#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/56/7205625.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7205625
loop_
_publ_author_name
'Urbanczyk-Lipkowska, Zofia'
'Kalicki, Przemyslaw'
'Gawinkowski, Sylwester'
'Waluk, Jacek'
'Yokoyama, Masashi'
'Tanaka, Koichi'
_publ_section_title
;
 1,4-Bis(1,3-dioxo-2-indenylidene)cyclohexane: polymorphism, gas phase
 oxidation and enol form mediated radical formation in the solid state
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3170
_journal_paper_doi               10.1039/c0ce00509f
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C24 H16 O4'
_chemical_formula_weight         368.37
_chemical_name_common            'orange polymorph'
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.228(2)
_cell_angle_beta                 97.055(2)
_cell_angle_gamma                119.4050(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9787(2)
_cell_length_b                   8.0272(2)
_cell_length_c                   15.4271(5)
_cell_measurement_reflns_used    4544
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     848.61(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9547
_diffrn_reflns_theta_full        65.05
_diffrn_reflns_theta_max         65.05
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.9104
_exptl_absorpt_correction_T_min  0.8316
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.2295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                2472
_reflns_number_total             2832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00509f.txt
_cod_data_source_block           tana1_orange_0ma
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9212(2) 0.2773(2) 0.19585(10) 0.0352(3) Uani 1 1 d . . .
C2 C 1.0131(2) 0.4044(2) 0.28187(9) 0.0371(4) Uani 1 1 d . . .
H2A H 0.9279 0.4509 0.2974 0.045 Uiso 1 1 calc R . .
H2B H 1.1352 0.5153 0.2742 0.045 Uiso 1 1 calc R . .
C3 C 1.0530(2) 0.3049(2) 0.35813(10) 0.0404(4) Uani 1 1 d . . .
H3A H 1.1693 0.2978 0.3530 0.049 Uiso 1 1 calc R . .
H3B H 1.0772 0.3815 0.4133 0.049 Uiso 1 1 calc R . .
C4 C 0.8863(2) 0.1066(2) 0.35932(10) 0.0353(3) Uani 1 1 d . . .
C5 C 0.8080(2) -0.0159(2) 0.27225(10) 0.0417(4) Uani 1 1 d . . .
H5A H 0.6702 -0.0586 0.2574 0.050 Uiso 1 1 calc R . .
H5B H 0.8207 -0.1294 0.2777 0.050 Uiso 1 1 calc R . .
C6 C 0.9104(3) 0.0865(2) 0.19751(10) 0.0431(4) Uani 1 1 d . . .
H6A H 1.0411 0.1047 0.2052 0.052 Uiso 1 1 calc R . .
H6B H 0.8397 0.0079 0.1419 0.052 Uiso 1 1 calc R . .
C7 C 0.8541(2) 0.3320(2) 0.12394(10) 0.0352(3) Uani 1 1 d . . .
C8 C 0.7655(2) 0.2227(2) 0.03459(10) 0.0356(3) Uani 1 1 d . . .
C9 C 0.7203(2) 0.3480(2) -0.02078(9) 0.0341(3) Uani 1 1 d . . .
C10 C 0.6345(2) 0.3115(2) -0.10784(10) 0.0423(4) Uani 1 1 d . . .
H10A H 0.5970 0.1958 -0.1409 0.051 Uiso 1 1 calc R . .
C11 C 0.6060(2) 0.4520(2) -0.14462(11) 0.0460(4) Uani 1 1 d . . .
H11A H 0.5474 0.4303 -0.2030 0.055 Uiso 1 1 calc R . .
C12 C 0.6640(2) 0.6251(2) -0.09500(10) 0.0448(4) Uani 1 1 d . . .
H12 H 0.6433 0.7175 -0.1209 0.054 Uiso 1 1 calc R . .
C13 C 0.7515(2) 0.6630(2) -0.00854(10) 0.0411(4) Uani 1 1 d . . .
H13 H 0.7920 0.7799 0.0241 0.049 Uiso 1 1 calc R . .
C14 C 0.7773(2) 0.5206(2) 0.02820(9) 0.0344(3) Uani 1 1 d . . .
C15 C 0.8606(2) 0.5199(2) 0.11952(10) 0.0375(4) Uani 1 1 d . . .
C16 C 0.8080(2) 0.0387(2) 0.43193(10) 0.0352(3) Uani 1 1 d . . .
C17 C 0.6363(2) -0.1548(2) 0.43449(10) 0.0372(4) Uani 1 1 d . . .
C18 C 0.5993(2) -0.1665(2) 0.52685(10) 0.0366(3) Uani 1 1 d . . .
C19 C 0.4606(2) -0.3186(2) 0.56349(11) 0.0451(4) Uani 1 1 d . . .
H19 H 0.3710 -0.4336 0.5292 0.054 Uiso 1 1 calc R . .
C20 C 0.4593(3) -0.2945(3) 0.65246(12) 0.0501(4) Uani 1 1 d . . .
H20 H 0.3690 -0.3955 0.6788 0.060 Uiso 1 1 calc R . .
C21 C 0.5914(3) -0.1210(3) 0.70311(11) 0.0499(4) Uani 1 1 d . . .
H21 H 0.5859 -0.1069 0.7626 0.060 Uiso 1 1 calc R . .
C22 C 0.7309(3) 0.0310(2) 0.66686(10) 0.0442(4) Uani 1 1 d . . .
H22 H 0.8195 0.1466 0.7010 0.053 Uiso 1 1 calc R . .
C23 C 0.7339(2) 0.0051(2) 0.57787(10) 0.0363(3) Uani 1 1 d . . .
C24 C 0.8711(2) 0.1393(2) 0.52309(10) 0.0373(4) Uani 1 1 d . . .
O1 O 0.73525(18) 0.06413(16) 0.00825(7) 0.0520(3) Uani 1 1 d . . .
O2 O 0.9200(2) 0.65035(17) 0.17830(8) 0.0591(4) Uani 1 1 d . . .
O3 O 0.53957(18) -0.28164(16) 0.37390(7) 0.0536(3) Uani 1 1 d . . .
O4 O 1.00937(19) 0.29776(16) 0.55076(8) 0.0572(4) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C6 123.49(14) . . ?
C7 C1 C2 122.67(13) . . ?
C6 C1 C2 113.84(12) . . ?
C1 C2 C3 114.18(12) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 112.08(12) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C16 C4 C3 123.99(14) . . ?
C16 C4 C5 121.20(14) . . ?
C3 C4 C5 114.81(13) . . ?
C4 C5 C6 113.81(13) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C1 C6 C5 110.45(12) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C1 C7 C15 125.28(13) . . ?
C1 C7 C8 128.00(13) . . ?
C15 C7 C8 106.70(12) . . ?
O1 C8 C9 124.36(14) . . ?
O1 C8 C7 129.05(14) . . ?
C9 C8 C7 106.58(12) . . ?
C10 C9 C14 120.93(14) . . ?
C10 C9 C8 129.14(14) . . ?
C14 C9 C8 109.93(12) . . ?
C9 C10 C11 118.14(15) . . ?
C9 C10 H10A 120.9 . . ?
C11 C10 H10A 120.9 . . ?
C10 C11 C12 120.53(15) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 121.55(15) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 117.59(15) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C9 C14 C13 121.25(14) . . ?
C9 C14 C15 109.72(13) . . ?
C13 C14 C15 129.03(14) . . ?
O2 C15 C14 124.98(14) . . ?
O2 C15 C7 127.96(14) . . ?
C14 C15 C7 107.06(12) . . ?
C4 C16 C17 125.30(14) . . ?
C4 C16 C24 127.84(14) . . ?
C17 C16 C24 106.86(12) . . ?
O3 C17 C18 124.94(14) . . ?
O3 C17 C16 128.12(14) . . ?
C18 C17 C16 106.93(12) . . ?
C19 C18 C23 121.14(15) . . ?
C19 C18 C17 129.25(14) . . ?
C23 C18 C17 109.58(13) . . ?
C20 C19 C18 118.06(16) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 C21 120.71(16) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 121.41(16) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 117.66(16) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C22 C23 C18 120.98(15) . . ?
C22 C23 C24 129.08(14) . . ?
C18 C23 C24 109.93(13) . . ?
O4 C24 C23 124.71(14) . . ?
O4 C24 C16 128.59(14) . . ?
C23 C24 C16 106.68(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C7 1.354(2) . ?
C1 C6 1.493(2) . ?
C1 C2 1.504(2) . ?
C2 C3 1.534(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.494(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C16 1.352(2) . ?
C4 C5 1.500(2) . ?
C5 C6 1.523(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C15 1.488(2) . ?
C7 C8 1.492(2) . ?
C8 O1 1.2158(18) . ?
C8 C9 1.489(2) . ?
C9 C10 1.380(2) . ?
C9 C14 1.383(2) . ?
C10 C11 1.384(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.484(2) . ?
C15 O2 1.2151(18) . ?
C16 C17 1.490(2) . ?
C16 C24 1.491(2) . ?
C17 O3 1.2180(18) . ?
C17 C18 1.487(2) . ?
C18 C19 1.384(2) . ?
C18 C23 1.388(2) . ?
C19 C20 1.381(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.488(2) . ?
C24 O4 1.2170(18) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 C3 171.89(14) . . . . ?
C6 C1 C2 C3 -7.85(19) . . . . ?
C1 C2 C3 C4 -43.18(18) . . . . ?
C2 C3 C4 C16 -131.95(15) . . . . ?
C2 C3 C4 C5 47.73(18) . . . . ?
C16 C4 C5 C6 178.33(14) . . . . ?
C3 C4 C5 C6 -1.37(19) . . . . ?
C7 C1 C6 C5 -125.51(16) . . . . ?
C2 C1 C6 C5 54.23(18) . . . . ?
C4 C5 C6 C1 -49.79(18) . . . . ?
C6 C1 C7 C15 179.57(14) . . . . ?
C2 C1 C7 C15 -0.2(2) . . . . ?
C6 C1 C7 C8 -2.1(3) . . . . ?
C2 C1 C7 C8 178.17(14) . . . . ?
C1 C7 C8 O1 0.2(3) . . . . ?
C15 C7 C8 O1 178.74(16) . . . . ?
C1 C7 C8 C9 -178.89(15) . . . . ?
C15 C7 C8 C9 -0.32(16) . . . . ?
O1 C8 C9 C10 2.0(3) . . . . ?
C7 C8 C9 C10 -178.91(15) . . . . ?
O1 C8 C9 C14 -178.29(15) . . . . ?
C7 C8 C9 C14 0.83(16) . . . . ?
C14 C9 C10 C11 -0.4(2) . . . . ?
C8 C9 C10 C11 179.30(15) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C8 C9 C14 C13 179.77(13) . . . . ?
C10 C9 C14 C15 178.76(14) . . . . ?
C8 C9 C14 C15 -1.00(17) . . . . ?
C12 C13 C14 C9 1.2(2) . . . . ?
C12 C13 C14 C15 -177.90(15) . . . . ?
C9 C14 C15 O2 -178.58(16) . . . . ?
C13 C14 C15 O2 0.6(3) . . . . ?
C9 C14 C15 C7 0.78(17) . . . . ?
C13 C14 C15 C7 179.93(15) . . . . ?
C1 C7 C15 O2 -2.3(3) . . . . ?
C8 C7 C15 O2 179.09(16) . . . . ?
C1 C7 C15 C14 178.37(14) . . . . ?
C8 C7 C15 C14 -0.25(16) . . . . ?
C3 C4 C16 C17 177.05(13) . . . . ?
C5 C4 C16 C17 -2.6(2) . . . . ?
C3 C4 C16 C24 -1.9(2) . . . . ?
C5 C4 C16 C24 178.40(14) . . . . ?
C4 C16 C17 O3 0.1(3) . . . . ?
C24 C16 C17 O3 179.22(15) . . . . ?
C4 C16 C17 C18 -179.01(14) . . . . ?
C24 C16 C17 C18 0.15(15) . . . . ?
O3 C17 C18 C19 3.3(3) . . . . ?
C16 C17 C18 C19 -177.63(15) . . . . ?
O3 C17 C18 C23 -178.38(15) . . . . ?
C16 C17 C18 C23 0.73(16) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
C17 C18 C19 C20 178.45(15) . . . . ?
C18 C19 C20 C21 1.2(2) . . . . ?
C19 C20 C21 C22 -1.5(2) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C21 C22 C23 C18 1.1(2) . . . . ?
C21 C22 C23 C24 -177.23(15) . . . . ?
C19 C18 C23 C22 -1.4(2) . . . . ?
C17 C18 C23 C22 -179.91(13) . . . . ?
C19 C18 C23 C24 177.19(13) . . . . ?
C17 C18 C23 C24 -1.32(16) . . . . ?
C22 C23 C24 O4 1.5(3) . . . . ?
C18 C23 C24 O4 -176.96(15) . . . . ?
C22 C23 C24 C16 179.83(15) . . . . ?
C18 C23 C24 C16 1.39(16) . . . . ?
C4 C16 C24 O4 -3.5(3) . . . . ?
C17 C16 C24 O4 177.37(16) . . . . ?
C4 C16 C24 C23 178.23(14) . . . . ?
C17 C16 C24 C23 -0.90(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26666950
