#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/09/2100929.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_2100929
loop_
_publ_author_name
'Clark, G. R.'
'Robinson, K.'
'Denny, W. A.'
'Lee, H. H.'
_publ_section_title
;
 Structures of quinone imine metabolites related to the anti-cancer
 drug amsacrine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              342
_journal_page_last               347
_journal_paper_doi               10.1107/S0108768192009169
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.3
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                96.45(3)
_cell_angle_beta                 105.30(2)
_cell_angle_gamma                110.110(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3650(10)
_cell_length_b                   13.318(2)
_cell_length_c                   6.918(3)
_cell_volume                     761.6(4)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71069
_exptl_absorpt_coefficient_mu    0.098
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      1.350(10)
_exptl_crystal_F_000             656
_cod_data_source_file            hu0417.cif
_cod_data_source_block           hu0417b
_cod_original_cell_volume        761.4(5)
_cod_database_code               2100929
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1'') .7801(8) .4421(5) -.3544(10)
O(2'') .7373(7) .5126(5) -.0088(11)
N(9') .8987(8) .2445(5) .2695(11)
N(10) 1.0645(8) -.0157(6) .2536(10)
C(1) 1.2333(12) .2873(7) .3167(15)
C(1A) 1.1154(11) .1807(6) .2822(13)
C(1') .7979(9) .3934(7) -.2168(15)
C(2) 1.3877(12) .3051(7) .3419(15)
C(2') .7824(10) .4273(7) -.0160(16)
C(2'') .7170(12) .5512(8) .1790(19)
C(3) 1.4368(11) .2158(8) .3372(15)
C(3') .8167(9) .3771(6) .1420(14)
C(4) 1.3274(10) .1115(7) .3052(14)
C(4A) 1.1648(10) .0893(7) .2806(13)
C(4') .8671(9) .2858(6) .1116(14)
C(5) .8059(11) -.1437(7) .2129(13)
C(5A) .9113(10) -.0326(6) .2368(12)
C(5') .8738(10) .2466(7) -.0901(14)
C(6) .6506(12) -.1690(7) .1950(14)
C(6') .8417(9) .2979(6) -.2436(14)
C(7) .5875(11) -.0862(8) .1973(15)
C(8) .6833(11) .0201(8) .2182(14)
C(8A) .8480(11) .0501(7) .2377(12)
C(9) .9530(11) .1578(7) .2572(14)
H(1) 1.2023(12) .3481(7) .3220(15)
H(2) 1.4641(12) .3775(7) .3631(15)
H(2") .6681(12) .6026(8) .1585(19)
H(2") .8148(12) .5841(8) .2908(19)
H(2") .6465(12) .4888(8) .2087(19)
H(3) 1.5463(11) .2286(8) .3562(15)
H(3') .8080(9) .4017(6) .2712(14)
H(4) 1.3620(10) .0523(7) .2995(14)
H(5) .8461(11) -.2001(7) .2097(13)
H(5') .9008(10) .1849(7) -.1134(14)
H(6) .5822(12) -.2431(7) .1807(14)
H(6') .8476(9) .2715(6) -.3735(14)
H(7) .4773(11) -.1054(8) .1842(15)
H(8) .6397(11) .0747(8) .2196(14)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2'') O(2'') C(2') 116.6(8)
C(9) N(9') C(4') 119.7(8)
C(5A) N(10) C(4A) 116.2(7)
C(2) C(1) C(1A) 121.9(9)
C(4A) C(1A) C(1) 118.5(8)
C(9) C(1A) C(1) 124.2(8)
C(9) C(1A) C(4A) 117.3(8)
C(2') C(1') O(1'') 123.0(8)
C(6') C(1') O(1'') 120.4(9)
C(6') C(1') C(2') 116.5(8)
C(3) C(2) C(1) 119.9(9)
C(1') C(2') O(2'') 112.1(8)
C(3') C(2') O(2'') 126.1(10)
C(3') C(2') C(1') 121.8(8)
C(4) C(3) C(2) 120.3(9)
C(4') C(3') C(2') 119.8(9)
C(4A) C(4) C(3) 121.6(8)
C(1A) C(4A) N(10) 124.1(8)
C(4) C(4A) N(10) 118.2(8)
C(4) C(4A) C(1A) 117.7(9)
C(3') C(4') N(9') 115.4(8)
C(5') C(4') N(9') 125.3(7)
C(5') C(4') C(3') 119.3(8)
C(6) C(5) C(5A) 120.6(9)
C(5) C(5A) N(10) 116.1(8)
C(8A) C(5A) N(10) 125.2(8)
C(8A) C(5A) C(5) 118.7(8)
C(6') C(5') C(4') 120.2(8)
C(7) C(6) C(5) 120.6(9)
C(5') C(6') C(1') 122.3(9)
C(8) C(7) C(6) 120.5(10)
C(8A) C(8) C(7) 120.5(9)
C(8) C(8A) C(5A) 119.0(8)
C(9) C(8A) C(5A) 117.6(8)
C(9) C(8A) C(8) 123.5(8)
C(1A) C(9) N(9') 120.0(8)
C(8A) C(9) N(9') 120.1(8)
C(8A) C(9) C(1A) 119.7(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1') O(1'') 1.217(10)
C(2') O(2'') 1.342(9)
C(2'') O(2'') 1.426(11)
C(4') N(9') 1.288(10)
C(9) N(9') 1.415(10)
C(4A) N(10) 1.348(10)
C(5A) N(10) 1.344(10)
C(1A) C(1) 1.413(11)
C(2) C(1) 1.342(12)
C(4A) C(1A) 1.443(10)
C(9) C(1A) 1.402(12)
C(2') C(1') 1.472(12)
C(6') C(1') 1.472(10)
C(3) C(2) 1.414(12)
C(3') C(2') 1.368(11)
C(4) C(3) 1.364(11)
C(4') C(3') 1.462(10)
C(4A) C(4) 1.406(11)
C(5') C(4') 1.458(11)
C(5A) C(5) 1.430(11)
C(6) C(5) 1.342(11)
C(8A) C(5A) 1.419(10)
C(6') C(5') 1.349(11)
C(7) C(6) 1.420(12)
C(8) C(7) 1.357(12)
C(8A) C(8) 1.417(11)
C(9) C(8A) 1.400(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 14246737