#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/77/2007719.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_2007719
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            isocalanone
_chemical_name_systematic
;
 ?
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.3030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0017(3)
_cell_length_b                   27.3003(13)
_cell_length_c                   12.8273(6)
_cell_measurement_reflns_used    5944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.36
_cell_measurement_theta_min      1.76
_cell_volume                     2092.73(17)
_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      293(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  0.026
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12794
_diffrn_reflns_theta_max         29.36
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   'empirical (SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut long needle'
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.176
_refine_ls_extinction_coef       0.0117(11)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_all   1.053
_refine_ls_goodness_of_fit_obs   1.153
_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         5131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_restrained_S_obs      1.153
_refine_ls_R_factor_all          0.080
_refine_ls_R_factor_obs          0.049
_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)+(0.0462P)²+0.3604P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.120
_refine_ls_wR_factor_obs         0.107
_reflns_number_observed          3487
_reflns_number_total             5131
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            de1085.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0462P)^2^+0.3604P] 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^)+(0.0462P)^2^+0.3604P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2092.7(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2007719
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_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 0.4168(2) 0.04196(4) 0.22364(9) 0.0487(3) Uani d . 1 . O
O2 0.5607(2) -0.00661(5) 0.34900(10) 0.0701(4) Uani d . 1 . O
C1 0.4256(3) 0.02532(6) 0.32607(13) 0.0530(4) Uani d . 1 . C
C2 0.2790(3) 0.04873(6) 0.39268(13) 0.0534(4) Uani d . 1 . C
H2 0.2867(3) 0.03942(6) 0.46266(13) 0.064 Uiso calc R 1 . H
C3 0.1305(3) 0.08358(5) 0.35899(12) 0.0435(4) Uani d . 1 . C
C4 0.1088(3) 0.09623(5) 0.24812(12) 0.0398(3) Uani d . 1 . C
C5 0.2585(3) 0.07500(5) 0.18405(12) 0.0400(3) Uani d . 1 . C
C6 0.2582(2) 0.08345(5) 0.07713(12) 0.0389(3) Uani d . 1 . C
C7 0.0959(3) 0.11469(5) 0.03007(11) 0.0372(3) Uani d . 1 . C
C8 -0.0614(2) 0.13864(5) 0.08924(11) 0.0369(3) Uani d . 1 . C
C9 -0.0594(3) 0.12636(5) 0.19687(12) 0.0391(3) Uani d . 1 . C
C10 -0.0004(3) 0.10882(6) 0.43680(12) 0.0448(4) Uani d . 1 . C
C11 -0.1623(3) 0.08413(7) 0.48555(14) 0.0600(5) Uani d . 1 . C
H11 -0.1877(3) 0.05104(7) 0.47194(14) 0.072 Uiso calc R 1 . H
C12 -0.2872(4) 0.10863(9) 0.5549(2) 0.0743(6) Uani d . 1 . C
H12 -0.3991(4) 0.09209(9) 0.5861(2) 0.089 Uiso calc R 1 . H
C13 -0.2470(4) 0.15685(9) 0.57765(15) 0.0713(6) Uani d . 1 . C
H13 -0.3335(4) 0.17324(9) 0.62303(15) 0.086 Uiso calc R 1 . H
C14 -0.0788(4) 0.18112(7) 0.53357(14) 0.0655(5) Uani d . 1 . C
H14 -0.0475(4) 0.21359(7) 0.55133(14) 0.079 Uiso calc R 1 . H
C15 0.0438(3) 0.15748(6) 0.46302(13) 0.0563(5) Uani d . 1 . C
H15 0.1566(3) 0.17418(6) 0.43281(13) 0.068 Uiso calc R 1 . H
O3 -0.2220(2) 0.14252(5) 0.25310(9) 0.0526(3) Uani d . 1 . O
H1 -0.324(4) 0.1566(8) 0.2042(17) 0.079(7) Uiso d . 1 . H
C16 0.4210(3) 0.06237(6) 0.01227(13) 0.0473(4) Uani d . 1 . C
H16 0.5502(3) 0.04763(6) 0.04329(13) 0.057 Uiso calc R 1 . H
C17 0.3838(3) 0.06434(6) -0.09072(13) 0.0494(4) Uani d . 1 . C
H17 0.4913(3) 0.05223(6) -0.13168(13) 0.059 Uiso calc R 1 . H
C18 0.1731(3) 0.08554(6) -0.14282(12) 0.0426(4) Uani d . 1 . C
C19 0.2108(3) 0.11275(7) -0.24223(13) 0.0565(5) Uani d . 1 . C
H19A 0.0711(3) 0.12568(7) -0.27289(13) 0.085 Uiso calc R 1 . H
H19B 0.2713(3) 0.09072(7) -0.29068(13) 0.085 Uiso calc R 1 . H
H19C 0.3140(3) 0.13915(7) -0.22628(13) 0.085 Uiso calc R 1 . H
C20 -0.0051(3) 0.04631(7) -0.1626(2) 0.0672(5) Uani d . 1 . C
H20A -0.1390(3) 0.06072(7) -0.1961(2) 0.101 Uiso calc R 1 . H
H20B -0.0367(3) 0.03203(7) -0.0972(2) 0.101 Uiso calc R 1 . H
H20C 0.0476(3) 0.02136(7) -0.2070(2) 0.101 Uiso calc R 1 . H
O4 0.0849(2) 0.12308(4) -0.07378(8) 0.0465(3) Uani d . 1 . O
O5 -0.4055(2) 0.18036(4) 0.08860(9) 0.0531(3) Uani d . 1 . O
C21 -0.2330(3) 0.17297(5) 0.04380(12) 0.0384(3) Uani d . 1 . C
C22 -0.2073(2) 0.20243(5) -0.05199(11) 0.0369(3) Uani d . 1 . C
C23 -0.3932(3) 0.21014(6) -0.12226(12) 0.0444(4) Uani d . 1 . C
H23 -0.5288(3) 0.19545(6) -0.11102(12) 0.053 Uiso calc R 1 . H
C24 -0.3785(3) 0.23951(7) -0.20890(13) 0.0542(4) Uani d . 1 . C
H24 -0.5025(3) 0.24369(7) -0.25714(13) 0.065 Uiso calc R 1 . H
C25 -0.1794(3) 0.26272(7) -0.22396(14) 0.0576(5) Uani d . 1 . C
H25 -0.1691(3) 0.28243(7) -0.28246(14) 0.069 Uiso calc R 1 . H
C26 0.0034(3) 0.25661(7) -0.1523(2) 0.0577(5) Uani d . 1 . C
H26 0.1357(3) 0.27320(7) -0.1612(2) 0.069 Uiso calc R 1 . H
C27 -0.0079(3) 0.22605(6) -0.06730(14) 0.0471(4) Uani d . 1 . C
H27 0.1177(3) 0.22128(6) -0.02032(14) 0.056 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
C5 O1 C1 122.03(13) y
O2 C1 O1 115.7(2) y
O2 C1 C2 127.8(2) y
O1 C1 C2 116.56(14) y
C3 C2 C1 123.3(2) y
C2 C3 C4 118.49(14) y
C2 C3 C10 118.97(14) y
C4 C3 C10 122.51(14) y
C5 C4 C9 115.92(13) y
C5 C4 C3 118.10(14) y
C9 C4 C3 125.88(14) y
O1 C5 C6 114.31(13) y
O1 C5 C4 121.01(13) y
C6 C5 C4 124.65(14) y
C7 C6 C5 117.84(13) y
C7 C6 C16 118.28(13) y
C5 C6 C16 123.87(14) y
O4 C7 C6 120.12(12) y
O4 C7 C8 118.35(13) y
C6 C7 C8 121.53(13) y
C9 C8 C7 117.61(13) y
C9 C8 C21 118.57(12) y
C7 C8 C21 123.73(13) y
O3 C9 C4 117.68(13) y
O3 C9 C8 120.27(14) y
C4 C9 C8 122.04(13) y
C11 C10 C15 119.0(2) ?
C11 C10 C3 120.89(15) ?
C15 C10 C3 120.14(15) ?
C10 C11 C12 120.0(2) ?
C13 C12 C11 120.5(2) ?
C12 C13 C14 120.0(2) ?
C13 C14 C15 120.1(2) ?
C14 C15 C10 120.3(2) ?
C17 C16 C6 119.6(2) y
C16 C17 C18 121.47(14) y
O4 C18 C17 109.58(12) y
O4 C18 C19 104.69(12) y
C17 C18 C19 112.48(13) y
O4 C18 C20 107.58(12) y
C17 C18 C20 110.86(14) y
C19 C18 C20 111.3(2) y
C7 O4 C18 119.02(11) y
O5 C21 C8 120.07(13) y
O5 C21 C22 116.58(13) y
C8 C21 C22 123.26(12) y
C23 C22 C27 119.37(14) ?
C23 C22 C21 118.72(13) ?
C27 C22 C21 121.61(14) ?
C24 C23 C22 120.3(2) ?
C23 C24 C25 120.0(2) ?
C26 C25 C24 119.9(2) ?
C25 C26 C27 120.5(2) ?
C26 C27 C22 119.9(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 C5 . 1.373(2) y
O1 C1 . 1.387(2) y
O2 C1 . 1.208(2) y
C1 C2 . 1.432(2) y
C2 C3 . 1.347(2) y
C3 C4 . 1.458(2) y
C3 C10 . 1.494(2) y
C4 C5 . 1.398(2) y
C4 C9 . 1.416(2) y
C5 C6 . 1.391(2) y
C6 C7 . 1.390(2) y
C6 C16 . 1.458(2) y
C7 O4 . 1.347(2) y
C7 C8 . 1.424(2) y
C8 C9 . 1.420(2) y
C8 C21 . 1.472(2) y
C9 O3 . 1.341(2) y
C10 C11 . 1.379(2) ?
C10 C15 . 1.390(2) ?
C11 C12 . 1.387(3) ?
C12 C13 . 1.365(3) ?
C13 C14 . 1.372(3) ?
C14 C15 . 1.378(2) ?
C16 C17 . 1.320(2) y
C17 C18 . 1.491(2) y
C18 O4 . 1.484(2) y
C18 C19 . 1.511(2) y
C18 C20 . 1.519(2) y
O5 C21 . 1.246(2) y
C21 C22 . 1.488(2) y
C22 C23 . 1.384(2) ?
C22 C27 . 1.389(2) ?
C23 C24 . 1.380(2) ?
C24 C25 . 1.381(3) ?
C25 C26 . 1.375(3) ?
C26 C27 . 1.379(2) ?
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 174.22(15)
C5 O1 C1 C2 -7.4(2)
O2 C1 C2 C3 -178.8(2)
O1 C1 C2 C3 3.1(3)
C1 C2 C3 C4 3.5(3)
C1 C2 C3 C10 -174.6(2)
C2 C3 C4 C5 -6.1(2)
C10 C3 C4 C5 171.97(14)
C2 C3 C4 C9 170.2(2)
C10 C3 C4 C9 -11.7(2)
C1 O1 C5 C6 -173.11(14)
C1 O1 C5 C4 4.9(2)
C9 C4 C5 O1 -174.59(13)
C3 C4 C5 O1 2.1(2)
C9 C4 C5 C6 3.2(2)
C3 C4 C5 C6 179.88(14)
O1 C5 C6 C7 177.01(13)
C4 C5 C6 C7 -0.9(2)
O1 C5 C6 C16 -4.4(2)
C4 C5 C6 C16 177.64(15)
C5 C6 C7 O4 -178.30(13)
C16 C6 C7 O4 3.1(2)
C5 C6 C7 C8 1.9(2)
C16 C6 C7 C8 -176.73(14)
O4 C7 C8 C9 175.00(13)
C6 C7 C8 C9 -5.2(2)
O4 C7 C8 C21 -1.3(2)
C6 C7 C8 C21 178.44(14)
C5 C4 C9 O3 172.04(14)
C3 C4 C9 O3 -4.3(2)
C5 C4 C9 C8 -6.7(2)
C3 C4 C9 C8 176.96(14)
C7 C8 C9 O3 -170.95(13)
C21 C8 C9 O3 5.6(2)
C7 C8 C9 C4 7.7(2)
C21 C8 C9 C4 -175.73(13)
C2 C3 C10 C11 -69.2(2)
C4 C3 C10 C11 112.7(2)
C2 C3 C10 C15 109.2(2)
C4 C3 C10 C15 -68.9(2)
C15 C10 C11 C12 3.8(3)
C3 C10 C11 C12 -177.8(2)
C10 C11 C12 C13 -1.8(3)
C11 C12 C13 C14 -1.4(3)
C12 C13 C14 C15 2.6(3)
C13 C14 C15 C10 -0.6(3)
C11 C10 C15 C14 -2.6(3)
C3 C10 C15 C14 179.0(2)
C7 C6 C16 C17 -14.6(2)
C5 C6 C16 C17 166.8(2)
C6 C16 C17 C18 -3.0(3)
C16 C17 C18 O4 28.3(2)
C16 C17 C18 C19 144.3(2)
C16 C17 C18 C20 -90.3(2)
C6 C7 O4 C18 25.5(2)
C8 C7 O4 C18 -154.69(13)
C17 C18 O4 C7 -39.7(2)
C19 C18 O4 C7 -160.58(14)
C20 C18 O4 C7 80.9(2)
C9 C8 C21 O5 -19.4(2)
C7 C8 C21 O5 156.91(15)
C9 C8 C21 C22 156.97(14)
C7 C8 C21 C22 -26.7(2)
O5 C21 C22 C23 -40.8(2)
C8 C21 C22 C23 142.69(15)
O5 C21 C22 C27 132.9(2)
C8 C21 C22 C27 -43.6(2)
C27 C22 C23 C24 2.5(2)
C21 C22 C23 C24 176.37(14)
C22 C23 C24 C25 -2.2(2)
C23 C24 C25 C26 -0.2(3)
C24 C25 C26 C27 2.3(3)
C25 C26 C27 C22 -2.0(3)
C23 C22 C27 C26 -0.4(2)
C21 C22 C27 C26 -174.08(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9179595
