#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/74/1517440.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_1517440
loop_
_publ_author_name
'Liu, Gang'
'Mei, Guangjian'
'Chen, Runwen'
'Yuan, Haina'
'Yang, Zhen'
'Li, Chuang-Chuang'
_publ_section_title
;
 Total Synthesis of Aplykurodinone-1.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4380
_journal_paper_doi               10.1021/ol502220r
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H14 O3'
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 100.429(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1115(2)
_cell_length_b                   9.6680(2)
_cell_length_c                   10.4467(7)
_cell_measurement_reflns_used    5409
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      7.20
_cell_volume                     1004.38(8)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_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  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5691
_diffrn_reflns_theta_full        68.26
_diffrn_reflns_theta_max         68.26
_diffrn_reflns_theta_min         7.24
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.1366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                1481
_reflns_number_total             1783
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol502220r_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1517440.cif.'
_cod_original_cell_volume        1004.38(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1517440
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 0.64435(10) 0.95476(14) 0.67517(11) 0.0314(3) Uani 1 1 d .
O2 O 0.01702(11) 1.16029(12) 0.55481(11) 0.0310(3) Uani 1 1 d .
O3 O 0.43925(10) 0.87264(11) 0.60277(10) 0.0223(3) Uani 1 1 d .
C1 C 0.05568(16) 0.97589(17) 0.84318(16) 0.0263(4) Uani 1 1 d .
H1 H 0.0236 0.9254 0.9069 0.032 Uiso 1 1 calc R
C2 C 0.20282(15) 1.00503(16) 0.84883(14) 0.0204(4) Uani 1 1 d .
C3 C 0.20272(14) 1.10168(15) 0.72995(14) 0.0185(4) Uani 1 1 d .
H3 H 0.2253 1.1950 0.7634 0.022 Uiso 1 1 calc R
C4 C 0.30022(14) 1.06464(16) 0.63873(14) 0.0193(4) Uani 1 1 d .
H4 H 0.2751 1.1186 0.5586 0.023 Uiso 1 1 calc R
C5 C 0.44775(16) 1.09446(17) 0.69453(16) 0.0254(4) Uani 1 1 d .
H5A H 0.4771 1.1782 0.6568 0.030 Uiso 1 1 calc R
H5B H 0.4609 1.1056 0.7883 0.030 Uiso 1 1 calc R
C6 C 0.52465(15) 0.97147(17) 0.65940(13) 0.0221(4) Uani 1 1 d .
C7 C 0.05619(16) 1.10389(16) 0.65901(16) 0.0235(4) Uani 1 1 d .
C8 C -0.02488(16) 1.02838(17) 0.73940(17) 0.0276(4) Uani 1 1 d .
H8 H -0.1179 1.0187 0.7208 0.033 Uiso 1 1 calc R
C9 C 0.27581(16) 0.86726(17) 0.83291(15) 0.0233(4) Uani 1 1 d .
H9A H 0.3722 0.8808 0.8571 0.028 Uiso 1 1 calc R
H9B H 0.2492 0.7984 0.8908 0.028 Uiso 1 1 calc R
C10 C 0.24251(15) 0.81518(16) 0.69344(15) 0.0221(4) Uani 1 1 d .
H10A H 0.2797 0.7232 0.6887 0.026 Uiso 1 1 calc R
H10B H 0.1457 0.8089 0.6669 0.026 Uiso 1 1 calc R
C11 C 0.29861(15) 0.91045(16) 0.60139(14) 0.0203(4) Uani 1 1 d .
H11 H 0.2471 0.8987 0.5132 0.024 Uiso 1 1 calc R
C12 C 0.26283(17) 1.07259(19) 0.97913(15) 0.0284(4) Uani 1 1 d .
H12A H 0.2114 1.1532 0.9920 0.043 Uiso 1 1 calc R
H12B H 0.3543 1.0988 0.9785 0.043 Uiso 1 1 calc R
H12C H 0.2604 1.0081 1.0485 0.043 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
C6 O3 C11 111.72(12)
C8 C1 C2 114.51(15)
C8 C1 H1 122.7
C2 C1 H1 122.7
C1 C2 C12 110.14(12)
C1 C2 C9 108.80(13)
C12 C2 C9 110.04(12)
C1 C2 C3 102.92(12)
C12 C2 C3 113.36(13)
C9 C2 C3 111.30(12)
C4 C3 C7 112.16(12)
C4 C3 C2 116.68(12)
C7 C3 C2 104.81(12)
C4 C3 H3 107.6
C7 C3 H3 107.6
C2 C3 H3 107.6
C5 C4 C3 114.35(12)
C5 C4 C11 104.13(12)
C3 C4 C11 113.90(12)
C5 C4 H4 108.1
C3 C4 H4 108.1
C11 C4 H4 108.1
C6 C5 C4 105.68(12)
C6 C5 H5A 110.6
C4 C5 H5A 110.6
C6 C5 H5B 110.6
C4 C5 H5B 110.6
H5A C5 H5B 108.7
O1 C6 O3 120.86(15)
O1 C6 C5 128.73(15)
O3 C6 C5 110.41(13)
O2 C7 C8 127.48(15)
O2 C7 C3 124.62(15)
C8 C7 C3 107.90(13)
C1 C8 C7 109.39(14)
C1 C8 H8 125.3
C7 C8 H8 125.3
C10 C9 C2 111.17(12)
C10 C9 H9A 109.4
C2 C9 H9A 109.4
C10 C9 H9B 109.4
C2 C9 H9B 109.4
H9A C9 H9B 108.0
C11 C10 C9 111.33(13)
C11 C10 H10A 109.4
C9 C10 H10A 109.4
C11 C10 H10B 109.4
C9 C10 H10B 109.4
H10A C10 H10B 108.0
O3 C11 C10 108.44(12)
O3 C11 C4 105.85(11)
C10 C11 C4 114.58(12)
O3 C11 H11 109.3
C10 C11 H11 109.3
C4 C11 H11 109.3
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.2025(18)
O2 C7 1.2178(19)
O3 C6 1.3505(19)
O3 C11 1.4659(18)
C1 C8 1.333(2)
C1 C2 1.505(2)
C1 H1 0.9300
C2 C12 1.533(2)
C2 C9 1.546(2)
C2 C3 1.554(2)
C3 C4 1.532(2)
C3 C7 1.532(2)
C3 H3 0.9800
C4 C5 1.528(2)
C4 C11 1.540(2)
C4 H4 0.9800
C5 C6 1.502(2)
C5 H5A 0.9700
C5 H5B 0.9700
C7 C8 1.469(2)
C8 H8 0.9300
C9 C10 1.521(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.514(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11 0.9800
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 46896150
