#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/41/1514177.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_1514177
loop_
_publ_author_name
'Li, Hanxiang'
'Jiang, Jieyi'
'Liu, Zhaoming'
'Lin, Shaoe'
'Xia, Guoping'
'Xia, Xuekui'
'Ding, Bo'
'He, Lei'
'Lu, Yongjun'
'She, Zhigang'
_publ_section_title
;
 Peniphenones A-D from the Mangrove Fungus Penicillium dipodomyicola
 HN4-3A as Inhibitors of Mycobacterium tuberculosis Phosphatase MptpB.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              800
_journal_page_last               806
_journal_paper_doi               10.1021/np400880w
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H16 O6'
_chemical_formula_weight         292.28
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.52790(10)
_cell_length_b                   15.4658(3)
_cell_length_c                   19.9377(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1396.19(5)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17232
_diffrn_reflns_theta_full        62.71
_diffrn_reflns_theta_max         62.71
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0255
_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)+(0.0532P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                2079
_reflns_number_total             2233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np400880w_si_005.cif
_cod_data_source_block           peniphenone_D
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1514176--1514179.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1514177
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_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
O5 O 0.1857(3) 0.51850(6) -0.05387(5) 0.0366(3) Uani 1 1 d .
H5 H 0.2540 0.5676 -0.0549 0.055 Uiso 1 1 calc R
O4 O 0.3285(3) 0.35740(6) 0.06870(5) 0.0378(3) Uani 1 1 d .
O1 O 0.8607(3) 0.56166(7) 0.19963(5) 0.0403(3) Uani 1 1 d .
H1A H 0.7997 0.5167 0.1827 0.061 Uiso 1 1 calc R
O2 O 0.2332(2) 0.70706(6) 0.04677(4) 0.0316(2) Uani 1 1 d .
H2A H 0.1191 0.7482 0.0449 0.047 Uiso 1 1 calc R
C3 C 0.4290(4) 0.75427(9) 0.22178(7) 0.0329(4) Uani 1 1 d .
H3A H 0.3915 0.7947 0.2552 0.039 Uiso 1 1 calc R
C6 C 0.5549(3) 0.63583(9) 0.11983(7) 0.0285(3) Uani 1 1 d .
O3 O 0.6475(3) 0.41393(7) 0.14256(5) 0.0451(3) Uani 1 1 d .
O6 O -0.0443(2) 0.83968(6) 0.09097(5) 0.0356(3) Uani 1 1 d .
C4 C 0.2863(4) 0.76377(9) 0.15942(6) 0.0291(3) Uani 1 1 d .
C12 C 0.7684(4) 0.67680(11) 0.30257(7) 0.0419(4) Uani 1 1 d .
H12A H 0.7067 0.7225 0.3320 0.063 Uiso 1 1 calc R
H12B H 0.9789 0.6789 0.2971 0.063 Uiso 1 1 calc R
H12C H 0.7133 0.6220 0.3215 0.063 Uiso 1 1 calc R
C11 C 0.2888(4) 0.47716(9) -0.00029(6) 0.0299(3) Uani 1 1 d .
C5 C 0.3532(3) 0.70284(9) 0.10847(6) 0.0279(3) Uani 1 1 d .
C1 C 0.6759(3) 0.62753(9) 0.18376(7) 0.0318(3) Uani 1 1 d .
C13 C 0.0836(4) 0.83398(9) 0.14640(7) 0.0318(4) Uani 1 1 d .
C7 C 0.6526(3) 0.57928(9) 0.06208(7) 0.0303(3) Uani 1 1 d .
H7A H 0.6503 0.6140 0.0215 0.036 Uiso 1 1 calc R
H7B H 0.8556 0.5621 0.0700 0.036 Uiso 1 1 calc R
C2 C 0.6213(4) 0.68775(10) 0.23521(7) 0.0329(4) Uani 1 1 d .
C9 C 0.4977(4) 0.42362(9) 0.09221(7) 0.0336(4) Uani 1 1 d .
C8 C 0.4732(3) 0.49887(9) 0.04945(7) 0.0298(3) Uani 1 1 d .
C15 C 0.2834(4) 0.32889(9) -0.05073(7) 0.0393(4) Uani 1 1 d .
H15A H 0.2148 0.2709 -0.0437 0.059 Uiso 1 1 calc R
H15B H 0.4949 0.3290 -0.0539 0.059 Uiso 1 1 calc R
H15C H 0.2007 0.3512 -0.0916 0.059 Uiso 1 1 calc R
C14 C 0.0297(4) 0.90281(10) 0.19793(8) 0.0436(4) Uani 1 1 d .
H14A H -0.1095 0.9440 0.1807 0.065 Uiso 1 1 calc R
H14B H 0.2122 0.9315 0.2081 0.065 Uiso 1 1 calc R
H14C H -0.0480 0.8769 0.2380 0.065 Uiso 1 1 calc R
C10 C 0.1886(4) 0.38489(9) 0.00729(7) 0.0341(4) Uani 1 1 d .
H10A H -0.0266 0.3828 0.0122 0.041 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 0.0181 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
_geom_angle_site_symmetry_1
C11 O5 H5 109.5 .
C9 O4 C10 108.51(10) .
C1 O1 H1A 109.5 .
C5 O2 H2A 109.5 .
C2 C3 C4 122.73(13) .
C2 C3 H3A 118.6 .
C4 C3 H3A 118.6 .
C1 C6 C5 118.22(13) .
C1 C6 C7 121.88(13) .
C5 C6 C7 119.73(12) .
O6 O6 C13 0(10) 1
C3 C4 C5 117.70(13) .
C3 C4 C13 121.88(12) .
C5 C4 C13 120.40(12) .
C2 C12 H12A 109.5 .
C2 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C2 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
O5 C11 C8 133.89(13) .
O5 C11 C10 115.52(13) .
C8 C11 C10 110.57(12) .
O2 C5 C6 116.55(11) .
O2 C5 C4 122.42(13) .
C6 C5 C4 121.02(13) .
O1 C1 C6 121.70(13) .
O1 C1 C2 115.83(12) .
C6 C1 C2 122.45(14) .
O6 C13 O6 0.00(9) 1
O6 C13 C4 120.39(12) 1
O6 C13 C4 120.39(12) .
O6 C13 C14 118.68(14) 1
O6 C13 C14 118.68(14) .
C4 C13 C14 120.90(13) .
C8 C7 C6 116.55(12) .
C8 C7 H7A 108.2 .
C6 C7 H7A 108.2 .
C8 C7 H7B 108.2 .
C6 C7 H7B 108.2 .
H7A C7 H7B 107.3 .
C3 C2 C1 117.70(13) .
C3 C2 C12 122.50(13) .
C1 C2 C12 119.80(13) .
O3 C9 O4 120.20(13) .
O3 C9 C8 128.75(15) .
O4 C9 C8 111.03(13) .
C11 C8 C9 106.41(13) .
C11 C8 C7 131.83(13) .
C9 C8 C7 121.61(13) .
C10 C15 H15A 109.5 .
C10 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C10 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
O4 C10 C11 103.43(12) .
O4 C10 C15 110.91(12) .
C11 C10 C15 112.46(12) .
O4 C10 H10A 110.0 .
C11 C10 H10A 110.0 .
C15 C10 H10A 110.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O5 C11 1.3296(16) .
O5 H5 0.8200 .
O4 C9 1.3622(18) .
O4 C10 1.4427(17) .
O1 C1 1.3555(18) .
O1 H1A 0.8200 .
O2 C5 1.3463(17) .
O2 H2A 0.8200 .
C3 C2 1.374(2) .
C3 C4 1.409(2) .
C3 H3A 0.9300 .
C6 C1 1.393(2) .
C6 C5 1.400(2) .
C6 C7 1.5120(19) .
O3 C9 1.2206(19) .
O6 O6 0.000(4) 1
O6 C13 1.2507(18) .
C4 C5 1.4182(19) .
C4 C13 1.445(2) .
C12 C2 1.509(2) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C11 C8 1.339(2) .
C11 C10 1.505(2) .
C1 C2 1.408(2) .
C13 O6 1.2507(18) 1
C13 C14 1.499(2) .
C7 C8 1.507(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C9 C8 1.447(2) .
C15 C10 1.5074(19) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C10 H10A 0.9800 .
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
O2 H2A O6 0.82 1.84 2.5619(13) 145.7 1
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C3 C4 C5 -1.8(2) . .
C2 C3 C4 C13 179.67(14) . .
C1 C6 C5 O2 -177.81(12) . .
C7 C6 C5 O2 6.80(19) . .
C1 C6 C5 C4 3.6(2) . .
C7 C6 C5 C4 -171.81(14) . .
C3 C4 C5 O2 -178.74(13) . .
C13 C4 C5 O2 -0.2(2) . .
C3 C4 C5 C6 -0.2(2) . .
C13 C4 C5 C6 178.35(13) . .
C5 C6 C1 O1 176.49(14) . .
C7 C6 C1 O1 -8.2(2) . .
C5 C6 C1 C2 -5.2(2) . .
C7 C6 C1 C2 170.06(14) . .
O6 O6 C13 C4 0.00(6) 1 .
O6 O6 C13 C14 0.00(8) 1 .
C3 C4 C13 O6 -178.54(14) . 1
C5 C4 C13 O6 3.0(2) . 1
C3 C4 C13 O6 -178.54(14) . .
C5 C4 C13 O6 3.0(2) . .
C3 C4 C13 C14 3.5(2) . .
C5 C4 C13 C14 -175.03(15) . .
C1 C6 C7 C8 93.99(17) . .
C5 C6 C7 C8 -90.80(16) . .
C4 C3 C2 C1 0.3(2) . .
C4 C3 C2 C12 -178.65(15) . .
O1 C1 C2 C3 -178.30(13) . .
C6 C1 C2 C3 3.3(2) . .
O1 C1 C2 C12 0.7(2) . .
C6 C1 C2 C12 -177.70(14) . .
C10 O4 C9 O3 -176.98(13) . .
C10 O4 C9 C8 1.74(16) . .
O5 C11 C8 C9 -179.31(16) . .
C10 C11 C8 C9 -1.17(16) . .
O5 C11 C8 C7 -3.9(3) . .
C10 C11 C8 C7 174.24(14) . .
O3 C9 C8 C11 178.25(16) . .
O4 C9 C8 C11 -0.33(17) . .
O3 C9 C8 C7 2.3(2) . .
O4 C9 C8 C7 -176.32(12) . .
C6 C7 C8 C11 110.03(17) . .
C6 C7 C8 C9 -75.14(18) . .
C9 O4 C10 C11 -2.28(15) . .
C9 O4 C10 C15 118.50(13) . .
O5 C11 C10 O4 -179.34(12) . .
C8 C11 C10 O4 2.15(16) . .
O5 C11 C10 C15 60.94(18) . .
C8 C11 C10 C15 -117.57(14) . .
