#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228277.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_2228277
loop_
_publ_author_name
'Rohlíček, Jan'
'Cibulka, Radek'
'Cibulková, Jana'
'Maixner, Jaroslav'
'Hušák, Michal'
_publ_section_title
;
 10-Methylisoalloxazine 5-oxide from synchrotron powder diffraction
 data
;
_journal_coeditor_code           CV5002
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3350
_journal_page_last               o3351
_journal_paper_doi               10.1107/S1600536810048932
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H8 N4 O3'
_chemical_formula_moiety         'C11 H8 N4 O3'
_chemical_formula_sum            'C11 H8 N4 O3'
_chemical_formula_weight         244.21
_chemical_name_common
;
10-Methylisoalloxazine 5-oxide
;
_chemical_name_systematic
;
10-methylbenzo[g]pteridine-2,4(3H,10H)-dione 5-oxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90.0
_cell_angle_beta                 90.830(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   13.8774(6)
_cell_length_b                   14.5321(4)
_cell_length_c                   4.9305(2)
_cell_measurement_temperature    293
_cell_volume                     994.22(6)
_computing_cell_refinement       'GSAS (Larson & Von Dreele, 1994)'
_computing_data_collection
'ESRF SPEC (Certified Scientific Software, 2003)'
_computing_data_reduction        'CRYSFIRE (Shirley, 2000)'
_computing_molecular_graphics
'Mercury (Macrae et al., 2006) and PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'GSAS (Larson & Von Dreele, 1994)'
_computing_structure_solution    'FOX (Favre-Nicolin & Černý, 2002)'
_diffrn_measurement_device_type  'ESRF Grenoble, BM20'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.8856
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             504
_pd_calc_method                  'Rietveld Refinement'
_pd_char_colour                  yellow
_pd_meas_2theta_range_inc        0.01
_pd_meas_2theta_range_max        36.5
_pd_meas_2theta_range_min        4.0
_pd_meas_number_of_points        3251
_pd_meas_scan_method             step
_pd_phase_name
'from C:/PiGi/skola/flavin2/gsas/02/FLAVIN2-RIETVELD-RESTR-complete'
_pd_proc_2theta_range_inc        0.01
_pd_proc_2theta_range_max        36.5
_pd_proc_2theta_range_min        4.0
_pd_proc_info_datetime           2010-10-27T10:43:09
_pd_proc_info_excluded_regions   none
_pd_proc_ls_background_function
;   GSAS Background function number 1 with 20 terms.
 Shifted Chebyshev function of 1st kind
      1:    1199.79     2:   -234.522     3:   -315.536     4:    152.956
      5:    123.532     6:   -246.657     7:    116.810     8:    83.9272
      9:   -107.809    10:   -12.4938    11:    79.2500    12:   -25.2804
     13:   -27.8174    14:    13.6120    15:    6.03858    16:   -3.86487
     17:    2.09281    18:    9.92947    19:   -18.6000    20:    1.36657
;
_pd_proc_ls_peak_cutoff          0.00010
_pd_proc_ls_pref_orient_corr
;
March-Dollase
AXIS  1 Ratio=   0.89956  h= 0.000  k= 0.000  l= 1.000
Prefered orientation correction range: Min=   0.85318, Max=   1.37377
;
_pd_proc_ls_profile_function
;
CW Profile function number 4 with  21 terms
Pseudovoigt profile coefficients as parameterized in
P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl.
Cryst.,20,79-83.
Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994).
J. Appl. Cryst.,27,892-900.
Microstrain broadening by P.W. Stephens,  (1999). J. Appl.
Cryst.,32,281-289.
Peak tails are ignored  where the intensity is below 0.0001 times the peak
  Aniso. broadening axis   0.0   0.0   1.0
;
_pd_proc_ls_prof_R_factor        0.0420
_pd_proc_ls_prof_wR_expected     0.0213
_pd_proc_ls_prof_wR_factor       0.0558
_pd_proc_number_of_points        3251
_pd_spec_mounting                capilary
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_spec_size_axial              20
_pd_spec_size_equat              1
_pd_spec_size_thick              1
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.183
_refine_ls_goodness_of_fit_all   2.67
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     73
_refine_ls_number_restraints     57
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.01
_refine_ls_weighting_scheme      sigma
_reflns_number_total             371
_cod_data_source_file            cv5002.cif
_cod_data_source_block           I
_cod_original_cell_volume        994.22(5)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2228277
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x+1/2,+y+1/2,-z
-x,-y,-z
+x+1/2,-y+1/2,+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_thermal_displace_type
_atom_site_occupancy
N N1 0.0773(7) 0.1443(5) 1.0053(18) 0.036(6) Uiso 1.0
C C2 0.0483(8) 0.0827(7) 1.194(3) 0.075(8) Uiso 1.0
N N3 0.0977(7) -0.0028(6) 1.2303(19) 0.068(6) Uiso 1.0
C C4 0.1784(5) -0.0297(5) 1.0946(14) 0.028(8) Uiso 1.0
C C4a 0.2075(5) 0.0367(5) 0.8768(14) 0.049(7) Uiso 1.0
N N5 0.2843(7) 0.0175(6) 0.725(2) 0.120(8) Uiso 1.0
C C5a 0.3110(6) 0.0833(6) 0.5319(18) 0.077(9) Uiso 1.0
C C6 0.3917(7) 0.0645(6) 0.365(2) 0.037(7) Uiso 1.0
C C7 0.4210(6) 0.1290(8) 0.180(2) 0.052(7) Uiso 1.0
C C8 0.3703(8) 0.2112(7) 0.1520(18) 0.059(8) Uiso 1.0
C C9 0.2917(7) 0.2332(6) 0.311(2) 0.054(8) Uiso 1.0
C C9a 0.2610(6) 0.1684(6) 0.5019(18) 0.045(9) Uiso 1.0
N N10 0.1787(7) 0.1824(7) 0.6664(19) 0.078(7) Uiso 1.0
C C10a 0.1522(5) 0.1216(5) 0.8572(14) 0.046(8) Uiso 1.0
O O11 -0.0238(7) 0.1000(7) 1.338(2) 0.063(5) Uiso 1.0
O O12 0.2230(7) -0.1014(5) 1.1524(17) 0.037(4) Uiso 1.0
O O13 0.3291(8) -0.0597(7) 0.748(2) 0.100(5) Uiso 1.0
C C14 0.1211(10) 0.2660(9) 0.619(3) 0.095(9) Uiso 1.0
H H1N3 0.0746 -0.0405 1.3466 0.0804 Uiso 1.0
H H1C6 0.425 0.0076 0.3816 0.0456 Uiso 1.0
H H1C7 0.4758 0.1173 0.0718 0.0612 Uiso 1.0
H H1C8 0.3906 0.254 0.0188 0.0708 Uiso 1.0
H H1C9 0.2597 0.2905 0.2901 0.0636 Uiso 1.0
H H1C14 0.1488 0.3013 0.479 0.114 Uiso 1.0
H H2C14 0.119 0.3013 0.781 0.114 Uiso 1.0
H H3C14 0.057 0.249 0.567 0.114 Uiso 1.0
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.000 0.000 International_Tables_Vol_C
N 0.000 0.000 International_Tables_Vol_C
O 0.000 0.000 International_Tables_Vol_C
H 0.000 0.000 International_Tables_Vol_C
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C10A 1_555 . 1_555 117.3(8) n
C2 N3 C4 1_555 . 1_555 125.5(9) n
O13 N5 C4A 1_555 . 1_555 121.3(9) n
O13 N5 C5A 1_555 . 1_555 121.5(9) n
C4A N5 C5A 1_555 . 1_555 117.2(8) n
C9A N10 C10A 1_555 . 1_555 122.3(9) n
C9A N10 C14 1_555 . 1_555 117.8(9) n
C10A N10 C14 1_555 . 1_555 120.0(9) n
O11 C2 N1 1_555 . 1_555 120.0(10) n
O11 C2 N3 1_555 . 1_555 119.1(11) n
N1 C2 N3 1_555 . 1_555 120.9(10) n
O12 C4 N3 1_555 . 1_555 122.4(8) n
O12 C4 C4A 1_555 . 1_555 124.3(7) n
N3 C4 C4A 1_555 . 1_555 113.3(7) n
N5 C4A C4 1_555 . 1_555 119.3(7) n
N5 C4A C10A 1_555 . 1_555 124.2(7) n
C4 C4A C10A 1_555 . 1_555 116.4(6) n
N5 C5A C6 1_555 . 1_555 118.6(8) n
N5 C5A C9A 1_555 . 1_555 121.9(8) n
C6 C5A C9A 1_555 . 1_555 119.5(8) n
C5A C6 C7 1_555 . 1_555 119.7(8) n
C6 C7 C8 1_555 . 1_555 119.8(9) n
C7 C8 C9 1_555 . 1_555 122.8(9) n
C8 C9 C9A 1_555 . 1_555 118.2(8) n
N10 C9A C5A 1_555 . 1_555 117.3(8) n
N10 C9A C9 1_555 . 1_555 122.7(8) n
C5A C9A C9 1_555 . 1_555 120.0(8) n
N1 C10A N10 1_555 . 1_555 116.6(8) n
N1 C10A C4A 1_555 . 1_555 126.4(7) n
N10 C10A C4A 1_555 . 1_555 117.0(7) n
C2 N3 H1N3 1_555 . 1_555 117 n
C4 N3 H1N3 1_555 . 1_555 117 n
C5A C6 H1C6 1_555 . 1_555 120 n
C7 C6 H1C6 1_555 . 1_555 120 n
C6 C7 H1C7 1_555 . 1_555 120 n
C8 C7 H1C7 1_555 . 1_555 120 n
C7 C8 H1C8 1_555 . 1_555 118 n
C9 C8 H1C8 1_555 . 1_555 119 n
C8 C9 H1C9 1_555 . 1_555 121 n
C9A C9 H1C9 1_555 . 1_555 121 n
N10 C14 H1C14 1_555 . 1_555 110 n
N10 C14 H2C14 1_555 . 1_555 110 n
N10 C14 H3C14 1_555 . 1_555 109 n
H1C14 C14 H2C14 1_555 . 1_555 110 n
H1C14 C14 H3C14 1_555 . 1_555 109 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C2 . 1_555 1.261(16) n
C4 C4a . 1_555 1.503(10) n
O12 C4 . 1_555 1.243(11) n
C5a C9a . 1_555 1.425(12) n
O13 N5 . 1_555 1.287(14) n
C5a C6 . 1_555 1.426(13) n
N1 C10a . 1_555 1.321(12) n
C6 C7 . 1_555 1.374(14) n
N1 C2 . 1_555 1.356(15) n
C7 C8 . 1_555 1.392(15) n
N10 C10a . 1_555 1.346(12) n
C8 C9 . 1_555 1.390(14) n
N10 C14 . 1_555 1.471(17) n
C9 C9a . 1_555 1.402(13) n
N10 C9a . 1_555 1.425(13) n
N3 C2 . 1_555 1.429(14) n
N3 C4 . 1_555 1.370(12) n
N5 C5a . 1_555 1.403(13) n
N5 C4a . 1_555 1.341(12) n
C10a C4a . 1_555 1.455(10) n
C14 H1C14 . 1_555 0.9500 n
C14 H2C14 . 1_555 0.9500 n
C14 H3C14 . 1_555 0.9500 n
C6 H1C6 . 1_555 0.9500 n
C7 H1C7 . 1_555 0.9500 n
N3 H1N3 . 1_555 0.8600 n
C8 H1C8 . 1_555 0.9500 n
C9 H1C9 . 1_555 0.9500 n
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cg1 Cg2 3.560(10) . 1_556 ?
Cg1 Cg3 3.540(10) . 1_556 ?
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 H1N3 O11 3_558 0.86 1.92 2.764(14) 166 yes
C14 H2C14 O12 2_557 0.95 2.63 3.097(16) 111 yes
C14 H1C14 O13 2_556 0.95 2.33 3.194(17) 151 yes
loop_
_pd_calc_intensity_total
1326.11328
1327.44678
1328.48975
1329.25464
1329.75464
1330.00110
1330.00586
1329.78101
1329.33704
1328.68494
1327.83582
1326.79907
1325.58545
1324.20374
1322.66418
1320.97571
1319.14746
1317.18750
1315.10474
1312.90735
1310.60376
1308.20032
1305.70581
1303.12732
1300.47156
1297.74609
1294.95752
1292.11255
1289.21753
1286.27869
1283.30237
1280.29456
1277.26099
1274.20715
1271.13965
1268.06372
1264.98425
1261.90735
1258.83813
1255.78198
1252.74390
1249.72986
1246.74463
1243.79321
1240.88159
1238.01404
1235.19751
1232.43701
1229.73755
1227.10645
1224.54846
1222.07056
1219.67920
1217.38159
1215.18542
1213.09802
1211.12805
1209.28418
1207.57751
1206.01709
1204.61597
1203.38586
1202.34155
1201.49915
1200.87573
1200.49036
1200.36633
1200.52832
1201.00427
1201.82739
1203.03491
1204.66919
1206.78088
1209.42737
1212.67773
1216.61182
1221.32471
1226.93054
1233.56543
1241.39539
1250.62134
1261.49243
1274.31580
1289.47913
1307.47168
1328.92334
1354.65234
1385.74634
1423.70129
1470.75964
1530.88281
1612.59717
1736.26782
1949.10303
2348.02808
3100.35059
4439.27197
6611.37256
9774.84863
13877.83594
18608.51367
23490.70703
27944.37695
31227.49805
32449.42773
30836.96875
26339.61133
20119.53906
13911.18848
8928.21973
5557.88379
3587.59521
2561.38940
2058.19775
1803.67566
1657.32300
1558.94385
1485.22925
1426.89026
1379.48035
1340.33264
1307.61145
1279.97473
1256.41516
1236.16260
1218.62158
1203.32446
1189.90259
1178.05823
1167.55237
1158.18945
1151.15771
1143.64197
1136.86426
1130.73145
1125.16516
1120.09766
1115.47205
1111.23999
1107.35803
1103.78992
1100.50378
1097.47156
1094.66846
1092.07373
1089.66711
1087.43274
1085.35474
1083.42053
1081.61731
1079.93481
1078.36267
1076.89270
1075.51672
1074.22754
1073.01880
1071.88379
1070.81787
1069.81580
1068.87305
1067.98535
1067.14868
1066.35938
1065.61426
1064.91052
1064.24512
1063.61572
1063.01892
1062.45325
1061.91699
1061.40698
1060.92236
1060.46094
1060.02124
1059.60181
1059.20093
1058.81750
1058.45032
1058.09778
1057.75977
1057.43408
1057.15991
1056.85754
1056.56567
1056.28271
1056.00879
1055.74231
1055.48303
1055.23071
1054.98425
1054.74280
1054.50684
1054.27539
1054.04773
1053.82361
1053.60339
1053.38586
1053.17102
1052.95850
1052.74780
1052.53955
1052.33289
1052.12732
1051.92371
1051.72119
1051.51941
1051.31958
1051.12012
1050.92236
1050.72534
1050.52942
1050.33496
1050.14136
1049.94958
1049.75903
1049.57043
1049.38367
1049.19897
1049.01660
1048.83728
1048.66064
1048.48767
1050.81860
1050.68408
1050.55432
1050.43066
1050.31372
1050.20288
1050.10034
1050.00574
1049.92053
1049.84521
1049.78052
1049.72729
1049.68750
1049.66125
1049.65027
1049.65576
1049.67908
1049.72192
1049.78564
1049.87219
1049.98340
1050.12158
1050.28845
1050.48718
1050.72009
1050.99011
1051.30078
1051.65491
1052.05701
1052.51147
1053.02258
1053.59570
1054.23645
1054.95129
1055.74744
1056.63293
1057.61670
1058.70874
1059.92041
1061.26477
1062.75598
1064.41101
1066.24902
1068.29211
1070.56494
1073.09753
1075.92444
1079.08521
1079.79749
1083.81201
1088.33191
1093.43787
1099.22815
1105.82288
1113.36963
1122.05212
1132.10388
1143.82727
1157.64075
1174.18652
1194.61230
1221.24695
1259.09753
1318.73438
1421.01428
1603.29077
1925.01086
2468.35181
3328.17041
4586.84961
6274.37109
8321.10547
10522.40723
12550.55078
14031.10840
14642.92773
14213.27344
12804.39648
10731.07617
8432.98926
6293.80078
4547.13818
3271.14575
2428.03589
1919.92188
1638.56018
1495.55750
1432.25354
1416.65906
1435.83801
1489.00110
1583.05298
1730.27869
1947.16821
2253.49219
2671.00903
3221.46680
3923.79907
4790.60986
5824.29443
7013.29688
8329.17676
9725.13379
11136.60059
12484.37500
13680.57422
14637.32227
15277.37695
15545.00293
15414.97656
14897.50195
14037.10938
12905.24219
11588.78516
10178.09375
8757.18262
7396.83838
6150.65430
5053.57324
4122.66699
3359.63232
2754.37524
2288.99536
1941.55945
1689.23792
1510.57239
1386.86340
1302.78418
1246.41565
1208.91577
1183.99756
1167.36438
1156.18726
1148.66602
1143.69385
1140.61584
1139.05920
1138.82959
1139.84229
1142.08569
1145.59985
1150.46814
1156.81653
1164.81580
1174.69214
1186.73730
1201.33020
1218.96033
1240.26770
1266.09448
1297.57153
1336.28223
1384.66394
1447.18774
1533.77356
1668.49695
1907.87585
2370.41724
3268.01978
4911.19824
7647.57422
11705.66992
16956.76367
22693.84375
27685.89453
30588.60742
30411.25977
27011.33008
21431.25391
15366.10352
10158.81836
6399.83740
4054.41846
2761.39404
2110.86938
1795.80334
1638.43127
1554.19312
1508.35754
1487.50452
1485.68286
1498.92322
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0.000909 834.57507
0.000918 834.06189
0.000988 833.54956
0.000956 833.03778
0.000932 832.52698
0.001001 832.01721
0.000961 831.50916
0.000985 831.00250
0.001054 830.49762
0.000978 829.99506
0.000967 829.49451
0.001003 828.99646
0.001026 828.50092
0.001052 828.00842
0.000993 827.51904
0.001003 827.03296
0.001013 826.55054
0.000974 826.07214
0.000975 825.59778
0.001086 825.12744
0.001005 824.66187
0.001010 824.20074
0.001022 823.74493
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0.001007 822.84894
0.001056 822.40955
0.000996 821.97565
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0.001155 820.71277
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0.001139 807.21051
0.001179 806.36615
0.001152 805.45056
0.001206 804.45966
0.001190 803.39050
0.001134 802.23840
0.001142 801.00037
0.001134 799.67096
0.001121 798.24725
0.001136 796.72424
. .
loop_
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1 PubChem 12247624
