#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/77/2007720.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_2007720
loop_
_publ_author_name
'Vittal, Jagadese J.'
'Cao, Shu-Geng'
'Goh, Swee-Hock'
'Tan, Goek-Kheng'
'Sim, Keng-Yeow'
_publ_section_title
;
 Three Novel Isomeric Pyranocoumarins from Calophyllum
 teysmannii: Calanone, Isocalanone and Teysmanone A
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1536
_journal_page_last               1540
_journal_paper_doi               10.1107/S0108270198005691
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C27 H20 O5'
_chemical_formula_sum            'C27 H20 O5'
_chemical_formula_weight         424.452
_chemical_name_common            'teysmanone A'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 106.3150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0418(5)
_cell_length_b                   16.7577(10)
_cell_length_c                   14.1879(9)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.27
_cell_measurement_theta_min      1.93
_cell_volume                     2063.2(2)
_computing_cell_refinement       'SAINT (Siemens, 1996a)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL (Siemens, 1996b)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device       'Siemens SMART CCD'
_diffrn_measurement_method       'frames and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12285
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   'empirical (SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut long thin needle'
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.181
_refine_ls_extinction_coef       0.0024(7)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_all   1.057
_refine_ls_goodness_of_fit_obs   1.151
_refine_ls_hydrogen_treatment
;
The positional and isotropic thermal parameters of the hydroxyl H atom were
refined in the least-squares cycles.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_restrained_S_obs      1.151
_refine_ls_R_factor_all          0.092
_refine_ls_R_factor_obs          0.056
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0430P)²+0.7114P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.128
_refine_ls_wR_factor_obs         0.114
_reflns_number_observed          3475
_reflns_number_total             5047
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            de1085.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.7114P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.7114P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2007720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.16250(13) 0.03658(7) 0.62605(9) 0.0382(3) Uani d . 1 . O
O2 -0.06470(14) 0.08411(9) 0.54591(11) 0.0534(4) Uani d . 1 . O
C1 0.0732(2) 0.08517(12) 0.55498(14) 0.0392(4) Uani d . 1 . C
C2 0.1511(2) 0.13444(12) 0.50225(14) 0.0417(4) Uani d . 1 . C
H2 0.0925(2) 0.16809(12) 0.45391(14) 0.050 Uiso calc R 1 . H
C3 0.3065(2) 0.13468(10) 0.51911(13) 0.0331(4) Uani d . 1 . C
C4 0.3975(2) 0.07793(10) 0.58913(12) 0.0315(4) Uani d . 1 . C
C5 0.3196(2) 0.03048(10) 0.64132(12) 0.0319(4) Uani d . 1 . C
C6 0.3908(2) -0.02383(10) 0.71332(12) 0.0323(4) Uani d . 1 . C
C7 0.5497(2) -0.03018(10) 0.73562(12) 0.0320(4) Uani d . 1 . C
C8 0.6359(2) 0.01271(10) 0.68419(13) 0.0337(4) Uani d . 1 . C
C9 0.5586(2) 0.06415(10) 0.60934(13) 0.0324(4) Uani d . 1 . C
C10 0.3697(2) 0.19939(10) 0.46919(13) 0.0347(4) Uani d . 1 . C
C11 0.4710(2) 0.25589(12) 0.52383(15) 0.0430(5) Uani d . 1 . C
H11 0.5153(2) 0.24783(12) 0.59069(15) 0.052 Uiso calc R 1 . H
C12 0.5061(2) 0.32360(12) 0.4795(2) 0.0524(5) Uani d . 1 . C
H12 0.5725(2) 0.36147(12) 0.5169(2) 0.063 Uiso calc R 1 . H
C13 0.4436(3) 0.33556(14) 0.3806(2) 0.0619(6) Uani d . 1 . C
H13 0.4661(3) 0.38186(14) 0.3511(2) 0.074 Uiso calc R 1 . H
C14 0.3479(3) 0.27896(15) 0.3252(2) 0.0686(7) Uani d . 1 . C
H14 0.3088(3) 0.28587(15) 0.2577(2) 0.082 Uiso calc R 1 . H
C15 0.3093(2) 0.21151(12) 0.3697(2) 0.0498(5) Uani d . 1 . C
H15 0.2420(2) 0.17411(12) 0.3321(2) 0.060 Uiso calc R 1 . H
C16 0.8023(2) -0.00029(11) 0.71408(14) 0.0383(4) Uani d . 1 . C
H16 0.8615(2) 0.01655(11) 0.67383(14) 0.046 Uiso calc R 1 . H
C17 0.8687(2) -0.03616(11) 0.79878(14) 0.0411(4) Uani d . 1 . C
H17 0.9747(2) -0.04444(11) 0.81699(14) 0.049 Uiso calc R 1 . H
C18 0.7769(2) -0.06368(12) 0.86585(14) 0.0393(4) Uani d . 1 . C
C19 0.8395(2) -0.14129(13) 0.9167(2) 0.0565(6) Uani d . 1 . C
H19A 0.7785(2) -0.15729(13) 0.9590(2) 0.085 Uiso calc R 1 . H
H19B 0.9444(2) -0.13372(13) 0.9550(2) 0.085 Uiso calc R 1 . H
H19C 0.8352(2) -0.18194(13) 0.8683(2) 0.085 Uiso calc R 1 . H
C20 0.7644(3) 0.00038(15) 0.9383(2) 0.0596(6) Uani d . 1 . C
H20A 0.7050(3) -0.01938(15) 0.9798(2) 0.089 Uiso calc R 1 . H
H20B 0.7145(3) 0.04650(15) 0.9033(2) 0.089 Uiso calc R 1 . H
H20C 0.8656(3) 0.01468(15) 0.9778(2) 0.089 Uiso calc R 1 . H
O3 0.6319(2) 0.10297(8) 0.55186(10) 0.0441(3) Uani d . 1 . O
H1 0.724(3) 0.0911(15) 0.5659(17) 0.069(8) Uiso d . 1 . H
O4 0.61931(13) -0.08308(7) 0.80704(9) 0.0393(3) Uani d . 1 . O
O5 0.2781(2) -0.03669(9) 0.84298(11) 0.0591(4) Uani d . 1 . O
C21 0.3008(2) -0.06831(11) 0.77181(13) 0.0361(4) Uani d . 1 . C
C22 0.2422(2) -0.14936(11) 0.73980(13) 0.0355(4) Uani d . 1 . C
C23 0.2596(2) -0.18386(12) 0.6550(2) 0.0469(5) Uani d . 1 . C
H23 0.3135(2) -0.15707(12) 0.6177(2) 0.056 Uiso calc R 1 . H
C24 0.1967(3) -0.25842(14) 0.6257(2) 0.0643(6) Uani d . 1 . C
H24 0.2068(3) -0.28112(14) 0.5680(2) 0.077 Uiso calc R 1 . H
C25 0.1196(3) -0.29871(14) 0.6816(2) 0.0704(7) Uani d . 1 . C
H25 0.0772(3) -0.34854(14) 0.6614(2) 0.084 Uiso calc R 1 . H
C26 0.1047(3) -0.26593(14) 0.7672(2) 0.0643(7) Uani d . 1 . C
H26 0.0544(3) -0.29414(14) 0.8055(2) 0.077 Uiso calc R 1 . H
C27 0.1641(2) -0.19140(12) 0.7963(2) 0.0492(5) Uani d . 1 . C
H27 0.1522(2) -0.16893(12) 0.8537(2) 0.059 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 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
_geom_angle_publ_flag
C1 O1 C5 121.87(13) y
O2 C1 O1 116.4(2) y
O2 C1 C2 126.5(2) y
O1 C1 C2 117.06(15) y
C3 C2 C1 123.3(2) y
C2 C3 C4 118.5(2) y
C2 C3 C10 115.7(2) y
C4 C3 C10 125.54(14) y
C5 C4 C9 116.04(15) y
C5 C4 C3 117.43(14) y
C9 C4 C3 126.52(15) y
O1 C5 C6 114.18(14) y
O1 C5 C4 121.49(15) y
C6 C5 C4 124.30(15) y
C5 C6 C7 117.16(15) y
C5 C6 C21 121.24(15) y
C7 C6 C21 121.3(2) y
O4 C7 C6 116.96(15) y
O4 C7 C8 120.77(15) y
C6 C7 C8 122.2(2) y
C9 C8 C7 118.65(15) y
C9 C8 C16 124.7(2) y
C7 C8 C16 116.7(2) y
O3 C9 C8 122.09(15) y
O3 C9 C4 116.60(15) y
C8 C9 C4 121.31(15) y
C15 C10 C11 118.7(2) ?
C15 C10 C3 119.9(2) ?
C11 C10 C3 120.6(2) ?
C12 C11 C10 120.4(2) ?
C13 C12 C11 120.4(2) ?
C14 C13 C12 119.8(2) ?
C13 C14 C15 120.1(2) ?
C10 C15 C14 120.6(2) ?
C17 C16 C8 119.9(2) y
C16 C17 C18 121.5(2) y
O4 C18 C17 109.19(14) y
O4 C18 C20 107.28(15) y
C17 C18 C20 111.9(2) y
O4 C18 C19 104.65(15) y
C17 C18 C19 111.5(2) y
C20 C18 C19 112.0(2) y
C7 O4 C18 116.77(13) y
O5 C21 C22 121.9(2) y
O5 C21 C6 119.1(2) y
C22 C21 C6 119.0(2) ?
C23 C22 C27 119.2(2) ?
C23 C22 C21 122.1(2) ?
C27 C22 C21 118.7(2) ?
C22 C23 C24 120.0(2) ?
C25 C24 C23 120.1(2) ?
C24 C25 C26 120.4(2) ?
C25 C26 C27 120.1(2) ?
C26 C27 C22 120.2(2) ?
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 C1 . 1.369(2) y
O1 C5 . 1.379(2) y
O2 C1 . 1.217(2) y
C1 C2 . 1.426(2) y
C2 C3 . 1.358(2) y
C3 C4 . 1.452(2) y
C3 C10 . 1.494(2) y
C4 C5 . 1.403(2) y
C4 C9 . 1.423(2) y
C5 C6 . 1.385(2) y
C6 C7 . 1.385(2) y
C6 C21 . 1.512(2) y
C7 O4 . 1.360(2) y
C7 C8 . 1.406(2) y
C8 C9 . 1.394(2) y
C8 C16 . 1.460(2) y
C9 O3 . 1.353(2) y
C10 C15 . 1.378(3) ?
C10 C11 . 1.392(2) ?
C11 C12 . 1.377(3) ?
C12 C13 . 1.373(3) ?
C13 C14 . 1.373(3) ?
C14 C15 . 1.386(3) ?
C16 C17 . 1.327(3) y
C17 C18 . 1.501(2) y
C18 O4 . 1.471(2) y
C18 C20 . 1.512(3) y
C18 C19 . 1.518(3) y
O5 C21 . 1.208(2) y
C21 C22 . 1.482(3) ?
C22 C23 . 1.383(3) ?
C22 C27 . 1.399(2) ?
C23 C24 . 1.387(3) ?
C24 C25 . 1.372(3) ?
C25 C26 . 1.374(4) ?
C26 C27 . 1.376(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
C5 O1 C1 O2 177.8(2)
C5 O1 C1 C2 -4.9(3)
O2 C1 C2 C3 177.2(2)
O1 C1 C2 C3 0.3(3)
C1 C2 C3 C4 4.7(3)
C1 C2 C3 C10 -170.2(2)
C2 C3 C4 C5 -5.2(2)
C10 C3 C4 C5 169.1(2)
C2 C3 C4 C9 173.6(2)
C10 C3 C4 C9 -12.1(3)
C1 O1 C5 C6 -177.4(2)
C1 O1 C5 C4 4.4(2)
C9 C4 C5 O1 -178.1(2)
C3 C4 C5 O1 0.8(2)
C9 C4 C5 C6 3.9(3)
C3 C4 C5 C6 -177.2(2)
O1 C5 C6 C7 -177.05(15)
C4 C5 C6 C7 1.1(3)
O1 C5 C6 C21 -2.8(2)
C4 C5 C6 C21 175.3(2)
C5 C6 C7 O4 179.41(15)
C21 C6 C7 O4 5.2(2)
C5 C6 C7 C8 -3.7(3)
C21 C6 C7 C8 -177.9(2)
O4 C7 C8 C9 177.8(2)
C6 C7 C8 C9 1.0(3)
O4 C7 C8 C16 -2.3(2)
C6 C7 C8 C16 -179.1(2)
C7 C8 C9 O3 -175.1(2)
C16 C8 C9 O3 5.0(3)
C7 C8 C9 C4 4.4(3)
C16 C8 C9 C4 -175.5(2)
C5 C4 C9 O3 172.8(2)
C3 C4 C9 O3 -5.9(3)
C5 C4 C9 C8 -6.7(2)
C3 C4 C9 C8 174.6(2)
C2 C3 C10 C15 -51.2(2)
C4 C3 C10 C15 134.3(2)
C2 C3 C10 C11 118.2(2)
C4 C3 C10 C11 -56.3(2)
C15 C10 C11 C12 2.0(3)
C3 C10 C11 C12 -167.6(2)
C10 C11 C12 C13 -1.1(3)
C11 C12 C13 C14 -1.2(4)
C12 C13 C14 C15 2.7(4)
C11 C10 C15 C14 -0.5(3)
C3 C10 C15 C14 169.1(2)
C13 C14 C15 C10 -1.8(4)
C9 C8 C16 C17 165.2(2)
C7 C8 C16 C17 -14.7(3)
C8 C16 C17 C18 -0.4(3)
C16 C17 C18 O4 28.8(2)
C16 C17 C18 C20 -89.8(2)
C16 C17 C18 C19 143.9(2)
C6 C7 O4 C18 -149.4(2)
C8 C7 O4 C18 33.6(2)
C17 C18 O4 C7 -44.9(2)
C20 C18 O4 C7 76.6(2)
C19 C18 O4 C7 -164.3(2)
C5 C6 C21 O5 -84.1(2)
C7 C6 C21 O5 89.9(2)
C5 C6 C21 C22 95.6(2)
C7 C6 C21 C22 -90.5(2)
O5 C21 C22 C23 175.9(2)
C6 C21 C22 C23 -3.7(3)
O5 C21 C22 C27 -2.7(3)
C6 C21 C22 C27 177.6(2)
C27 C22 C23 C24 1.6(3)
C21 C22 C23 C24 -177.1(2)
C22 C23 C24 C25 -1.2(3)
C23 C24 C25 C26 -0.4(4)
C24 C25 C26 C27 1.5(4)
C25 C26 C27 C22 -1.1(3)
C23 C22 C27 C26 -0.4(3)
C21 C22 C27 C26 178.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136849
