#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/43/2204318.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_2204318
loop_
_publ_author_name
'Ohba, Shigeru'
'Yohei, Yamamoto'
'Tanaka, Koichi'
_publ_section_title
;(2RS,3RS,1'SR,2'SR,3'RS)-2-(2',3'-Dihydro-1'-hydroxy-3'-phenyl-1H-inden-2'-yl)-2,3-dihydro-3-phenylinden-1-one:
 isomer (I)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1793
_journal_page_last               o1794
_journal_paper_doi               10.1107/S1600536804022457
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C30 H24 O2 '
_chemical_formula_moiety         'C30 H24 O2 '
_chemical_formula_sum            'C30 H24 O2'
_chemical_formula_weight         416.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 99.63(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.985(3)
_cell_length_b                   9.529(3)
_cell_length_c                   13.154(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      12.8
_cell_measurement_theta_min      10.1
_cell_volume                     2222.6(10)
_computing_cell_refinement       ' WinAFC Diffractometer Control Software'
_computing_data_collection
' WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 2001)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6053
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5110
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0731P)²+0.206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1668
_reflns_number_gt                2464
_reflns_number_total             5110
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6373.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C30 H24 O2 '
_cod_database_code               2204318
_cod_database_fobs_code          2204318
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O1 0.72250(10) 0.0544(2) 0.37300(10) 0.0598(5) Uani d 1.00 O
O2 0.66800(10) 0.5763(2) 0.27190(10) 0.0621(5) Uani d 1.00 O
C3 0.65750(10) 0.1102(2) 0.3129(2) 0.0452(6) Uani d 1.00 C
C4 0.66090(10) 0.2682(2) 0.2896(2) 0.0447(5) Uani d 1.00 C
C5 0.61180(10) 0.2905(2) 0.1818(2) 0.0440(5) Uani d 1.00 C
C6 0.61320(10) 0.1459(2) 0.1341(2) 0.0431(5) Uani d 1.00 C
C7 0.63590(10) 0.0452(2) 0.2079(2) 0.0448(6) Uani d 1.00 C
C8 0.63770(10) -0.0958(2) 0.1814(2) 0.0565(7) Uani d 1.00 C
C9 0.6178(2) -0.1326(3) 0.0790(2) 0.0633(8) Uani d 1.00 C
C10 0.5965(2) -0.0318(3) 0.0055(2) 0.0649(8) Uani d 1.00 C
C11 0.59360(10) 0.1082(3) 0.0317(2) 0.0547(6) Uani d 1.00 C
C12 0.67160(10) 0.5196(2) 0.3559(2) 0.0449(5) Uani d 1.00 C
C13 0.64930(10) 0.3698(2) 0.3729(2) 0.0480(6) Uani d 1.00 C
C14 0.68540(10) 0.3358(2) 0.4871(2) 0.0447(5) Uani d 1.00 C
C15 0.71230(10) 0.4784(2) 0.5306(2) 0.0431(5) Uani d 1.00 C
C16 0.70240(10) 0.5810(2) 0.4568(2) 0.0439(5) Uani d 1.00 C
C17 0.7223(2) 0.7204(3) 0.4796(2) 0.0559(7) Uani d 1.00 C
C18 0.7535(2) 0.7527(3) 0.5792(2) 0.0628(7) Uani d 1.00 C
C19 0.7656(2) 0.6496(3) 0.6536(2) 0.0657(8) Uani d 1.00 C
C20 0.7449(2) 0.5119(3) 0.6310(2) 0.0574(7) Uani d 1.00 C
C21 0.53150(10) 0.3381(2) 0.1824(2) 0.0422(5) Uani d 1.00 C
C22 0.5045(2) 0.4589(3) 0.1337(3) 0.0762(9) Uani d 1.00 C
C23 0.4298(2) 0.4982(4) 0.1296(3) 0.1090(10) Uani d 1.00 C
C24 0.3821(2) 0.4193(4) 0.1755(3) 0.0844(10) Uani d 1.00 C
C25 0.4076(2) 0.3017(3) 0.2251(3) 0.0725(8) Uani d 1.00 C
C26 0.48130(10) 0.2603(3) 0.2279(2) 0.0625(7) Uani d 1.00 C
C27 0.63040(10) 0.2658(3) 0.5471(2) 0.0469(6) Uani d 1.00 C
C28 0.5741(2) 0.3407(3) 0.5812(3) 0.0771(9) Uani d 1.00 C
C29 0.5224(2) 0.2750(4) 0.6328(3) 0.1070(10) Uani d 1.00 C
C30 0.5275(2) 0.1341(5) 0.6513(3) 0.1060(10) Uani d 1.00 C
C31 0.5828(2) 0.0586(4) 0.6179(3) 0.0900(10) Uani d 1.00 C
C32 0.6345(2) 0.1230(3) 0.5671(2) 0.0620(7) Uani d 1.00 C
H1 0.7571 0.0545 0.3396 0.0598 Uiso calc 1.00 H
H3 0.6168 0.0957 0.3494 0.0542 Uiso calc 1.00 H
H4 0.7112 0.2841 0.2791 0.0536 Uiso calc 1.00 H
H5 0.6362 0.3554 0.1435 0.0527 Uiso calc 1.00 H
H8 0.6523 -0.1653 0.2327 0.0678 Uiso calc 1.00 H
H9 0.6189 -0.2284 0.0592 0.0760 Uiso calc 1.00 H
H10 0.5836 -0.0587 -0.0648 0.0778 Uiso calc 1.00 H
H11 0.5783 0.1772 -0.0197 0.0656 Uiso calc 1.00 H
H13 0.5964 0.3720 0.3722 0.0576 Uiso calc 1.00 H
H14 0.7277 0.2762 0.4873 0.0536 Uiso calc 1.00 H
H17 0.7145 0.7908 0.4278 0.0671 Uiso calc 1.00 H
H18 0.7669 0.8470 0.5970 0.0754 Uiso calc 1.00 H
H19 0.7885 0.6736 0.7218 0.0789 Uiso calc 1.00 H
H20 0.7529 0.4417 0.6830 0.0688 Uiso calc 1.00 H
H22 0.5372 0.5166 0.1022 0.0915 Uiso calc 1.00 H
H23 0.4118 0.5816 0.0943 0.1305 Uiso calc 1.00 H
H24 0.3310 0.4472 0.1725 0.1013 Uiso calc 1.00 H
H25 0.3748 0.2467 0.2585 0.0869 Uiso calc 1.00 H
H26 0.4981 0.1755 0.2622 0.0750 Uiso calc 1.00 H
H28 0.5705 0.4390 0.5692 0.0926 Uiso calc 1.00 H
H29 0.4834 0.3281 0.6552 0.1279 Uiso calc 1.00 H
H30 0.4926 0.0890 0.6873 0.1267 Uiso calc 1.00 H
H31 0.5858 -0.0397 0.6298 0.1084 Uiso calc 1.00 H
H32 0.6733 0.0689 0.5455 0.0744 Uiso calc 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, 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_publ_flag
C3 O1 H1 109.5 no
O1 C3 C4 115.2(2) ?
O1 C3 C7 115.1(2) ?
O1 C3 H3 107.5 no
C4 C3 C7 103.4(2) ?
C4 C3 H3 107.5 no
C7 C3 H3 107.5 no
C3 C4 C5 106.3(2) ?
C3 C4 C13 118.0(2) ?
C3 C4 H4 104.7 no
C5 C4 C13 116.9(2) ?
C5 C4 H4 104.7 no
C13 C4 H4 104.7 no
C4 C5 C6 102.0(2) ?
C4 C5 C21 115.6(2) ?
C4 C5 H5 109.4 no
C6 C5 C21 110.9(2) ?
C6 C5 H5 109.4 no
C21 C5 H5 109.4 no
C5 C6 C7 111.4(2) ?
C5 C6 C11 128.3(2) ?
C7 C6 C11 120.2(2) ?
C3 C7 C6 111.2(2) ?
C3 C7 C8 127.9(2) ?
C6 C7 C8 120.9(2) ?
C7 C8 C9 118.5(2) ?
C7 C8 H8 120.8 no
C9 C8 H8 120.8 no
C8 C9 C10 120.4(3) ?
C8 C9 H9 119.8 no
C10 C9 H9 119.8 no
C9 C10 C11 121.3(3) ?
C9 C10 H10 119.4 no
C11 C10 H10 119.4 no
C6 C11 C10 118.7(2) ?
C6 C11 H11 120.7 no
C10 C11 H11 120.7 no
O2 C12 C13 125.2(2) ?
O2 C12 C16 126.5(2) ?
C13 C12 C16 108.2(2) ?
C4 C13 C12 115.4(2) ?
C4 C13 C14 118.8(2) ?
C4 C13 H13 105.5 no
C12 C13 C14 105.1(2) ?
C12 C13 H13 105.5 no
C14 C13 H13 105.5 no
C13 C14 C15 103.3(2) ?
C13 C14 C27 112.8(2) ?
C13 C14 H14 109.2 no
C15 C14 C27 113.0(2) ?
C15 C14 H14 109.2 no
C27 C14 H14 109.2 no
C14 C15 C16 112.1(2) ?
C14 C15 C20 128.3(2) ?
C16 C15 C20 119.6(2) ?
C12 C16 C15 109.9(2) ?
C12 C16 C17 128.1(2) ?
C15 C16 C17 121.9(2) ?
C16 C17 C18 117.9(2) ?
C16 C17 H17 121.0 no
C18 C17 H17 121.0 no
C17 C18 C19 120.7(3) ?
C17 C18 H18 119.7 no
C19 C18 H18 119.7 no
C18 C19 C20 121.2(2) ?
C18 C19 H19 119.4 no
C20 C19 H19 119.4 no
C15 C20 C19 118.6(2) ?
C15 C20 H20 120.7 no
C19 C20 H20 120.7 no
C5 C21 C22 121.0(2) ?
C5 C21 C26 122.3(2) ?
C22 C21 C26 116.7(2) ?
C21 C22 C23 120.8(3) ?
C21 C22 H22 119.6 no
C23 C22 H22 119.6 no
C22 C23 C24 121.0(3) ?
C22 C23 H23 119.5 no
C24 C23 H23 119.5 no
C23 C24 C25 119.3(3) ?
C23 C24 H24 120.3 no
C25 C24 H24 120.3 no
C24 C25 C26 120.2(3) ?
C24 C25 H25 119.9 no
C26 C25 H25 119.9 no
C21 C26 C25 122.1(3) ?
C21 C26 H26 119.0 no
C25 C26 H26 119.0 no
C14 C27 C28 121.4(2) ?
C14 C27 C32 120.8(2) ?
C28 C27 C32 117.8(3) ?
C27 C28 C29 121.0(3) ?
C27 C28 H28 119.5 no
C29 C28 H28 119.5 no
C28 C29 C30 120.0(4) ?
C28 C29 H29 120.0 no
C30 C29 H29 120.0 no
C29 C30 C31 119.6(4) ?
C29 C30 H30 120.2 no
C31 C30 H30 120.2 no
C30 C31 C32 120.8(3) ?
C30 C31 H31 119.6 no
C32 C31 H31 119.6 no
C27 C32 C31 120.8(3) ?
C27 C32 H32 119.6 no
C31 C32 H32 119.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.401(3) yes
O1 H1 0.820 no
O2 C12 1.222(3) yes
C3 C4 1.541(3) ?
C3 C7 1.505(3) ?
C3 H3 0.950 no
C4 C5 1.554(3) ?
C4 C13 1.502(3) ?
C4 H4 0.950 no
C5 C6 1.516(3) ?
C5 C21 1.516(3) ?
C5 H5 0.950 no
C6 C7 1.376(3) ?
C6 C11 1.383(3) ?
C7 C8 1.390(3) ?
C8 C9 1.381(4) ?
C8 H8 0.950 no
C9 C10 1.371(4) ?
C9 H9 0.950 no
C10 C11 1.381(4) ?
C10 H10 0.950 no
C11 H11 0.950 no
C12 C13 1.509(3) ?
C12 C16 1.470(3) ?
C13 C14 1.567(3) ?
C13 H13 0.950 no
C14 C15 1.522(3) ?
C14 C27 1.518(4) ?
C14 H14 0.950 no
C15 C16 1.369(3) ?
C15 C20 1.390(3) ?
C16 C17 1.396(3) ?
C17 C18 1.370(4) ?
C17 H17 0.950 no
C18 C19 1.379(4) ?
C18 H18 0.950 no
C19 C20 1.382(4) ?
C19 H19 0.950 no
C20 H20 0.950 no
C21 C22 1.366(4) ?
C21 C26 1.379(4) ?
C22 C23 1.386(5) ?
C22 H22 0.950 no
C23 C24 1.357(6) ?
C23 H23 0.950 no
C24 C25 1.338(5) ?
C24 H24 0.950 no
C25 C26 1.379(4) ?
C25 H25 0.950 no
C26 H26 0.950 no
C27 C28 1.374(4) ?
C27 C32 1.385(4) ?
C28 C29 1.390(6) ?
C28 H28 0.950 no
C29 C30 1.365(6) ?
C29 H29 0.950 no
C30 C31 1.359(6) ?
C30 H30 0.950 no
C31 C32 1.376(5) ?
C31 H31 0.950 no
C32 H32 0.950 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 2_645 0.82 2.16 2.969(3) 168 yes
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
O1 C3 C4 C5 148.4(2) ?
O1 C3 C4 C13 -78.2(3) ?
O1 C3 C7 C6 -138.2(2) ?
O1 C3 C7 C8 41.1(4) ?
O2 C12 C13 C4 31.5(3) ?
O2 C12 C13 C14 164.3(2) ?
O2 C12 C16 C15 -166.9(2) ?
O2 C12 C16 C17 11.1(4) ?
C3 C4 C5 C6 -23.6(2) ?
C3 C4 C5 C21 96.8(2) yes
C3 C4 C13 C12 165.8(2) yes
C3 C4 C13 C14 39.7(3) yes
C3 C7 C6 C5 -3.8(3) ?
C3 C7 C6 C11 177.7(2) ?
C3 C7 C8 C9 -177.7(3) ?
C4 C3 C7 C6 -11.6(3) ?
C4 C3 C7 C8 167.6(2) ?
C4 C5 C6 C7 17.2(3) ?
C4 C5 C6 C11 -164.4(2) ?
C4 C5 C21 C22 123.2(3) ?
C4 C5 C21 C26 -59.4(3) ?
C4 C13 C12 C16 -145.1(2) ?
C4 C13 C14 C15 141.2(2) ?
C4 C13 C14 C27 -96.5(3) ?
C5 C4 C3 C7 21.8(2) ?
C5 C4 C13 C12 -65.6(3) yes
C5 C4 C13 C14 168.4(2) yes
C5 C6 C7 C8 176.9(2) ?
C5 C6 C11 C10 -177.7(2) ?
C5 C21 C22 C23 176.5(3) ?
C5 C21 C26 C25 -177.7(2) ?
C6 C5 C4 C13 -157.7(2) ?
C6 C5 C21 C22 -121.4(3) ?
C6 C5 C21 C26 55.9(3) ?
C6 C7 C8 C9 1.4(4) ?
C6 C11 C10 C9 0.6(4) ?
C7 C3 C4 C13 155.3(2) ?
C7 C6 C5 C21 -106.4(2) ?
C7 C6 C11 C10 0.6(4) ?
C7 C8 C9 C10 -0.3(4) ?
C8 C7 C6 C11 -1.6(4) ?
C8 C9 C10 C11 -0.7(4) ?
C11 C6 C5 C21 72.0(3) ?
C12 C13 C14 C15 10.4(2) ?
C12 C13 C14 C27 132.7(2) yes
C12 C16 C15 C14 -2.6(3) ?
C12 C16 C15 C20 176.3(2) ?
C12 C16 C17 C18 -176.9(2) ?
C13 C4 C5 C21 -37.3(3) ?
C13 C12 C16 C15 9.7(3) ?
C13 C12 C16 C17 -172.4(2) ?
C13 C14 C15 C16 -5.1(3) ?
C13 C14 C15 C20 176.1(2) ?
C13 C14 C27 C28 -74.8(3) ?
C13 C14 C27 C32 103.6(2) ?
C14 C13 C12 C16 -12.3(3) ?
C14 C15 C16 C17 179.2(2) ?
C14 C15 C20 C19 179.7(2) ?
C14 C27 C28 C29 177.7(3) ?
C14 C27 C32 C31 -177.4(2) ?
C15 C14 C27 C28 41.9(3) ?
C15 C14 C27 C32 -139.6(2) ?
C15 C16 C17 C18 0.9(4) ?
C15 C20 C19 C18 0.8(4) ?
C16 C15 C14 C27 -127.3(2) ?
C16 C15 C20 C19 1.0(4) ?
C16 C17 C18 C19 0.9(4) ?
C17 C16 C15 C20 -1.8(4) ?
C17 C18 C19 C20 -1.7(5) ?
C20 C15 C14 C27 53.8(3) ?
C21 C22 C23 C24 1.2(5) ?
C21 C26 C25 C24 1.3(5) ?
C22 C21 C26 C25 -0.3(4) ?
C22 C23 C24 C25 -0.1(6) ?
C23 C22 C21 C26 -1.0(4) ?
C23 C24 C25 C26 -1.1(5) ?
C27 C28 C29 C30 0.7(5) ?
C27 C32 C31 C30 -1.2(5) ?
C28 C27 C32 C31 1.1(4) ?
C28 C29 C30 C31 -0.8(6) ?
C29 C28 C27 C32 -0.8(4) ?
C29 C30 C31 C32 1.1(6) ?
C29 C30 C31 C32 1.1(6) ?
