#------------------------------------------------------------------------------
#$Date: 2019-11-04 12:51:47 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/42/4034252.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_4034252
loop_
_publ_author_name
'Qiao, Liang'
'Duan, Zhongwei'
'Chen, Yinghan'
'Luan, Yepeng'
'Gu, Qianqun'
'Liu, Yan-Kai'
'Li, Dehai'
_publ_section_title
;
 Aspergiolides A and B: Core Structural Establishment and Synthesis of
 Structural Analogues.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4451
_journal_page_last               4457
_journal_paper_doi               10.1021/acs.joc.8b03185
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         C25H16O4
_chemical_formula_sum            'C25 H16 O4'
_chemical_formula_weight         380.38
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.578(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.417(4)
_cell_length_b                   16.255(7)
_cell_length_c                   12.488(5)
_cell_measurement_reflns_used    3247
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.11
_cell_volume                     1841.4(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Bruker
_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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9988
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0435
_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)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                1925
_reflns_number_total             3247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b03185_si_002.cif
_cod_data_source_block           2
_cod_original_cell_volume        1841.4(12)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4034252
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.37388(17) 0.23163(10) 0.25077(12) 0.0706(5) Uani 1 1 d .
O2 O 0.12685(16) 0.10872(10) 0.26528(12) 0.0686(5) Uani 1 1 d .
O3 O 0.20073(14) 0.03031(9) 0.41363(11) 0.0524(4) Uani 1 1 d .
O4 O 0.6933(2) 0.09580(13) 0.82393(13) 0.1088(7) Uani 1 1 d .
C1 C 0.1871(2) 0.30741(14) 0.45082(17) 0.0586(6) Uani 1 1 d .
H1A H 0.2136 0.2662 0.5042 0.070 Uiso 1 1 calc R
C2 C 0.1038(3) 0.37294(15) 0.4687(2) 0.0712(7) Uani 1 1 d .
H2A H 0.0750 0.3761 0.5342 0.085 Uiso 1 1 calc R
C3 C 0.0631(3) 0.43398(15) 0.3895(2) 0.0746(7) Uani 1 1 d .
H3A H 0.0064 0.4781 0.4016 0.089 Uiso 1 1 calc R
C4 C 0.1063(3) 0.42969(15) 0.2931(2) 0.0761(7) Uani 1 1 d .
H4A H 0.0786 0.4709 0.2399 0.091 Uiso 1 1 calc R
C5 C 0.1908(2) 0.36419(14) 0.27459(19) 0.0631(6) Uani 1 1 d .
H5A H 0.2199 0.3617 0.2092 0.076 Uiso 1 1 calc R
C6 C 0.2322(2) 0.30218(12) 0.35336(15) 0.0464(5) Uani 1 1 d U
C7 C 0.3211(2) 0.23191(13) 0.33020(16) 0.0500(5) Uani 1 1 d U
C8 C 0.3342(2) 0.15685(12) 0.40451(15) 0.0447(5) Uani 1 1 d .
C9 C 0.2152(2) 0.09964(13) 0.35521(17) 0.0507(5) Uani 1 1 d .
C10 C 0.2923(2) 0.01642(12) 0.51912(16) 0.0451(5) Uani 1 1 d .
C11 C 0.2547(2) -0.05252(13) 0.57269(18) 0.0513(5) Uani 1 1 d .
C12 C 0.1227(2) -0.10517(13) 0.51968(19) 0.0668(7) Uani 1 1 d .
H12A H 0.1158 -0.1494 0.5690 0.100 Uiso 1 1 calc R
H12B H 0.1335 -0.1274 0.4510 0.100 Uiso 1 1 calc R
H12C H 0.0349 -0.0723 0.5052 0.100 Uiso 1 1 calc R
C13 C 0.3444(3) -0.06829(14) 0.67833(19) 0.0614(6) Uani 1 1 d .
H13A H 0.3231 -0.1142 0.7156 0.074 Uiso 1 1 calc R
C14 C 0.4642(2) -0.01982(14) 0.73223(17) 0.0576(6) Uani 1 1 d .
C15 C 0.5481(3) -0.04443(17) 0.84941(18) 0.0898(9) Uani 1 1 d .
H15A H 0.5056 -0.0936 0.8702 0.135 Uiso 1 1 calc R
H15B H 0.5422 -0.0009 0.9000 0.135 Uiso 1 1 calc R
H15C H 0.6495 -0.0544 0.8521 0.135 Uiso 1 1 calc R
C16 C 0.4977(2) 0.04944(13) 0.67610(15) 0.0479(5) Uani 1 1 d .
C17 C 0.4101(2) 0.06812(12) 0.56642(15) 0.0424(5) Uani 1 1 d .
C18 C 0.4341(2) 0.14124(12) 0.50440(15) 0.0424(5) Uani 1 1 d .
C19 C 0.5636(2) 0.19352(13) 0.55539(16) 0.0468(5) Uani 1 1 d .
C20 C 0.6517(2) 0.17578(13) 0.66280(16) 0.0512(5) Uani 1 1 d .
C21 C 0.7767(2) 0.22323(15) 0.71090(19) 0.0648(6) Uani 1 1 d .
H21A H 0.8335 0.2105 0.7822 0.078 Uiso 1 1 calc R
C22 C 0.8169(3) 0.28758(16) 0.6555(2) 0.0713(7) Uani 1 1 d .
H22A H 0.9002 0.3185 0.6886 0.086 Uiso 1 1 calc R
C23 C 0.7322(3) 0.30640(16) 0.5495(2) 0.0715(7) Uani 1 1 d .
H23A H 0.7588 0.3503 0.5112 0.086 Uiso 1 1 calc R
C24 C 0.6077(2) 0.26025(14) 0.49968(19) 0.0627(6) Uani 1 1 d .
H24A H 0.5524 0.2736 0.4282 0.075 Uiso 1 1 calc R
C25 C 0.6190(2) 0.10575(15) 0.72844(17) 0.0601(6) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 O3 C10 121.01(16)
C2 C1 C6 120.6(2)
C1 C2 C3 120.1(2)
C4 C3 C2 120.1(2)
C3 C4 C5 120.2(2)
C4 C5 C6 120.3(2)
C5 C6 C1 118.7(2)
C5 C6 C7 118.98(18)
C1 C6 C7 122.33(19)
O1 C7 C6 122.2(2)
O1 C7 C8 120.59(19)
C6 C7 C8 117.08(17)
C18 C8 C9 121.88(19)
C18 C8 C7 128.98(18)
C9 C8 C7 109.11(16)
O2 C9 O3 116.84(19)
O2 C9 C8 124.8(2)
O3 C9 C8 118.36(18)
O3 C10 C17 121.82(18)
O3 C10 C11 114.36(18)
C17 C10 C11 123.82(19)
C13 C11 C10 115.8(2)
C13 C11 C12 122.2(2)
C10 C11 C12 121.98(19)
C11 C13 C14 124.3(2)
C13 C14 C16 118.24(19)
C13 C14 C15 117.5(2)
C16 C14 C15 124.3(2)
C14 C16 C17 119.9(2)
C14 C16 C25 121.84(19)
C17 C16 C25 118.22(19)
C10 C17 C16 117.92(18)
C10 C17 C18 118.91(17)
C16 C17 C18 123.09(18)
C8 C18 C17 117.69(18)
C8 C18 C19 124.73(19)
C17 C18 C19 117.58(17)
C20 C19 C24 116.91(19)
C20 C19 C18 119.94(19)
C24 C19 C18 123.11(18)
C21 C20 C19 120.6(2)
C21 C20 C25 117.45(19)
C19 C20 C25 121.92(19)
C22 C21 C20 121.4(2)
C21 C22 C23 119.2(2)
C22 C23 C24 120.6(2)
C23 C24 C19 121.3(2)
O4 C25 C16 121.6(2)
O4 C25 C20 119.5(2)
C16 C25 C20 118.90(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.223(2)
O2 C9 1.214(2)
O3 C9 1.369(2)
O3 C10 1.386(2)
O4 C25 1.220(2)
C1 C2 1.376(3)
C1 C6 1.395(3)
C2 C3 1.380(3)
C3 C4 1.373(3)
C4 C5 1.385(3)
C5 C6 1.389(3)
C6 C7 1.490(3)
C7 C8 1.518(3)
C8 C18 1.370(2)
C8 C9 1.459(3)
C10 C17 1.390(3)
C10 C11 1.398(3)
C11 C13 1.386(3)
C11 C12 1.508(3)
C13 C14 1.393(3)
C14 C16 1.406(3)
C14 C15 1.518(3)
C16 C17 1.429(3)
C16 C25 1.473(3)
C17 C18 1.469(3)
C18 C19 1.483(3)
C19 C20 1.404(3)
C19 C24 1.410(3)
C20 C21 1.401(3)
C20 C25 1.483(3)
C21 C22 1.362(3)
C22 C23 1.384(3)
C23 C24 1.390(3)
