#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/19/2001950.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_2001950
loop_
_publ_author_name
'Lloyd, B. A.'
'Ericson, C.'
'Arif, A. M.'
'Allred, E. L.'
_publ_section_title
;
 Ketone pyramidalization in a tetracyclic perpendicular enone
 derivative
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              257
_journal_page_last               261
_journal_paper_doi               10.1107/S0108270192006838
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C14 H18 O3'
_chemical_formula_weight         234.3
_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_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 103.550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.113(2)
_cell_length_b                   10.0320(10)
_cell_length_c                   17.086(2)
_cell_volume                     2351.7(5)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54056
_exptl_absorpt_coefficient_mu    0.7038
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             1008
_cod_data_source_file            hh1005.cif
_cod_data_source_block           hh1005_structure_1_of_1
_cod_original_cell_volume        2351.74
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2001950
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
O1 .12880(10) -.5084(2) .16190(10)
O2 .23050(10) -.0091(2) .02147(9)
O3 .12480(10) .0685(2) .09617(9)
C1 .09460(10) -.1547(2) .04320(10)
C2 .16260(10) -.2644(2) .02270(10)
C3 .1317(2) -.4095(2) .02910(10)
C4 .2076(2) -.4985(2) .00150(10)
C5 .3019(2) -.4832(2) .07150(10)
C6 .2698(2) -.3881(2) .13200(10)
C7 .25790(10) -.2496(2) .09300(10)
C8 .2320(2) -.1310(2) .14310(10)
C9 .1511(2) -.1772(2) .18120(10)
C10 .0707(2) -.1927(2) .12240(10)
C11 .17130(10) -.0449(2) .07410(10)
C12 .1658(2) -.4396(2) .11870(10)
C13 .1778(2) .0523(3) -.05140(10)
C14 .1906(2) .1680(2) .1370(2)
H1 .040(2) -.127(4) -.002(2)
H3 .064(2) -.429(4) .004(2)
H6 .309(2) -.394(4) .188(2)
H8 .290(2) -.086(4) .179(2)
H9 .159(2) -.194(4) .246(2)
H10 .004(2) -.233(4) .127(2)
O1' .61800(10) .1911(2) .29708(9)
O2' .52910(10) -.3014(2) .10905(8)
O3' .61110(10) -.3845(2) .23280(9)
C1' .66050(10) -.1659(2) .19870(10)
C2' .60560(10) -.0505(2) .14570(10)
C3' .6398(2) .0927(2) .16870(10)
C4' .5772(2) .1848(2) .10380(10)
C5' .4724(2) .1780(2) .12180(10)
C6' .4861(2) .0827(2) .19480(10)
C7' .50010(10) -.0572(2) .16360(10)
C8' .50970(10) -.1753(2) .22390(10)
C9' .5804(2) -.1330(2) .30100(10)
C10' .6694(2) -.1274(2) .28560(10)
C11' .5766(2) -.2686(2) .18910(10)
C12' .5891(2) .1264(2) .23610(10)
C13' .5899(2) -.3713(3) .06650(10)
C14' .5358(2) -.4715(2) .2459(2)
H1' .722(2) -.186(4) .184(2)
H2 .179(2) -.244(4) -.032(2)
H2' .602(2) -.068(4) .086(2)
H3' .713(2) .109(4) .182(2)
H4a .185(2) -.599(4) -.003(2)
H4a' .602(2) .281(4) .112(2)
H4b .216(2) -.468(4) -.052(2)
H4b' .579(2) .155(4) .048(2)
H5a .321(2) -.577(4) .098(2)
H5a' .454(2) .271(4) .137(2)
H5b .360(2) -.446(4) .053(2)
H5b' .423(2) .142(4) .076(2)
H6' .436(2) .090(4) .227(2)
H7 .316(2) -.225(4) .072(2)
H7' .451(2) -.079(4) .112(2)
H8' .053(2) .285(4) .271(2)
H9' .560(2) -.107(4) .351(2)
H10' .733(2) -.092(4) .322(2)
H13c' .611(2) -.462(4) .094(2)
H13a .220(2) .068(4) -.084(2)
H13b .125(2) -.003(4) -.078(2)
H13a' .550(2) -.387(4) .008(2)
H13b' .647(2) -.316(4) .064(2)
H13c .152(2) .149(4) -.037(2)
H14c' .489(2) -.494(4) .191(2)
H14b' .570(2) -.562(4) .266(2)
H14a .237(2) .201(4) .100(2)
H14c .234(2) .131(4) .189(2)
H14b .152(2) .247(4) .147(2)
H14a' .502(2) -.431(4) .287(2)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 O3 C14 113.8(2)
C2 C1 C10 107.6(2)
C10 C1 C11 99.2(2)
C1 C2 C7 102.8(2)
C2 C3 C4 107.2(2)
C4 C3 C12 96.5(2)
C4 C5 C6 103.9(2)
C5 C6 C12 96.5(2)
C2 C7 C6 103.4(2)
C6 C7 C8 118.0(2)
C7 C8 C11 99.6(2)
C8 C9 C10 107.9(2)
O2 C11 O3 110.4(2)
O2 C11 C1 115.8(2)
O2 C11 C8 108.8(2)
C3 C12 C6 98.7(2)
O1 C12 C6 129.7(2)
C11 O2 C13 113.5(2)
C2 C1 C11 99.3(2)
C1 C2 C3 117.1(2)
C3 C2 C7 103.9(2)
C2 C3 C12 103.4(2)
C3 C4 C5 103.5(2)
C5 C6 C7 106.7(2)
C7 C6 C12 103.8(2)
C2 C7 C8 102.8(2)
C7 C8 C9 107.4(2)
C9 C8 C11 99.2(2)
C1 C10 C9 108.2(2)
C1 C11 O3 109.5(2)
O3 C11 C8 117.1(2)
C1 C11 C8 94.6(2)
O1 C12 C3 130.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.215(3)
O2 C11 1.410(2)
O2 C13 1.432(3)
O3 C11 1.408(2)
O3 C14 1.430(3)
C1 C2 1.554(3)
C1 C10 1.519(3)
C1 C11 1.547(3)
C2 C3 1.532(3)
C2 C7 1.586(3)
C3 C4 1.551(3)
C3 C12 1.523(3)
C4 C5 1.574(3)
C5 C6 1.550(3)
C6 C7 1.534(3)
C6 C12 1.522(3)
C7 C8 1.558(3)
C8 C9 1.513(3)
C8 C11 1.549(3)
C9 C10 1.337(3)
O1' C12' 1.214(3)
O2' C11' 1.413(2)
O2' C13' 1.432(3)
O3' C11' 1.406(2)
O3' C14' 1.432(3)
C1' C2' 1.559(3)
C1' C10' 1.510(3)
C1' C11' 1.549(3)
C2' C3' 1.537(3)
C2' C7' 1.589(3)
C3' C4' 1.550(3)
C3' C12' 1.528(3)
C4' C5' 1.581(3)
C5' C6' 1.548(3)
C6' C7' 1.532(3)
C6' C12' 1.524(3)
C7' C8' 1.555(3)
C8' C9' 1.516(3)
C8' C11' 1.544(3)
C9' C10' 1.344(3)
