#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:48:14 +0100 (lun 21 de mar de 2016) $
#$Revision: 178406 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/27/4022742.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_4022742
loop_
_publ_author_name
'Gary A. Molander'
'Barbara Czakó'
'Michael Rheam'
_publ_section_title
;
 Construction of Bicyclic Ring Systems via a Transannular
 SmI₂-Mediated Ketone-Olefin Cyclization Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1755
_journal_page_last               1764
_journal_paper_doi               10.1021/jo062292d
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C9 H15 O'
_chemical_formula_weight         139.21
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   12.2331(7)
_cell_length_b                   12.2331(7)
_cell_length_c                   27.5112(12)
_cell_measurement_temperature    143(1)
_cell_volume                     3565.4(3)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9373
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8923
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             1386
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0476
_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)+(0.0529P)²+7.0085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                1310
_reflns_number_total             1413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062292dsi20061107_122917.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'R -3     '
_cod_database_code               4022742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.38010(14) 0.30512(14) 0.27188(5) 0.0215(4) Uani 1 1 d .
C2 C 0.48245(16) 0.40952(16) 0.23943(6) 0.0309(4) Uani 1 1 d .
H2A H 0.5626 0.4515 0.2565 0.041 Uiso 1 1 calc R
H2B H 0.4932 0.3729 0.2098 0.041 Uiso 1 1 calc R
C3 C 0.43939(18) 0.50341(17) 0.22746(7) 0.0372(5) Uani 1 1 d .
H3A H 0.3969 0.4844 0.1962 0.050 Uiso 1 1 calc R
H3B H 0.5104 0.5889 0.2268 0.050 Uiso 1 1 calc R
C4 C 0.34813(16) 0.48689(15) 0.26877(6) 0.0285(4) Uani 1 1 d .
H4A H 0.3939 0.5334 0.2974 0.038 Uiso 1 1 calc R
H4B H 0.2907 0.5159 0.2589 0.038 Uiso 1 1 calc R
C5 C 0.27641(14) 0.34470(13) 0.27866(5) 0.0195(4) Uani 1 1 d .
C6 C 0.17908(16) 0.26860(17) 0.23818(6) 0.0307(4) Uani 1 1 d .
H6A H 0.0973 0.2122 0.2525 0.041 Uiso 1 1 calc R
H6B H 0.1701 0.3256 0.2162 0.041 Uiso 1 1 calc R
C7 C 0.22744(19) 0.19271(18) 0.21056(6) 0.0376(5) Uani 1 1 d .
H7A H 0.1581 0.1115 0.2004 0.050 Uiso 1 1 calc R
H7B H 0.2756 0.2383 0.1822 0.050 Uiso 1 1 calc R
C8 C 0.31072(16) 0.17668(16) 0.24748(6) 0.0300(4) Uani 1 1 d .
H8A H 0.2605 0.1109 0.2708 0.040 Uiso 1 1 calc R
H8B H 0.3692 0.1564 0.2316 0.040 Uiso 1 1 calc R
C9 C 0.21435(14) 0.31115(14) 0.32907(5) 0.0214(4) Uani 1 1 d .
H9A H 0.1718 0.2203 0.3332 0.028 Uiso 1 1 calc R
H9B H 0.2798 0.3486 0.3536 0.028 Uiso 1 1 calc R
O1 O 0.43342(10) 0.29183(10) 0.31634(4) 0.0235(3) Uani 1 1 d .
H1 H 0.4870 0.3617 0.3261 0.035 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
C1 0.0234(8) 0.0247(8) 0.0184(7) -0.0003(6) 0.0021(6) 0.0135(6)
C2 0.0274(8) 0.0386(10) 0.0268(8) 0.0068(7) 0.0095(6) 0.0165(7)
C3 0.0418(10) 0.0314(9) 0.0377(10) 0.0111(8) 0.0191(8) 0.0177(8)
C4 0.0333(9) 0.0233(8) 0.0298(8) 0.0057(6) 0.0107(7) 0.0148(7)
C5 0.0219(7) 0.0202(7) 0.0174(7) 0.0007(5) 0.0021(6) 0.0113(6)
C6 0.0280(9) 0.0416(10) 0.0250(8) -0.0088(7) -0.0043(6) 0.0193(8)
C7 0.0444(11) 0.0409(10) 0.0314(9) -0.0144(8) -0.0099(8) 0.0243(9)
C8 0.0379(9) 0.0292(9) 0.0285(8) -0.0084(7) -0.0033(7) 0.0210(8)
C9 0.0245(8) 0.0220(7) 0.0192(7) 0.0025(6) 0.0043(6) 0.0127(6)
O1 0.0234(6) 0.0223(5) 0.0244(6) -0.0010(4) -0.0035(4) 0.0111(5)
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
O1 C1 C8 108.09(12) .
O1 C1 C2 111.07(12) .
C8 C1 C2 113.68(13) .
O1 C1 C5 114.53(11) .
C8 C1 C5 104.50(12) .
C2 C1 C5 104.92(12) .
C3 C2 C1 107.79(13) .
C2 C3 C4 104.14(13) .
C5 C4 C3 104.31(13) .
C4 C5 C9 112.96(12) .
C4 C5 C6 112.66(13) .
C9 C5 C6 111.03(12) .
C4 C5 C1 103.63(12) .
C9 C5 C1 112.99(11) .
C6 C5 C1 102.95(11) .
C7 C6 C5 107.85(13) .
C8 C7 C6 103.54(13) .
C1 C8 C7 103.06(13) .
C9 C9 C5 113.98(15) 16
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.4330(18) .
C1 C8 1.519(2) .
C1 C2 1.548(2) .
C1 C5 1.579(2) .
C2 C3 1.520(2) .
C3 C4 1.534(2) .
C4 C5 1.531(2) .
C5 C9 1.5351(19) .
C5 C6 1.554(2) .
C6 C7 1.529(2) .
C7 C8 1.519(2) .
C9 C9 1.531(3) 16
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.82 1.98 2.7973(12) 175.6 17
