#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/54/2005412.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_2005412
loop_
_publ_author_name
'Moriwaki, H.'
'Kawamoto, T.'
'Oshima, T.'
_publ_section_title
;
 Half-Chair Conformation of
 trans-1,4-Dimethyl-7,7-diphenylbicyclo[4.1.0]hepta-2,5-dione
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2269
_journal_page_last               2271
_journal_paper_doi               10.1107/S0108270196003435
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C21 H20 O2'
_chemical_formula_sum            'C21 H20 O2'
_chemical_formula_weight         304.37
_chemical_name_systematic
;
trans-1,4-dimethyl-7,7-diphenylbicyclo[4.1.0]hepta-2,5-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 96.36(3)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   8.925(4)
_cell_length_b                   23.480(12)
_cell_length_c                   8.049(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    296
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      15.9
_cell_volume                     1676.4(13)
_computing_cell_refinement       Crystan-GM
_computing_data_collection       Crystan-GM
_computing_data_reduction        Crystan-GM
_computing_molecular_graphics    Crystan-GM
_computing_publication_material  Crystan-GM
_computing_structure_refinement  Crystan-GM
_computing_structure_solution    Crystan-GM
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Mac Science MXC3'
_diffrn_measurement_method       θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4531
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        'not significant'
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   refdelf
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.21
_exptl_crystal_density_meas      1.21
_exptl_crystal_density_method    flotation
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.42
_refine_ls_extinction_coef       0.0000
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   0.81
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2597
_refine_ls_R_factor_obs          0.0699
_refine_ls_shift/esd_max         0.0180
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
'Weighting scheme based on counting statistics'
_refine_ls_wR_factor_obs         0.0709
_reflns_number_observed          3340
_reflns_number_total             3840
_reflns_observed_criterion       refl_observed_if_F_>_3_sigma(F)
_cod_data_source_file            oa1000.cif
_cod_data_source_block           I
_cod_original_cell_volume        1676.0(10)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2005412
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-y,+z
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
O(1) 1.000 0.9667(3) 0.4727(1) 0.6955(4) 0.067 Uij
O(2) 1.000 0.7183(4) 0.2646(1) 0.6329(5) 0.076 Uij
C(1) 1.000 0.9684(2) 0.3864(1) 0.5495(3) 0.039 Uij
C(2) 1.000 0.9002(3) 0.4295(1) 0.6541(3) 0.046 Uij
C(3) 1.000 0.7465(3) 0.4188(1) 0.7101(4) 0.056 Uij
C(4) 1.000 0.7078(3) 0.3573(1) 0.7492(4) 0.054 Uij
C(5) 1.000 0.7672(3) 0.3130(1) 0.6383(4) 0.049 Uij
C(6) 1.000 0.8969(2) 0.3272(1) 0.5419(3) 0.042 Uij
C(7) 1.000 0.8736(2) 0.3656(1) 0.3894(3) 0.038 Uij
C(8) 1.000 1.1372(2) 0.3913(1) 0.5487(3) 0.052 Uij
C(9) 1.000 0.5384(4) 0.3501(2) 0.7624(7) 0.078 Uij
C(10) 1.000 0.9555(2) 0.3486(1) 0.2430(3) 0.042 Uij
C(11) 1.000 0.9602(6) 0.2917(2) 0.1942(5) 0.071 Uij
C(12) 1.000 1.0342(8) 0.2767(2) 0.0574(5) 0.091 Uij
C(13) 1.000 1.0993(5) 0.3170(2) -0.0342(4) 0.080 Uij
C(14) 1.000 1.0925(3) 0.3736(2) 0.0113(4) 0.062 Uij
C(15) 1.000 1.0206(3) 0.3896(1) 0.1483(3) 0.050 Uij
C(16) 1.000 0.7222(2) 0.3914(1) 0.3317(3) 0.040 Uij
C(17) 1.000 0.7089(3) 0.4491(1) 0.2948(4) 0.053 Uij
C(18) 1.000 0.5689(4) 0.4719(2) 0.2354(6) 0.071 Uij
C(19) 1.000 0.4422(3) 0.4374(2) 0.2145(6) 0.072 Uij
C(20) 1.000 0.4548(3) 0.3798(2) 0.2488(5) 0.061 Uij
C(21) 1.000 0.5945(3) 0.3567(1) 0.3069(4) 0.049 Uij
H(3A) 1.000 0.67239 0.43188 0.62293 0.08 Uiso
H(3B) 1.000 0.73899 0.44098 0.80903 0.07 Uiso
H(4) 1.000 0.74810 0.34941 0.86236 0.09 Uiso
H(6) 1.000 0.95934 0.29388 0.54050 0.036 Uiso
H(8A) 1.000 1.19622 0.40431 0.64853 0.07 Uiso
H(8B) 1.000 1.15492 0.41721 0.46063 0.08 Uiso
H(8C) 1.000 1.17412 0.35431 0.52313 0.10 Uiso
H(9A) 1.000 0.51411 0.31143 0.78719 0.10 Uiso
H(9B) 1.000 0.48301 0.36103 0.65819 0.11 Uiso
H(9C) 1.000 0.50971 0.37443 0.84929 0.09 Uiso
H(11) 1.000 0.91233 0.26289 0.25459 0.10 Uiso
H(12) 1.000 1.03990 0.23730 0.02662 0.15 Uiso
H(13) 1.000 1.14934 0.30613 -0.12892 0.08 Uiso
H(14) 1.000 1.13779 0.40213 -0.05253 0.07 Uiso
H(15) 1.000 1.01549 0.42910 0.17798 0.09 Uiso
H(17) 1.000 0.79595 0.47326 0.31047 0.05 Uiso
H(18) 1.000 0.56044 0.51166 0.20837 0.09 Uiso
H(19) 1.000 0.34552 0.45347 0.17689 0.10 Uiso
H(20) 1.000 0.36752 0.35567 0.23198 0.06 Uiso
H(21) 1.000 0.60311 0.31671 0.33034 0.05 Uiso
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(6) 116.5(2) yes
C(2) C(1) C(7) 117.9(2) yes
C(2) C(1) C(8) 114.8(3) yes
C(6) C(1) C(7) 59.4(2) yes
C(6) C(1) C(8) 118.8(2) yes
C(7) C(1) C(8) 118.4(2) yes
O(1) C(2) C(1) 120.6(3) yes
O(1) C(2) C(3) 119.6(3) yes
C(1) C(2) C(3) 119.7(3) yes
C(2) C(3) C(4) 116.9(3) yes
C(2) C(3) H(3A) 107.6(3) ?
C(2) C(3) H(3B) 107.8(3) ?
C(4) C(3) H(3A) 107.5(3) ?
C(4) C(3) H(3B) 107.8(3) ?
H(3A) C(3) H(3B) 109.1(3) ?
C(3) C(4) C(5) 115.5(3) yes
C(3) C(4) C(9) 111.4(3) yes
C(3) C(4) H(4) 108.0(3) ?
C(5) C(4) C(9) 112.3(3) yes
C(5) C(4) H(4) 108.0(3) ?
C(9) C(4) H(4) 100.4(3) ?
O(2) C(5) C(4) 121.3(3) yes
O(2) C(5) C(6) 118.9(3) yes
C(4) C(5) C(6) 119.7(3) yes
C(1) C(6) C(5) 121.6(3) yes
C(1) C(6) C(7) 60.7(2) yes
C(1) C(6) H(6) 120.1(2) ?
C(5) C(6) C(7) 120.4(2) yes
C(5) C(6) H(6) 107.9(3) ?
C(7) C(6) H(6) 120.1(3) ?
C(1) C(7) C(6) 59.9(2) yes
C(1) C(7) C(10) 118.0(2) yes
C(1) C(7) C(16) 121.4(2) yes
C(6) C(7) C(10) 116.1(2) yes
C(6) C(7) C(16) 121.7(2) yes
C(10) C(7) C(16) 111.2(2) yes
C(1) C(8) H(8A) 118.4(3) ?
C(1) C(8) H(8B) 107.3(3) ?
C(1) C(8) H(8C) 107.3(3) ?
H(8A) C(8) H(8B) 107.3(3) ?
H(8A) C(8) H(8C) 107.3(3) ?
H(8B) C(8) H(8C) 109.0(3) ?
C(4) C(9) H(9A) 111.4(4) ?
C(4) C(9) H(9B) 109.0(4) ?
C(4) C(9) H(9C) 109.2(4) ?
H(9A) C(9) H(9B) 109.1(5) ?
H(9A) C(9) H(9C) 109.1(5) ?
H(9B) C(9) H(9C) 109.0(5) ?
C(7) C(10) C(11) 120.4(3) yes
C(7) C(10) C(15) 120.8(3) yes
C(11) C(10) C(15) 118.7(3) no
C(10) C(11) C(12) 119.8(4) no
C(10) C(11) H(11) 120.2(4) ?
C(12) C(11) H(11) 120.0(4) ?
C(11) C(12) C(13) 121.3(5) no
C(11) C(12) H(12) 119.4(5) ?
C(13) C(12) H(12) 119.3(6) ?
C(12) C(13) C(14) 119.3(4) no
C(12) C(13) H(13) 120.4(6) ?
C(14) C(13) H(13) 120.3(5) ?
C(13) C(14) C(15) 120.6(4) no
C(13) C(14) H(14) 119.7(4) ?
C(15) C(14) H(14) 119.7(4) ?
C(10) C(15) C(14) 120.4(3) no
C(10) C(15) H(15) 119.8(3) ?
C(14) C(15) H(15) 119.9(3) ?
C(7) C(16) C(17) 120.7(2) yes
C(7) C(16) C(21) 120.0(2) yes
C(17) C(16) C(21) 119.2(3) no
C(16) C(17) C(18) 120.0(3) no
C(16) C(17) H(17) 120.0(3) ?
C(18) C(17) H(17) 120.0(3) ?
C(17) C(18) C(19) 120.3(4) no
C(17) C(18) H(18) 119.8(4) ?
C(19) C(18) H(18) 119.9(4) ?
C(18) C(19) C(20) 120.0(4) no
C(18) C(19) H(19) 120.1(4) ?
C(20) C(19) H(19) 119.9(4) ?
C(19) C(20) C(21) 119.9(3) no
C(19) C(20) H(20) 120.1(3) ?
C(21) C(20) H(20) 120.0(4) ?
C(16) C(21) C(20) 120.5(3) no
C(16) C(21) H(21) 119.7(3) ?
C(20) C(21) H(21) 119.7(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.202(4) yes
O(2) C(5) 1.217(4) yes
C(1) C(2) 1.490(4) yes
C(1) C(6) 1.527(4) yes
C(1) C(7) 1.540(4) yes
C(1) C(8) 1.512(3) yes
C(2) C(3) 1.512(4) yes
C(3) C(4) 1.525(5) yes
C(3) H(3A) 0.960(4) ?
C(3) H(3B) 0.960(4) ?
C(4) C(5) 1.505(5) yes
C(4) C(9) 1.537(5) yes
C(4) H(4) 0.960(4) ?
C(5) C(6) 1.501(4) yes
C(6) C(7) 1.519(4) yes
C(6) H(6) 0.961(3) ?
C(7) C(10) 1.508(4) yes
C(7) C(16) 1.506(3) yes
C(8) H(8A) 0.960(3) ?
C(8) H(8B) 0.960(3) ?
C(8) H(8C) 0.960(4) ?
C(9) H(9A) 0.960(6) ?
C(9) H(9B) 0.960(5) ?
C(9) H(9C) 0.959(6) ?
C(10) C(11) 1.395(5) no
C(10) C(15) 1.394(4) no
C(11) C(12) 1.390(7) no
C(11) H(11) 0.960(4) ?
C(12) C(13) 1.369(8) no
C(12) H(12) 0.961(5) ?
C(13) C(14) 1.382(8) no
C(13) H(13) 0.960(5) ?
C(14) C(15) 1.388(5) no
C(14) H(14) 0.960(4) ?
C(15) H(15) 0.960(3) ?
C(16) C(17) 1.389(4) no
C(16) C(21) 1.397(4) no
C(17) C(18) 1.394(5) no
C(17) H(17) 0.960(3) ?
C(18) C(19) 1.386(5) no
C(18) H(18) 0.961(4) ?
C(19) C(20) 1.382(6) no
C(19) H(19) 0.960(4) ?
C(20) C(21) 1.392(4) no
C(20) H(20) 0.960(3) ?
C(21) H(21) 0.959(3) ?
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_publ_flag
C(6) C(1) C(2) O(1) 164.3(4) no
C(6) C(1) C(2) C(3) -15.1(3) no
C(2) C(1) C(6) C(5) -1.5(3) no
C(2) C(1) C(6) C(7) 108.1(3) no
C(2) C(1) C(6) H(6) -142.0(4) no
C(7) C(1) C(2) O(1) -128.0(4) no
C(7) C(1) C(2) C(3) 52.5(3) no
C(2) C(1) C(7) C(6) -105.9(3) no
C(2) C(1) C(7) C(10) 148.6(3) no
C(2) C(1) C(7) C(16) 5.0(2) no
C(8) C(1) C(2) O(1) 18.8(3) no
C(8) C(1) C(2) C(3) -160.6(4) no
C(2) C(1) C(8) H(8A) 33.2(3) no
C(2) C(1) C(8) H(8B) -88.2(3) no
C(2) C(1) C(8) H(8C) 154.8(4) no
C(7) C(1) C(6) C(5) -109.6(3) no
C(6) C(1) C(7) C(6) 0.0(2) no
C(7) C(1) C(6) C(7) 0.0(2) no
C(6) C(1) C(7) C(10) -105.5(3) no
C(6) C(1) C(7) C(16) 111.0(3) no
C(7) C(1) C(6) H(6) 109.9(3) no
C(8) C(1) C(6) C(5) 142.6(4) no
C(8) C(1) C(6) C(7) -107.8(3) no
C(8) C(1) C(6) H(6) 2.1(3) no
C(6) C(1) C(8) H(8A) -111.4(4) no
C(6) C(1) C(8) H(8B) 127.2(4) no
C(6) C(1) C(8) H(8C) 10.1(3) no
C(8) C(1) C(7) C(6) 108.4(3) no
C(8) C(1) C(7) C(10) 2.9(3) no
C(8) C(1) C(7) C(16) -140.6(3) no
C(7) C(1) C(8) H(8A) 179.9(4) no
C(7) C(1) C(8) H(8B) 58.5(3) no
C(7) C(1) C(8) H(8C) -58.6(3) no
O(1) C(2) C(3) C(4) -144.7(4) no
O(1) C(2) C(3) H(3A) 94.3(4) no
O(1) C(2) C(3) H(3B) -23.2(3) no
C(1) C(2) C(3) C(4) 34.7(3) no
C(1) C(2) C(3) H(3A) -86.3(3) no
C(1) C(2) C(3) H(3B) 156.2(4) no
C(2) C(3) C(4) C(5) -36.5(3) no
C(2) C(3) C(4) C(9) -166.1(4) no
C(2) C(3) C(4) H(4) 84.5(4) no
H(3A) C(3) C(4) C(5) 84.6(4) no
H(3A) C(3) C(4) C(9) -45.1(4) no
H(3A) C(3) C(4) H(4) -154.4(4) no
H(3B) C(3) C(4) C(5) -158.0(4) no
H(3B) C(3) C(4) C(9) 72.4(4) no
H(3B) C(3) C(4) H(4) -37.0(3) no
C(3) C(4) C(5) O(2) -164.1(5) no
C(3) C(4) C(5) C(6) 20.4(3) no
C(3) C(4) C(9) H(9A) -179.9(5) no
C(3) C(4) C(9) H(9B) 59.6(4) no
C(3) C(4) C(9) H(9C) -59.3(4) no
C(9) C(4) C(5) O(2) -34.9(4) no
C(9) C(4) C(5) C(6) 149.6(4) no
C(5) C(4) C(9) H(9A) 48.8(4) no
C(5) C(4) C(9) H(9B) -71.6(4) no
C(5) C(4) C(9) H(9C) 169.4(5) no
H(4) C(4) C(5) O(2) 74.9(4) no
H(4) C(4) C(5) C(6) -100.5(4) no
H(4) C(4) C(9) H(9A) -65.7(5) no
H(4) C(4) C(9) H(9B) 173.8(5) no
H(4) C(4) C(9) H(9C) 54.8(4) no
O(2) C(5) C(6) C(1) -177.2(4) no
O(2) C(5) C(6) C(7) 110.6(4) no
O(2) C(5) C(6) H(6) -32.5(3) no
C(4) C(5) C(6) C(1) -1.7(3) no
C(4) C(5) C(6) C(7) -73.9(3) no
C(4) C(5) C(6) H(6) 143.0(4) no
C(1) C(6) C(7) C(1) 0.0(2) no
C(1) C(6) C(7) C(10) 108.7(3) no
C(1) C(6) C(7) C(16) -110.5(3) no
C(5) C(6) C(7) C(1) 111.6(3) no
C(5) C(6) C(7) C(10) -139.7(3) no
C(5) C(6) C(7) C(16) 1.1(3) no
H(6) C(6) C(7) C(1) -109.8(3) no
H(6) C(6) C(7) C(10) -1.1(3) no
H(6) C(6) C(7) C(16) 139.7(4) no
C(1) C(7) C(10) C(11) 110.8(4) no
C(1) C(7) C(10) C(15) -72.8(3) no
C(1) C(7) C(16) C(17) 59.8(3) no
C(1) C(7) C(16) C(21) -123.4(3) no
C(6) C(7) C(10) C(11) 42.6(3) no
C(6) C(7) C(10) C(15) -140.9(4) no
C(6) C(7) C(16) C(17) 131.5(4) no
C(6) C(7) C(16) C(21) -51.7(3) no
C(16) C(7) C(10) C(11) -102.2(4) no
C(16) C(7) C(10) C(15) 74.3(3) no
C(10) C(7) C(16) C(17) -86.0(3) no
C(10) C(7) C(16) C(21) 90.8(3) no
C(7) C(10) C(11) C(12) 179.1(6) no
C(7) C(10) C(11) H(11) -0.7(4) no
C(7) C(10) C(15) C(14) -178.4(4) no
C(7) C(10) C(15) H(15) 1.5(3) no
C(15) C(10) C(11) C(12) 2.5(4) no
C(11) C(10) C(15) C(14) -1.9(4) no
C(15) C(10) C(11) H(11) -177.3(6) no
C(11) C(10) C(15) H(15) 178.0(5) no
C(10) C(11) C(12) C(13) -1.9(5) no
C(10) C(11) C(12) H(12) 178.0(8) no
H(11) C(11) C(12) C(13) 177.9(8) no
H(11) C(11) C(12) H(12) -2.2(5) no
C(11) C(12) C(13) C(14) 0.6(5) no
C(11) C(12) C(13) H(13) -179.5(9) no
H(12) C(12) C(13) C(14) -179.3(8) no
H(12) C(12) C(13) H(13) 0.6(5) no
C(12) C(13) C(14) C(15) 0.0(5) no
C(12) C(13) C(14) H(14) -179.9(7) no
H(13) C(13) C(14) C(15) -179.9(7) no
H(13) C(13) C(14) H(14) 0.2(5) no
C(13) C(14) C(15) C(10) 0.6(4) no
C(13) C(14) C(15) H(15) -179.3(6) no
H(14) C(14) C(15) C(10) -179.4(5) no
H(14) C(14) C(15) H(15) 0.7(4) no
C(7) C(16) C(17) C(18) 177.5(5) no
C(7) C(16) C(17) H(17) -2.7(3) no
C(7) C(16) C(21) C(20) -178.0(4) no
C(7) C(16) C(21) H(21) 2.1(3) no
C(21) C(16) C(17) C(18) 0.7(3) no
C(17) C(16) C(21) C(20) -1.2(3) no
C(21) C(16) C(17) H(17) -179.5(5) no
C(17) C(16) C(21) H(21) 178.9(4) no
C(16) C(17) C(18) C(19) 0.7(4) no
C(16) C(17) C(18) H(18) -179.1(6) no
H(17) C(17) C(18) C(19) -179.1(6) no
H(17) C(17) C(18) H(18) 1.1(4) no
C(17) C(18) C(19) C(20) -1.6(4) no
C(17) C(18) C(19) H(19) 178.0(7) no
H(18) C(18) C(19) C(20) 178.2(7) no
H(18) C(18) C(19) H(19) -2.2(4) no
C(18) C(19) C(20) C(21) 1.1(4) no
C(18) C(19) C(20) H(20) -178.6(6) no
H(19) C(19) C(20) C(21) -178.5(6) no
H(19) C(19) C(20) H(20) 1.8(4) no
C(19) C(20) C(21) C(16) 0.3(4) no
C(19) C(20) C(21) H(21) -179.8(5) no
H(20) C(20) C(21) C(16) 180.0(5) no
H(20) C(20) C(21) H(21) -0.1(3) no
