#------------------------------------------------------------------------------
#$Date: 2018-08-23 04:23:19 +0300 (Thu, 23 Aug 2018) $
#$Revision: 210089 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024788.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_4024788
loop_
_publ_author_name
'Singh, Vishwakarma'
'Sahu, Pramod K.'
'Sahu, Bharat C.'
'Mobin, Shaikh M.'
_publ_section_title
;
 Diels--Alder Cycloaddition and Ring-Closing Metathesis:
 A Versatile, Stereoselective, and General Route to Embellished Bridged
 Bicyclic Systems, Carbocyclic Framework of Secoatisanes, and Homologues
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   16
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6092
_journal_page_last               6104
_journal_paper_doi               10.1021/jo901279g
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C20 H20 O4'
_chemical_formula_weight         324.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.92(2)
_cell_angle_beta                 94.53(2)
_cell_angle_gamma                116.86(3)
_cell_formula_units_Z            2
_cell_length_a                   8.663(2)
_cell_length_b                   9.548(3)
_cell_length_c                   10.915(3)
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.5623
_cell_measurement_theta_min      3.0797
_cell_volume                     801.5(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'OXFORD DIFFRACTION XCALIBUR-S'
_diffrn_measurement_method       ω/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6636
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0319
_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)+(0.0441P)²+0.1161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                2305
_reflns_number_total             2818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901279g_si_002.cif
_cod_data_source_block           vks020
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024788
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21219(12) -0.02241(10) 0.01224(8) 0.0266(2) Uani 1 1 d . . .
O2 O -0.07299(11) -0.19537(10) 0.15260(8) 0.0269(2) Uani 1 1 d . . .
O3 O -0.11316(11) 0.15070(11) 0.44988(8) 0.0270(2) Uani 1 1 d . . .
O4 O 0.18423(13) 0.41712(11) 0.53413(8) 0.0330(3) Uani 1 1 d . . .
C1 C 0.20540(15) 0.02912(14) 0.11238(11) 0.0196(3) Uani 1 1 d . . .
C2 C 0.08880(15) -0.07067(14) 0.20491(11) 0.0200(3) Uani 1 1 d . . .
C3 C 0.05318(17) -0.23651(15) 0.21455(13) 0.0258(3) Uani 1 1 d . . .
H3A H 0.1155 -0.2768 0.1634 0.031 Uiso 1 1 calc R . .
H3B H 0.0294 -0.2821 0.2959 0.031 Uiso 1 1 calc R . .
C4 C 0.08880(16) 0.02964(14) 0.31341(11) 0.0195(3) Uani 1 1 d . . .
H4 H 0.0108 -0.0352 0.3751 0.023 Uiso 1 1 calc R . .
C5 C 0.27450(16) 0.11443(14) 0.36679(11) 0.0202(3) Uani 1 1 d . . .
H5 H 0.3103 0.1079 0.4501 0.024 Uiso 1 1 calc R . .
C6 C 0.38492(16) 0.19940(14) 0.28819(11) 0.0196(3) Uani 1 1 d . . .
H6 H 0.5062 0.2562 0.3118 0.024 Uiso 1 1 calc R . .
C7 C 0.30885(15) 0.20165(14) 0.15965(11) 0.0187(3) Uani 1 1 d . . .
C8 C 0.16544(15) 0.26187(14) 0.17500(11) 0.0186(3) Uani 1 1 d . . .
H8 H 0.1023 0.2536 0.0923 0.022 Uiso 1 1 calc R . .
C9 C 0.03247(15) 0.15288(14) 0.26133(11) 0.0188(3) Uani 1 1 d . . .
H9 H -0.0819 0.0939 0.2110 0.023 Uiso 1 1 calc R . .
C10 C 0.00590(16) 0.24378(14) 0.36589(11) 0.0208(3) Uani 1 1 d . . .
C11 C -0.15985(17) 0.24931(16) 0.37222(13) 0.0277(3) Uani 1 1 d . . .
H11A H -0.1569 0.3450 0.4110 0.033 Uiso 1 1 calc R . .
H11B H -0.2515 0.1976 0.3032 0.033 Uiso 1 1 calc R . .
C12 C 0.16211(17) 0.38478(15) 0.42400(11) 0.0228(3) Uani 1 1 d . . .
C13 C 0.27303(16) 0.48798(15) 0.33470(12) 0.0220(3) Uani 1 1 d . . .
C14 C 0.25905(16) 0.43229(14) 0.21936(12) 0.0206(3) Uani 1 1 d . . .
H14 H 0.3129 0.5067 0.1602 0.025 Uiso 1 1 calc R . .
C15 C 0.39488(18) 0.65517(16) 0.38102(13) 0.0296(3) Uani 1 1 d . . .
H15A H 0.3254 0.7120 0.3936 0.035 Uiso 1 1 calc R . .
H15B H 0.4538 0.6532 0.4620 0.035 Uiso 1 1 calc R . .
C16 C 0.52959(17) 0.74405(16) 0.29711(13) 0.0299(3) Uani 1 1 d . . .
H16 H 0.6148 0.7098 0.2847 0.036 Uiso 1 1 calc R . .
C17 C 0.53839(19) 0.86649(17) 0.23913(14) 0.0369(4) Uani 1 1 d . . .
H17A H 0.4552 0.9038 0.2494 0.044 Uiso 1 1 calc R . .
H17B H 0.6279 0.9178 0.1869 0.044 Uiso 1 1 calc R . .
C18 C 0.44070(16) 0.29881(15) 0.07103(12) 0.0223(3) Uani 1 1 d . . .
H18A H 0.3793 0.2834 -0.0123 0.027 Uiso 1 1 calc R . .
H18B H 0.4890 0.4116 0.0973 0.027 Uiso 1 1 calc R . .
C19 C 0.58811(17) 0.25806(16) 0.06389(12) 0.0248(3) Uani 1 1 d . . .
H19 H 0.5610 0.1520 0.0428 0.030 Uiso 1 1 calc R . .
C20 C 0.75171(18) 0.36045(19) 0.08512(14) 0.0364(4) Uani 1 1 d . . .
H20A H 0.7826 0.4673 0.1064 0.044 Uiso 1 1 calc R . .
H20B H 0.8398 0.3280 0.0793 0.044 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C3 61.81(8) . . ?
C10 O3 C11 61.44(8) . . ?
O1 C1 C2 123.12(11) . . ?
O1 C1 C7 124.87(11) . . ?
C2 C1 C7 112.00(10) . . ?
O2 C2 C3 59.50(8) . . ?
O2 C2 C1 114.75(10) . . ?
C3 C2 C1 120.55(11) . . ?
O2 C2 C4 118.94(10) . . ?
C3 C2 C4 122.54(11) . . ?
C1 C2 C4 111.05(10) . . ?
O2 C3 C2 58.70(8) . . ?
O2 C3 H3A 117.9 . . ?
C2 C3 H3A 117.9 . . ?
O2 C3 H3B 117.9 . . ?
C2 C3 H3B 117.9 . . ?
H3A C3 H3B 115.1 . . ?
C5 C4 C2 105.22(10) . . ?
C5 C4 C9 108.68(10) . . ?
C2 C4 C9 107.16(10) . . ?
C5 C4 H4 111.8 . . ?
C2 C4 H4 111.8 . . ?
C9 C4 H4 111.8 . . ?
C6 C5 C4 114.52(11) . . ?
C6 C5 H5 122.7 . . ?
C4 C5 H5 122.7 . . ?
C5 C6 C7 116.86(11) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
C6 C7 C1 105.93(10) . . ?
C6 C7 C18 115.32(10) . . ?
C1 C7 C18 111.67(10) . . ?
C6 C7 C8 105.91(10) . . ?
C1 C7 C8 105.13(9) . . ?
C18 C7 C8 112.15(10) . . ?
C14 C8 C9 114.68(10) . . ?
C14 C8 C7 107.86(10) . . ?
C9 C8 C7 108.87(10) . . ?
C14 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
C7 C8 H8 108.4 . . ?
C10 C9 C8 112.65(10) . . ?
C10 C9 C4 110.20(10) . . ?
C8 C9 C4 110.67(10) . . ?
C10 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
C4 C9 H9 107.7 . . ?
O3 C10 C11 59.79(8) . . ?
O3 C10 C12 114.82(10) . . ?
C11 C10 C12 114.90(11) . . ?
O3 C10 C9 115.65(10) . . ?
C11 C10 C9 121.20(11) . . ?
C12 C10 C9 117.48(11) . . ?
O3 C11 C10 58.78(8) . . ?
O3 C11 H11A 117.9 . . ?
C10 C11 H11A 117.9 . . ?
O3 C11 H11B 117.9 . . ?
C10 C11 H11B 117.9 . . ?
H11A C11 H11B 115.0 . . ?
O4 C12 C13 123.75(12) . . ?
O4 C12 C10 122.08(12) . . ?
C13 C12 C10 113.80(11) . . ?
C14 C13 C12 119.59(12) . . ?
C14 C13 C15 123.95(12) . . ?
C12 C13 C15 116.45(11) . . ?
C13 C14 C8 125.59(12) . . ?
C13 C14 H14 117.2 . . ?
C8 C14 H14 117.2 . . ?
C16 C15 C13 114.20(11) . . ?
C16 C15 H15A 108.7 . . ?
C13 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C13 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 124.39(14) . . ?
C17 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C19 C18 C7 114.08(11) . . ?
C19 C18 H18A 108.7 . . ?
C7 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C7 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 123.58(13) . . ?
C20 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2080(15) . ?
O2 C2 1.4322(16) . ?
O2 C3 1.4443(16) . ?
O3 C10 1.4287(15) . ?
O3 C11 1.4438(17) . ?
O4 C12 1.2145(15) . ?
C1 C2 1.5068(18) . ?
C1 C7 1.5324(18) . ?
C2 C3 1.4774(18) . ?
C2 C4 1.5111(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.4974(18) . ?
C4 C9 1.5629(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.3266(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.5069(17) . ?
C6 H6 0.9500 . ?
C7 C18 1.5319(18) . ?
C7 C8 1.6054(17) . ?
C8 C14 1.5032(18) . ?
C8 C9 1.5548(18) . ?
C8 H8 1.0000 . ?
C9 C10 1.5161(17) . ?
C9 H9 1.0000 . ?
C10 C11 1.4675(18) . ?
C10 C12 1.4954(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4723(19) . ?
C13 C14 1.3336(18) . ?
C13 C15 1.5116(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.490(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.313(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C18 C19 1.5007(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.306(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O2 C2 C1 112.21(12) . . . . ?
C3 O2 C2 C4 -112.81(13) . . . . ?
O1 C1 C2 O2 -33.35(17) . . . . ?
C7 C1 C2 O2 145.31(10) . . . . ?
O1 C1 C2 C3 34.51(18) . . . . ?
C7 C1 C2 C3 -146.83(11) . . . . ?
O1 C1 C2 C4 -171.80(11) . . . . ?
C7 C1 C2 C4 6.86(14) . . . . ?
C1 C2 C3 O2 -102.50(12) . . . . ?
C4 C2 C3 O2 106.88(13) . . . . ?
O2 C2 C4 C5 164.43(10) . . . . ?
C3 C2 C4 C5 94.02(14) . . . . ?
C1 C2 C4 C5 -59.06(13) . . . . ?
O2 C2 C4 C9 -80.01(13) . . . . ?
C3 C2 C4 C9 -150.43(11) . . . . ?
C1 C2 C4 C9 56.49(13) . . . . ?
C2 C4 C5 C6 56.81(13) . . . . ?
C9 C4 C5 C6 -57.69(14) . . . . ?
C4 C5 C6 C7 1.38(16) . . . . ?
C5 C6 C7 C1 -55.00(14) . . . . ?
C5 C6 C7 C18 -179.04(11) . . . . ?
C5 C6 C7 C8 56.32(14) . . . . ?
O1 C1 C7 C6 -133.59(13) . . . . ?
C2 C1 C7 C6 47.77(13) . . . . ?
O1 C1 C7 C18 -7.30(17) . . . . ?
C2 C1 C7 C18 174.07(10) . . . . ?
O1 C1 C7 C8 114.54(13) . . . . ?
C2 C1 C7 C8 -64.09(12) . . . . ?
C6 C7 C8 C14 69.07(12) . . . . ?
C1 C7 C8 C14 -179.05(9) . . . . ?
C18 C7 C8 C14 -57.52(13) . . . . ?
C6 C7 C8 C9 -55.94(12) . . . . ?
C1 C7 C8 C9 55.95(12) . . . . ?
C18 C7 C8 C9 177.47(9) . . . . ?
C14 C8 C9 C10 7.55(15) . . . . ?
C7 C8 C9 C10 128.46(10) . . . . ?
C14 C8 C9 C4 -116.33(11) . . . . ?
C7 C8 C9 C4 4.58(13) . . . . ?
C5 C4 C9 C10 -74.36(13) . . . . ?
C2 C4 C9 C10 172.41(10) . . . . ?
C5 C4 C9 C8 50.91(13) . . . . ?
C2 C4 C9 C8 -62.32(12) . . . . ?
C11 O3 C10 C12 105.52(13) . . . . ?
C11 O3 C10 C9 -112.67(12) . . . . ?
C8 C9 C10 O3 -179.21(9) . . . . ?
C4 C9 C10 O3 -55.08(14) . . . . ?
C8 C9 C10 C11 112.00(13) . . . . ?
C4 C9 C10 C11 -123.86(12) . . . . ?
C8 C9 C10 C12 -38.45(15) . . . . ?
C4 C9 C10 C12 85.69(13) . . . . ?
C12 C10 C11 O3 -105.38(12) . . . . ?
C9 C10 C11 O3 103.47(13) . . . . ?
O3 C10 C12 O4 -0.43(18) . . . . ?
C11 C10 C12 O4 66.21(17) . . . . ?
C9 C10 C12 O4 -141.51(13) . . . . ?
O3 C10 C12 C13 -173.74(10) . . . . ?
C11 C10 C12 C13 -107.11(13) . . . . ?
C9 C10 C12 C13 45.17(15) . . . . ?
O4 C12 C13 C14 168.18(13) . . . . ?
C10 C12 C13 C14 -18.63(17) . . . . ?
O4 C12 C13 C15 -13.25(19) . . . . ?
C10 C12 C13 C15 159.93(11) . . . . ?
C12 C13 C14 C8 -13.4(2) . . . . ?
C15 C13 C14 C8 168.15(12) . . . . ?
C9 C8 C14 C13 18.92(18) . . . . ?
C7 C8 C14 C13 -102.55(14) . . . . ?
C14 C13 C15 C16 -14.0(2) . . . . ?
C12 C13 C15 C16 167.51(12) . . . . ?
C13 C15 C16 C17 114.15(16) . . . . ?
C6 C7 C18 C19 52.55(14) . . . . ?
C1 C7 C18 C19 -68.43(13) . . . . ?
C8 C7 C18 C19 173.88(10) . . . . ?
C7 C18 C19 C20 -123.96(14) . . . . ?
