#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008323.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_2008323
loop_
_publ_author_name
'Singh, A.'
'Parmar, V. S.'
'Errington, W.'
'Howarth, O. W.'
'Lawrie, S.'
_publ_section_title
;
 Diosbulbin B, a constituent of <i>Dioscorea pentaphylla</i>
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              559
_journal_page_last               561
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C19 H20 O6'
_chemical_formula_weight         344.35
_chemical_name_common            Diosbulbin-B
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.915(4)
_cell_length_b                   10.623(4)
_cell_length_c                   17.243(5)
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.25
_cell_volume                     1633.0(11)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1994)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_sigmaI/netI    0.050
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8492
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.3(13)
_refine_ls_extinction_coef       0.0090(12)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+0.5866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.097
_reflns_number_gt                2376
_reflns_number_total             2872
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1291.cif
_[local]_cod_data_source_block   asj
_cod_original_cell_volume        1633.0(10)
_cod_database_code               2008323
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.2389(2) 0.92433(19) 0.61399(12) 0.0447(5) Uani d . 1 O
O2 0.0941(3) 0.7996(2) 0.68594(15) 0.0614(7) Uani d . 1 O
O3 0.3896(2) 0.86110(17) 0.89606(12) 0.0415(5) Uani d . 1 O
O4 0.16591(19) 0.92667(17) 0.85451(11) 0.0371(5) Uani d . 1 O
O5 0.44260(19) 1.11590(16) 0.94399(9) 0.0308(4) Uani d . 1 O
O6 0.9099(2) 1.01694(18) 1.01976(11) 0.0413(5) Uani d . 1 O
C1 0.3599(3) 1.1160(3) 0.65927(14) 0.0364(7) Uani d . 1 C
H1A 0.3586 1.2089 0.6554 0.044 Uiso calc R 1 H
H1B 0.4629 1.0867 0.6478 0.044 Uiso calc R 1 H
C2 0.2509(3) 1.0602(3) 0.60041(16) 0.0411(7) Uani d . 1 C
H2 0.2840 1.0784 0.5461 0.049 Uiso calc R 1 H
C3 0.0912(3) 1.1038(3) 0.61381(17) 0.0463(8) Uani d . 1 C
H3A 0.0240 1.0798 0.5705 0.056 Uiso calc R 1 H
H3B 0.0852 1.1958 0.6226 0.056 Uiso calc R 1 H
C4 0.0577(3) 1.0293(3) 0.68739(16) 0.0388(7) Uani d . 1 C
H4 -0.0523 1.0231 0.6981 0.047 Uiso calc R 1 H
C5 0.1448(3) 1.0907(2) 0.75517(14) 0.0305(6) Uani d . 1 C
H5 0.1237 1.1830 0.7519 0.037 Uiso calc R 1 H
C6 0.1009(3) 1.0505(3) 0.83779(15) 0.0347(6) Uani d . 1 C
H6 -0.0105 1.0496 0.8445 0.042 Uiso calc R 1 H
C7 0.1758(3) 1.1341(3) 0.89831(15) 0.0342(6) Uani d . 1 C
H7A 0.1637 1.2247 0.8866 0.041 Uiso calc R 1 H
H7B 0.1395 1.1163 0.9514 0.041 Uiso calc R 1 H
C8 0.3354(3) 1.0892(2) 0.88572(14) 0.0274(5) Uani d . 1 C
C9 0.4016(3) 1.1385(2) 0.80846(14) 0.0259(6) Uani d . 1 C
C10 0.3158(3) 1.0759(2) 0.74168(13) 0.0264(6) Uani d . 1 C
H10 0.3375 0.9837 0.7453 0.032 Uiso calc R 1 H
C11 0.5652(3) 1.0994(2) 0.82115(14) 0.0290(6) Uani d . 1 C
H11A 0.6339 1.1475 0.7871 0.035 Uiso calc R 1 H
H11B 0.5795 1.0082 0.8118 0.035 Uiso calc R 1 H
C12 0.5894(3) 1.1328(2) 0.90704(14) 0.0281(6) Uani d . 1 C
H12 0.6168 1.2239 0.9103 0.034 Uiso calc R 1 H
C13 0.7051(3) 1.0592(2) 0.94975(15) 0.0282(6) Uani d . 1 C
C14 0.7142(3) 0.9268(3) 0.96273(16) 0.0364(7) Uani d . 1 C
H14 0.6455 0.8648 0.9449 0.044 Uiso calc R 1 H
C15 0.8382(3) 0.9064(3) 1.00485(16) 0.0411(7) Uani d . 1 C
H15 0.8714 0.8260 1.0219 0.049 Uiso calc R 1 H
C16 0.8253(3) 1.1086(3) 0.98565(15) 0.0337(6) Uani d . 1 C
H16 0.8484 1.1959 0.9871 0.040 Uiso calc R 1 H
C17 0.1253(3) 0.9038(3) 0.66522(18) 0.0439(7) Uani d . 1 C
C18 0.3072(3) 0.9464(3) 0.87992(15) 0.0310(6) Uani d . 1 C
C19 0.3937(3) 1.2831(2) 0.80351(16) 0.0361(7) Uani d . 1 C
H19A 0.4248 1.3196 0.8532 0.054 Uiso calc R 1 H
H19B 0.2906 1.3089 0.7919 0.054 Uiso calc R 1 H
H19C 0.4608 1.3127 0.7623 0.054 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0483(12) 0.0438(13) 0.0420(11) 0.0002(10) -0.0039(10) -0.0142(10)
O2 0.0620(15) 0.0424(14) 0.0797(17) -0.0163(12) -0.0030(14) -0.0111(12)
O3 0.0428(11) 0.0298(10) 0.0520(13) 0.0011(10) -0.0017(10) 0.0107(10)
O4 0.0326(10) 0.0351(10) 0.0435(11) -0.0047(9) 0.0013(9) 0.0062(9)
O5 0.0321(10) 0.0373(11) 0.0228(9) 0.0035(8) 0.0021(8) -0.0030(8)
O6 0.0387(12) 0.0426(12) 0.0427(12) 0.0006(9) -0.0113(10) -0.0011(9)
C1 0.0441(16) 0.0377(16) 0.0274(14) -0.0019(13) -0.0010(13) 0.0018(13)
C2 0.0507(18) 0.0451(17) 0.0275(15) 0.0001(14) -0.0050(14) 0.0001(14)
C3 0.0493(17) 0.0514(19) 0.0381(16) 0.0070(15) -0.0138(15) -0.0038(15)
C4 0.0305(15) 0.0437(18) 0.0422(17) 0.0024(13) -0.0079(14) -0.0048(14)
C5 0.0309(14) 0.0295(14) 0.0311(14) 0.0028(11) -0.0020(11) -0.0026(12)
C6 0.0258(13) 0.0416(16) 0.0368(16) 0.0047(12) 0.0036(13) 0.0033(13)
C7 0.0328(14) 0.0412(16) 0.0286(15) 0.0061(13) 0.0057(12) 0.0013(13)
C8 0.0285(12) 0.0289(13) 0.0248(12) 0.0015(11) 0.0011(11) -0.0005(12)
C9 0.0329(14) 0.0216(13) 0.0232(13) -0.0004(12) 0.0017(11) -0.0009(11)
C10 0.0298(14) 0.0258(13) 0.0236(13) 0.0007(11) 0.0027(11) 0.0001(11)
C11 0.0316(14) 0.0300(14) 0.0255(13) -0.0040(11) 0.0055(11) -0.0009(11)
C12 0.0299(14) 0.0250(13) 0.0294(14) -0.0030(11) 0.0000(12) -0.0027(11)
C13 0.0301(14) 0.0292(14) 0.0252(13) -0.0004(11) 0.0011(12) -0.0058(11)
C14 0.0394(16) 0.0321(15) 0.0376(16) 0.0006(13) -0.0048(13) -0.0010(13)
C15 0.0471(17) 0.0333(16) 0.0427(17) 0.0050(14) -0.0030(15) 0.0015(13)
C16 0.0379(15) 0.0305(15) 0.0326(15) 0.0021(13) 0.0002(13) -0.0021(12)
C17 0.0368(16) 0.0460(19) 0.0488(18) -0.0078(14) -0.0101(15) -0.0092(16)
C18 0.0315(14) 0.0347(15) 0.0269(14) -0.0012(12) 0.0059(12) 0.0064(12)
C19 0.0480(17) 0.0268(15) 0.0336(15) -0.0006(13) -0.0040(14) 0.0018(12)
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
C17 O1 C2 108.4(2) ?
C18 O4 C6 107.1(2) ?
C8 O5 C12 108.60(17) ?
C15 O6 C16 105.9(2) ?
C2 C1 C10 110.2(2) ?
O1 C2 C3 102.0(2) ?
O1 C2 C1 108.8(2) ?
C3 C2 C1 112.3(2) ?
C2 C3 C4 98.8(2) y
C17 C4 C3 99.8(2) y
C17 C4 C5 111.3(2) ?
C3 C4 C5 108.2(2) ?
C6 C5 C4 117.1(2) ?
C6 C5 C10 111.2(2) ?
C4 C5 C10 109.7(2) ?
O4 C6 C7 102.4(2) ?
O4 C6 C5 109.3(2) ?
C7 C6 C5 111.2(2) ?
C8 C7 C6 97.4(2) y
O5 C8 C7 118.0(2) ?
O5 C8 C18 110.7(2) ?
C7 C8 C18 99.5(2) ?
O5 C8 C9 106.59(19) ?
C7 C8 C9 112.0(2) ?
C18 C8 C9 109.8(2) ?
C11 C9 C10 117.7(2) ?
C11 C9 C19 108.7(2) ?
C10 C9 C19 111.6(2) ?
C11 C9 C8 98.54(19) ?
C10 C9 C8 108.02(19) ?
C19 C9 C8 111.6(2) ?
C9 C10 C1 116.6(2) ?
C9 C10 C5 109.51(19) ?
C1 C10 C5 111.3(2) ?
C9 C11 C12 102.04(19) ?
O5 C12 C13 109.8(2) ?
O5 C12 C11 105.36(19) ?
C13 C12 C11 116.9(2) ?
C16 C13 C14 105.5(2) ?
C16 C13 C12 125.1(2) ?
C14 C13 C12 129.4(2) ?
C15 C14 C13 106.9(3) ?
C14 C15 O6 110.5(3) ?
C13 C16 O6 111.1(2) ?
O2 C17 O1 121.0(3) ?
O2 C17 C4 130.4(3) ?
O1 C17 C4 108.6(3) ?
O3 C18 O4 122.0(2) ?
O3 C18 C8 128.9(2) ?
O4 C18 C8 109.0(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.362(4)
O1 C2 1.467(4)
O2 C17 1.196(4)
O3 C18 1.199(3)
O4 C18 1.350(3)
O4 C6 1.466(3)
O5 C8 1.416(3)
O5 C12 1.467(3)
O6 C15 1.362(3)
O6 C16 1.365(3)
C1 C2 1.524(4)
C1 C10 1.535(3)
C2 C3 1.515(4)
C3 C4 1.525(4)
C4 C17 1.512(4)
C4 C5 1.547(4)
C5 C6 1.538(4)
C5 C10 1.550(4)
C6 C7 1.524(4)
C7 C8 1.516(4)
C8 C18 1.541(4)
C8 C9 1.548(3)
C9 C11 1.532(3)
C9 C10 1.534(3)
C9 C19 1.540(3)
C11 C12 1.538(4)
C12 C13 1.489(4)
C13 C16 1.345(4)
C13 C14 1.426(4)
C14 C15 1.340(4)
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
C17 O1 C2 C3 -28.6(3) ?
C17 O1 C2 C1 90.2(3) ?
C10 C1 C2 O1 -51.6(3) ?
C10 C1 C2 C3 60.5(3) ?
O1 C2 C3 C4 44.5(3) ?
C1 C2 C3 C4 -71.8(3) y
C2 C3 C4 C17 -43.4(3) ?
C2 C3 C4 C5 73.0(3) ?
C17 C4 C5 C6 -84.9(3) ?
C3 C4 C5 C6 166.5(2) ?
C17 C4 C5 C10 43.0(3) ?
C3 C4 C5 C10 -65.6(3) ?
C18 O4 C6 C7 -32.8(2) ?
C18 O4 C6 C5 85.1(2) ?
C4 C5 C6 O4 77.5(3) ?
C10 C5 C6 O4 -49.7(3) ?
C4 C5 C6 C7 -170.1(2) ?
C10 C5 C6 C7 62.7(3) ?
O4 C6 C7 C8 47.6(2) ?
C5 C6 C7 C8 -69.0(2) ?
C12 O5 C8 C7 -148.2(2) ?
C12 O5 C8 C18 98.1(2) ?
C12 O5 C8 C9 -21.3(2) ?
C6 C7 C8 O5 -163.0(2) ?
C6 C7 C8 C18 -43.4(2) ?
C6 C7 C8 C9 72.7(2) y
O5 C8 C9 C11 39.4(2) ?
C7 C8 C9 C11 169.8(2) ?
C18 C8 C9 C11 -80.6(2) ?
O5 C8 C9 C10 162.28(19) ?
C7 C8 C9 C10 -67.3(3) ?
C18 C8 C9 C10 42.3(3) ?
O5 C8 C9 C19 -74.7(3) ?
C7 C8 C9 C19 55.7(3) ?
C18 C8 C9 C19 165.3(2) ?
C11 C9 C10 C1 -72.0(3) ?
C19 C9 C10 C1 54.7(3) ?
C8 C9 C10 C1 177.6(2) ?
C11 C9 C10 C5 160.6(2) ?
C19 C9 C10 C5 -72.7(3) ?
C8 C9 C10 C5 50.3(3) ?
C2 C1 C10 C9 -172.0(2) ?
C2 C1 C10 C5 -45.5(3) ?
C6 C5 C10 C9 -49.7(3) y
C4 C5 C10 C9 179.2(2) ?
C6 C5 C10 C1 -180.0(2) ?
C4 C5 C10 C1 48.9(3) y
C10 C9 C11 C12 -156.8(2) ?
C19 C9 C11 C12 75.2(2) ?
C8 C9 C11 C12 -41.2(2) ?
C8 O5 C12 C13 -132.8(2) ?
C8 O5 C12 C11 -6.1(2) ?
C9 C11 C12 O5 30.8(2) ?
C9 C11 C12 C13 153.1(2) ?
O5 C12 C13 C16 -118.2(3) ?
C11 C12 C13 C16 121.9(3) ?
O5 C12 C13 C14 60.9(3) ?
C11 C12 C13 C14 -59.0(4) ?
C16 C13 C14 C15 -0.2(3) ?
C12 C13 C14 C15 -179.5(3) ?
C13 C14 C15 O6 -0.1(3) ?
C16 O6 C15 C14 0.4(3) ?
C14 C13 C16 O6 0.5(3) ?
C12 C13 C16 O6 179.8(2) ?
C15 O6 C16 C13 -0.5(3) ?
C2 O1 C17 O2 -179.5(3) ?
C2 O1 C17 C4 -0.1(3) ?
C3 C4 C17 O2 -152.3(3) ?
C5 C4 C17 O2 93.7(4) ?
C3 C4 C17 O1 28.3(3) ?
C5 C4 C17 O1 -85.7(3) ?
C6 O4 C18 O3 -177.8(2) ?
C6 O4 C18 C8 3.8(3) ?
O5 C8 C18 O3 -26.8(4) ?
C7 C8 C18 O3 -151.7(3) ?
C9 C8 C18 O3 90.6(3) ?
O5 C8 C18 O4 151.39(19) ?
C7 C8 C18 O4 26.5(3) ?
C9 C8 C18 O4 -91.2(2) ?