#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:45:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178442 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/63/4026307.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_4026307
loop_
_publ_author_name
'Chih-Wei Chang'
'Rong-Jie Chein'
_publ_section_title
;
 Absolute Configuration of Anti-HIV-1 Agent (-)-Concentricolide: Total
 Synthesis of (+)-(R)-Concentricolide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4154
_journal_page_last               4157
_journal_paper_doi               10.1021/jo2004132
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C24 H20 O6'
_chemical_formula_sum            'C24 H20 O6'
_chemical_formula_weight         404.4
_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
_cell_angle_alpha                90
_cell_angle_beta                 99.295(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4716(11)
_cell_length_b                   8.2895(8)
_cell_length_c                   12.6979(16)
_cell_measurement_reflns_used    730
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.221
_cell_measurement_theta_min      2.9157
_cell_volume                     983.9(2)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.4875
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0213794
_diffrn_orient_matrix_UB_12      0.0816405
_diffrn_orient_matrix_UB_13      0.0032358
_diffrn_orient_matrix_UB_21      0.0715227
_diffrn_orient_matrix_UB_22      0.0253176
_diffrn_orient_matrix_UB_23      -0.0000315
_diffrn_orient_matrix_UB_31      -0.0134831
_diffrn_orient_matrix_UB_32      0.0045195
_diffrn_orient_matrix_UB_33      -0.0565035
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19106
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         30.46
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.93248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.003(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0646P)²+0.1231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1831
_reflns_number_gt                1456
_reflns_number_total             2841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2004132_si_003.cif
_cod_data_source_block           i12889
_cod_original_cell_volume        983.88(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026307
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 0.75997(19) 0.63347(18) 1.04902(13) 0.0370(5) Uani 1 1 d .
O2 O 0.8426(2) 0.60222(19) 0.89414(15) 0.0492(6) Uani 1 1 d .
O3 O 0.90031(17) 0.96426(17) 0.80712(12) 0.0279(4) Uani 1 1 d .
C1 C 0.7189(3) 0.7659(3) 1.11423(18) 0.0299(6) Uani 1 1 d .
H1 H 0.7776 0.7625 1.1871 0.036 Uiso 1 1 calc R
C2 C 0.7429(3) 1.0764(3) 1.08231(17) 0.0288(6) Uani 1 1 d .
H2 H 0.7066 1.1059 1.1451 0.035 Uiso 1 1 calc R
C3 C 0.7847(3) 1.1938(3) 1.01563(17) 0.0279(5) Uani 1 1 d .
H3 H 0.7785 1.3047 1.033 0.033 Uiso 1 1 calc R
C4 C 0.8879(3) 1.2315(3) 0.83772(18) 0.0266(5) Uani 1 1 d .
H4 H 0.895 1.345 0.8298 0.032 Uiso 1 1 calc R
C5 C 0.9243(3) 1.1191(3) 0.77199(18) 0.0278(5) Uani 1 1 d .
H5 H 0.9621 1.1421 0.7087 0.033 Uiso 1 1 calc R
C6 C 0.8078(3) 0.6911(3) 0.96061(19) 0.0340(6) Uani 1 1 d .
C7 C 0.7552(2) 0.9143(3) 1.05551(17) 0.0246(5) Uani 1 1 d .
C8 C 0.8359(2) 1.1480(2) 0.92295(16) 0.0218(5) Uani 1 1 d .
C9 C 0.8463(2) 0.9848(3) 0.89920(17) 0.0232(5) Uani 1 1 d .
C10 C 0.8060(2) 0.8669(3) 0.96497(17) 0.0241(5) Uani 1 1 d .
C11 C 0.5631(3) 0.7483(3) 1.1218(2) 0.0363(6) Uani 1 1 d .
H11A H 0.507 0.7491 1.0488 0.044 Uiso 1 1 calc R
H11B H 0.5326 0.8423 1.1606 0.044 Uiso 1 1 calc R
C12 C 0.5289(3) 0.5941(3) 1.1784(2) 0.0460(7) Uani 1 1 d .
H12A H 0.5802 0.5947 1.2518 0.069 Uiso 1 1 calc R
H12B H 0.5587 0.5002 1.1405 0.069 Uiso 1 1 calc R
H12C H 0.4257 0.5883 1.1791 0.069 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
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 O1 C1 110.92(17)
C9 O3 C5 105.30(16)
O1 C1 C11 108.48(19)
O1 C1 C7 103.27(17)
C11 C1 C7 114.6(2)
O1 C1 H1 110.1
C11 C1 H1 110.1
C7 C1 H1 110.1
C3 C2 C7 118.9(2)
C3 C2 H2 120.6
C7 C2 H2 120.6
C2 C3 C8 119.7(2)
C2 C3 H3 120.1
C8 C3 H3 120.1
C5 C4 C8 106.86(19)
C5 C4 H4 126.6
C8 C4 H4 126.6
C4 C5 O3 111.9(2)
C4 C5 H5 124.1
O3 C5 H5 124.1
O2 C6 O1 121.8(2)
O2 C6 C10 130.0(2)
O1 C6 C10 108.15(19)
C10 C7 C2 122.3(2)
C10 C7 C1 108.61(19)
C2 C7 C1 129.1(2)
C9 C8 C3 119.5(2)
C9 C8 C4 105.05(18)
C3 C8 C4 135.4(2)
O3 C9 C10 127.67(19)
O3 C9 C8 110.93(18)
C10 C9 C8 121.4(2)
C7 C10 C9 118.2(2)
C7 C10 C6 108.99(19)
C9 C10 C6 132.8(2)
C1 C11 C12 113.4(2)
C1 C11 H11A 108.9
C12 C11 H11A 108.9
C1 C11 H11B 108.9
C12 C11 H11B 108.9
H11A C11 H11B 107.7
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 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 1.363(3)
O1 C1 1.465(3)
O2 C6 1.206(3)
O3 C9 1.361(3)
O3 C5 1.390(3)
C1 C11 1.501(3)
C1 C7 1.507(3)
C1 H1 1
C2 C3 1.389(3)
C2 C7 1.395(3)
C2 H2 0.95
C3 C8 1.396(3)
C3 H3 0.95
C4 C5 1.333(3)
C4 C8 1.437(3)
C4 H4 0.95
C5 H5 0.95
C6 C10 1.459(3)
C7 C10 1.374(3)
C8 C9 1.393(3)
C9 C10 1.379(3)
C11 C12 1.527(3)
C11 H11A 0.99
C11 H11B 0.99
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
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
C6 O1 C1 C11 119.3(2)
C6 O1 C1 C7 -2.6(3)
C7 C2 C3 C8 0.9(4)
C8 C4 C5 O3 0.0(3)
C9 O3 C5 C4 0.0(3)
C1 O1 C6 O2 -177.5(2)
C1 O1 C6 C10 2.2(3)
C3 C2 C7 C10 -0.6(4)
C3 C2 C7 C1 179.4(2)
O1 C1 C7 C10 2.0(3)
C11 C1 C7 C10 -115.7(2)
O1 C1 C7 C2 -177.9(2)
C11 C1 C7 C2 64.3(3)
C2 C3 C8 C9 -0.9(3)
C2 C3 C8 C4 -179.6(2)
C5 C4 C8 C9 -0.1(3)
C5 C4 C8 C3 178.8(2)
C5 O3 C9 C10 -179.5(2)
C5 O3 C9 C8 -0.1(2)
C3 C8 C9 O3 -179.02(19)
C4 C8 C9 O3 0.1(2)
C3 C8 C9 C10 0.5(3)
C4 C8 C9 C10 179.6(2)
C2 C7 C10 C9 0.2(3)
C1 C7 C10 C9 -179.8(2)
C2 C7 C10 C6 179.1(2)
C1 C7 C10 C6 -0.8(3)
O3 C9 C10 C7 179.3(2)
C8 C9 C10 C7 -0.1(3)
O3 C9 C10 C6 0.6(4)
C8 C9 C10 C6 -178.8(2)
O2 C6 C10 C7 178.8(3)
O1 C6 C10 C7 -0.8(3)
O2 C6 C10 C9 -2.4(5)
O1 C6 C10 C9 177.9(2)
O1 C1 C11 C12 63.3(3)
C7 C1 C11 C12 178.1(2)
