#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:49:28 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178407 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/28/4022822.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_4022822
loop_
_publ_author_name
'Yit Wooi Goh'
'Stephen M. Danczak'
'Tang Kuan Lim'
'Jonathan M. White'
_publ_section_title
;
 Manifestations of the Alder-Rickert Reaction in the Structures
 of Bicyclo[2.2.2]octadiene and Bicyclo[2.2.2]octene Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2929
_journal_page_last               2935
_journal_paper_doi               10.1021/jo0625610
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_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                 100.102(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.348(3)
_cell_length_b                   7.9547(18)
_cell_length_c                   14.484(4)
_cell_measurement_reflns_used    445
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      17.76
_cell_measurement_theta_min      2.86
_cell_volume                     1173.8(5)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0917
_diffrn_reflns_av_sigmaI/netI    0.1432
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5875
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0004(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.732
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.732
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.075
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0335P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                713
_reflns_number_total             2077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0625610si20061219_073713_3.cif
_cod_data_source_block           CMPD12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022822
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
C1 C 0.8830(4) -0.0891(5) 0.3188(3) 0.0612(10) Uani 1 1 d .
C2 C 0.7835(3) 0.0213(4) 0.2821(3) 0.0556(10) Uani 1 1 d .
C3 C 0.7431(4) 0.1846(5) 0.3235(3) 0.0628(10) Uani 1 1 d .
C4 C 0.5977(4) 0.1735(4) 0.3263(3) 0.0678(11) Uani 1 1 d .
H4 H 0.5624 0.1887 0.3805 0.081 Uiso 1 1 calc R
C5 C 0.5230(3) 0.1382(4) 0.2396(3) 0.0680(11) Uani 1 1 d .
H5 H 0.4322 0.1272 0.2294 0.082 Uiso 1 1 calc R
C6 C 0.6045(3) 0.1194(4) 0.1624(2) 0.0627(10) Uani 1 1 d .
H6 H 0.5511 0.0926 0.1013 0.075 Uiso 1 1 calc R
C7 C 0.7085(3) -0.0120(4) 0.1948(3) 0.0556(10) Uani 1 1 d .
C8 C 0.7343(4) -0.1526(5) 0.1439(3) 0.0595(10) Uani 1 1 d .
C9 C 0.7587(3) 0.3240(4) 0.2539(3) 0.0756(12) Uani 1 1 d .
H9A H 0.7306 0.4302 0.2767 0.091 Uiso 1 1 calc R
H9B H 0.8504 0.3343 0.2482 0.091 Uiso 1 1 calc R
C10 C 0.6798(4) 0.2859(4) 0.1617(3) 0.0786(12) Uani 1 1 d .
H10A H 0.7370 0.2794 0.1154 0.094 Uiso 1 1 calc R
H10B H 0.6177 0.3765 0.1435 0.094 Uiso 1 1 calc R
C11 C 0.9049(3) -0.2316(5) 0.2694(3) 0.0667(11) Uani 1 1 d .
H11 H 0.9696 -0.3072 0.2955 0.080 Uiso 1 1 calc R
C12 C 0.8324(4) -0.2639(4) 0.1820(3) 0.0682(11) Uani 1 1 d .
H12 H 0.8491 -0.3593 0.1488 0.082 Uiso 1 1 calc R
C13 C 0.8215(4) 0.3683(5) 0.4554(3) 0.1101(16) Uani 1 1 d .
H13A H 0.7326 0.3993 0.4580 0.165 Uiso 1 1 calc R
H13B H 0.8590 0.4493 0.4187 0.165 Uiso 1 1 calc R
H13C H 0.8717 0.3652 0.5178 0.165 Uiso 1 1 calc R
C14 C 0.6930(4) -0.3014(5) -0.0020(2) 0.0989(14) Uani 1 1 d .
H14A H 0.6870 -0.4093 0.0267 0.148 Uiso 1 1 calc R
H14B H 0.7816 -0.2824 -0.0107 0.148 Uiso 1 1 calc R
H14C H 0.6355 -0.2988 -0.0617 0.148 Uiso 1 1 calc R
O1 O 0.9605(2) -0.0582(3) 0.40504(19) 0.0778(8) Uani 1 1 d .
H15 H 1.0041 -0.1421 0.4224 0.117 Uiso 1 1 calc R
O2 O 0.6556(2) -0.1743(3) 0.05662(19) 0.0746(8) Uani 1 1 d .
O5 O 0.8232(2) 0.2068(3) 0.41353(19) 0.0830(8) 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 0.0000 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
C11 C1 O1 119.5(4)
C11 C1 C2 120.0(4)
O1 C1 C2 120.5(4)
C1 C2 C7 119.1(4)
C1 C2 C3 128.9(4)
C7 C2 C3 112.0(3)
O5 C3 C4 113.8(3)
O5 C3 C2 108.1(3)
C4 C3 C2 107.7(3)
O5 C3 C9 113.7(3)
C4 C3 C9 106.3(3)
C2 C3 C9 107.0(3)
C5 C4 C3 112.7(3)
C5 C4 H4 123.6
C3 C4 H4 123.6
C4 C5 C6 113.2(3)
C4 C5 H5 123.4
C6 C5 H5 123.4
C7 C6 C5 107.2(3)
C7 C6 C10 105.2(3)
C5 C6 C10 105.4(3)
C7 C6 H6 112.8
C5 C6 H6 112.8
C10 C6 H6 112.8
C2 C7 C8 120.5(3)
C2 C7 C6 113.8(3)
C8 C7 C6 125.6(4)
C12 C8 O2 123.6(4)
C12 C8 C7 119.8(4)
O2 C8 C7 116.5(4)
C10 C9 C3 110.2(3)
C10 C9 H9A 109.6
C3 C9 H9A 109.6
C10 C9 H9B 109.6
C3 C9 H9B 109.6
H9A C9 H9B 108.1
C9 C10 C6 111.9(3)
C9 C10 H10A 109.2
C6 C10 H10A 109.2
C9 C10 H10B 109.2
C6 C10 H10B 109.2
H10A C10 H10B 107.9
C12 C11 C1 121.1(4)
C12 C11 H11 119.4
C1 C11 H11 119.4
C11 C12 C8 119.3(4)
C11 C12 H12 120.4
C8 C12 H12 120.4
O5 C13 H13A 109.5
O5 C13 H13B 109.5
H13A C13 H13B 109.5
O5 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C1 O1 H15 109.5
C8 O2 C14 117.1(3)
C13 O5 C3 116.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C11 1.380(4)
C1 O1 1.383(4)
C1 C2 1.387(4)
C2 C7 1.388(4)
C2 C3 1.520(4)
C3 O5 1.428(4)
C3 C4 1.515(4)
C3 C9 1.526(4)
C4 C5 1.383(4)
C4 H4 0.9300
C5 C6 1.521(4)
C5 H5 0.9300
C6 C7 1.515(4)
C6 C10 1.538(4)
C6 H6 0.9800
C7 C8 1.390(4)
C8 C12 1.386(4)
C8 O2 1.389(4)
C9 C10 1.470(4)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.378(4)
C11 H11 0.9300
C12 H12 0.9300
C13 O5 1.422(4)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 O2 1.417(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
O1 H15 0.8200
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
C11 C1 C2 C7 -1.2(5)
O1 C1 C2 C7 179.1(3)
C11 C1 C2 C3 -179.5(3)
O1 C1 C2 C3 0.9(5)
C1 C2 C3 O5 -2.8(5)
C7 C2 C3 O5 178.9(3)
C1 C2 C3 C4 -126.1(4)
C7 C2 C3 C4 55.6(4)
C1 C2 C3 C9 120.0(4)
C7 C2 C3 C9 -58.3(4)
O5 C3 C4 C5 -175.0(3)
C2 C3 C4 C5 -55.3(4)
C9 C3 C4 C5 59.1(4)
C3 C4 C5 C6 -0.1(4)
C4 C5 C6 C7 54.3(4)
C4 C5 C6 C10 -57.4(4)
C1 C2 C7 C8 -1.2(5)
C3 C2 C7 C8 177.4(3)
C1 C2 C7 C6 -179.2(3)
C3 C2 C7 C6 -0.7(4)
C5 C6 C7 C2 -53.9(4)
C10 C6 C7 C2 58.0(4)
C5 C6 C7 C8 128.1(3)
C10 C6 C7 C8 -120.0(3)
C2 C7 C8 C12 2.4(5)
C6 C7 C8 C12 -179.8(3)
C2 C7 C8 O2 -179.0(3)
C6 C7 C8 O2 -1.2(5)
O5 C3 C9 C10 176.3(3)
C4 C3 C9 C10 -57.8(4)
C2 C3 C9 C10 57.1(4)
C3 C9 C10 C6 0.4(4)
C7 C6 C10 C9 -56.9(4)
C5 C6 C10 C9 56.3(4)
O1 C1 C11 C12 -177.9(3)
C2 C1 C11 C12 2.4(5)
C1 C11 C12 C8 -1.2(5)
O2 C8 C12 C11 -179.7(3)
C7 C8 C12 C11 -1.2(5)
C12 C8 O2 C14 -10.9(5)
C7 C8 O2 C14 170.6(3)
C4 C3 O5 C13 -73.8(4)
C2 C3 O5 C13 166.7(3)
C9 C3 O5 C13 48.1(4)
