#------------------------------------------------------------------------------
#$Date: 2016-03-21 16:11:36 +0100 (lun 21 de mar de 2016) $
#$Revision: 178772 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/26/4102686.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_4102686
loop_
_publ_author_name
'Yandong Zhang'
'Samuel J. Danishefsky'
_publ_section_title
;
 Total Synthesis of (\+-)-Aplykurodinone-1: Traceless Stereochemical
 Guidance
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9928
_journal_page_last               9928
_journal_paper_doi               10.1021/ja105280j
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_chemical_name_systematic
; 
 ? 
;
_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                 110.181(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.052(7)
_cell_length_b                   10.973(5)
_cell_length_c                   8.450(4)
_cell_measurement_reflns_used    3677
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.59
_cell_volume                     1048.9(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.1120
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13730
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_correction_T_min  0.9538
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0698
_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)+(0.0607P)²+1.9674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.2051
_reflns_number_gt                1463
_reflns_number_total             2604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105280j_si_001.cif
_cod_data_source_block           ydws10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'EMPIRICAL' changed to
'empirical' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4102686
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 0.5344(2) 0.1305(2) 0.1149(3) 0.0346(6) Uani 1 1 d .
O2 O 0.7180(2) 0.0770(2) 0.1413(3) 0.0298(6) Uani 1 1 d .
O3 O 0.9251(2) 0.2253(2) -0.1992(3) 0.0305(6) Uani 1 1 d .
C1 C 0.6082(3) 0.1144(3) 0.0492(5) 0.0264(8) Uani 1 1 d .
C2 C 0.7864(3) 0.0545(3) 0.0289(4) 0.0247(7) Uani 1 1 d .
H2A H 0.8698 0.0830 0.0836 0.030 Uiso 1 1 calc R
C3 C 0.7844(3) -0.0824(3) -0.0068(4) 0.0261(7) Uani 1 1 d .
H3A H 0.7022 -0.1130 -0.0403 0.031 Uiso 1 1 calc R
H3B H 0.8325 -0.1260 0.0967 0.031 Uiso 1 1 calc R
C4 C 0.8339(3) -0.1072(3) -0.1483(4) 0.0264(8) Uani 1 1 d .
H4A H 0.8360 -0.1963 -0.1655 0.032 Uiso 1 1 calc R
H4B H 0.9160 -0.0764 -0.1137 0.032 Uiso 1 1 calc R
C5 C 0.7595(3) -0.0464(3) -0.3163(4) 0.0210(7) Uani 1 1 d .
C6 C 0.6401(3) -0.1099(3) -0.3939(5) 0.0328(8) Uani 1 1 d .
H6A H 0.6527 -0.1946 -0.4207 0.049 Uiso 1 1 calc R
H6B H 0.5932 -0.0674 -0.4973 0.049 Uiso 1 1 calc R
H6C H 0.5979 -0.1086 -0.3134 0.049 Uiso 1 1 calc R
C7 C 0.8286(3) -0.0485(3) -0.4409(4) 0.0254(7) Uani 1 1 d .
H7A H 0.8719 -0.1264 -0.4315 0.031 Uiso 1 1 calc R
H7B H 0.7737 -0.0394 -0.5584 0.031 Uiso 1 1 calc R
C8 C 0.9156(3) 0.0589(3) -0.3921(4) 0.0244(7) Uani 1 1 d .
H8A H 0.9968 0.0299 -0.3304 0.029 Uiso 1 1 calc R
H8B H 0.9155 0.1038 -0.4938 0.029 Uiso 1 1 calc R
C9 C 0.8720(3) 0.1392(3) -0.2810(4) 0.0248(7) Uani 1 1 d .
C10 C 0.7511(3) 0.0918(3) -0.2837(4) 0.0224(7) Uani 1 1 d .
H10A H 0.6892 0.1273 -0.3849 0.027 Uiso 1 1 calc R
C11 C 0.7235(3) 0.1322(3) -0.1270(4) 0.0226(7) Uani 1 1 d .
H11A H 0.7520 0.2179 -0.1007 0.027 Uiso 1 1 calc R
C12 C 0.5954(3) 0.1282(3) -0.1339(4) 0.0250(7) Uani 1 1 d .
H12A H 0.5531 0.2043 -0.1820 0.030 Uiso 1 1 calc R
H12B H 0.5528 0.0580 -0.2013 0.030 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0395(15) 0.0280(13) 0.0476(16) -0.0059(11) 0.0292(13) -0.0052(11)
O2 0.0345(14) 0.0315(13) 0.0264(13) -0.0011(10) 0.0144(11) -0.0014(11)
O3 0.0306(14) 0.0259(12) 0.0422(15) -0.0048(11) 0.0219(12) -0.0067(10)
C1 0.0246(17) 0.0218(16) 0.039(2) -0.0086(15) 0.0181(16) -0.0050(13)
C2 0.0221(17) 0.0231(15) 0.0304(18) -0.0042(14) 0.0111(14) -0.0002(13)
C3 0.0276(18) 0.0234(16) 0.0292(18) 0.0050(14) 0.0120(15) 0.0014(14)
C4 0.0303(18) 0.0189(15) 0.033(2) 0.0041(13) 0.0155(15) 0.0041(13)
C5 0.0208(16) 0.0200(15) 0.0251(17) -0.0007(13) 0.0116(14) 0.0021(12)
C6 0.032(2) 0.0287(18) 0.039(2) -0.0085(16) 0.0131(17) -0.0051(15)
C7 0.0277(18) 0.0248(16) 0.0276(18) -0.0014(14) 0.0143(15) 0.0034(14)
C8 0.0241(17) 0.0246(16) 0.0310(18) 0.0024(14) 0.0177(14) 0.0048(13)
C9 0.0292(18) 0.0211(15) 0.0301(18) 0.0042(14) 0.0177(15) 0.0025(14)
C10 0.0220(16) 0.0211(15) 0.0267(17) 0.0018(13) 0.0116(14) 0.0028(12)
C11 0.0251(17) 0.0185(14) 0.0274(17) -0.0006(13) 0.0133(14) -0.0031(12)
C12 0.0258(18) 0.0217(15) 0.0296(18) 0.0013(13) 0.0121(15) 0.0029(13)
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
C1 O2 C2 109.5(3)
O1 C1 O2 120.6(3)
O1 C1 C12 128.6(3)
O2 C1 C12 110.8(3)
O2 C2 C3 108.4(3)
O2 C2 C11 103.8(2)
C3 C2 C11 114.0(3)
C2 C3 C4 110.1(3)
C3 C4 C5 112.4(3)
C6 C5 C4 111.0(3)
C6 C5 C10 114.4(3)
C4 C5 C10 108.2(3)
C6 C5 C7 110.4(3)
C4 C5 C7 109.9(3)
C10 C5 C7 102.6(2)
C8 C7 C5 106.4(3)
C9 C8 C7 105.3(3)
O3 C9 C8 125.5(3)
O3 C9 C10 125.5(3)
C8 C9 C10 108.9(3)
C11 C10 C9 112.0(3)
C11 C10 C5 118.8(3)
C9 C10 C5 102.3(2)
C12 C11 C2 102.2(3)
C12 C11 C10 118.4(3)
C2 C11 C10 112.9(3)
C1 C12 C11 102.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.213(4)
O2 C1 1.347(4)
O2 C2 1.478(4)
O3 C9 1.214(4)
C1 C12 1.508(5)
C2 C3 1.530(5)
C2 C11 1.532(5)
C3 C4 1.533(5)
C4 C5 1.545(5)
C5 C6 1.528(5)
C5 C10 1.551(4)
C5 C7 1.552(4)
C7 C8 1.536(5)
C8 C9 1.507(4)
C9 C10 1.540(5)
C10 C11 1.538(4)
C11 C12 1.525(5)
