#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:36:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178907 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/36/4113683.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_4113683
loop_
_publ_author_name
'Chaomin Li'
'Richard P. Johnson'
'John A. Porco'
_publ_contact_author
;
     John A. Porco, Jr.
        Department of Chemistry and Center for Streamlined Synthesis
    590 Commonwealth Avenue
    Boston, MA 02215
        USA
;
_publ_contact_author_email       porco@chem.bu.edu
_publ_section_title
;
 Total Synthesis of the Quinone Epoxide Dimer (+)-Torreyanic Acid:
 Application of a Biomimetic Oxidation/Electrocyclization/Diels-Alder
 Dimerization Cascade1
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5095
_journal_page_last               5106
_journal_paper_doi               10.1021/ja021396c
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C17 H20 O4'
_chemical_formula_weight         288.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.599(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.105(3)
_cell_length_b                   6.3582(6)
_cell_length_c                   19.2691(18)
_cell_measurement_temperature    173(2)
_cell_volume                     3051.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker 1K CCD area detector'
_diffrn_measurement_method       '0.3 deg. omega 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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8470
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.8488
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       rod
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+1.2406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                1900
_reflns_number_total             2587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021396c_4.cif
_cod_data_source_block           porco17
_cod_database_code               4113683
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59379(6) 0.0333(2) 0.53705(9) 0.0373(4) Uani 1 1 d . . .
O2 O 0.66926(6) 0.2993(2) 0.70936(9) 0.0329(4) Uani 1 1 d . . .
O3 O 0.79260(6) 0.2113(3) 0.75469(8) 0.0296(4) Uani 1 1 d . . .
H3O H 0.8005(10) 0.070(5) 0.7537(15) 0.055(8) Uiso 1 1 d . . .
O4 O 0.67556(6) -0.3816(2) 0.55712(9) 0.0399(4) Uani 1 1 d . . .
C1 C 0.61765(8) -0.1569(3) 0.58062(13) 0.0317(6) Uani 1 1 d . . .
C2 C 0.61716(9) 0.0378(4) 0.62142(13) 0.0315(5) Uani 1 1 d . . .
H2 H 0.5931(8) 0.048(3) 0.6437(12) 0.027(6) Uiso 1 1 d . . .
C3 C 0.66669(8) 0.1681(3) 0.66133(13) 0.0261(5) Uani 1 1 d . . .
C4 C 0.71066(8) 0.1317(3) 0.64151(12) 0.0247(5) Uani 1 1 d . . .
C5 C 0.75866(8) 0.2758(3) 0.67558(13) 0.0263(5) Uani 1 1 d . . .
H5 H 0.7482(7) 0.419(3) 0.6788(11) 0.020(5) Uiso 1 1 d . . .
C6 C 0.78821(9) 0.2809(4) 0.62591(13) 0.0308(5) Uani 1 1 d . . .
H6 H 0.7659(8) 0.367(3) 0.5802(12) 0.030(6) Uiso 1 1 d . . .
C7 C 0.79242(10) 0.0655(4) 0.59736(13) 0.0359(6) Uani 1 1 d . . .
H7 H 0.8239(10) 0.039(4) 0.5884(14) 0.050(7) Uiso 1 1 d . . .
C8 C 0.75696(9) -0.0842(4) 0.58740(13) 0.0338(6) Uani 1 1 d . . .
H8 H 0.7596(10) -0.224(4) 0.5708(15) 0.051(7) Uiso 1 1 d . . .
C9 C 0.71164(8) -0.0439(3) 0.60252(12) 0.0270(5) Uani 1 1 d . . .
C10 C 0.66919(9) -0.2092(3) 0.57860(12) 0.0297(5) Uani 1 1 d . . .
C11 C 0.58075(10) -0.3394(4) 0.5719(2) 0.0441(7) Uani 1 1 d . . .
H11B H 0.5745(11) -0.399(4) 0.5240(17) 0.056(8) Uiso 1 1 d . . .
H11 H 0.5985(10) -0.437(4) 0.6166(16) 0.055(8) Uiso 1 1 d . . .
C12 C 0.52902(11) -0.2793(5) 0.5699(2) 0.0542(9) Uani 1 1 d . . .
H12 H 0.5076(14) -0.207(5) 0.530(2) 0.081(12) Uiso 1 1 d . . .
C13 C 0.51508(17) -0.3351(6) 0.6226(3) 0.0828(12) Uani 1 1 d . . .
H13A H 0.4823(15) -0.309(5) 0.618(2) 0.093(12) Uiso 1 1 d . . .
H13B H 0.5409(16) -0.436(6) 0.670(2) 0.118(15) Uiso 1 1 d . . .
C14 C 0.84223(10) 0.3943(4) 0.66905(15) 0.0376(6) Uani 1 1 d . . .
H14B H 0.8666(9) 0.300(4) 0.7130(14) 0.042(7) Uiso 1 1 d . . .
H14A H 0.8371(11) 0.523(4) 0.6974(16) 0.064(9) Uiso 1 1 d . . .
C15 C 0.86840(11) 0.4616(6) 0.61916(18) 0.0558(8) Uani 1 1 d . A .
H15B H 0.8436(10) 0.563(4) 0.5784(16) 0.054(8) Uiso 1 1 d . . .
H15 H 0.8744(10) 0.334(4) 0.5952(16) 0.054(9) Uiso 1 1 d . . .
C16 C 0.92154(13) 0.5749(8) 0.6660(2) 0.0885(14) Uani 1 1 d . . .
H16 H 0.9436(11) 0.488(4) 0.7036(16) 0.052(8) Uiso 1 1 d . . .
C17 C 0.9451(2) 0.7089(11) 0.6333(3) 0.056(2) Uani 0.473(7) 1 d P A 1
H17A H 0.9788 0.7645 0.6748 0.083 Uiso 0.473(7) 1 calc PR A 1
H17B H 0.9206 0.8255 0.6066 0.083 Uiso 0.473(7) 1 calc PR A 1
H17C H 0.9525 0.6306 0.5955 0.083 Uiso 0.473(7) 1 calc PR A 1
C17 C 0.9189(2) 0.7704(11) 0.6772(4) 0.071(2) Uani 0.527(7) 1 d P A 2
H17D H 0.9552 0.8268 0.7078 0.106 Uiso 0.527(7) 1 calc PR A 2
H17E H 0.8981 0.7925 0.7058 0.106 Uiso 0.527(7) 1 calc PR A 2
H17F H 0.9012 0.8428 0.6266 0.106 Uiso 0.527(7) 1 calc PR A 2
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
C2 O1 C1 61.10(14)
O1 C1 C2 59.35(13)
O1 C1 C10 111.26(18)
C2 C1 C10 116.61(19)
O1 C1 C11 117.83(18)
C2 C1 C11 122.0(2)
C10 C1 C11 116.48(19)
O1 C2 C1 59.55(14)
O1 C2 C3 114.86(19)
C1 C2 C3 120.38(19)
O2 C3 C4 122.78(19)
O2 C3 C2 118.89(19)
C4 C3 C2 118.34(19)
C9 C4 C3 120.63(19)
C9 C4 C5 119.94(19)
C3 C4 C5 118.80(18)
O3 C5 C4 108.06(17)
O3 C5 C6 112.62(17)
C4 C5 C6 112.10(18)
C7 C6 C14 113.7(2)
C7 C6 C5 111.55(19)
C14 C6 C5 111.05(19)
C8 C7 C6 121.8(2)
C7 C8 C9 120.9(2)
C4 C9 C8 120.1(2)
C4 C9 C10 122.21(19)
C8 C9 C10 117.55(19)
O4 C10 C9 121.2(2)
O4 C10 C1 120.3(2)
C9 C10 C1 118.52(19)
C12 C11 C1 114.7(2)
C13 C12 C11 123.8(4)
C15 C14 C6 116.0(2)
C14 C15 C16 112.8(3)
C17 C16 C17 63.7(4)
C17 C16 C15 116.4(4)
C17 C16 C15 124.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.444(3)
O1 C1 1.447(3)
O2 C3 1.223(2)
O3 C5 1.433(3)
O4 C10 1.214(3)
C1 C2 1.470(3)
C1 C10 1.504(3)
C1 C11 1.513(3)
C2 C3 1.491(3)
C3 C4 1.471(3)
C4 C9 1.353(3)
C4 C5 1.507(3)
C5 C6 1.531(3)
C6 C7 1.501(3)
C6 C14 1.532(3)
C7 C8 1.326(3)
C8 C9 1.455(3)
C9 C10 1.493(3)
C11 C12 1.486(4)
C12 C13 1.297(5)
C14 C15 1.518(4)
C15 C16 1.521(5)
C16 C17 1.270(7)
C16 C17 1.396(6)
