#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/52/1505218.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_1505218
loop_
_publ_author_name
'Fei, Dong-Qing'
'Li, Shi-Gang'
'Liu, Chun-Mei'
'Wu, Gang'
'Gao, Kun'
_publ_section_title
;
 Eremophilane-type sesquiterpene derivatives from the roots of Ligularia
 lapathifolia.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              241
_journal_page_last               245
_journal_paper_doi               10.1021/np060304k
_journal_volume                  70
_journal_year                    2007
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_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                 99.390(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.340(2)
_cell_length_b                   9.715(3)
_cell_length_c                   9.555(3)
_cell_measurement_temperature    294(2)
_cell_volume                     672.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3736
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_correction_T_min  0.9543
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(10)
_refine_ls_extinction_coef       0.054(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0350
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2253
_reflns_number_total             2421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np060304ksi20060630_032454.cif
_cod_data_source_block           p21
_cod_original_cell_volume        672.3(4)
_cod_database_code               1505218
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_calc_flag
_atom_site_refinement_flags
C1 C 1.0087(4) 0.6622(3) 0.3377(3) 0.0652(6) Uani 1 1 d .
H1A H 0.9600 0.5693 0.3366 0.078 Uiso 1 1 calc R
H1B H 1.1352 0.6562 0.3207 0.078 Uiso 1 1 calc R
C2 C 1.0082(4) 0.7250(3) 0.4853(3) 0.0712(7) Uani 1 1 d .
H2A H 1.0367 0.6532 0.5560 0.085 Uiso 1 1 calc R
H2B H 1.1053 0.7935 0.5030 0.085 Uiso 1 1 calc R
C3 C 0.8300(3) 0.7904(2) 0.5029(2) 0.0588(6) Uani 1 1 d .
H3 H 0.8153 0.8229 0.5919 0.071 Uiso 1 1 calc R
C4 C 0.6918(3) 0.8037(2) 0.39570(18) 0.0444(4) Uani 1 1 d .
C5 C 0.6952(3) 0.75675(18) 0.24524(17) 0.0393(4) Uani 1 1 d .
C6 C 0.5736(2) 0.87280(19) 0.16578(18) 0.0379(4) Uani 1 1 d .
H6 H 0.5096 0.8385 0.0744 0.046 Uiso 1 1 calc R
C7 C 0.6819(2) 0.99806(17) 0.14376(15) 0.0334(3) Uani 1 1 d .
C8 C 0.8616(2) 0.97370(18) 0.09168(18) 0.0360(4) Uani 1 1 d .
C9 C 0.9860(2) 0.8847(2) 0.19827(19) 0.0421(4) Uani 1 1 d .
H9A H 1.0104 0.9316 0.2890 0.050 Uiso 1 1 calc R
H9B H 1.1030 0.8702 0.1658 0.050 Uiso 1 1 calc R
C10 C 0.8944(3) 0.74500(19) 0.21647(19) 0.0438(4) Uani 1 1 d .
H10 H 0.8919 0.6928 0.1284 0.053 Uiso 1 1 calc R
C11 C 0.6587(2) 1.13190(18) 0.16947(16) 0.0370(4) Uani 1 1 d .
C12 C 0.8217(3) 1.2034(2) 0.13128(18) 0.0410(4) Uani 1 1 d .
C13 C 0.5086(3) 1.2094(2) 0.2236(2) 0.0547(5) Uani 1 1 d .
H13A H 0.5260 1.2031 0.3251 0.082 Uiso 1 1 calc R
H13B H 0.3911 1.1707 0.1842 0.082 Uiso 1 1 calc R
H13C H 0.5124 1.3043 0.1961 0.082 Uiso 1 1 calc R
C14 C 0.5916(4) 0.6188(2) 0.2161(2) 0.0587(6) Uani 1 1 d .
H14A H 0.4645 0.6310 0.2259 0.088 Uiso 1 1 calc R
H14B H 0.6470 0.5509 0.2828 0.088 Uiso 1 1 calc R
H14C H 0.5988 0.5886 0.1215 0.088 Uiso 1 1 calc R
C15 C 0.5176(3) 0.8795(2) 0.3958(2) 0.0545(5) Uani 1 1 d .
O1 O 0.4398(3) 0.9162(2) 0.4907(2) 0.0842(6) Uani 1 1 d .
O2 O 0.44032(18) 0.90544(16) 0.25794(15) 0.0515(4) Uani 1 1 d .
O3 O 0.94147(18) 1.11273(14) 0.09116(13) 0.0443(3) Uani 1 1 d .
O4 O 0.8533(3) 1.32653(16) 0.13506(18) 0.0611(4) Uani 1 1 d .
O5 O 0.82836(19) 0.92296(15) -0.04431(13) 0.0471(3) Uani 1 1 d .
H5 H 0.9250 0.8939 -0.0658 0.071 Uiso 1 1 calc R
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
C2 C1 C10 113.6(2)
C3 C2 C1 114.0(2)
C4 C3 C2 122.0(2)
C3 C4 C15 127.05(19)
C3 C4 C5 125.2(2)
C15 C4 C5 107.45(16)
C4 C5 C10 110.89(15)
C4 C5 C14 110.44(16)
C10 C5 C14 111.03(16)
C4 C5 C6 98.51(14)
C10 C5 C6 116.96(14)
C14 C5 C6 108.33(15)
O2 C6 C7 109.57(14)
O2 C6 C5 104.56(14)
C7 C6 C5 112.62(14)
C11 C7 C6 132.99(16)
C11 C7 C8 110.99(15)
C6 C7 C8 115.86(15)
O5 C8 O3 109.58(14)
O5 C8 C7 109.87(13)
O3 C8 C7 103.19(14)
O5 C8 C9 115.07(15)
O3 C8 C9 109.12(14)
C7 C8 C9 109.34(14)
C8 C9 C10 110.60(14)
C5 C10 C9 113.66(14)
C5 C10 C1 108.76(16)
C9 C10 C1 110.60(17)
C7 C11 C12 106.18(15)
C7 C11 C13 132.49(17)
C12 C11 C13 121.33(17)
O4 C12 O3 121.49(18)
O4 C12 C11 127.68(18)
O3 C12 C11 110.83(15)
O1 C15 O2 119.9(2)
O1 C15 C4 131.8(2)
O2 C15 C4 108.31(16)
C15 O2 C6 109.17(15)
C12 O3 C8 108.72(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.537(4)
C1 C10 1.541(3)
C2 C3 1.488(4)
C3 C4 1.326(3)
C4 C15 1.476(3)
C4 C5 1.512(2)
C5 C10 1.536(3)
C5 C14 1.544(3)
C5 C6 1.557(2)
C6 O2 1.454(2)
C6 C7 1.487(2)
C7 C11 1.339(3)
C7 C8 1.502(2)
C8 O5 1.374(2)
C8 O3 1.473(2)
C8 C9 1.522(2)
C9 C10 1.537(3)
C11 C12 1.480(2)
C11 C13 1.495(2)
C12 O4 1.218(3)
C12 O3 1.344(2)
C15 O1 1.202(3)
C15 O2 1.370(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
C10 C1 C2 C3 35.6(3)
C1 C2 C3 C4 -6.0(4)
C2 C3 C4 C15 -172.7(2)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C10 -22.5(3)
C15 C4 C5 C10 151.15(16)
C3 C4 C5 C14 101.0(2)
C15 C4 C5 C14 -85.3(2)
C3 C4 C5 C6 -145.7(2)
C15 C4 C5 C6 27.93(18)
C4 C5 C6 O2 -33.75(16)
C10 C5 C6 O2 -152.48(14)
C14 C5 C6 O2 81.18(17)
C4 C5 C6 C7 85.14(17)
C10 C5 C6 C7 -33.6(2)
C14 C5 C6 C7 -159.93(16)
O2 C6 C7 C11 -13.8(3)
C5 C6 C7 C11 -129.7(2)
O2 C6 C7 C8 161.18(13)
C5 C6 C7 C8 45.3(2)
C11 C7 C8 O5 -116.50(16)
C6 C7 C8 O5 67.44(19)
C11 C7 C8 O3 0.29(18)
C6 C7 C8 O3 -175.76(13)
C11 C7 C8 C9 116.31(17)
C6 C7 C8 C9 -59.74(18)
O5 C8 C9 C10 -63.96(19)
O3 C8 C9 C10 172.42(13)
C7 C8 C9 C10 60.23(18)
C4 C5 C10 C9 -74.64(19)
C14 C5 C10 C9 162.19(16)
C6 C5 C10 C9 37.2(2)
C4 C5 C10 C1 49.0(2)
C14 C5 C10 C1 -74.1(2)
C6 C5 C10 C1 160.86(17)
C8 C9 C10 C5 -50.2(2)
C8 C9 C10 C1 -172.88(16)
C2 C1 C10 C5 -57.4(3)
C2 C1 C10 C9 68.0(2)
C6 C7 C11 C12 176.68(17)
C8 C7 C11 C12 1.54(18)
C6 C7 C11 C13 -3.9(3)
C8 C7 C11 C13 -179.01(19)
C7 C11 C12 O4 177.9(2)
C13 C11 C12 O4 -1.6(3)
C7 C11 C12 O3 -3.07(19)
C13 C11 C12 O3 177.41(16)
C3 C4 C15 O1 -20.3(4)
C5 C4 C15 O1 166.2(3)
C3 C4 C15 O2 161.0(2)
C5 C4 C15 O2 -12.5(2)
O1 C15 O2 C6 170.4(2)
C4 C15 O2 C6 -10.8(2)
C7 C6 O2 C15 -91.88(18)
C5 C6 O2 C15 29.05(19)
O4 C12 O3 C8 -177.64(19)
C11 C12 O3 C8 3.27(18)
O5 C8 O3 C12 114.79(15)
C7 C8 O3 C12 -2.21(17)
C9 C8 O3 C12 -118.39(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17267195
