#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/18/1501806.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_1501806
loop_
_publ_author_name
'Wong, Su-Ling'
'Chang, Hsun-Shuo'
'Wang, Guei-Jane'
'Chiang, Michael Y.'
'Huang, Hung-Yi'
'Chen, Chu-Huang'
'Tsai, Shiow-Chwen'
'Lin, Chu-Hung'
'Chen, Ih-Sheng'
_publ_section_title
;
 Secondary metabolites from the roots of Neolitsea daibuensis and their
 anti-inflammatory activity.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              2489
_journal_page_last               2496
_journal_paper_doi               10.1021/np100874f
_journal_volume                  74
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H18 O5'
_chemical_formula_sum            'C17 H18 O5'
_chemical_formula_weight         302.31
_chemical_name_systematic
;
 ?
;
_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                 107.807(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3433(3)
_cell_length_b                   11.4642(4)
_cell_length_c                   9.1189(3)
_cell_measurement_reflns_used    3914
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.35
_cell_volume                     730.90(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4751
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6422
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0254
_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)+(0.0335P)²+0.1693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0637
_reflns_number_gt                2362
_reflns_number_total             2404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np100874f_si_002.cif
_cod_data_source_block           i12452
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1501806
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
O1 O 1.08227(15) 0.66018(10) 0.76055(12) 0.0204(2) Uani 1 1 d .
O2 O 0.74669(14) 0.33956(9) 0.76841(11) 0.0180(2) Uani 1 1 d .
O3 O 0.69763(16) 0.18492(10) 0.61004(13) 0.0247(3) Uani 1 1 d .
O4 O 0.44007(15) 0.38728(9) 0.10405(12) 0.0184(2) Uani 1 1 d .
O5 O 0.44326(16) 0.19170(10) 0.07992(13) 0.0242(3) Uani 1 1 d .
C1 C 0.8155(2) 0.50948(13) 0.41769(15) 0.0142(3) Uani 1 1 d .
C2 C 0.6424(2) 0.49397(13) 0.31727(16) 0.0154(3) Uani 1 1 d .
H10 H 0.5696 0.5597 0.2783 0.018 Uiso 1 1 calc R
C3 C 0.5590(2) 0.37751(13) 0.26387(17) 0.0160(3) Uani 1 1 d .
H9 H 0.6602 0.3195 0.2741 0.019 Uiso 1 1 calc R
C4 C 0.4273(2) 0.34195(14) 0.36212(16) 0.0179(3) Uani 1 1 d .
H8A H 0.3083 0.3853 0.3276 0.022 Uiso 1 1 calc R
H8B H 0.3973 0.2595 0.3481 0.022 Uiso 1 1 calc R
C5 C 0.5244(2) 0.36645(13) 0.52972(17) 0.0160(3) Uani 1 1 d .
C6 C 0.5345(2) 0.46699(13) 0.60400(17) 0.0149(3) Uani 1 1 d .
H5 H 0.4595 0.5320 0.5652 0.018 Uiso 1 1 calc R
C7 C 0.6823(2) 0.46147(13) 0.75793(17) 0.0158(3) Uani 1 1 d .
H4 H 0.6217 0.4765 0.8381 0.019 Uiso 1 1 calc R
C8 C 0.8512(2) 0.54093(13) 0.78189(16) 0.0150(3) Uani 1 1 d .
C9 C 0.9190(2) 0.60184(13) 0.68016(17) 0.0153(3) Uani 1 1 d .
C10 C 0.8654(2) 0.62144(13) 0.50847(17) 0.0158(3) Uani 1 1 d .
H12A H 0.9714 0.6586 0.4845 0.019 Uiso 1 1 calc R
H12B H 0.7567 0.6739 0.4773 0.019 Uiso 1 1 calc R
C11 C 0.9808(2) 0.56379(13) 0.93387(18) 0.0173(3) Uani 1 1 d .
C12 C 1.1154(2) 0.63517(14) 0.91393(18) 0.0217(3) Uani 1 1 d .
H1 H 1.2177 0.6640 0.9933 0.026 Uiso 1 1 calc R
C13 C 0.9661(2) 0.51402(16) 1.08135(17) 0.0222(3) Uani 1 1 d .
H14A H 0.9872 0.4313 1.0828 0.033 Uiso 1 1 calc R
H14B H 0.8410 0.5293 1.0894 0.033 Uiso 1 1 calc R
H14C H 1.0607 0.5495 1.1666 0.033 Uiso 1 1 calc R
C14 C 0.9704(2) 0.41855(13) 0.45989(17) 0.0180(3) Uani 1 1 d .
H15A H 0.9713 0.3815 0.5545 0.027 Uiso 1 1 calc R
H15B H 1.0921 0.4549 0.4726 0.027 Uiso 1 1 calc R
H15C H 0.9468 0.3612 0.3795 0.027 Uiso 1 1 calc R
C15 C 0.6601(2) 0.28468(14) 0.63271(16) 0.0166(3) Uani 1 1 d .
C16 C 0.3897(2) 0.28603(15) 0.02586(17) 0.0186(3) Uani 1 1 d .
C17 C 0.2603(2) 0.30818(16) -0.13394(18) 0.0266(4) Uani 1 1 d .
H17A H 0.2982 0.2598 -0.2054 0.040 Uiso 1 1 calc R
H17B H 0.2689 0.3887 -0.1600 0.040 Uiso 1 1 calc R
H17C H 0.1308 0.2903 -0.1388 0.040 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
C9 O1 C12 107.20(12)
C15 O2 C7 109.22(11)
C16 O4 C3 116.42(12)
C2 C1 C14 124.86(14)
C2 C1 C10 120.72(13)
C14 C1 C10 114.27(12)
C1 C2 C3 123.78(14)
C1 C2 H10 118.1
C3 C2 H10 118.1
O4 C3 C2 108.64(12)
O4 C3 C4 107.92(11)
C2 C3 C4 108.19(12)
O4 C3 H9 110.7
C2 C3 H9 110.7
C4 C3 H9 110.7
C5 C4 C3 110.53(12)
C5 C4 H8A 109.5
C3 C4 H8A 109.5
C5 C4 H8B 109.5
C3 C4 H8B 109.5
H8A C4 H8B 108.1
C6 C5 C15 107.76(13)
C6 C5 C4 128.07(14)
C15 C5 C4 123.11(13)
C5 C6 C7 110.78(13)
C5 C6 H5 124.6
C7 C6 H5 124.6
O2 C7 C6 103.23(11)
O2 C7 C8 109.44(11)
C6 C7 C8 116.30(12)
O2 C7 H4 109.2
C6 C7 H4 109.2
C8 C7 H4 109.2
C9 C8 C11 106.73(13)
C9 C8 C7 131.76(14)
C11 C8 C7 121.49(13)
C8 C9 O1 108.99(13)
C8 C9 C10 138.09(14)
O1 C9 C10 112.92(12)
C9 C10 C1 112.61(12)
C9 C10 H12A 109.1
C1 C10 H12A 109.1
C9 C10 H12B 109.1
C1 C10 H12B 109.1
H12A C10 H12B 107.8
C12 C11 C8 106.13(14)
C12 C11 C13 127.97(15)
C8 C11 C13 125.89(14)
C11 C12 O1 110.95(14)
C11 C12 H1 124.5
O1 C12 H1 124.5
C11 C13 H14A 109.5
C11 C13 H14B 109.5
H14A C13 H14B 109.5
C11 C13 H14C 109.5
H14A C13 H14C 109.5
H14B C13 H14C 109.5
C1 C14 H15A 109.5
C1 C14 H15B 109.5
H15A C14 H15B 109.5
C1 C14 H15C 109.5
H15A C14 H15C 109.5
H15B C14 H15C 109.5
O3 C15 O2 121.70(14)
O3 C15 C5 129.53(14)
O2 C15 C5 108.76(13)
O5 C16 O4 123.53(14)
O5 C16 C17 125.55(15)
O4 C16 C17 110.92(14)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.3728(18)
O1 C12 1.3746(18)
O2 C15 1.3603(18)
O2 C7 1.4691(18)
O3 C15 1.209(2)
O4 C16 1.353(2)
O4 C3 1.4562(17)
O5 C16 1.204(2)
C1 C2 1.332(2)
C1 C14 1.504(2)
C1 C10 1.510(2)
C2 C3 1.488(2)
C2 H10 0.9300
C3 C4 1.560(2)
C3 H9 0.9800
C4 C5 1.502(2)
C4 H8A 0.9700
C4 H8B 0.9700
C5 C6 1.327(2)
C5 C15 1.477(2)
C6 C7 1.490(2)
C6 H5 0.9300
C7 C8 1.500(2)
C7 H4 0.9800
C8 C9 1.371(2)
C8 C11 1.445(2)
C9 C10 1.510(2)
C10 H12A 0.9700
C10 H12B 0.9700
C11 C12 1.338(2)
C11 C13 1.495(2)
C12 H1 0.9300
C13 H14A 0.9600
C13 H14B 0.9600
C13 H14C 0.9600
C14 H15A 0.9600
C14 H15B 0.9600
C14 H15C 0.9600
C16 C17 1.498(2)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
C14 C1 C2 C3 16.9(2)
C10 C1 C2 C3 -158.47(13)
C16 O4 C3 C2 164.85(12)
C16 O4 C3 C4 -78.07(15)
C1 C2 C3 O4 -146.18(13)
C1 C2 C3 C4 96.92(16)
O4 C3 C4 C5 -162.27(12)
C2 C3 C4 C5 -44.89(17)
C3 C4 C5 C6 82.37(19)
C3 C4 C5 C15 -84.39(17)
C15 C5 C6 C7 2.44(16)
C4 C5 C6 C7 -165.95(13)
C15 O2 C7 C6 4.87(14)
C15 O2 C7 C8 -119.58(12)
C5 C6 C7 O2 -4.48(16)
C5 C6 C7 C8 115.37(14)
O2 C7 C8 C9 100.72(18)
C6 C7 C8 C9 -15.7(2)
O2 C7 C8 C11 -77.93(16)
C6 C7 C8 C11 165.63(13)
C11 C8 C9 O1 0.20(17)
C7 C8 C9 O1 -178.60(14)
C11 C8 C9 C10 179.84(17)
C7 C8 C9 C10 1.0(3)
C12 O1 C9 C8 -0.15(16)
C12 O1 C9 C10 -179.89(13)
C8 C9 C10 C1 -46.4(2)
O1 C9 C10 C1 133.27(12)
C2 C1 C10 C9 119.29(15)
C14 C1 C10 C9 -56.57(16)
C9 C8 C11 C12 -0.17(17)
C7 C8 C11 C12 178.78(14)
C9 C8 C11 C13 -178.84(15)
C7 C8 C11 C13 0.1(2)
C8 C11 C12 O1 0.08(18)
C13 C11 C12 O1 178.71(15)
C9 O1 C12 C11 0.04(18)
C7 O2 C15 O3 176.09(13)
C7 O2 C15 C5 -3.67(14)
C6 C5 C15 O3 -178.96(15)
C4 C5 C15 O3 -9.9(2)
C6 C5 C15 O2 0.78(16)
C4 C5 C15 O2 169.87(12)
C3 O4 C16 O5 -2.69(19)
C3 O4 C16 C17 177.24(12)
