#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/13/2001399.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_2001399
loop_
_publ_author_name
'Iulek, J.'
'Zukerman-Schpector, J.'
'Brocksom, T. J.'
'Silva, Jnr, F.'
_publ_section_title
;
 Structures of the Diels--Alder reaction products of thymoquinone and
 1-vinylcyclohexene. I.
 2-Isopropyl-5-methyltricyclo[8.4.0.0^2,7^]tetradeca-4,9-diene-3,6-dione
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1657
_journal_page_last               1659
_journal_paper_doi               10.1107/S010827019300229X
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C18 H24 O2'
_chemical_formula_weight         272.39
_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'
_atom_type_scat_source           'SHELX76 (Sheldrick, 1976)'
_cell_angle_alpha                90.0
_cell_angle_beta                 107.530(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   12.6640(10)
_cell_length_b                   9.4240(10)
_cell_length_c                   12.8830(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291
_cell_measurement_theta_max      20
_cell_measurement_theta_min      9
_cell_volume                     1466.1(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2410
_diffrn_reflns_theta_max         24
_diffrn_standards_decay_%        +-1.4
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.73
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_description       Irregular
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.16
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1311
_refine_ls_R_factor_obs          0.055
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w=[σ²F + 0.0005F²]⁻¹'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.059
_reflns_number_observed          1311
_reflns_number_total             2297
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            li1046.cif
_cod_data_source_block           li1046_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=[\s^2^F + 0.0005F^2^]^-1^' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w=[\s^2^F +
0.0005F^2^]^-1^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1466.1(3)
_cod_database_code               2001399
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
O(1) .5029(2) .2458(3) .4635(2)
O(2) .9089(2) .1916(3) .4447(3)
C(1) .7128(3) .4441(4) .5368(3)
C(2) .6544(3) .3696(4) .4261(3)
C(3) .5935(3) .2371(5) .4499(3)
C(4) .6468(4) .0969(4) .4596(3)
C(5) .7478(3) .0752(4) .4514(3)
C(6) .8090(3) .1968(4) .4250(3)
C(7) .7402(3) .3221(4) .3685(3)
C(8) .8138(3) .4444(4) .3537(3)
C(9) .8542(3) .5340(4) .4522(3)
C(10) .8096(3) .5352(4) .5343(3)
C(11) .8580(3) .6212(4) .6351(3)
C(12) .8957(3) .5241(5) .7344(3)
C(13) .8008(3) .4304(5) .7425(3)
C(14) .7510(3) .3456(4) .6375(3)
C(15) .5619(3) .4679(5) .3541(3)
C(16) .5915(4) .6228(5) .3430(4)
C(17) .5071(4) .4054(6) .2413(4)
C(18) .8047(4) -.0655(5) .4694(4)
H(C1) .6447 .5090 .5534
H(C4) .6011 .0142 .4866
H(C7) .6957 .2708 .2831
H(C8) .8638 .3953 .3244
H'(C8) .7717 .5036 .2956
H(C9) .9293 .5944 .4830
H(C11) .8066 .7105 .6588
H'(C11) .9056 .7031 .6269
H(C12) .9613 .4590 .7321
H'(C12) .9296 .5669 .7976
H(C13) .7406 .4910 .7606
H'(C13) .8201 .3600 .8156
H(C14) .6973 .2850 .6567
H'(C14) .8047 .2808 .6207
H(C15) .4872 .4802 .3735
H(C16) .6244 .6661 .4125
H'(C16) .6413 .6347 .3004
H"(C16) .5257 .6799 .3070
H(C17) .4884 .3065 .2472
H'(C17) .4401 .4535 .2033
H"(C17) .5558 .4083 .1967
H(C18) .7572 -.1365 .4862
H'(C18) .8208 -.0937 .4052
H"(C18) .8707 -.0600 .5280
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) C(1) C(10) 113.7(3) yes
C(2) C(1) C(14) 116.0(3) yes
C(10) C(1) C(14) 108.0(3) yes
C(1) C(2) C(3) 108.0(3) yes
C(1) C(2) C(7) 111.0(3) yes
C(1) C(2) C(15) 109.9(3) yes
C(3) C(2) C(7) 108.9(3) yes
C(3) C(2) C(15) 105.5(3) yes
C(7) C(2) C(15) 113.2(3) yes
O(1) C(3) C(2) 121.6(4) yes
O(1) C(3) C(4) 118.5(4) yes
C(2) C(3) C(4) 119.9(4) yes
C(3) C(4) C(5) 124.0(4) yes
C(4) C(5) C(6) 118.8(4) yes
C(4) C(5) C(18) 123.7(4) yes
C(6) C(5) C(18) 117.5(4) yes
O(2) C(6) C(5) 120.4(4) yes
O(2) C(6) C(7) 122.9(4) yes
C(5) C(6) C(7) 116.6(3) yes
C(2) C(7) C(6) 112.2(3) yes
C(2) C(7) C(8) 112.5(3) yes
C(6) C(7) C(8) 111.3(3) yes
C(7) C(8) C(9) 112.9(3) yes
C(8) C(9) C(10) 124.2(4) yes
C(1) C(10) C(9) 123.5(4) yes
C(1) C(10) C(11) 114.4(3) yes
C(9) C(10) C(11) 122.0(4) yes
C(10) C(11) C(12) 110.2(4) yes
C(11) C(12) C(13) 110.6(4) yes
C(12) C(13) C(14) 111.4(4) yes
C(1) C(14) C(13) 111.6(3) yes
C(2) C(15) C(16) 117.5(4) yes
C(2) C(15) C(17) 112.4(3) yes
C(16) C(15) C(17) 109.5(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(3) 1.215(5) yes
C(1) C(2) 1.562(5) yes
C(1) C(14) 1.549(5) yes
C(2) C(7) 1.555(6) yes
C(3) C(4) 1.472(6) yes
C(5) C(6) 1.479(6) yes
C(6) C(7) 1.517(6) yes
C(8) C(9) 1.481(6) yes
C(10) C(11) 1.496(6) yes
C(12) C(13) 1.520(6) yes
C(15) C(16) 1.525(7) yes
O(2) C(6) 1.214(6) yes
C(1) C(10) 1.505(6) yes
C(2) C(3) 1.546(6) yes
C(2) C(15) 1.561(6) yes
C(4) C(5) 1.331(7) yes
C(5) C(18) 1.493(6) yes
C(7) C(8) 1.530(6) yes
C(9) C(10) 1.341(6) yes
C(11) C(12) 1.528(6) yes
C(13) C(14) 1.534(6) yes
C(15) C(17) 1.527(6) yes
