#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/20/2002067.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_2002067
loop_
_publ_author_name
'Sekar, K.'
'Parthasarathy, S.'
'Prabahar, K. J.'
'Ramakrishnan, V. T.'
_publ_section_title
;
 Structure of
 1,8-dimethyl-4-oxo-1,2,2a,3,4,5-hexahydrocyclopenta[de]quinoline
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              97
_journal_page_last               99
_journal_paper_doi               10.1107/S0108270192004219
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.3
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_cell_angle_alpha                103.79(2)
_cell_angle_beta                 116.71(2)
_cell_angle_gamma                67.86(2)
_cell_formula_units_Z            2
_cell_length_a                   8.929(2)
_cell_length_b                   8.990(2)
_cell_length_c                   8.094(2)
_cell_volume                     535.7(2)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    0.583
_exptl_crystal_density_diffrn    1.25
_exptl_crystal_F_000             216
_cod_data_source_file            ab0271.cif
_cod_data_source_block           ab0271a
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-14
;
_cod_original_cell_volume        535.7(3)
_cod_original_formula_sum        'C13 H15 N1 O1'
_cod_database_code               2002067
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
_atom_site_U_iso_or_equiv
N(1) 1.3039(2) .1030(2) .8033(2) .0530(10)
C(2) 1.3894(3) -.0196(2) .7129(3) .0520(10)
C(3) 1.2982(3) -.0420(2) .5024(3) .0540(10)
C(3a) 1.1893(3) .1194(2) .4179(2) .0480(10)
C(4) 1.0490(3) .1194(2) .2194(2) .0540(10)
C(5) .9012(3) .2827(2) .2144(3) .0550(10)
C(5a) .9168(2) .3140(2) .4152(2) .0460(10)
C(6) .8041(2) .4190(2) .4986(3) .0490(10)
C(7) .8650(3) .4166(2) .6905(3) .0540(10)
C(8) 1.0271(3) .3155(2) .7985(2) .0520(10)
C(8a) 1.1372(2) .2130(2) .7115(2) .0440(10)
C(8b) 1.0802(2) .2196(2) .5238(2) .0440(10)
O(9) 1.5336(2) -.1148(2) .7980(2) .0700(10)
C(10) .7244(3) .2762(3) .0619(3) .0760(10)
C(11) .6270(3) .5316(3) .3902(4) .0680(10)
H1N1 1.373(4) .109(3) .961(5) ?
H1C3 1.210(3) -.113(3) .474(3) ?
H2C3 1.392(3) -.106(3) .448(3) ?
H1C3a 1.278(3) .185(3) .442(3) ?
H1C4 .996(3) .025(2) .198(3) ?
H2C4 1.098(3) .107(3) .122(3) ?
H1C5 .926(3) .377(3) .194(4) ?
H1C7 .779(3) .496(3) .755(4) ?
H1C8 1.073(3) .308(3) .942(3) ?
H1C10 .635(4) .381(4) .030(4) ?
H2C10 .674(4) .199(4) .102(5) ?
H3C10 .745(4) .249(4) -.049(5) ?
H1C11 .574(4) .618(4) .500(4) ?
H2C11 .634(4) .588(4) .298(5) ?
H3C11 .545(3) .475(3) .310(4) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(1) C(2) O(9) 121.2(2)
N(1) C(2) C(3) 117.9(2)
O(9) C(2) C(3) 120.8(2)
C(2) C(3) C(3a) 111.6(2)
C(3) C(3a) C(4) 118.1(2)
C(3) C(3a) C(8b) 108.8(2)
C(8b) C(3a) C(4) 101.6(2)
C(3a) C(4) C(5) 104.90(10)
C(4) C(5) C(10) 111.7(2)
C(4) C(5) C(5a) 102.10(10)
C(5a) C(5) C(10) 117.6(2)
C(5) C(5a) C(8b) 108.0(2)
C(5) C(5a) C(6) 132.6(2)
C(8b) C(5a) C(6) 119.4(2)
C(5a) C(6) C(11) 122.4(2)
C(5a) C(6) C(7) 116.6(2)
C(7) C(6) C(11) 121.0(2)
C(7) C(8) C(8a) 118.2(2)
C(8) C(8a) N(1) 124.3(2)
C(8) C(8a) C(8b) 118.0(2)
N(1) C(8a) C(8b) 117.7(2)
C(8a) C(8b) C(5a) 123.9(2)
C(8a) C(8b) C(3a) 122.5(2)
C(3a) C(8b) C(5a) 113.60(10)
C(6) C(7) C(8) 123.8(2)
C(2) N(1) C(8a) 123.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
H1N1 N(1) 1.14(4)
H1C3 C(3) 1.11(3)
H2C3 C(3) 1.04(3)
H1C3a C(3a) 1.08(3)
H1C4 C(4) 1.06(3)
H2C4 C(4) 1.03(3)
H1C5 C(5) 1.02(3)
H1C7 C(7) 1.07(3)
N(1) C(2) 1.348(3)
C(2) C(3) 1.523(3)
C(2) O(9) 1.232(2)
C(3) C(3a) 1.527(2)
C(3a) C(8b) 1.489(3)
C(3a) C(4) 1.530(2)
C(4) C(5) 1.555(3)
C(5) C(5a) 1.532(3)
N(1) C(8a) 1.411(2)
H1C8 C(8) 1.05(2)
H1C10 C(10) 0.98(3)
H2C10 C(10) 1.12(5)
H3C10 C(10) 0.95(4)
H1C11 C(11) 1.18(3)
H2C11 C(11) 1.03(5)
H3C11 C(11) 0.96(3)
C(5) C(10) 1.517(3)
C(5a) C(6) 1.397(3)
C(5a) C(8b) 1.375(2)
C(6) C(11) 1.505(3)
C(6) C(7) 1.399(3)
C(7) C(8) 1.391(2)
C(8) C(8a) 1.393(3)
C(8a) C(8b) 1.377(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139054063
