#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012522.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_2012522
loop_
_publ_author_name
'Usman, Anwar'
'Razak, Ibrahim Abdul'
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
'Zhao, Bao-Guo'
'Xu, Jian-Hua'
_publ_section_title
;Ethyl
 (6aRS,8RS,12bRS)-6-oxo-8-phenyl-6a,7,8,12b-tetrahydro-6H-benzo[b]naphtho[1,2-d]pyran-6a-carboxylate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o57
_journal_page_last               o58
_journal_paper_doi               10.1107/S0108270101017164
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C26 H22 O4'
_chemical_formula_moiety         'C26 H22 O4'
_chemical_formula_sum            'C26 H22 O4'
_chemical_formula_weight         398.44
_chemical_melting_point          435
_chemical_name_systematic
;
Ethyl (6aRS,8RS,12bRS)-6-oxo-8-phenyl-6a,7,8,12b-tetrahydro-6H-benzo[b]-
naphtho[1,2-d]pyran-6a-carboxylate
;
_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                94.8480(10)
_cell_angle_beta                 99.0910(10)
_cell_angle_gamma                119.0640(10)
_cell_formula_units_Z            2
_cell_length_a                   10.5692(2)
_cell_length_b                   10.6982(2)
_cell_length_c                   10.76870(10)
_cell_measurement_reflns_used    4216
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.95
_cell_volume                     1032.43(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .979
_diffrn_measured_fraction_theta_max .979
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0837
_diffrn_reflns_av_sigmaI/netI    .1486
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6894
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .086
_exptl_absorpt_correction_T_max  .9881
_exptl_absorpt_correction_T_min  .9698
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             420
_exptl_crystal_size_max          .36
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .14
_refine_diff_density_max         .569
_refine_diff_density_min         -.593
_refine_ls_extinction_coef       .226(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .874
_refine_ls_R_factor_all          .1117
_refine_ls_R_factor_gt           .0746
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0916P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1751
_refine_ls_wR_factor_ref         .2087
_reflns_number_gt                2402
_reflns_number_total             4425
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1509.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '435K' was changed to '435' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '435K' was changed to '435' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2012522
_cod_database_fobs_code          2012522
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .2491(2) .5661(2) .35589(19) .0495(6) Uani d . 1 . . O
O2 .2382(2) .4991(2) .1549(2) .0564(6) Uani d . 1 . . O
O3 .1815(2) .7109(2) -.02682(18) .0513(6) Uani d . 1 . . O
O4 .40941(19) .8018(2) .09736(17) .0441(5) Uani d . 1 . . O
C1 .2103(3) .7073(3) .2001(2) .0302(6) Uani d . 1 . . C
C2 .2992(3) .8420(3) .3095(2) .0318(6) Uani d . 1 . . C
H2A .4055 .8795 .3159 .038 Uiso calc R 1 . . H
C3 .2661(3) .9592(3) .2788(2) .0345(6) Uani d . 1 . . C
C4 .3750(3) 1.1048(3) .3189(3) .0462(7) Uani d . 1 . . C
H4A .4693 1.1284 .3626 .055 Uiso calc R 1 . . H
C5 .3482(4) 1.2150(3) .2964(3) .0600(9) Uani d . 1 . . C
H5A .4233 1.3117 .3244 .072 Uiso calc R 1 . . H
C6 .2092(4) 1.1812(4) .2320(3) .0637(10) Uani d . 1 . . C
H6A .1893 1.2552 .2179 .076 Uiso calc R 1 . . H
C7 .0986(4) 1.0369(3) .1880(3) .0501(8) Uani d . 1 . . C
H7A .0059 1.0150 .1420 .060 Uiso calc R 1 . . H
C8 .1243(3) .9240(3) .2116(2) .0341(6) Uani d . 1 . . C
C9 -.0002(3) .7678(3) .1611(2) .0328(6) Uani d . 1 . . C
H9A -.0318 .7578 .0685 .039 Uiso calc R 1 . . H
C10 .0433(3) .6524(3) .1824(2) .0330(6) Uani d . 1 . . C
H10A -.0106 .5725 .1097 .040 Uiso calc R 1 . . H
H10B .0120 .6142 .2576 .040 Uiso calc R 1 . . H
C11 .2344(3) .5839(3) .2323(3) .0381(6) Uani d . 1 . . C
C12 .2392(3) .6569(3) .4504(3) .0431(7) Uani d . 1 . . C
C13 .2054(4) .6027(4) .5602(3) .0589(9) Uani d . 1 . . C
H13A .1911 .5112 .5689 .071 Uiso calc R 1 . . H
C14 .1935(4) .6867(4) .6560(3) .0697(11) Uani d . 1 . . C
H14A .1711 .6520 .7307 .084 Uiso calc R 1 . . H
C15 .2144(4) .8210(4) .6426(3) .0692(10) Uani d . 1 . . C
H15A .2044 .8763 .7076 .083 Uiso calc R 1 . . H
C16 .2504(3) .8754(4) .5323(3) .0516(8) Uani d . 1 . . C
H16A .2665 .9677 .5249 .062 Uiso calc R 1 . . H
C17 .2626(3) .7929(3) .4334(2) .0363(6) Uani d . 1 . . C
C18 -.1358(3) .7301(3) .2171(3) .0370(6) Uani d . 1 . . C
C19 -.1227(3) .7930(3) .3398(3) .0512(8) Uani d . 1 . . C
H19A -.0302 .8654 .3886 .061 Uiso calc R 1 . . H
C20 -.2497(4) .7470(4) .3900(4) .0663(10) Uani d . 1 . . C
H20A -.2408 .7896 .4723 .080 Uiso calc R 1 . . H
C21 -.3848(4) .6414(4) .3204(4) .0657(10) Uani d . 1 . . C
H21A -.4682 .6114 .3548 .079 Uiso calc R 1 . . H
C22 -.3981(3) .5793(4) .1997(4) .0625(9) Uani d . 1 . . C
H22A -.4913 .5070 .1520 .075 Uiso calc R 1 . . H
C23 -.2773(3) .6213(3) .1479(3) .0496(8) Uani d . 1 . . C
H23A -.2890 .5771 .0654 .060 Uiso calc R 1 . . H
C24 .2626(3) .7401(3) .0760(2) .0336(6) Uani d . 1 . . C
C25 .4751(3) .8142(3) -.0124(3) .0483(7) Uani d . 1 . . C
H25A .4454 .8654 -.0695 .058 Uiso calc R 1 . . H
H25C .4429 .7183 -.0592 .058 Uiso calc R 1 . . H
C26 .6405(3) .8970(4) .0371(3) .0556(8) Uani d . 1 . . C
H26D .6879 .9073 -.0334 .083 Uiso calc R 1 . . H
H26A .6685 .8452 .0933 .083 Uiso calc R 1 . . H
H26B .6710 .9916 .0831 .083 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C11 O1 C12 120.9(2) ?
C24 O4 C25 117.9(2) ?
C11 C1 C24 105.24(18) yes
C11 C1 C10 107.43(19) yes
C24 C1 C10 112.1(2) yes
C11 C1 C2 111.0(2) ?
C24 C1 C2 111.6(2) ?
C10 C1 C2 109.34(19) ?
C3 C2 C17 113.8(2) yes
C3 C2 C1 109.9(2) ?
C17 C2 C1 108.0(2) ?
C3 C2 H2A 108.3 ?
C17 C2 H2A 108.3 ?
C1 C2 H2A 108.3 ?
C4 C3 C8 118.8(3) ?
C4 C3 C2 120.2(2) ?
C8 C3 C2 121.0(2) ?
C5 C4 C3 122.1(3) ?
C5 C4 H4A 118.9 ?
C3 C4 H4A 118.9 ?
C4 C5 C6 119.4(3) ?
C4 C5 H5A 120.3 ?
C6 C5 H5A 120.3 ?
C5 C6 C7 120.0(3) ?
C5 C6 H6A 120.0 ?
C7 C6 H6A 120.0 ?
C6 C7 C8 121.0(3) ?
C6 C7 H7A 119.5 ?
C8 C7 H7A 119.5 ?
C7 C8 C3 118.6(2) ?
C7 C8 C9 119.0(2) ?
C3 C8 C9 122.3(2) ?
C8 C9 C18 112.33(19) yes
C8 C9 C10 114.9(2) yes
C18 C9 C10 107.8(2) ?
C8 C9 H9A 107.2 ?
C18 C9 H9A 107.2 ?
C10 C9 H9A 107.2 ?
C9 C10 C1 114.8(2) ?
C9 C10 H10A 108.6 ?
C1 C10 H10A 108.6 ?
C9 C10 H10B 108.6 ?
C1 C10 H10B 108.6 ?
H10A C10 H10B 107.6 ?
O2 C11 O1 117.8(3) ?
O2 C11 C1 124.2(2) ?
O1 C11 C1 118.1(2) ?
C13 C12 C17 122.8(3) ?
C13 C12 O1 115.9(3) ?
C17 C12 O1 121.3(2) ?
C14 C13 C12 118.6(3) ?
C14 C13 H13A 120.7 ?
C12 C13 H13A 120.7 ?
C15 C14 C13 120.5(3) ?
C15 C14 H14A 119.7 ?
C13 C14 H14A 119.7 ?
C14 C15 C16 120.4(3) ?
C14 C15 H15A 119.8 ?
C16 C15 H15A 119.8 ?
C17 C16 C15 120.5(3) ?
C17 C16 H16A 119.8 ?
C15 C16 H16A 119.8 ?
C12 C17 C16 117.2(2) ?
C12 C17 C2 118.6(2) ?
C16 C17 C2 124.2(3) ?
C19 C18 C23 118.0(2) ?
C19 C18 C9 121.9(2) ?
C23 C18 C9 120.0(2) ?
C18 C19 C20 119.6(3) ?
C18 C19 H19A 120.2 ?
C20 C19 H19A 120.2 ?
C21 C20 C19 120.9(3) ?
C21 C20 H20A 119.6 ?
C19 C20 H20A 119.6 ?
C20 C21 C22 119.7(3) ?
C20 C21 H21A 120.2 ?
C22 C21 H21A 120.2 ?
C23 C22 C21 121.1(3) ?
C23 C22 H22A 119.5 ?
C21 C22 H22A 119.5 ?
C22 C23 C18 120.8(3) ?
C22 C23 H23A 119.6 ?
C18 C23 H23A 119.6 ?
O3 C24 O4 124.8(2) ?
O3 C24 C1 124.5(2) ?
O4 C24 C1 110.6(2) ?
O4 C25 C26 107.2(2) ?
O4 C25 H25A 110.3 ?
C26 C25 H25A 110.3 ?
O4 C25 H25C 110.3 ?
C26 C25 H25C 110.3 ?
H25A C25 H25C 108.5 ?
C25 C26 H26D 109.5 ?
C25 C26 H26A 109.5 ?
H26D C26 H26A 109.5 ?
C25 C26 H26B 109.5 ?
H26D C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
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 C11 . 1.356(3) yes
O1 C12 . 1.399(3) yes
O2 C11 . 1.199(3) ?
O3 C24 . 1.200(3) ?
O4 C24 . 1.328(3) ?
O4 C25 . 1.447(3) ?
C1 C11 . 1.518(4) yes
C1 C24 . 1.530(3) ?
C1 C10 . 1.537(3) yes
C1 C2 . 1.548(3) yes
C2 C3 . 1.504(4) yes
C2 C17 . 1.513(3) yes
C2 H2A . .9800 ?
C3 C4 . 1.388(4) ?
C3 C8 . 1.404(4) yes
C4 C5 . 1.372(4) ?
C4 H4A . .9300 ?
C5 C6 . 1.375(5) ?
C5 H5A . .9300 ?
C6 C7 . 1.386(5) ?
C6 H6A . .9300 ?
C7 C8 . 1.396(4) ?
C7 H7A . .9300 ?
C8 C9 . 1.518(3) yes
C9 C18 . 1.527(3) yes
C9 C10 . 1.535(3) yes
C9 H9A . .9800 ?
C10 H10A . .9700 ?
C10 H10B . .9700 ?
C12 C13 . 1.382(4) ?
C12 C17 . 1.387(4) ?
C13 C14 . 1.372(5) ?
C13 H13A . .9300 ?
C14 C15 . 1.368(5) ?
C14 H14A . .9300 ?
C15 C16 . 1.393(4) ?
C15 H15A . .9300 ?
C16 C17 . 1.387(4) ?
C16 H16A . .9300 ?
C18 C19 . 1.385(4) ?
C18 C23 . 1.399(4) ?
C19 C20 . 1.403(4) ?
C19 H19A . .9300 ?
C20 C21 . 1.352(5) ?
C20 H20A . .9300 ?
C21 C22 . 1.363(5) ?
C21 H21A . .9300 ?
C22 C23 . 1.362(4) ?
C22 H22A . .9300 ?
C23 H23A . .9300 ?
C25 C26 . 1.498(4) ?
C25 H25A . .9700 ?
C25 H25C . .9700 ?
C26 H26D . .9600 ?
C26 H26A . .9600 ?
C26 H26B . .9600 ?
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
C2 H2A O4 1_555 .98 2.4423 2.815(3) 102 yes
C6 H6A O2 1_565 .93 2.5760 3.449(4) 156 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
C11 C1 C2 C3 -176.57(18)
C24 C1 C2 C3 66.4(3)
C10 C1 C2 C3 -58.2(3)
C11 C1 C2 C17 -51.9(3)
C24 C1 C2 C17 -168.91(19)
C10 C1 C2 C17 66.5(3)
C17 C2 C3 C4 91.6(3)
C1 C2 C3 C4 -147.1(2)
C17 C2 C3 C8 -87.1(3)
C1 C2 C3 C8 34.2(3)
C8 C3 C4 C5 .8(4)
C2 C3 C4 C5 -178.0(3)
C3 C4 C5 C6 .0(4)
C4 C5 C6 C7 -1.4(5)
C5 C6 C7 C8 2.1(4)
C6 C7 C8 C3 -1.4(4)
C6 C7 C8 C9 -179.9(2)
C4 C3 C8 C7 -.1(3)
C2 C3 C8 C7 178.7(2)
C4 C3 C8 C9 178.4(2)
C2 C3 C8 C9 -2.9(3)
C7 C8 C9 C18 -61.3(3)
C3 C8 C9 C18 120.3(2)
C7 C8 C9 C10 175.1(2)
C3 C8 C9 C10 -3.4(3)
C8 C9 C10 C1 -23.2(3)
C18 C9 C10 C1 -149.2(2)
C11 C1 C10 C9 174.71(19)
C24 C1 C10 C9 -70.1(3)
C2 C1 C10 C9 54.2(3)
C12 O1 C11 O2 -177.2(2)
C12 O1 C11 C1 1.3(4)
C24 C1 C11 O2 -24.8(3)
C10 C1 C11 O2 94.8(3)
C2 C1 C11 O2 -145.7(3)
C24 C1 C11 O1 156.8(2)
C10 C1 C11 O1 -83.6(3)
C2 C1 C11 O1 35.9(3)
C11 O1 C12 C13 158.9(3)
C11 O1 C12 C17 -21.2(4)
C17 C12 C13 C14 .4(5)
O1 C12 C13 C14 -179.7(3)
C12 C13 C14 C15 .2(5)
C13 C14 C15 C16 -1.1(5)
C14 C15 C16 C17 1.4(5)
C13 C12 C17 C16 -.1(4)
O1 C12 C17 C16 -180.0(2)
C13 C12 C17 C2 179.9(3)
O1 C12 C17 C2 .0(4)
C15 C16 C17 C12 -.8(4)
C15 C16 C17 C2 179.2(3)
C3 C2 C17 C12 158.1(2)
C1 C2 C17 C12 35.9(3)
C3 C2 C17 C16 -21.8(3)
C1 C2 C17 C16 -144.1(3)
C8 C9 C18 C19 -32.0(4)
C10 C9 C18 C19 95.5(3)
C8 C9 C18 C23 153.0(3)
C10 C9 C18 C23 -79.5(3)
C23 C18 C19 C20 -.3(5)
C9 C18 C19 C20 -175.4(3)
C18 C19 C20 C21 .3(5)
C19 C20 C21 C22 -.3(6)
C20 C21 C22 C23 .2(5)
C21 C22 C23 C18 -.3(5)
C19 C18 C23 C22 .3(4)
C9 C18 C23 C22 175.5(3)
C25 O4 C24 O3 -10.3(4)
C25 O4 C24 C1 168.1(2)
C11 C1 C24 O3 108.2(3)
C10 C1 C24 O3 -8.3(3)
C2 C1 C24 O3 -131.4(3)
C11 C1 C24 O4 -70.2(2)
C10 C1 C24 O4 173.3(2)
C2 C1 C24 O4 50.2(3)
C24 O4 C25 C26 175.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21134957
