#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/19/1511964.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_1511964
loop_
_publ_author_name
'Asai, Teigo'
'Otsuki, Sae'
'Sakurai, Hiroaki'
'Yamashita, Kouwa'
'Ozeki, Tomoji'
'Oshima, Yoshiteru'
_publ_section_title
;
 Benzophenones from an Endophytic Fungus, Graphiopsis chlorocephala, from
 Paeonia lactiflora Cultivated in the Presence of an NAD(+)-Dependent HDAC
 Inhibitor.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2058
_journal_page_last               2061
_journal_paper_doi               10.1021/ol400781b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C21 H20 O7'
_chemical_formula_sum            'C21 H20 O7'
_chemical_formula_weight         384.37
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.443(1)
_cell_angle_beta                 79.217(1)
_cell_angle_gamma                69.002(2)
_cell_formula_units_Z            2
_cell_length_a                   9.075(1)
_cell_length_b                   9.818(1)
_cell_length_c                   11.417(1)
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.78
_cell_volume                     917.25(16)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection
'Crystal Clear (Molecular Structure Corporation, 2001)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       'oscillation method, ω scans'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_radiation_source         'KEK PF-AR NW2A beamline'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6890
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11519
_diffrn_reflns_theta_full        24.45
_diffrn_reflns_theta_max         27.21
_diffrn_reflns_theta_min         2.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.0508
_exptl_absorpt_correction_T_min  0.9574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'PLATON MULABS'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0684
_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)+(0.1285P)²+0.0609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1935
_refine_ls_wR_factor_ref         0.2086
_reflns_number_gt                2832
_reflns_number_total             3763
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol400781b_si_001.cif
_cod_data_source_block           PL2-7
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1511964
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.5328(3) 0.3073(3) 0.2466(2) 0.0320(5) Uani 1 1 d .
C1' C 0.4909(3) 0.2463(3) -0.0942(2) 0.0339(6) Uani 1 1 d .
C2' C 0.3654(3) 0.1738(3) -0.0623(2) 0.0330(5) Uani 1 1 d .
C2 C 0.6531(3) 0.3268(2) 0.14165(19) 0.0290(5) Uani 1 1 d .
C3 C 0.6325(3) 0.3200(3) 0.0245(2) 0.0292(5) Uani 1 1 d .
C3' C 0.2888(3) 0.1469(3) -0.13823(19) 0.0299(5) Uani 1 1 d .
C4' C 0.1697(3) 0.0723(3) -0.0803(2) 0.0308(5) Uani 1 1 d .
C4 C 0.7420(3) 0.3455(3) -0.0736(2) 0.0325(5) Uani 1 1 d .
C5 C 0.8740(3) 0.3741(3) -0.0548(2) 0.0335(5) Uani 1 1 d .
C5' C 0.3119(4) 0.1872(4) -0.2736(2) 0.0395(6) Uani 1 1 d .
C6 C 0.8988(3) 0.3772(3) 0.0604(2) 0.0333(6) Uani 1 1 d .
C7 C 0.7876(3) 0.3534(3) 0.1595(2) 0.0293(5) Uani 1 1 d .
C8 C 0.8225(3) 0.3585(3) 0.2810(2) 0.0315(5) Uani 1 1 d .
C9 C 0.7950(3) 0.2544(3) 0.39232(19) 0.0297(5) Uani 1 1 d .
C10 C 0.8793(3) 0.2352(3) 0.4921(2) 0.0330(5) Uani 1 1 d .
C11 C 0.8757(3) 0.1260(3) 0.5943(2) 0.0354(6) Uani 1 1 d .
C12 C 0.7864(3) 0.0352(3) 0.6035(2) 0.0337(6) Uani 1 1 d D
C13 C 0.6975(3) 0.0551(3) 0.5100(2) 0.0319(5) Uani 1 1 d .
C14 C 0.6991(3) 0.1631(3) 0.40742(19) 0.0290(5) Uani 1 1 d .
C15 C 0.7799(3) -0.0842(3) 0.7131(2) 0.0423(6) Uani 1 1 d D
C16 C 0.3521(4) 0.4309(4) 0.3957(3) 0.0594(9) Uani 1 1 d D
O1 O 0.4829(2) 0.4294(2) 0.30208(15) 0.0401(5) Uani 1 1 d D
O3 O 0.5017(2) 0.2866(2) 0.01635(14) 0.0357(4) Uani 1 1 d .
O4A O 0.0842(2) 0.0599(2) -0.15545(15) 0.0379(5) Uani 1 1 d .
O4B O 0.1510(2) 0.0279(2) 0.02989(14) 0.0385(5) Uani 1 1 d .
O8 O 0.8931(2) 0.4462(2) 0.28226(16) 0.0416(5) Uani 1 1 d .
O10 O 0.9699(2) 0.3190(2) 0.49037(17) 0.0409(5) Uani 1 1 d .
O14 O 0.59786(19) 0.17086(18) 0.32910(14) 0.0321(4) Uani 1 1 d .
H1 H 0.427(3) 0.314(2) 0.231(2) 0.019(5) Uiso 1 1 d .
H1'A H 0.465(3) 0.335(3) -0.157(3) 0.037(7) Uiso 1 1 d .
H1'B H 0.592(4) 0.177(3) -0.122(2) 0.035(7) Uiso 1 1 d .
H2' H 0.340(3) 0.145(3) 0.024(2) 0.032(7) Uiso 1 1 d .
H4 H 0.732(3) 0.345(3) -0.157(2) 0.029(6) Uiso 1 1 d .
H4'A H 0.006(5) 0.026(4) -0.112(3) 0.066(10) Uiso 1 1 d .
H5 H 0.957(4) 0.394(4) -0.125(3) 0.050(8) Uiso 1 1 d .
H5'A H 0.213(5) 0.254(4) -0.300(3) 0.067(10) Uiso 1 1 d .
H5'B H 0.342(4) 0.098(4) -0.308(3) 0.066(10) Uiso 1 1 d .
H5'C H 0.382(4) 0.242(3) -0.301(3) 0.041(7) Uiso 1 1 d .
H6 H 0.999(4) 0.390(3) 0.075(3) 0.043(7) Uiso 1 1 d .
H10 H 0.960(4) 0.379(4) 0.415(4) 0.066(10) Uiso 1 1 d .
H11 H 0.936(4) 0.125(4) 0.649(3) 0.053(9) Uiso 1 1 d .
H13 H 0.626(3) -0.003(3) 0.517(2) 0.031(6) Uiso 1 1 d .
H15A H 0.817(3) -0.183(3) 0.692(3) 0.066(10) Uiso 1 1 d D
H15B H 0.670(3) -0.063(3) 0.752(3) 0.058(9) Uiso 1 1 d D
H15C H 0.849(3) -0.088(3) 0.771(2) 0.049(8) Uiso 1 1 d D
H16A H 0.265(3) 0.418(3) 0.357(2) 0.035(7) Uiso 1 1 d D
H16B H 0.320(4) 0.533(3) 0.423(3) 0.101(14) Uiso 1 1 d D
H16C H 0.390(5) 0.346(4) 0.469(3) 0.103(15) 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 0.0029 0.0015 '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 0.0101 0.0057 '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
O1 C1 O14 112.17(19)
O1 C1 C2 108.86(19)
O14 C1 C2 110.33(19)
O1 C1 H1 96.5(13)
O14 C1 H1 109.3(13)
C2 C1 H1 119.0(13)
O3 C1' C2' 105.07(19)
O3 C1' H1'A 109.3(16)
C2' C1' H1'A 113.6(16)
O3 C1' H1'B 111.0(15)
C2' C1' H1'B 110.2(16)
H1'A C1' H1'B 108(2)
C3' C2' C1' 127.4(2)
C3' C2' H2' 119.0(15)
C1' C2' H2' 113.6(15)
C7 C2 C3 119.4(2)
C7 C2 C1 119.6(2)
C3 C2 C1 120.9(2)
O3 C3 C4 124.3(2)
O3 C3 C2 115.41(19)
C4 C3 C2 120.3(2)
C2' C3' C4' 115.5(2)
C2' C3' C5' 125.4(2)
C4' C3' C5' 119.1(2)
O4B C4' O4A 122.6(2)
O4B C4' C3' 122.7(2)
O4A C4' C3' 114.74(19)
C5 C4 C3 119.6(2)
C5 C4 H4 116.7(15)
C3 C4 H4 123.6(15)
C6 C5 C4 121.0(2)
C6 C5 H5 117.3(17)
C4 C5 H5 121.7(17)
C3' C5' H5'A 108(2)
C3' C5' H5'B 109(2)
H5'A C5' H5'B 110(3)
C3' C5' H5'C 112.2(17)
H5'A C5' H5'C 104(3)
H5'B C5' H5'C 114(3)
C5 C6 C7 119.6(2)
C5 C6 H6 120.8(16)
C7 C6 H6 119.4(16)
C2 C7 C6 120.0(2)
C2 C7 C8 123.5(2)
C6 C7 C8 116.5(2)
O8 C8 C9 120.3(2)
O8 C8 C7 116.13(19)
C9 C8 C7 123.1(2)
C14 C9 C10 116.17(19)
C14 C9 C8 125.8(2)
C10 C9 C8 117.9(2)
O10 C10 C11 116.8(2)
O10 C10 C9 121.8(2)
C11 C10 C9 121.4(2)
C12 C11 C10 120.6(2)
C12 C11 H11 128(2)
C10 C11 H11 112(2)
C11 C12 C13 119.3(2)
C11 C12 C15 121.9(2)
C13 C12 C15 118.7(2)
C14 C13 C12 121.1(2)
C14 C13 H13 117.9(15)
C12 C13 H13 120.9(15)
O14 C14 C13 112.37(19)
O14 C14 C9 126.41(18)
C13 C14 C9 121.2(2)
C12 C15 H15A 112.0(18)
C12 C15 H15B 109.1(18)
H15A C15 H15B 109(2)
C12 C15 H15C 110.7(17)
H15A C15 H15C 106.4(19)
H15B C15 H15C 109.7(19)
O1 C16 H16A 106.4(15)
O1 C16 H16B 105(2)
H16A C16 H16B 114(2)
O1 C16 H16C 110(2)
H16A C16 H16C 112(2)
H16B C16 H16C 109(2)
C1 O1 C16 113.5(2)
C3 O3 C1' 118.33(18)
C4' O4A H4'A 109(2)
C10 O10 H10 103(2)
C14 O14 C1 120.16(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.379(3)
C1 O14 1.442(3)
C1 C2 1.489(3)
C1 H1 0.98(2)
C1' O3 1.437(3)
C1' C2' 1.497(3)
C1' H1'A 0.98(3)
C1' H1'B 0.98(3)
C2' C3' 1.330(3)
C2' H2' 0.97(3)
C2 C7 1.395(3)
C2 C3 1.405(3)
C3 O3 1.365(3)
C3 C4 1.391(3)
C3' C4' 1.488(3)
C3' C5' 1.497(3)
C4' O4B 1.232(3)
C4' O4A 1.311(3)
C4 C5 1.388(3)
C4 H4 0.97(3)
C5 C6 1.384(3)
C5 H5 1.03(3)
C5' H5'A 0.95(4)
C5' H5'B 0.97(4)
C5' H5'C 0.94(3)
C6 C7 1.404(3)
C6 H6 1.01(3)
C7 C8 1.495(3)
C8 O8 1.247(3)
C8 C9 1.475(3)
C9 C14 1.422(3)
C9 C10 1.428(3)
C10 O10 1.351(3)
C10 C11 1.393(3)
C11 C12 1.380(4)
C11 H11 0.90(3)
C12 C13 1.393(3)
C12 C15 1.509(3)
C13 C14 1.385(3)
C13 H13 0.99(3)
C14 O14 1.369(3)
C15 H15A 0.98(2)
C15 H15B 0.98(2)
C15 H15C 0.98(2)
C16 O1 1.440(4)
C16 H16A 1.03(2)
C16 H16B 1.04(3)
C16 H16C 1.04(3)
O4A H4'A 0.90(4)
O10 H10 0.92(4)
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
O4A H4'A O4B 0.90(4) 1.73(4) 2.636(2) 176(4) 2
O10 H10 O8 0.92(4) 1.64(4) 2.509(3) 156(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
O3 C1' C2' C3' 164.1(2)
O1 C1 C2 C7 55.3(3)
O14 C1 C2 C7 -68.2(3)
O1 C1 C2 C3 -124.2(2)
O14 C1 C2 C3 112.3(2)
C7 C2 C3 O3 177.0(2)
C1 C2 C3 O3 -3.5(3)
C7 C2 C3 C4 -2.6(3)
C1 C2 C3 C4 176.9(2)
C1' C2' C3' C4' 179.8(2)
C1' C2' C3' C5' -1.1(4)
C2' C3' C4' O4B -5.3(4)
C5' C3' C4' O4B 175.6(2)
C2' C3' C4' O4A 173.5(2)
C5' C3' C4' O4A -5.6(3)
O3 C3 C4 C5 -177.9(2)
C2 C3 C4 C5 1.6(4)
C3 C4 C5 C6 0.2(4)
C4 C5 C6 C7 -1.0(4)
C3 C2 C7 C6 1.7(3)
C1 C2 C7 C6 -177.8(2)
C3 C2 C7 C8 -178.2(2)
C1 C2 C7 C8 2.3(3)
C5 C6 C7 C2 0.1(4)
C5 C6 C7 C8 -180.0(2)
C2 C7 C8 O8 -147.0(2)
C6 C7 C8 O8 33.0(3)
C2 C7 C8 C9 40.5(3)
C6 C7 C8 C9 -139.5(2)
O8 C8 C9 C14 171.3(2)
C7 C8 C9 C14 -16.5(4)
O8 C8 C9 C10 -13.0(3)
C7 C8 C9 C10 159.2(2)
C14 C9 C10 O10 -177.7(2)
C8 C9 C10 O10 6.2(4)
C14 C9 C10 C11 4.3(4)
C8 C9 C10 C11 -171.8(2)
O10 C10 C11 C12 -179.9(2)
C9 C10 C11 C12 -1.8(4)
C10 C11 C12 C13 -0.9(4)
C10 C11 C12 C15 -180.0(2)
C11 C12 C13 C14 0.9(4)
C15 C12 C13 C14 180.0(2)
C12 C13 C14 O14 -176.7(2)
C12 C13 C14 C9 1.8(4)
C10 C9 C14 O14 174.0(2)
C8 C9 C14 O14 -10.3(4)
C10 C9 C14 C13 -4.3(3)
C8 C9 C14 C13 171.4(2)
O14 C1 O1 C16 -64.9(3)
C2 C1 O1 C16 172.7(2)
C4 C3 O3 C1' 12.8(3)
C2 C3 O3 C1' -166.8(2)
C2' C1' O3 C3 163.4(2)
C13 C14 O14 C1 154.4(2)
C9 C14 O14 C1 -24.0(3)
O1 C1 O14 C14 -43.5(3)
C2 C1 O14 C14 78.0(3)
