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#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/09/2100930.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_2100930
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_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C22 H19 N3 O2'
_chemical_formula_weight         347.4
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                108.39(2)
_cell_angle_beta                 99.63(4)
_cell_angle_gamma                95.87(3)
_cell_formula_units_Z            2
_cell_length_a                   8.091(7)
_cell_length_b                   10.078(2)
_cell_length_c                   11.716(3)
_cell_volume                     881.4(8)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71069
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      1.330(10)
_exptl_crystal_F_000             376
_[local]_cod_data_source_file    hu0417.cif
_[local]_cod_data_source_block   hu0417c
_cod_original_cell_volume        881.4(9)
_cod_database_code               2100930
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N(5'') .8640(3) .3467(2) .16864(19)
N(9') .7556(3) .2271(2) .33363(17)
N(10) .6875(3) .0459(2) .60767(17)
O(1'') .2792(3) .2710(2) -.01558(17)
O(2'') .2084(2) .05399(18) .05804(14)
C(1) .8211(3) -.0602(3) .3062(2)
C(1A) .7610(3) .0263(3) .4086(2)
C(1') .3996(4) .2418(3) .0476(2)
C(2) .8629(4) -.1876(3) .3040(2)
C(2') .3661(3) .1298(3) .1034(2)
C(2'') .1604(3) -.0549(3) .1079(2)
C(3) .8458(4) -.2390(3) .4011(2)
C(3') .4844(3) .1174(3) .1937(2)
C(4) .7861(3) -.1624(3) .4979(2)
C(4A) .7428(3) -.0263(3) .5070(2)
C(4') .6501(3) .2062(2) .2320(2)
C(5) .6021(3) .2578(3) .7251(2)
C(5A) .6566(3) .1783(3) .6181(2)
C(5') .6999(3) .2885(2) .1521(2)
C(5'') .9055(4) .4435(3) .1041(3)
C(5''') 1.0115(4) .2992(3) .2258(3)
C(6) .5748(4) .3921(3) .7428(2)
C(6') .5712(4) .3085(3) .0701(2)
C(7) .5982(4) .4573(3) .6555(2)
C(8) .6467(3) .3854(3) .5505(2)
C(8A) .6766(3) .2433(3) .5273(2)
C(9) .7241(3) .1626(3) .4202(2)
H(1) .664(3) .433(2) .492(2)
H(2) .579(3) .546(2) .6623(18)
H(3) .535(3) .437(2) .8107(18)
H(4) .585(3) .208(2) .781(2)
H(5) .769(3) -.194(2) .5587(18)
H(6) .874(3) -.333(2) .397(2)
H(7) .901(3) -.242(2) .236(2)
H(8) .834(3) -.023(2) .2378(19)
H(3') .460(3) .059(2) .2362(18)
H(6') .587(3) .366(2) .0216(17)
H(2''A) .235(3) -.127(2) .0848(18)
H(2''B) .177(3) -.018(2) .203(2)
H(2''C) .042(3) -.096(2) .063(2)
H(5''A) .832(3) .513(3) .105(2)
H(5''B) .904(4) .380(3) .011(2)
H(5''C) 1.014(3) .496(3) .136(2)
H(5'''A) .986(3) .197(3) .224(2)
H(5'''B) 1.056(4) .356(3) .312(3)
H(5'''C) 1.095(4) .299(3) .171(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(5') N(5'') 1.351(3)
C(5'') N(5'') 1.454(4)
C(5''') N(5'') 1.467(4)
C(4') N(9') 1.286(3)
C(9) N(9') 1.406(4)
C(4A) N(10) 1.347(3)
C(5A) N(10) 1.352(3)
C(1') O(1'') 1.240(4)
C(2') O(2'') 1.346(3)
C(2'') O(2'') 1.443(4)
C(1A) C(1) 1.432(3)
C(2) C(1) 1.353(4)
C(4A) C(1A) 1.433(4)
C(9) C(1A) 1.404(4)
C(2') C(1') 1.493(4)
C(6') C(1') 1.422(4)
C(3) C(2) 1.409(4)
C(3') C(2') 1.348(4)
C(4) C(3) 1.348(4)
C(4') C(3') 1.449(3)
C(4A) C(4) 1.424(4)
C(5') C(4') 1.505(4)
C(5A) C(5) 1.423(3)
C(6) C(5) 1.348(4)
C(8A) C(5A) 1.434(4)
C(6') C(5') 1.370(4)
C(7) C(6) 1.403(4)
C(8) C(7) 1.358(4)
C(8A) C(8) 1.423(4)
C(9) C(8A) 1.400(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(5'') N(5'') C(5') 119.0(2)
C(5''') N(5'') C(5') 125.4(2)
C(5'') N(5'') C(5''') 114.4(2)
C(9) N(9') C(4') 123.4(2)
C(5A) N(10) C(4A) 117.4(2)
C(2'') O(2'') C(2') 117.4(2)
C(2) C(1) C(1A) 120.5(3)
C(4A) C(1A) C(1) 118.7(2)
C(9) C(1A) C(1) 123.6(3)
C(9) C(1A) C(4A) 117.7(2)
C(2') C(1') O(1'') 119.3(2)
C(6') C(1') O(1'') 123.7(3)
C(6') C(1') C(2') 117.0(2)
C(3) C(2) C(1) 120.9(3)
C(1') C(2') O(2'') 112.6(2)
C(3') C(2') O(2'') 126.8(3)
C(3') C(2') C(1') 120.5(2)
C(4) C(3) C(2) 120.6(3)
C(4') C(3') C(2') 120.4(3)
C(4A) C(4) C(3) 121.4(3)
C(1A) C(4A) N(10) 123.7(2)
C(4) C(4A) N(10) 118.3(3)
C(4) C(4A) c(1A) 118.0(2)
C(3') C(4') N(9') 124.9(3)
C(5') C(4') N(9') 116.7(2)
C(5') C(4') C(3') 118.3(2)
C(6) C(5) C(5A) 121.2(3)
C(5) C(5A) N(10) 118.4(3)
C(8A) C(5A) N(10) 123.5(2)
C(8A) C(5A) C(5) 118.1(2)
C(4') C(5') N(5'') 119.9(2)
C(6') C(5') N(5'') 122.9(3)
C(6') C(5') C(4') 117.0(2)
C(7) C(6) C(5) 120.8(2)
C(5') C(6') C(1') 123.2(3)
C(8) C(7) C(6) 120.5(3)
C(8A) C(8) C(7) 120.8(3)
C(8) C(8A) C(5A) 118.5(2)
C(9) C(8A) C(5A) 117.8(2)
C(9) C(8A) C(8) 123.6(3)
C(1A) C(9) N(9') 121.0(2)
C(8A) C(9) N(9') 118.8(2)
C(8A) C(9) C(1A) 119.6(2)
_journal_paper_doi 10.1107/S0108768192009169