#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:53:44 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180321 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/35/7153503.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_7153503
loop_
_publ_author_name
'Blanc, Romain'
'Héran, Virginie'
'Rahmani, Raphaël'
'Commeiras, Laurent'
'Parrain, Jean-Luc'
_publ_section_title
;
 Diels-Alder cycloaddition of o-quinonedimethides and
 alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores
 and arthrinone derivatives.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5490
_journal_page_last               5494
_journal_paper_doi               10.1039/c0ob00448k
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H10 O4'
_chemical_formula_sum            'C14 H10 O4'
_chemical_formula_weight         242.22
_chemical_name_systematic
;
?
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-05-19T10:48:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0794(3)
_cell_length_b                   5.2878(1)
_cell_length_c                   19.8876(6)
_cell_measurement_reflns_used    10207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      3.85
_cell_measurement_wavelength     0.71073
_cell_volume                     1165.13(5)
_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, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10207
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.85
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1457
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.0408
_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)+(0.0349P)²+0.1994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1273
_reflns_number_total             1457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00448k.txt
_cod_data_source_block           lcf265
_cod_database_code               7153503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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
C1 C 0.7263(2) 0.8593(4) 0.66772(13) 0.0430(5) Uani 1 1 d .
C2 C 0.67318(18) 0.9742(4) 0.73191(13) 0.0405(5) Uani 1 1 d .
C3 C 0.6916(2) 0.8314(4) 0.79510(12) 0.0408(5) Uani 1 1 d .
C4 C 0.6242(3) 0.8966(5) 0.85130(14) 0.0555(7) Uani 1 1 d .
H4 H 0.5694 1.0294 0.8489 0.067 Uiso 1 1 calc R
C5 C 0.6380(3) 0.7658(6) 0.91055(17) 0.0707(8) Uani 1 1 d .
H5 H 0.5921 0.81 0.9479 0.085 Uiso 1 1 calc R
C6 C 0.7195(3) 0.5695(6) 0.91489(17) 0.0697(8) Uani 1 1 d .
H6 H 0.7291 0.4829 0.9552 0.084 Uiso 1 1 calc R
C7 C 0.7867(3) 0.5017(5) 0.85965(16) 0.0602(7) Uani 1 1 d .
H7 H 0.8413 0.3687 0.8628 0.072 Uiso 1 1 calc R
C8 C 0.7738(2) 0.6304(4) 0.79890(14) 0.0454(5) Uani 1 1 d .
C9 C 0.84639(19) 0.5560(4) 0.73933(15) 0.0492(6) Uani 1 1 d .
C10 C 0.8483(2) 0.7361(6) 0.68107(15) 0.0558(7) Uani 1 1 d .
H10A H 0.8736 0.6456 0.6411 0.067 Uiso 1 1 calc R
H10B H 0.9074 0.8673 0.6898 0.067 Uiso 1 1 calc R
C11 C 0.63378(19) 0.6875(4) 0.63664(12) 0.0413(5) Uani 1 1 d .
H11 H 0.6075 0.5358 0.6552 0.05 Uiso 1 1 calc R
C12 C 0.5951(2) 0.7829(5) 0.57903(13) 0.0447(5) Uani 1 1 d .
C13 C 0.6624(3) 1.0184(5) 0.56697(13) 0.0520(6) Uani 1 1 d .
C14 C 0.5024(3) 0.6927(6) 0.53078(15) 0.0623(7) Uani 1 1 d .
H14A H 0.4324 0.799 0.5336 0.093 Uiso 1 1 calc R
H14B H 0.4804 0.5218 0.5416 0.093 Uiso 1 1 calc R
H14C H 0.5345 0.6987 0.486 0.093 Uiso 1 1 calc R
O1 O 0.61467(15) 1.1680(3) 0.72989(10) 0.0525(5) Uani 1 1 d .
O2 O 0.90366(17) 0.3605(4) 0.73855(13) 0.0704(6) Uani 1 1 d .
O3 O 0.74132(16) 1.0572(3) 0.61873(10) 0.0553(5) Uani 1 1 d .
O4 O 0.6566(2) 1.1639(4) 0.52085(11) 0.0768(7) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O3 C1 C11 103.88(19)
O3 C1 C10 109.05(19)
C11 C1 C10 114.7(2)
O3 C1 C2 108.66(18)
C11 C1 C2 108.69(18)
C10 C1 C2 111.4(2)
O1 C2 C3 122.2(2)
O1 C2 C1 120.9(2)
C3 C2 C1 116.87(18)
C4 C3 C8 119.6(2)
C4 C3 C2 118.9(2)
C8 C3 C2 121.5(2)
C5 C4 C3 120.4(3)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.3(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 120.1(3)
C7 C6 H6 120
C5 C6 H6 120
C6 C7 C8 120.7(3)
C6 C7 H7 119.7
C8 C7 H7 119.7
C7 C8 C3 118.9(2)
C7 C8 C9 120.4(2)
C3 C8 C9 120.6(2)
O2 C9 C8 121.3(3)
O2 C9 C10 121.6(3)
C8 C9 C10 117.1(2)
C9 C10 C1 113.2(2)
C9 C10 H10A 108.9
C1 C10 H10A 108.9
C9 C10 H10B 108.9
C1 C10 H10B 108.9
H10A C10 H10B 107.8
C12 C11 C1 110.3(2)
C12 C11 H11 124.9
C1 C11 H11 124.9
C11 C12 C13 107.4(2)
C11 C12 C14 131.4(2)
C13 C12 C14 121.2(2)
O4 C13 O3 121.0(3)
O4 C13 C12 129.8(3)
O3 C13 C12 109.2(2)
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 O3 C1 109.09(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O3 1.440(3)
C1 C11 1.503(3)
C1 C10 1.524(3)
C1 C2 1.532(4)
C2 O1 1.213(3)
C2 C3 1.480(3)
C3 C4 1.388(4)
C3 C8 1.402(3)
C4 C5 1.375(4)
C4 H4 0.93
C5 C6 1.379(5)
C5 H5 0.93
C6 C7 1.374(4)
C6 H6 0.93
C7 C8 1.394(4)
C7 H7 0.93
C8 C9 1.485(4)
C9 O2 1.213(3)
C9 C10 1.500(4)
C10 H10A 0.97
C10 H10B 0.97
C11 C12 1.323(3)
C11 H11 0.93
C12 C13 1.471(4)
C12 C14 1.484(4)
C13 O4 1.199(3)
C13 O3 1.366(3)
C14 H14A 0.96
C14 H14B 0.96
C14 H14C 0.96
