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#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/10/2001053.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_2001053
loop_
_publ_author_name
'Black, S. N.'
'Davey, R. J.'
'O'Mahoney, C. A.'
'Williams, D. J.'
_publ_section_title
;
 Structure of 1-amino-4-hydroxy-2-phenoxy-9,10-anthracenedione
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              321
_journal_page_last               323
_journal_paper_doi               10.1107/S0108270191009381
_journal_volume                  48
_journal_year                    1992
_chemical_formula_sum            'C20 H13 N O4'
_chemical_formula_weight         331.3
_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'
_cell_angle_alpha                90
_cell_angle_beta                 94.15(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.972(3)
_cell_length_b                   5.1410(10)
_cell_length_c                   19.853(3)
_cell_volume                     1524.1(5)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54178
_exptl_absorpt_coefficient_mu    0.8
_exptl_crystal_density_diffrn    1.44
_exptl_crystal_F_000             688
_cod_data_source_file            he0026.cif
_cod_data_source_block           he0026a
_cod_original_cell_volume        1524.0(10)
_cod_original_formula_sum        'C20 H13 N1 O4'
_cod_database_code               2001053
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) .72420(10) 1.1246(4) .20020(10) .0600(10)
C(1) .70730(10) .9362(4) .15310(10) .0510(10)
C(2) .6161(2) .8962(4) .12890(10) .0540(10)
O(2) .55840(10) 1.0624(3) .15760(10) .0710(10)
C(3) .5918(2) .7162(5) .08120(10) .0590(10)
C(4) .6576(2) .5572(4) .05490(10) .0520(10)
O(4) .62890(10) .3809(3) .00800(10) .0670(10)
C(5) .74730(10) .5833(4) .07800(10) .0490(10)
C(6) .8129(2) .4113(5) .05200(10) .0560(10)
O(6) .79160(10) .2456(4) .00710(10) .0730(10)
C(7) .9071(2) .4303(4) .07880(10) .0550(10)
C(8) .9704(2) .2620(6) .05600(10) .0710(10)
C(9) 1.0588(2) .2762(6) .08100(10) .0780(10)
C(10) 1.0840(2) .4582(6) .12930(10) .0800(10)
C(11) 1.0221(2) .6296(6) .15330(10) .0720(10)
C(12) .93270(10) .6155(5) .12810(10) .0560(10)
C(13) .8661(2) .7977(5) .15460(10) .0540(10)
O(13) .89120(10) .9581(3) .19890(10) .0690(10)
C(14) .77280(10) .7759(4) .12810(10) .0470(10)
C(15) .4668(2) 1.0032(5) .15330(10) .0590(10)
C(16) .4111(2) 1.1542(6) .11260(10) .0730(10)
C(17) .3209(2) 1.1139(6) .1110(2) .0870(10)
C(18) .2868(2) .9296(6) .1501(2) .0860(10)
C(19) .3426(2) .7735(6) .1910(2) .0920(10)
C(20) .4356(2) .8105(6) .19270(10) .0780(10)
H(1a) .6728(11) 1.228(4) .2121(13) ?
H(1b) .7872(5) 1.157(5) .2137(11) ?
H(3) .5299 .6966 .0656 ?
H(4) .6823(13) .282(5) -.0014(15) ?
H(8) .9528 .1336 .0225 ?
H(9) 1.1025 .1596 .0648 ?
H(10) 1.1455 .4668 .1467 ?
H(11) 1.0405 .7560 .1871 ?
H(16) .4352 1.2873 .0852 ?
H(17) .2806 1.2170 .0822 ?
H(18) .2232 .9055 .1499 ?
H(19) .3181 .6403 .2181 ?
H(20) .4758 .7030 .2204 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(1) 1.357(3)
C(1) C(14) 1.399(3)
C(2) C(3) 1.355(3)
C(3) C(4) 1.409(3)
C(4) C(5) 1.394(3)
C(5) C(14) 1.436(3)
C(6) C(7) 1.475(3)
C(7) C(12) 1.399(3)
C(9) C(10) 1.372(4)
C(11) C(12) 1.397(3)
C(13) O(13) 1.244(3)
C(15) C(16) 1.362(3)
C(16) C(17) 1.364(4)
C(18) C(19) 1.380(4)
C(1) C(2) 1.429(3)
C(2) O(2) 1.369(3)
O(2) C(15) 1.402(3)
C(4) O(4) 1.348(3)
C(5) C(6) 1.444(3)
C(6) O(6) 1.257(3)
C(7) C(8) 1.384(4)
C(8) C(9) 1.382(3)
C(10) C(11) 1.388(4)
C(12) C(13) 1.492(3)
C(13) C(14) 1.461(3)
C(15) C(20) 1.365(4)
C(17) C(18) 1.348(4)
C(19) C(20) 1.403(4)
