#------------------------------------------------------------------------------
#$Date: 2015-09-05 02:40:51 +0300 (Sat, 05 Sep 2015) $
#$Revision: 154293 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/97/1529712.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_1529712
loop_
_publ_author_name
'Liu, Yayue'
'Yang, Qin'
'Xia, Guoping'
'Huang, Hongbo'
'Li, Hanxiang'
'Ma, Lin'
'Lu, Yongjun'
'He, Lei'
'Xia, Xuekui'
'She, Zhigang'
_publ_section_title
;
 Polyketides with α-Glucosidase Inhibitory Activity from a Mangrove
 Endophytic Fungus, Penicillium sp. HN29-3B1.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1816
_journal_page_last               1822
_journal_paper_doi               10.1021/np500885f
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H14 O5'
_chemical_formula_weight         238.23
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8143(4)
_cell_length_b                   7.9133(3)
_cell_length_c                   18.3147(9)
_cell_measurement_temperature    293(2)
_cell_volume                     1132.52(9)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_laue_measured_fraction_full 0.983
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5807
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.963
_diffrn_reflns_theta_min         4.829
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.02(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0667P)²+0.8075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.669
_reflns_friedel_fraction_full    0.951
_reflns_friedel_fraction_max     0.965
_reflns_number_gt                1890
_reflns_number_total             1990
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np500885f_si_002.cif
_cod_data_source_block           compound_4
_cod_database_code               1529712
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O4 O -0.1479(3) 1.0537(3) 0.31466(12) 0.0232(5) Uani 1 1 d . .
H4 H -0.1405 1.0314 0.2710 0.035 Uiso 1 1 calc R U
O2 O 0.0993(4) 1.1979(3) 0.67960(14) 0.0322(6) Uani 1 1 d . .
H2 H 0.1708 1.2737 0.6775 0.048 Uiso 1 1 calc R U
O3 O 0.1179(3) 0.5162(3) 0.33017(12) 0.0243(6) Uani 1 1 d . .
H3 H 0.1536 0.4480 0.3602 0.036 Uiso 1 1 calc R U
C4 C -0.0118(4) 0.7822(4) 0.32261(18) 0.0205(7) Uani 1 1 d . .
H4A H -0.0294 0.7628 0.2731 0.025 Uiso 1 1 calc R U
C5 C -0.0367(4) 0.9628(4) 0.42808(17) 0.0202(7) Uani 1 1 d . .
H5 H -0.0721 1.0641 0.4490 0.024 Uiso 1 1 calc R U
O1 O 0.2138(4) 1.1552(3) 0.53148(14) 0.0323(6) Uani 1 1 d . .
C7 C 0.0680(4) 0.6620(4) 0.36538(17) 0.0194(7) Uani 1 1 d . .
C8 C -0.0652(4) 0.9319(4) 0.35439(17) 0.0192(7) Uani 1 1 d . .
C9 C 0.0401(4) 0.7919(4) 0.60821(18) 0.0206(7) Uani 1 1 d . .
C10 C 0.0448(4) 0.8416(4) 0.47027(18) 0.0193(7) Uani 1 1 d . .
C11 C 0.0756(5) 0.8877(4) 0.67743(18) 0.0234(8) Uani 1 1 d . .
H11A H 0.1458 0.8212 0.7103 0.028 Uiso 1 1 calc R U
H11B H -0.0303 0.9170 0.7020 0.028 Uiso 1 1 calc R U
C12 C 0.1591(5) 1.0409(4) 0.56997(19) 0.0244(8) Uani 1 1 d . .
C13 C 0.0787(5) 0.8811(4) 0.54763(17) 0.0209(7) Uani 1 1 d . .
C14 C 0.0965(4) 0.6880(4) 0.43923(18) 0.0204(7) Uani 1 1 d . .
H14 H 0.1488 0.6052 0.4676 0.024 Uiso 1 1 calc R U
C15 C -0.0344(5) 0.6193(4) 0.61216(19) 0.0254(8) Uani 1 1 d . .
H15A H 0.0522 0.5407 0.6272 0.038 Uiso 1 1 calc R U
H15B H -0.0771 0.5875 0.5650 0.038 Uiso 1 1 calc R U
H15C H -0.1265 0.6184 0.6469 0.038 Uiso 1 1 calc R U
C16 C 0.1709(5) 1.0470(4) 0.65269(19) 0.0274(8) Uani 1 1 d . .
H16 H 0.2911 1.0396 0.6676 0.033 Uiso 1 1 calc R U
O5 O 0.7784(4) 0.2218(4) 0.60726(18) 0.0458(8) Uani 1 1 d D .
H5A H 0.880(4) 0.252(8) 0.618(4) 0.09(2) Uiso 1 1 d D .
H5B H 0.760(9) 0.275(7) 0.567(2) 0.08(2) Uiso 1 1 d D .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C7 C4 C8 119.2(3)
C10 C5 C8 119.5(3)
O3 C7 C4 116.0(3)
O3 C7 C14 122.4(3)
C4 C7 C14 121.6(3)
O4 C8 C4 121.4(3)
O4 C8 C5 117.9(3)
C4 C8 C5 120.7(3)
C13 C9 C15 127.5(3)
C13 C9 C11 112.9(3)
C15 C9 C11 119.6(3)
C5 C10 C14 120.4(3)
C5 C10 C13 118.1(3)
C14 C10 C13 121.5(3)
C9 C11 C16 104.8(3)
O1 C12 C13 128.7(3)
O1 C12 C16 122.0(3)
C13 C12 C16 109.3(3)
C9 C13 C12 108.5(3)
C9 C13 C10 129.7(3)
C12 C13 C10 121.8(3)
C7 C14 C10 118.6(3)
O2 C16 C12 110.6(3)
O2 C16 C11 113.7(3)
C12 C16 C11 103.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C8 1.369(4)
O2 C16 1.407(4)
O3 C7 1.378(4)
C4 C7 1.381(5)
C4 C8 1.385(5)
C5 C10 1.387(5)
C5 C8 1.390(5)
O1 C12 1.223(4)
C7 C14 1.386(5)
C9 C13 1.349(5)
C9 C15 1.486(5)
C9 C11 1.503(5)
C10 C14 1.401(5)
C10 C13 1.475(5)
C11 C16 1.533(5)
C12 C13 1.471(5)
C12 C16 1.519(5)
