#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229680.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_2229680
loop_
_publ_author_name
'Qiao, Zhen'
'Liu, Li'
'Wang, Dong'
_publ_section_title
;
 10-Phenyl-6b,7,8,9,9a,10-hexahydro-6H-cyclopenta[4,5]pyrano[3,2-c]chromen-6,9-dione
;
_journal_coeditor_code           HG2800
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o855
_journal_paper_doi               10.1107/S1600536811006192
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H16 O4'
_chemical_formula_moiety         'C21 H16 O4'
_chemical_formula_sum            'C21 H16 O4'
_chemical_formula_weight         332.34
_chemical_name_common
;
10-Phenyl-6b,7,8,9,9a,10-hexahydro-6H-
cyclopenta[4,5]pyrano[3,2-c]chromen-6,9-dione
;
_chemical_name_systematic
;
16-phenyl-8,17-dioxatetracyclo[8.7.0.0^2,7^.0^11,15^]heptadeca-
1(10),2(7),3,5-tetraene-9,14-dione
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.295(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1672(14)
_cell_length_b                   8.6538(14)
_cell_length_c                   19.899(3)
_cell_measurement_reflns_used    4768
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      1.02
_cell_volume                     1578.2(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2007)'
_computing_data_collection       'CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13128
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9614
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0549
_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)+(0.0704P)²+0.6329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                3469
_reflns_number_total             3608
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2800.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229680
_cod_database_fobs_code          2229680
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.50827(10) 0.14483(13) 0.10143(5) 0.0292(2) Uani d . 1 . .
O O2 0.30494(11) 0.31578(13) -0.06936(5) 0.0342(3) Uani d . 1 . .
O O3 0.21059(14) -0.10952(16) 0.24113(6) 0.0472(3) Uani d . 1 . .
O O4 0.09368(13) 0.21341(18) -0.04206(7) 0.0509(4) Uani d . 1 . .
C C1 0.45295(15) 0.33318(17) -0.05937(7) 0.0293(3) Uani d . 1 . .
C C2 0.52778(18) 0.41320(18) -0.10830(8) 0.0344(3) Uani d . 1 . .
H H2A 0.4773 0.4543 -0.1465 0.041 Uiso calc R 1 . .
C C3 0.67665(18) 0.43206(18) -0.10057(8) 0.0358(3) Uani d . 1 . .
H H3A 0.7289 0.4869 -0.1337 0.043 Uiso calc R 1 . .
C C4 0.75115(17) 0.37144(19) -0.04468(8) 0.0358(3) Uani d . 1 . .
H H4A 0.8538 0.3846 -0.0400 0.043 Uiso calc R 1 . .
C C5 0.67574(16) 0.29218(18) 0.00397(8) 0.0321(3) Uani d . 1 . .
H H5A 0.7267 0.2512 0.0420 0.039 Uiso calc R 1 . .
C C6 0.52458(15) 0.27221(16) -0.00277(7) 0.0268(3) Uani d . 1 . .
C C7 0.43568(15) 0.19240(16) 0.04545(7) 0.0260(3) Uani d . 1 . .
C C8 0.41941(15) 0.10574(17) 0.15850(7) 0.0275(3) Uani d . 1 . .
H H8A 0.3765 0.2025 0.1771 0.033 Uiso calc R 1 . .
C C9 0.29535(15) -0.00278(17) 0.13564(7) 0.0289(3) Uani d . 1 . .
H H9A 0.3352 -0.1037 0.1198 0.035 Uiso calc R 1 . .
C C10 0.18782(18) -0.02793(19) 0.19294(8) 0.0356(3) Uani d . 1 . .
C C11 0.0505(2) 0.0604(3) 0.17786(11) 0.0564(5) Uani d . 1 . .
H H11A 0.0224 0.1227 0.2173 0.068 Uiso calc R 1 . .
H H11B -0.0305 -0.0110 0.1661 0.068 Uiso calc R 1 . .
C C12 0.08425(18) 0.1647(2) 0.11868(9) 0.0412(4) Uani d . 1 . .
H H12A 0.1231 0.2656 0.1342 0.049 Uiso calc R 1 . .
H H12B -0.0039 0.1824 0.0900 0.049 Uiso calc R 1 . .
C C13 0.20060(15) 0.07317(18) 0.08039(7) 0.0308(3) Uani d . 1 . .
H H13A 0.1506 -0.0100 0.0537 0.037 Uiso calc R 1 . .
C C14 0.29132(15) 0.16801(17) 0.03381(7) 0.0285(3) Uani d . 1 . .
C C15 0.22106(16) 0.22987(19) -0.02619(8) 0.0343(3) Uani d . 1 . .
C C16 0.51992(15) 0.03462(17) 0.21074(7) 0.0274(3) Uani d . 1 . .
C C17 0.62801(17) -0.06787(19) 0.19234(8) 0.0360(3) Uani d . 1 . .
H H17A 0.6423 -0.0896 0.1462 0.043 Uiso calc R 1 . .
C C18 0.71543(18) -0.1389(2) 0.24094(9) 0.0440(4) Uani d . 1 . .
H H18A 0.7886 -0.2101 0.2280 0.053 Uiso calc R 1 . .
C C19 0.69637(19) -0.1066(2) 0.30784(9) 0.0453(4) Uani d . 1 . .
H H19A 0.7564 -0.1553 0.3411 0.054 Uiso calc R 1 . .
C C20 0.59009(19) -0.0033(2) 0.32673(8) 0.0413(4) Uani d . 1 . .
H H20A 0.5775 0.0194 0.3729 0.050 Uiso calc R 1 . .
C C21 0.50157(17) 0.06724(18) 0.27822(7) 0.0325(3) Uani d . 1 . .
H H21A 0.4283 0.1380 0.2913 0.039 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C8 . . 116.22(10) ?
C1 O2 C15 . . 121.99(11) ?
O2 C1 C2 . . 117.04(13) ?
O2 C1 C6 . . 121.37(12) ?
C2 C1 C6 . . 121.59(14) ?
C3 C2 C1 . . 118.94(14) ?
C3 C2 H2A . . 120.5 ?
C1 C2 H2A . . 120.5 ?
C2 C3 C4 . . 120.66(14) ?
C2 C3 H3A . . 119.7 ?
C4 C3 H3A . . 119.7 ?
C5 C4 C3 . . 120.06(14) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C4 C5 C6 . . 120.20(14) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C1 C6 C5 . . 118.54(13) ?
C1 C6 C7 . . 116.98(12) ?
C5 C6 C7 . . 124.48(13) ?
O1 C7 C14 . . 123.74(13) ?
O1 C7 C6 . . 114.72(12) ?
C14 C7 C6 . . 121.54(13) ?
O1 C8 C16 . . 106.85(11) ?
O1 C8 C9 . . 109.60(11) ?
C16 C8 C9 . . 113.09(12) ?
O1 C8 H8A . . 109.1 ?
C16 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
C13 C9 C8 . . 110.72(12) ?
C13 C9 C10 . . 103.28(12) ?
C8 C9 C10 . . 110.45(12) ?
C13 C9 H9A . . 110.7 ?
C8 C9 H9A . . 110.7 ?
C10 C9 H9A . . 110.7 ?
O3 C10 C11 . . 126.03(15) ?
O3 C10 C9 . . 124.73(16) ?
C11 C10 C9 . . 109.21(13) ?
C10 C11 C12 . . 105.83(13) ?
C10 C11 H11A . . 110.6 ?
C12 C11 H11A . . 110.6 ?
C10 C11 H11B . . 110.6 ?
C12 C11 H11B . . 110.6 ?
H11A C11 H11B . . 108.7 ?
C11 C12 C13 . . 103.48(14) ?
C11 C12 H12A . . 111.1 ?
C13 C12 H12A . . 111.1 ?
C11 C12 H12B . . 111.1 ?
C13 C12 H12B . . 111.1 ?
H12A C12 H12B . . 109.0 ?
C14 C13 C9 . . 111.33(12) ?
C14 C13 C12 . . 114.99(13) ?
C9 C13 C12 . . 104.62(12) ?
C14 C13 H13A . . 108.6 ?
C9 C13 H13A . . 108.6 ?
C12 C13 H13A . . 108.6 ?
C7 C14 C15 . . 119.90(13) ?
C7 C14 C13 . . 122.11(13) ?
C15 C14 C13 . . 117.96(13) ?
O4 C15 O2 . . 116.59(14) ?
O4 C15 C14 . . 125.49(15) ?
O2 C15 C14 . . 117.93(13) ?
C17 C16 C21 . . 119.32(14) ?
C17 C16 C8 . . 120.64(13) ?
C21 C16 C8 . . 120.00(13) ?
C16 C17 C18 . . 120.36(15) ?
C16 C17 H17A . . 119.8 ?
C18 C17 H17A . . 119.8 ?
C19 C18 C17 . . 120.06(17) ?
C19 C18 H18A . . 120.0 ?
C17 C18 H18A . . 120.0 ?
C18 C19 C20 . . 120.08(15) ?
C18 C19 H19A . . 120.0 ?
C20 C19 H19A . . 120.0 ?
C19 C20 C21 . . 120.03(15) ?
C19 C20 H20A . . 120.0 ?
C21 C20 H20A . . 120.0 ?
C16 C21 C20 . . 120.14(15) ?
C16 C21 H21A . . 119.9 ?
C20 C21 H21A . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.3491(17) ?
O1 C8 . 1.4524(16) ?
O2 C1 . 1.3751(17) ?
O2 C15 . 1.3828(18) ?
O3 C10 . 1.205(2) ?
O4 C15 . 1.2112(19) ?
C1 C2 . 1.389(2) ?
C1 C6 . 1.394(2) ?
C2 C3 . 1.380(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.394(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.384(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3999(19) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.4483(19) ?
C7 C14 . 1.3548(19) ?
C8 C16 . 1.5050(19) ?
C8 C9 . 1.5359(19) ?
C8 H8A . 1.0000 ?
C9 C13 . 1.534(2) ?
C9 C10 . 1.540(2) ?
C9 H9A . 1.0000 ?
C10 C11 . 1.498(3) ?
C11 C12 . 1.521(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.543(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.503(2) ?
C13 H13A . 1.0000 ?
C14 C15 . 1.446(2) ?
C16 C17 . 1.385(2) ?
C16 C21 . 1.386(2) ?
C17 C18 . 1.386(2) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.375(3) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.380(3) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.388(2) ?
C20 H20A . 0.9500 ?
C21 H21A . 0.9500 ?
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
C8 H8A O3 2 1.00 2.45 3.4042(19) 160
C17 H17A O2 3_655 0.95 2.54 3.322(2) 140
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 O2 C1 C2 . . . . 175.79(14) ?
C15 O2 C1 C6 . . . . -3.8(2) ?
O2 C1 C2 C3 . . . . -179.40(13) ?
C6 C1 C2 C3 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . 0.2(2) ?
C2 C3 C4 C5 . . . . -0.4(2) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
O2 C1 C6 C5 . . . . 179.16(13) ?
C2 C1 C6 C5 . . . . -0.4(2) ?
O2 C1 C6 C7 . . . . -1.1(2) ?
C2 C1 C6 C7 . . . . 179.32(13) ?
C4 C5 C6 C1 . . . . 0.3(2) ?
C4 C5 C6 C7 . . . . -179.48(14) ?
C8 O1 C7 C14 . . . . -17.6(2) ?
C8 O1 C7 C6 . . . . 162.78(12) ?
C1 C6 C7 O1 . . . . -175.67(12) ?
C5 C6 C7 O1 . . . . 4.1(2) ?
C1 C6 C7 C14 . . . . 4.7(2) ?
C5 C6 C7 C14 . . . . -175.52(14) ?
C7 O1 C8 C16 . . . . 171.88(11) ?
C7 O1 C8 C9 . . . . 49.00(16) ?
O1 C8 C9 C13 . . . . -58.49(15) ?
C16 C8 C9 C13 . . . . -177.59(11) ?
O1 C8 C9 C10 . . . . -172.27(12) ?
C16 C8 C9 C10 . . . . 68.63(15) ?
C13 C9 C10 O3 . . . . 165.87(15) ?
C8 C9 C10 O3 . . . . -75.70(19) ?
C13 C9 C10 C11 . . . . -12.28(18) ?
C8 C9 C10 C11 . . . . 106.14(16) ?
O3 C10 C11 C12 . . . . 170.98(17) ?
C9 C10 C11 C12 . . . . -10.9(2) ?
C10 C11 C12 C13 . . . . 29.6(2) ?
C8 C9 C13 C14 . . . . 36.94(16) ?
C10 C9 C13 C14 . . . . 155.18(12) ?
C8 C9 C13 C12 . . . . -87.86(14) ?
C10 C9 C13 C12 . . . . 30.38(15) ?
C11 C12 C13 C14 . . . . -159.98(15) ?
C11 C12 C13 C9 . . . . -37.54(17) ?
O1 C7 C14 C15 . . . . 176.95(13) ?
C6 C7 C14 C15 . . . . -3.5(2) ?
O1 C7 C14 C13 . . . . -5.1(2) ?
C6 C7 C14 C13 . . . . 174.40(13) ?
C9 C13 C14 C7 . . . . -6.2(2) ?
C12 C13 C14 C7 . . . . 112.55(16) ?
C9 C13 C14 C15 . . . . 171.73(13) ?
C12 C13 C14 C15 . . . . -69.51(18) ?
C1 O2 C15 O4 . . . . -175.20(15) ?
C1 O2 C15 C14 . . . . 5.1(2) ?
C7 C14 C15 O4 . . . . 178.92(16) ?
C13 C14 C15 O4 . . . . 0.9(3) ?
C7 C14 C15 O2 . . . . -1.4(2) ?
C13 C14 C15 O2 . . . . -179.35(13) ?
O1 C8 C16 C17 . . . . -40.89(18) ?
C9 C8 C16 C17 . . . . 79.79(17) ?
O1 C8 C16 C21 . . . . 141.38(13) ?
C9 C8 C16 C21 . . . . -97.94(15) ?
C21 C16 C17 C18 . . . . 1.0(2) ?
C8 C16 C17 C18 . . . . -176.74(15) ?
C16 C17 C18 C19 . . . . -0.8(3) ?
C17 C18 C19 C20 . . . . 0.1(3) ?
C18 C19 C20 C21 . . . . 0.4(3) ?
C17 C16 C21 C20 . . . . -0.5(2) ?
C8 C16 C21 C20 . . . . 177.23(13) ?
C19 C20 C21 C16 . . . . -0.2(2) ?
