#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:46:30 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178915 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/44/4114425.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_4114425
loop_
_publ_author_name
'Brian H. White'
'Marc L. Snapper'
_publ_section_title
;
 Ring-Opening Metathesis/Oxy-Cope Rearrangement: A New Strategy for the
 Synthesis of Bicyclic Medium Ring-Containing Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14901
_journal_page_last               14904
_journal_paper_doi               10.1021/ja037656n
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C13 H20 O3'
_chemical_formula_weight         224.29
_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                 92.314(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1213(6)
_cell_length_b                   9.2198(11)
_cell_length_c                   25.200(3)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.35
_cell_volume                     1188.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8602
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0438
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                2133
_reflns_number_total             2965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037656nsi20030730_113104.cif
_cod_data_source_block           bwXVIIIt
_cod_database_code               4114425
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 0.34829(15) 0.90847(9) 0.43590(3) 0.0429(2) Uani 1 1 d .
C1 C 0.5849(2) 0.90143(12) 0.43477(4) 0.0308(3) Uani 1 1 d .
O3 O 0.90576(19) 0.71703(11) 0.25853(3) 0.0605(3) Uani 1 1 d .
O2 O 0.57316(19) 1.22326(9) 0.39117(4) 0.0535(3) Uani 1 1 d .
C13 C 0.7374(2) 0.80977(13) 0.47454(4) 0.0355(3) Uani 1 1 d .
H13A H 0.7152 0.8474 0.5100 0.043 Uiso 1 1 calc R
H13B H 0.9218 0.8138 0.4673 0.043 Uiso 1 1 calc R
C2 C 0.7327(2) 0.98467(12) 0.39421(4) 0.0312(3) Uani 1 1 d .
H2 H 0.9002 0.9373 0.3882 0.037 Uiso 1 1 calc R
C5 C 0.5797(2) 1.00815(12) 0.34110(4) 0.0337(3) Uani 1 1 d .
H5 H 0.4061 0.9646 0.3435 0.040 Uiso 1 1 calc R
C12 C 0.6433(2) 0.65305(13) 0.47160(5) 0.0417(3) Uani 1 1 d .
H12A H 0.7494 0.5950 0.4963 0.050 Uiso 1 1 calc R
H12B H 0.4643 0.6488 0.4827 0.050 Uiso 1 1 calc R
C11 C 0.6562(2) 0.58789(13) 0.41636(5) 0.0410(3) Uani 1 1 d .
H11A H 0.5691 0.6531 0.3912 0.049 Uiso 1 1 calc R
H11B H 0.5602 0.4972 0.4156 0.049 Uiso 1 1 calc R
C8 C 0.9541(2) 0.70250(14) 0.31494(5) 0.0425(3) Uani 1 1 d .
H8 H 1.0955 0.7642 0.3295 0.051 Uiso 1 1 calc R
C6 C 0.7108(3) 0.94410(14) 0.29317(5) 0.0421(3) Uani 1 1 d .
H6A H 0.6144 0.9742 0.2611 0.051 Uiso 1 1 calc R
H6B H 0.8862 0.9832 0.2918 0.051 Uiso 1 1 calc R
C7 C 0.7263(2) 0.78223(13) 0.29406(5) 0.0407(3) Uani 1 1 d .
H7 H 0.5587 0.7320 0.2967 0.049 Uiso 1 1 calc R
C3 C 0.7782(3) 1.14059(14) 0.41473(5) 0.0464(3) Uani 1 1 d .
H3A H 0.7729 1.1438 0.4531 0.056 Uiso 1 1 calc R
H3B H 0.9463 1.1768 0.4042 0.056 Uiso 1 1 calc R
C9 C 0.9489(3) 0.55385(14) 0.33826(5) 0.0473(3) Uani 1 1 d .
H9A H 1.1061 0.5022 0.3293 0.057 Uiso 1 1 calc R
H9B H 0.8000 0.5011 0.3231 0.057 Uiso 1 1 calc R
C10 C 0.9313(2) 0.55917(14) 0.39829(5) 0.0449(3) Uani 1 1 d .
H10A H 1.0466 0.6348 0.4122 0.054 Uiso 1 1 calc R
H10B H 0.9923 0.4676 0.4131 0.054 Uiso 1 1 calc R
C4 C 0.5496(3) 1.17274(14) 0.33795(5) 0.0504(4) Uani 1 1 d .
H4A H 0.6847 1.2147 0.3169 0.060 Uiso 1 1 calc R
H4B H 0.3803 1.1985 0.3220 0.060 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
O1 C1 C13 120.38(10)
O1 C1 C2 121.18(10)
C13 C1 C2 118.43(10)
C8 O3 C7 60.88(8)
C3 O2 C4 104.71(10)
C1 C13 C12 110.20(9)
C1 C2 C5 114.19(9)
C1 C2 C3 108.71(9)
C5 C2 C3 103.01(9)
C6 C5 C4 113.00(10)
C6 C5 C2 114.19(10)
C4 C5 C2 103.41(9)
C11 C12 C13 113.20(10)
C12 C11 C10 114.71(11)
O3 C8 C7 59.58(7)
O3 C8 C9 117.99(11)
C7 C8 C9 125.33(12)
C7 C6 C5 113.57(10)
O3 C7 C8 59.53(8)
O3 C7 C6 116.26(10)
C8 C7 C6 123.35(11)
O2 C3 C2 105.25(9)
C8 C9 C10 111.42(10)
C9 C10 C11 113.37(10)
O2 C4 C5 105.80(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2147(13)
C1 C13 1.5053(15)
C1 C2 1.5063(15)
O3 C8 1.4394(15)
O3 C7 1.4401(14)
O2 C3 1.4092(15)
O2 C4 1.4202(15)
C13 C12 1.5240(17)
C2 C5 1.5386(15)
C2 C3 1.5422(16)
C5 C6 1.5243(16)
C5 C4 1.5271(18)
C12 C11 1.5200(18)
C11 C10 1.5211(17)
C8 C7 1.4590(18)
C8 C9 1.4919(19)
C6 C7 1.4946(17)
C9 C10 1.5197(18)
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
O1 C1 C13 C12 57.38(14)
C2 C1 C13 C12 -123.22(11)
O1 C1 C2 C5 -30.50(15)
C13 C1 C2 C5 150.11(10)
O1 C1 C2 C3 83.88(13)
C13 C1 C2 C3 -95.51(12)
C1 C2 C5 C6 -120.45(11)
C3 C2 C5 C6 121.85(11)
C1 C2 C5 C4 116.36(11)
C3 C2 C5 C4 -1.34(12)
C1 C13 C12 C11 55.92(14)
C13 C12 C11 C10 70.42(14)
C7 O3 C8 C9 116.57(13)
C4 C5 C6 C7 -176.33(10)
C2 C5 C6 C7 65.83(13)
C8 O3 C7 C6 114.90(12)
C9 C8 C7 O3 -104.54(13)
O3 C8 C7 C6 -103.14(13)
C9 C8 C7 C6 152.32(12)
C5 C6 C7 O3 -163.94(10)
C5 C6 C7 C8 -94.56(14)
C4 O2 C3 C2 -41.86(13)
C1 C2 C3 O2 -95.69(11)
C5 C2 C3 O2 25.79(12)
O3 C8 C9 C10 -164.96(10)
C7 C8 C9 C10 -93.99(14)
C8 C9 C10 C11 79.52(14)
C12 C11 C10 C9 -156.54(11)
C3 O2 C4 C5 41.16(13)
C6 C5 C4 O2 -147.32(11)
C2 C5 C4 O2 -23.34(13)
