 120.7(2) yes
C(7) C(8) C(9) 122.4(2) yes
C(8) C(9) C(9a) 117.6(2) yes
C(8) C(9) C(91) 122.3(2) yes
C(91) C(9) C(9a) 120.0(2) yes
C(5a) C(9a) C(9) 120.0(2) yes
C(9) C(9a) N(10) 119.1(2) yes
C(5a) C(9a) N(10) 120.9(2) yes
C(9a) N(10) C(10a) 116.7(2) yes
C(4a) C(10a) N(10) 122.7(2) yes
N(1) C(10a) N(10) 118.5(2) yes
N(1) C(10a) C(4a) 118.7(2) yes
N(1) C(11) H(11C) 114 no
N(1) C(11) H(11B) 111 no
N(1) C(11) H(11A) 105 no
H(11B) C(11) H(11C) 108 no
H(11A) C(11) H(11C) 106 no
H(11A) C(11) H(11B) 113 no
N(3) C(31) H(31C) 114 no
N(3) C(31) H(31B) 106 no
N(3) C(31) H(31A) 112 no
H(31B) C(31) H(31C) 113 no
H(31A) C(31) H(31C) 106 no
H(31A) C(31) H(31B) 106 no
C(5a) C(6) H(6) 117 no
H(6) C(6) C(7) 124 no
C(6) C(7) H(7) 122 no
H(7) C(7) C(8) 118 no
C(7) C(8) H(8) 121 no
H(8) C(8) C(9) 116 no
C(9) C(91) H(91C) 109 no
C(9) C(91) H(91B) 111 no
C(9) C(91) H(91A) 115 no
H(91B) C(91) H(91C) 108 no
H(91A) C(91) H(91C) 109 no
H(91A) C(91) H(91B) 105 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(11) 1.468(3) yes
N(1) C(2) 1.373(3) yes
N(1) C(10a) 1.391(3) yes
C(2) O(2) 1.212(3) yes
C(2) N(3) 1.398(3) yes
N(3) C(31) 1.472(3) yes
N(3) C(4) 1.382(3) yes
C(4) O(4) 1.216(3) yes
C(4) C(4a) 1.474(3) yes
C(4a) N(5) 1.313(3) yes
C(4a) C(10a) 1.430(3) yes
N(5) C(5a) 1.358(3) yes
C(5a) C(6) 1.417(3) yes
C(5a) C(9a) 1.424(3) yes
C(6) C(7) 1.360(3) yes
C(7) C(8) 1.414(4) yes
C(8) C(9) 1.377(3) yes
C(9) C(91) 1.496(4) yes
C(9) C(9a) 1.419(3) yes
C(9a) N(10) 1.367(3) yes
N(10) C(10a) 1.304(3) yes
C(11) H(11A) 0.97 no
C(11) H(11B) 1.01 no
C(11) H(11C) 0.98 no
C(31) H(31A) 0.97 no
C(31) H(31B) 0.95 no
C(31) H(31C) 0.95 no
C(6) H(6) 1.04 no
C(7) H(7) 1.02 no
C(8) H(8) 1.04 no
C(91) H(91A) 0.98 no
C(91) H(91B) 0.96 no
C(91) H(91C) 1.02 no
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_publ_flag
C(11) N(1) C(2) N(3) 176.8(2) yes
C(11) N(1) C(10a) C(4a) -176.4(2) yes
C(11) N(1) C(2) O(2) -3.1(4) yes
C(11) N(1) C(10a) N(10) 3.7(3) yes
N(1) C(2) N(3) C(31) -178.6(2) yes
C(31) N(3) C(4) C(4a) 179.9(2) yes
C(31) N(3) C(4) O(4) -0.2(4) yes
O(2) C(2) N(3) C(31) 1.3(4) yes
C(91) C(9) C(9a) C(5a) 178.5(2) yes
C(7) C(8) C(9) C(91) -177.2(2) yes
C(91) C(9) C(9a) N(10) -0.9(3) yes
