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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/71/7107139.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_7107139
loop_
_publ_author_name
'Fuye Gao'
'Craig T. M. Stamp'
'Paul D. Thornton'
'T. Stanley Cameron'
'Lauren E. Doyle'
'David O. Miller'
'D. Jean Burnell'
_publ_section_title
;
 Selective formation of angular tricyclic compounds by ruthenium-mediated
 ring-rearrangement metathesis
;
_journal_name_full               Chem.Commun.
_journal_page_first              233
_journal_paper_doi               10.1039/c1cc15452d
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_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                   8.5343(9)
_cell_length_b                   12.8315(14)
_cell_length_c                   19.306(2)
_cell_measurement_reflns_used    8384
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.4
_cell_volume                     2114.2(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9373
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0517P)²+1.0967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2292
_reflns_number_total             2392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc15452d.txt
_cod_data_source_block           compound22
_cod_database_code               7107139
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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 0.42866(10) 0.16660(8) 0.51241(4) 0.0229(2) Uani 1 1 d .
O2 O 0.62975(10) 0.31588(7) 0.54289(5) 0.0219(2) Uani 1 1 d .
C1 C 0.43074(14) 0.14752(9) 0.58627(6) 0.0189(3) Uani 1 1 d .
C2 C 0.35899(15) 0.03962(10) 0.59451(7) 0.0241(3) Uani 1 1 d .
H1 H 0.2450 0.0440 0.5856 0.029 Uiso 1 1 calc R
H2 H 0.4050 -0.0076 0.5594 0.029 Uiso 1 1 calc R
C3 C 0.38490(15) -0.00575(10) 0.66506(7) 0.0248(3) Uani 1 1 d .
H3 H 0.3222 -0.0630 0.6794 0.030 Uiso 1 1 calc R
C4 C 0.49198(15) 0.03105(10) 0.70816(6) 0.0228(3) Uani 1 1 d .
H4 H 0.5046 -0.0033 0.7514 0.027 Uiso 1 1 calc R
C5 C 0.59471(15) 0.12313(10) 0.69347(6) 0.0207(3) Uani 1 1 d .
H5 H 0.7030 0.1059 0.7078 0.025 Uiso 1 1 calc R
H6 H 0.5590 0.1822 0.7224 0.025 Uiso 1 1 calc R
C6 C 0.59778(14) 0.15912(9) 0.61637(6) 0.0169(2) Uani 1 1 d .
C7 C 0.73232(14) 0.10647(9) 0.57796(6) 0.0206(3) Uani 1 1 d .
H7 H 0.7298 0.1270 0.5285 0.025 Uiso 1 1 calc R
H8 H 0.7200 0.0299 0.5806 0.025 Uiso 1 1 calc R
C8 C 0.89142(15) 0.13833(11) 0.61010(7) 0.0254(3) Uani 1 1 d .
H9 H 0.9212 0.0854 0.6450 0.031 Uiso 1 1 calc R
H10 H 0.9720 0.1371 0.5732 0.031 Uiso 1 1 calc R
C9 C 0.89410(15) 0.24399(11) 0.64408(7) 0.0259(3) Uani 1 1 d .
H11 H 0.9906 0.2668 0.6633 0.031 Uiso 1 1 calc R
C10 C 0.77173(15) 0.30797(10) 0.64924(6) 0.0237(3) Uani 1 1 d .
H12 H 0.7799 0.3711 0.6747 0.028 Uiso 1 1 calc R
C11 C 0.62103(14) 0.27896(9) 0.61436(6) 0.0188(3) Uani 1 1 d .
C12 C 0.46479(15) 0.32124(9) 0.64186(7) 0.0234(3) Uani 1 1 d .
H13 H 0.4377 0.3878 0.6189 0.028 Uiso 1 1 calc R
H14 H 0.4704 0.3329 0.6925 0.028 Uiso 1 1 calc R
C13 C 0.34166(14) 0.23573(10) 0.62438(6) 0.0217(3) Uani 1 1 d .
H15 H 0.2929 0.2088 0.6673 0.026 Uiso 1 1 calc R
H16 H 0.2583 0.2646 0.5944 0.026 Uiso 1 1 calc R
H17 H 0.492(2) 0.2224(16) 0.5064(11) 0.047 Uiso 1 1 d .
H18 H 0.730(7) 0.318(4) 0.529(3) 0.225 Uiso 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
O1 C1 C2 104.59(10)
O1 C1 C6 111.43(9)
C2 C1 C6 114.78(10)
O1 C1 C13 109.77(9)
C2 C1 C13 114.68(10)
C6 C1 C13 101.74(9)
C3 C2 C1 112.90(10)
C4 C3 C2 122.37(11)
C3 C4 C5 124.50(11)
C4 C5 C6 115.10(10)
C7 C6 C1 117.95(10)
C7 C6 C11 109.32(10)
C1 C6 C11 101.77(9)
C7 C6 C5 110.23(9)
C1 C6 C5 108.35(9)
C11 C6 C5 108.65(9)
C6 C7 C8 110.40(10)
C9 C8 C7 115.19(11)
C10 C9 C8 125.13(12)
C9 C10 C11 119.08(12)
O2 C11 C10 107.47(9)
O2 C11 C12 104.86(9)
C10 C11 C12 120.16(10)
O2 C11 C6 110.59(9)
C10 C11 C6 110.17(10)
C12 C11 C6 103.34(9)
C11 C12 C13 105.22(9)
C1 C13 C12 106.66(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4470(14)
O2 C11 1.4609(14)
C1 C2 1.5222(17)
C1 C6 1.5467(16)
C1 C13 1.5493(17)
C2 C3 1.4977(18)
C3 C4 1.3230(19)
C4 C5 1.4984(17)
C5 C6 1.5586(15)
C6 C7 1.5248(16)
C6 C11 1.5509(16)
C7 C8 1.5478(17)
C8 C9 1.506(2)
C9 C10 1.3321(19)
C10 C11 1.4988(16)
C11 C12 1.5343(17)
C12 C13 1.5563(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101553488
