#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:07:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180223 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/09/7110931.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110931
loop_
_publ_author_name
'Bassindale, Martin J.'
'Edwards, Andrew S.'
'Adams, Harry'
'Harrity, Joseph P. A.'
'Hamley, Peter'
_publ_section_title
;
 The synthesis of angularly fused tricyclic compounds via tandem ring
 closing metathesis reactions
;
_journal_issue                   12
_journal_name_full               'Chemical Communications'
_journal_page_first              1035
_journal_paper_doi               10.1039/b002136i
_journal_year                    2000
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.6041(5)
_cell_length_b                   13.1932(7)
_cell_length_c                   19.0521(10)
_cell_measurement_reflns_used    76
_cell_measurement_temperature    150(2)
_cell_volume                     2162.7(2)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13115
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0572
_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)+(0.1003P)²+0.8288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1589
_reflns_number_gt                2278
_reflns_number_total             2624
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002136isup1.cif
_cod_data_source_block           ohj12m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7110931
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.16240(13) 0.69115(9) 0.04679(5) 0.0313(3) Uani 1 1 d .
H1 H 0.1075 0.7228 0.0177 0.038 Uiso 1 1 calc R
O2 O -0.04160(12) 0.82949(9) 0.01079(5) 0.0320(3) Uani 1 1 d .
H2 H -0.1290 0.8243 -0.0085 0.038 Uiso 1 1 calc R
C1 C 0.09885(16) 0.84021(10) 0.11950(7) 0.0229(3) Uani 1 1 d .
C2 C 0.12351(17) 0.72392(11) 0.11719(7) 0.0264(3) Uani 1 1 d .
C3 C -0.03753(19) 0.68120(11) 0.13747(9) 0.0324(4) Uani 1 1 d .
H3A H -0.0410 0.6645 0.1881 0.039 Uiso 1 1 calc R
H3B H -0.0609 0.6192 0.1102 0.039 Uiso 1 1 calc R
C4 C -0.15605(17) 0.76660(12) 0.11982(8) 0.0297(3) Uani 1 1 d .
H4A H -0.2375 0.7409 0.0877 0.036 Uiso 1 1 calc R
H4B H -0.2064 0.7918 0.1632 0.036 Uiso 1 1 calc R
C5 C -0.06191(16) 0.85227(11) 0.08420(7) 0.0253(3) Uani 1 1 d .
C6 C -0.13258(18) 0.95817(12) 0.09105(9) 0.0335(4) Uani 1 1 d .
H6A H -0.0822 1.0038 0.0566 0.040 Uiso 1 1 calc R
H6B H -0.2445 0.9547 0.0793 0.040 Uiso 1 1 calc R
C7 C -0.11467(19) 1.00225(12) 0.16286(9) 0.0357(4) Uani 1 1 d .
H7A H -0.1770 1.0588 0.1755 0.043 Uiso 1 1 calc R
C8 C -0.01523(19) 0.96565(12) 0.20979(9) 0.0324(4) Uani 1 1 d .
H8A H -0.0078 0.9990 0.2539 0.039 Uiso 1 1 calc R
C9 C 0.08614(18) 0.87475(12) 0.19734(7) 0.0282(3) Uani 1 1 d .
H9A H 0.0452 0.8175 0.2254 0.034 Uiso 1 1 calc R
H9B H 0.1919 0.8901 0.2149 0.034 Uiso 1 1 calc R
C10 C 0.23700(17) 0.89337(12) 0.08444(8) 0.0301(3) Uani 1 1 d .
H10A H 0.2304 0.8850 0.0329 0.036 Uiso 1 1 calc R
H10B H 0.2340 0.9668 0.0952 0.036 Uiso 1 1 calc R
C11 C 0.38824(18) 0.84827(14) 0.11106(9) 0.0366(4) Uani 1 1 d .
H11A H 0.4812 0.8854 0.1032 0.044 Uiso 1 1 calc R
C12 C 0.39926(19) 0.76049(14) 0.14456(9) 0.0381(4) Uani 1 1 d .
H12A H 0.4996 0.7387 0.1589 0.046 Uiso 1 1 calc R
C13 C 0.2633(2) 0.69312(13) 0.16136(9) 0.0358(4) Uani 1 1 d .
H13A H 0.2372 0.6989 0.2118 0.043 Uiso 1 1 calc R
H13B H 0.2907 0.6217 0.1515 0.043 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0282(6) 0.0388(6) 0.0268(6) -0.0105(4) 0.0012(4) 0.0019(4)
O2 0.0252(5) 0.0496(7) 0.0211(5) 0.0003(4) -0.0026(4) -0.0036(5)
C1 0.0217(6) 0.0270(6) 0.0199(6) -0.0010(5) 0.0000(5) -0.0011(5)
C2 0.0267(7) 0.0274(7) 0.0251(7) -0.0025(5) 0.0016(5) 0.0010(5)
C3 0.0336(8) 0.0282(7) 0.0354(8) 0.0012(6) 0.0065(6) -0.0039(6)
C4 0.0239(7) 0.0350(8) 0.0303(8) 0.0011(6) 0.0041(5) -0.0056(6)
C5 0.0212(6) 0.0332(7) 0.0215(7) 0.0018(5) 0.0014(5) -0.0026(5)
C6 0.0269(7) 0.0358(8) 0.0379(9) 0.0086(6) 0.0012(6) 0.0042(6)
C7 0.0329(8) 0.0278(7) 0.0463(10) 0.0000(6) 0.0089(7) 0.0035(6)
C8 0.0339(8) 0.0306(7) 0.0327(8) -0.0084(6) 0.0077(6) -0.0029(6)
C9 0.0287(7) 0.0314(7) 0.0245(7) -0.0032(6) 0.0004(5) 0.0018(6)
C10 0.0264(7) 0.0336(8) 0.0303(7) -0.0028(6) 0.0045(5) -0.0070(6)
C11 0.0217(7) 0.0515(10) 0.0367(9) -0.0163(7) 0.0019(6) -0.0062(6)
C12 0.0260(8) 0.0520(10) 0.0363(9) -0.0149(7) -0.0055(6) 0.0076(7)
C13 0.0357(8) 0.0368(8) 0.0348(8) -0.0038(6) -0.0048(6) 0.0110(6)
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
C10 C1 C5 117.19(12)
C10 C1 C2 109.53(12)
C5 C1 C2 102.24(11)
C10 C1 C9 109.63(12)
C5 C1 C9 108.76(11)
C2 C1 C9 109.08(11)
O1 C2 C13 104.46(12)
O1 C2 C3 109.27(12)
C13 C2 C3 118.21(13)
O1 C2 C1 110.70(12)
C13 C2 C1 110.89(12)
C3 C2 C1 103.37(11)
C2 C3 C4 105.64(11)
C5 C4 C3 106.29(11)
O2 C5 C6 108.76(12)
O2 C5 C4 109.68(12)
C6 C5 C4 114.95(12)
O2 C5 C1 106.99(11)
C6 C5 C1 114.37(12)
C4 C5 C1 101.68(11)
C7 C6 C5 113.12(13)
C8 C7 C6 122.76(14)
C7 C8 C9 123.92(14)
C8 C9 C1 115.18(12)
C11 C10 C1 109.86(13)
C12 C11 C10 124.37(14)
C11 C12 C13 124.28(15)
C12 C13 C2 109.82(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.4482(17)
O2 C5 1.4412(17)
C1 C10 1.5333(19)
C1 C5 1.5462(19)
C1 C2 1.5496(19)
C1 C9 1.5554(19)
C2 C13 1.523(2)
C2 C3 1.545(2)
C3 C4 1.556(2)
C4 C5 1.547(2)
C5 C6 1.529(2)
C6 C7 1.495(2)
C7 C8 1.328(2)
C8 C9 1.502(2)
C10 C11 1.518(2)
C11 C12 1.326(3)
C12 C13 1.504(3)
