#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/19/8101929.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101929
loop_
_publ_author_name
'Zhang, X.-Q.'
'Zhang, Z.-T.'
'Zhang, X.-L.'
_publ_section_title
;
Crystal structure of kakkalidone, C₂₃H₂₄O₁₁
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              80
_journal_page_last               82
_journal_volume                  221
_journal_year                    2006
_chemical_formula_moiety         'C23 H24 O11'
_chemical_formula_sum            'C23 H24 O11'
_chemical_formula_weight         476.42
_chemical_name_systematic
; 
 kakkalidone
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.127(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.081(3)
_cell_length_b                   7.838(3)
_cell_length_c                   22.600(10)
_cell_measurement_reflns_used    1112
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.721
_cell_measurement_theta_min      2.706
_cell_volume                     1076.4(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       phi/omega
_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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5491
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     602
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0722
_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)+(0.1353P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.2258
_reflns_number_gt                1894
_reflns_number_total             3281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1724.cff
_cod_data_source_block           051017d
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      P12(1)1
_cod_database_code               8101929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1894(7) 0.2059(5) 0.86402(18) 0.0493(11) Uani 1 2 a d . . .
O2 O -0.3204(7) -0.0177(6) 0.94596(19) 0.0565(12) Uani 1 2 a d . . .
O3 O -0.4970(7) -0.0876(6) 0.8431(2) 0.0638(13) Uani 1 2 a d . . .
H3 H -0.4845 -0.0856 0.8793 0.096 Uiso 1 2 a calc R . .
O4 O -0.4877(8) -0.0509(7) 0.7241(2) 0.0635(13) Uani 1 2 a d . . .
O5 O -0.1387(7) 0.0858(10) 0.6738(2) 0.088(2) Uani 1 2 a d D . .
O6 O 0.1268(9) 0.0524(7) 1.20172(19) 0.0706(15) Uani 1 2 a d . . .
O7 O 0.1510(9) 0.2401(7) 0.6410(2) 0.0738(15) Uani 1 2 a d DU . .
O8 O -0.114(2) -0.088(2) 0.5731(6) 0.082(4) Uani 0.463(12) 2 a d PDU A 1
H8 H -0.1462 -0.1243 0.6058 0.123 Uiso 0.463(12) 2 a calc PRD A 1
O8' O -0.0329(19) -0.2068(15) 0.5998(4) 0.071(3) Uani 0.537(12) 2 a d PU A 2
H8' H -0.0070 -0.2634 0.5703 0.107 Uiso 0.537(12) 2 a calc PR A 2
O9 O 0.1962(11) -0.0703(10) 0.4947(3) 0.109(2) Uani 1 2 a d U . .
H9 H 0.2347 0.0002 0.4704 0.163 Uiso 1 2 a calc RD B 1
O10 O 0.5434(9) 0.1536(7) 0.52617(19) 0.0753(15) Uani 1 2 a d DU . .
H10 H 0.6020 0.2477 0.5248 0.113 Uiso 1 2 a calc R . .
O11 O 0.422(3) 0.5436(19) 0.5969(6) 0.075(4) Uani 0.463(12) 2 a d PDU A 1
H11 H 0.4102 0.5254 0.5612 0.112 Uiso 0.463(12) 2 a calc PR A 1
O11' O 0.292(3) 0.5222(15) 0.5749(7) 0.088(4) Uani 0.537(12) 2 a d PU A 2
H11' H 0.3213 0.4901 0.5416 0.133 Uiso 0.537(12) 2 a calc PR A 2
C1 C 0.1875(10) 0.1919(8) 0.9234(3) 0.0440(15) Uani 1 2 a d . . .
H1 H 0.3052 0.2387 0.9452 0.053 Uiso 1 2 a calc R . .
C2 C 0.0278(9) 0.1152(7) 0.9534(2) 0.0372(14) Uani 1 2 a d . . .
C3 C -0.1621(10) 0.0470(8) 0.9214(3) 0.0430(14) Uani 1 2 a d . . .
C4 C -0.1557(10) 0.0594(8) 0.8577(3) 0.0430(15) Uani 1 2 a d . . .
C5 C -0.3268(10) -0.0057(8) 0.8202(3) 0.0444(15) Uani 1 2 a d . . .
C6 C -0.3145(10) 0.0062(9) 0.7601(3) 0.0517(17) Uani 1 2 a d . . .
C7 C -0.1361(12) 0.0833(11) 0.7353(3) 0.0610(19) Uani 1 2 a d . . .
C8 C 0.0372(11) 0.1473(9) 0.7714(3) 0.0535(17) Uani 1 2 a d . . .
H8A H 0.1594 0.1972 0.7549 0.064 Uiso 1 2 a calc R A .
C9 C 0.0226(10) 0.1347(7) 0.8309(3) 0.0409(15) Uani 1 2 a d . . .
C10 C 0.0527(11) 0.1023(8) 1.0193(2) 0.0434(15) Uani 1 2 a d . . .
C11 C -0.1194(12) 0.1527(9) 1.0545(3) 0.0534(17) Uani 1 2 a d . . .
H11A H -0.2483 0.1963 1.0369 0.064 Uiso 1 2 a calc R . .
C12 C -0.0984(13) 0.1379(9) 1.1161(3) 0.063(2) Uani 1 2 a d . . .
H12 H -0.2137 0.1713 1.1393 0.076 Uiso 1 2 a calc R . .
C13 C 0.0927(12) 0.0737(10) 1.1426(3) 0.0578(19) Uani 1 2 a d . . .
C14 C 0.2645(13) 0.0250(10) 1.1066(3) 0.0598(18) Uani 1 2 a d . . .
H14 H 0.3946 -0.0178 1.1237 0.072 Uiso 1 2 a calc R . .
C15 C 0.2417(10) 0.0400(8) 1.0466(3) 0.0494(16) Uani 1 2 a d . . .
H15 H 0.3576 0.0071 1.0235 0.059 Uiso 1 2 a calc R . .
C16 C -0.4614(15) -0.2237(10) 0.7048(4) 0.076(2) Uani 1 2 a d . . .
H16A H -0.5863 -0.2563 0.6802 0.114 Uiso 1 2 a calc R A .
H16B H -0.4501 -0.2976 0.7387 0.114 Uiso 1 2 a calc R . .
H16C H -0.3301 -0.2329 0.6827 0.114 Uiso 1 2 a calc R . .
C17 C -0.0528(15) 0.0998(12) 1.2377(3) 0.081(3) Uani 1 2 a d . . .
H17A H -0.0129 0.0799 1.2786 0.121 Uiso 1 2 a calc R . .
H17B H -0.1799 0.0326 1.2267 0.121 Uiso 1 2 a calc R . .
H17C H -0.0860 0.2185 1.2319 0.121 Uiso 1 2 a calc R . .
C18 C 0.0626(12) 0.0742(10) 0.6462(3) 0.0634(16) Uani 0.463(12) 2 a d PDU A 1
H18 H 0.1648 -0.0101 0.6637 0.076 Uiso 0.463(12) 2 a calc PR A 1
C19 C 0.019(2) 0.055(3) 0.5800(6) 0.070(3) Uani 0.463(12) 2 a d PDU A 1
H19 H -0.0442 0.1580 0.5612 0.084 Uiso 0.463(12) 2 a calc PR A 1
C20 C 0.2347(12) -0.0044(11) 0.5529(3) 0.0695(17) Uani 0.463(12) 2 a d PDU A 1
H20 H 0.3178 -0.0837 0.5788 0.083 Uiso 0.463(12) 2 a calc PR A 1
C18' C 0.0626(12) 0.0742(10) 0.6462(3) 0.0634(16) Uani 0.537(12) 2 a d PU A 2
H18' H 0.1625 0.0115 0.6734 0.076 Uiso 0.537(12) 2 a calc PR A 2
C19' C 0.026(2) -0.040(2) 0.5906(5) 0.060(3) Uani 0.537(12) 2 a d PDU A 2
H19' H -0.0985 0.0110 0.5681 0.071 Uiso 0.537(12) 2 a calc PR A 2
C20' C 0.2347(12) -0.0044(11) 0.5529(3) 0.0695(17) Uani 0.537(12) 2 a d PU A 2
H20' H 0.3500 -0.0777 0.5706 0.083 Uiso 0.537(12) 2 a calc PR A 2
C21 C 0.3345(13) 0.1693(10) 0.5523(3) 0.0650(18) Uani 1 2 a d DU . .
H21 H 0.2401 0.2463 0.5285 0.078 Uiso 1 2 a calc R A 1
C22 C 0.3593(13) 0.2357(10) 0.6146(3) 0.0664(18) Uani 0.463(12) 2 a d PDU A 1
H22 H 0.4367 0.1433 0.6359 0.080 Uiso 0.463(12) 2 a calc PR A 1
C23 C 0.512(3) 0.3946(19) 0.6266(8) 0.063(3) Uani 0.463(12) 2 a d PDU A 1
H23A H 0.5256 0.4159 0.6688 0.076 Uiso 0.463(12) 2 a calc PR A 1
H23B H 0.6575 0.3712 0.6124 0.076 Uiso 0.463(12) 2 a calc PR A 1
C22' C 0.3593(13) 0.2357(10) 0.6146(3) 0.0664(18) Uani 0.537(12) 2 a d P A 2
H22' H 0.4689 0.1716 0.6385 0.080 Uiso 0.537(12) 2 a calc PR A 2
C23' C 0.403(3) 0.425(3) 0.6156(8) 0.070(3) Uani 0.537(12) 2 a d PU A 2
H23C H 0.3698 0.4679 0.6546 0.084 Uiso 0.537(12) 2 a calc PR A 2
H23D H 0.5593 0.4427 0.6106 0.084 Uiso 0.537(12) 2 a calc PR A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 118.8(4) . . ?
C5 O3 H3 109.5 . . ?
C6 O4 C16 113.2(5) . . ?
C7 O5 C18 117.9(5) . . ?
C13 O6 C17 115.8(6) . . ?
C18 O7 C22 111.2(5) . . ?
C19' O8' H8' 109.5 . . ?
C20 O9 H9 109.5 . . ?
C21 O10 H10 109.5 . . ?
C23 O11 H11 109.5 . . ?
C23' O11' H11' 109.5 . . ?
O1 C1 C2 124.9(5) . . ?
O1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 C10 119.0(5) . . ?
C3 C2 C10 121.6(5) . . ?
O2 C3 C2 123.2(5) . . ?
O2 C3 C4 121.7(6) . . ?
C2 C3 C4 115.1(5) . . ?
C9 C4 C5 117.3(5) . . ?
C9 C4 C3 120.8(6) . . ?
C5 C4 C3 121.8(5) . . ?
O3 C5 C6 119.3(6) . . ?
O3 C5 C4 120.2(5) . . ?
C6 C5 C4 120.4(6) . . ?
C5 C6 C7 120.5(6) . . ?
C5 C6 O4 119.7(6) . . ?
C7 C6 O4 119.7(6) . . ?
C6 C7 O5 115.6(6) . . ?
C6 C7 C8 120.4(6) . . ?
O5 C7 C8 123.9(6) . . ?
C9 C8 C7 118.5(6) . . ?
C9 C8 H8A 120.8 . . ?
C7 C8 H8A 120.8 . . ?
C8 C9 O1 116.2(5) . . ?
C8 C9 C4 122.9(6) . . ?
O1 C9 C4 120.8(5) . . ?
C15 C10 C11 118.5(5) . . ?
C15 C10 C2 121.7(5) . . ?
C11 C10 C2 119.9(6) . . ?
C10 C11 C12 120.1(7) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C13 C12 C11 120.5(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O6 C13 C12 124.6(6) . . ?
O6 C13 C14 116.7(7) . . ?
C12 C13 C14 118.7(6) . . ?
C15 C14 C13 120.2(7) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 122.1(6) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 O7 108.7(6) . . ?
O5 C18 C19 108.7(7) . . ?
O7 C18 C19 93.4(9) . . ?
O5 C18 H18 114.6 . . ?
O7 C18 H18 114.6 . . ?
C19 C18 H18 114.6 . . ?
O8 C19 C18 105.7(12) . . ?
O8 C19 C20 102.1(12) . . ?
C18 C19 C20 107.4(10) . . ?
O8 C19 H19 113.6 . . ?
C18 C19 H19 113.6 . . ?
C20 C19 H19 113.6 . . ?
O9 C20 C21 112.1(6) . . ?
O9 C20 C19 111.3(8) . . ?
C21 C20 C19 94.5(9) . . ?
O9 C20 H20 112.6 . . ?
C21 C20 H20 112.6 . . ?
C19 C20 H20 112.6 . . ?
O8' C19' H19' 105.6 . . ?
O10 C21 C20 107.1(6) . . ?
O10 C21 C22 111.0(6) . . ?
C20 C21 C22 109.6(6) . . ?
O10 C21 H21 109.7 . . ?
C20 C21 H21 109.7 . . ?
C22 C21 H21 109.7 . . ?
O7 C22 C21 109.9(6) . . ?
O7 C22 C23 116.1(9) . . ?
C21 C22 C23 118.3(8) . . ?
O7 C22 H22 103.4 . . ?
C21 C22 H22 103.4 . . ?
C23 C22 H22 103.4 . . ?
O11 C23 C22 110.5(13) . . ?
O11 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
O11 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
O11' C23' H23C 108.0 . . ?
O11' C23' H23D 108.0 . . ?
H23C C23' H23D 107.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.346(7) . ?
O1 C9 1.358(7) . ?
O2 C3 1.237(7) . ?
O3 C5 1.339(7) . ?
O3 H3 0.8200 . ?
O4 C6 1.381(7) . ?
O4 C16 1.434(9) . ?
O5 C7 1.388(8) . ?
O5 C18 1.398(8) . ?
O6 C13 1.355(8) . ?
O6 C17 1.435(9) . ?
O7 C18 1.414(9) . ?
O7 C22 1.420(8) . ?
O8 C19 1.392(16) . ?
O8 H8 0.8200 . ?
O8' C19' 1.372(19) . ?
O8' H8' 0.8200 . ?
O9 C20 1.425(8) . ?
O9 H9 0.8200 . ?
O10 C21 1.426(9) . ?
O10 H10 0.8200 . ?
O11 C23 1.444(16) . ?
O11 H11 0.8200 . ?
O11' C23' 1.35(2) . ?
O11' H11' 0.8200 . ?
C1 C2 1.348(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.443(8) . ?
C2 C10 1.493(8) . ?
C3 C4 1.444(8) . ?
C4 C9 1.393(8) . ?
C4 C5 1.414(9) . ?
C5 C6 1.365(9) . ?
C6 C7 1.380(10) . ?
C7 C8 1.401(10) . ?
C8 C9 1.355(8) . ?
C8 H8A 0.9300 . ?
C10 C15 1.374(9) . ?
C10 C11 1.395(9) . ?
C11 C12 1.398(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.401(10) . ?
C14 C15 1.362(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.517(14) . ?
C18 H18 0.9800 . ?
C19 C20 1.544(14) . ?
C19 H19 0.9800 . ?
C20 C21 1.490(10) . ?
C20 H20 0.9800 . ?
C19' H19' 0.9800 . ?
C21 C22 1.504(9) . ?
C21 H21 0.9800 . ?
C22 C23 1.570(15) . ?
C22 H22 0.9800 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23' H23C 0.9700 . ?
C23' H23D 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.85 2.583(6) 147.6 .
O8' H8' O11' 0.82 2.48 2.969(18) 119.7 1_545
O10 H10 O9 0.82 1.94 2.732(9) 161.4 2_656
O11' H11' O10 0.82 2.18 2.730(13) 124.4 2_656
O11 H11 O10 0.82 2.24 2.928(14) 141.2 2_656
C16 H16A O11 0.96 2.45 3.106(17) 125.3 1_445
C18 H18 O4 0.98 2.49 3.343(9) 144.9 1_655
C18' H18' O4 0.98 2.43 3.343(9) 155.3 1_655
