#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:56:42 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178451 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/72/4027216.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_4027216
loop_
_publ_author_name
'Björn Nelson'
'Sonja Herres-Pawlis'
'Wolf Hiller'
'Hans Preut'
'Carsten Strohmann'
'Martin Hiersemann'
_publ_section_title
;
 Palladium(II)-Catalyzed Cycloisomerization of Substituted 1,5-Hexadienes:
 A Combined Experimental and Computational Study on an Open and an
 Interrupted Hydropalladation/Carbopalladation/β-Hydride Elimination
 (HCHe) Catalytic Cycle
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4980
_journal_page_last               4995
_journal_paper_doi               10.1021/jo3004088
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C12 H20 O3'
_chemical_formula_weight         212.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.124(7)
_cell_angle_beta                 97.815(7)
_cell_angle_gamma                106.878(8)
_cell_formula_units_Z            2
_cell_length_a                   7.2223(6)
_cell_length_b                   8.8729(7)
_cell_length_c                   10.2165(8)
_cell_measurement_temperature    173(2)
_cell_volume                     611.38(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5898
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.9683
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0372
_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)+(0.0628P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1850
_reflns_number_total             2382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3004088_si_003.cif
_cod_data_source_block           preu
_cod_database_code               4027216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.2847(2) 0.93230(18) 0.36090(15) 0.0404(4) Uani 1 1 d .
H1A H 0.1596 0.9059 0.2986 0.061 Uiso 1 1 calc R
H1B H 0.3317 1.0473 0.3962 0.061 Uiso 1 1 calc R
H1C H 0.2653 0.8728 0.4352 0.061 Uiso 1 1 calc R
C2 C 0.4333(2) 0.88800(15) 0.28879(12) 0.0264(3) Uani 1 1 d .
H2 H 0.5604 0.9122 0.3525 0.032 Uiso 1 1 calc R
C3 C 0.4676(2) 0.97122(18) 0.17063(14) 0.0391(4) Uani 1 1 d .
H3A H 0.5654 0.9377 0.1270 0.059 Uiso 1 1 calc R
H3B H 0.5160 1.0872 0.2013 0.059 Uiso 1 1 calc R
H3C H 0.3439 0.9430 0.1066 0.059 Uiso 1 1 calc R
C4 C 0.38635(17) 0.61496(15) 0.31092(11) 0.0190(3) Uani 1 1 d .
C5 C 0.30005(16) 0.44192(14) 0.24161(11) 0.0174(3) Uani 1 1 d .
C6 C 0.27844(16) 0.41701(14) 0.08823(11) 0.0184(3) Uani 1 1 d .
H6 H 0.2107 0.4919 0.0545 0.022 Uiso 1 1 calc R
C7 C 0.46686(17) 0.44461(15) 0.03596(11) 0.0196(3) Uani 1 1 d .
H7 H 0.5444 0.3775 0.0560 0.024 Uiso 1 1 calc R
C8 C 0.13565(18) 0.24562(16) 0.04526(12) 0.0264(3) Uani 1 1 d .
H8A H 0.0520 0.2347 -0.0428 0.032 Uiso 1 1 calc R
H8B H 0.2094 0.1677 0.0380 0.032 Uiso 1 1 calc R
C9 C 0.0107(2) 0.21681(18) 0.15286(14) 0.0379(4) Uani 1 1 d .
H9A H 0.0220 0.1216 0.1906 0.046 Uiso 1 1 calc R
H9B H -0.1291 0.1975 0.1141 0.046 Uiso 1 1 calc R
C10 C 0.08417(17) 0.36615(15) 0.26416(12) 0.0228(3) Uani 1 1 d .
C11 C -0.03848(19) 0.47762(19) 0.24327(14) 0.0325(4) Uani 1 1 d .
H11A H -0.1749 0.4232 0.2501 0.049 Uiso 1 1 calc R
H11B H -0.0343 0.5073 0.1542 0.049 Uiso 1 1 calc R
H11C H 0.0149 0.5741 0.3120 0.049 Uiso 1 1 calc R
C12 C 0.0772(2) 0.32308(18) 0.40323(13) 0.0315(3) Uani 1 1 d .
H12A H 0.1386 0.4198 0.4710 0.047 Uiso 1 1 calc R
H12B H 0.1487 0.2460 0.4160 0.047 Uiso 1 1 calc R
H12C H -0.0600 0.2758 0.4123 0.047 Uiso 1 1 calc R
O1 O 0.42341(12) 0.35550(10) 0.29007(8) 0.0215(2) Uani 1 1 d .
H1 H 0.4471 0.3749 0.3743 0.032 Uiso 1 1 calc R
O2 O 0.46954(13) 0.65376(11) 0.42670(8) 0.0293(3) Uani 1 1 d .
O3 O 0.35950(12) 0.71737(10) 0.23233(8) 0.0221(2) 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
_geom_angle_site_symmetry_1
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
O3 C2 C1 109.30(10) .
O3 C2 C3 105.09(10) .
C1 C2 C3 112.84(12) .
O3 C2 H2 109.8 .
C1 C2 H2 109.8 .
C3 C2 H2 109.8 .
C2 C3 H3A 109.5 .
C2 C3 H3B 109.5 .
H3A C3 H3B 109.5 .
C2 C3 H3C 109.5 .
H3A C3 H3C 109.5 .
H3B C3 H3C 109.5 .
O2 C4 O3 124.00(11) .
O2 C4 C5 122.89(11) .
O3 C4 C5 113.11(9) .
O1 C5 C4 108.61(9) .
O1 C5 C6 107.66(9) .
C4 C5 C6 114.64(10) .
O1 C5 C10 110.93(10) .
C4 C5 C10 111.65(10) .
C6 C5 C10 103.23(9) .
C7 C6 C5 115.30(9) .
C7 C6 C8 114.34(10) .
C5 C6 C8 102.54(9) .
C7 C6 H6 108.1 .
C5 C6 H6 108.1 .
C8 C6 H6 108.1 .
C7 C7 C6 124.66(15) 2_665
C7 C7 H7 117.7 2_665
C6 C7 H7 117.7 .
C9 C8 C6 106.33(10) .
C9 C8 H8A 110.5 .
C6 C8 H8A 110.5 .
C9 C8 H8B 110.5 .
C6 C8 H8B 110.5 .
H8A C8 H8B 108.7 .
C8 C9 C10 108.32(10) .
C8 C9 H9A 110.0 .
C10 C9 H9A 110.0 .
C8 C9 H9B 110.0 .
C10 C9 H9B 110.0 .
H9A C9 H9B 108.4 .
C12 C10 C11 108.53(11) .
C12 C10 C9 112.19(11) .
C11 C10 C9 110.79(11) .
C12 C10 C5 112.47(10) .
C11 C10 C5 111.56(11) .
C9 C10 C5 101.20(10) .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C10 C12 H12A 109.5 .
C10 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C10 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C5 O1 H1 109.5 .
C4 O3 C2 118.16(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.496(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 O3 1.4629(14) .
C2 C3 1.5035(19) .
C2 H2 1.0000 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 O2 1.2100(13) .
C4 O3 1.3224(14) .
C4 C5 1.5172(16) .
C5 O1 1.4134(14) .
C5 C6 1.5351(16) .
C5 C10 1.5696(16) .
C6 C7 1.4944(16) .
C6 C8 1.5393(16) .
C6 H6 1.0000 .
C7 C7 1.318(2) 2_665
C7 H7 0.9500 .
C8 C9 1.5143(19) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.5441(18) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C12 1.5199(18) .
C10 C11 1.523(2) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
O1 H1 0.8400 .
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 O2 0.84 2.11 2.9094(11) 159.4 2_666
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
_geom_torsion_site_symmetry_4
O2 C4 C5 O1 -35.67(15) .
O3 C4 C5 O1 144.89(10) .
O2 C4 C5 C6 -156.11(11) .
O3 C4 C5 C6 24.45(14) .
O2 C4 C5 C10 86.96(14) .
O3 C4 C5 C10 -92.48(12) .
O1 C5 C6 C7 -49.54(13) .
C4 C5 C6 C7 71.43(14) .
C10 C5 C6 C7 -166.92(10) .
O1 C5 C6 C8 75.37(11) .
C4 C5 C6 C8 -163.67(10) .
C10 C5 C6 C8 -42.02(12) .
C5 C6 C7 C7 -117.75(16) 2_665
C8 C6 C7 C7 123.73(16) 2_665
C7 C6 C8 C9 153.39(11) .
C5 C6 C8 C9 27.86(14) .
C6 C8 C9 C10 -2.93(15) .
C8 C9 C10 C12 -142.57(12) .
C8 C9 C10 C11 95.96(14) .
C8 C9 C10 C5 -22.46(14) .
O1 C5 C10 C12 44.49(14) .
C4 C5 C10 C12 -76.80(13) .
C6 C5 C10 C12 159.55(11) .
O1 C5 C10 C11 166.72(9) .
C4 C5 C10 C11 45.42(13) .
C6 C5 C10 C11 -78.23(12) .
O1 C5 C10 C9 -75.42(11) .
C4 C5 C10 C9 163.28(10) .
C6 C5 C10 C9 39.64(13) .
O2 C4 O3 C2 -0.52(18) .
C5 C4 O3 C2 178.92(9) .
C1 C2 O3 C4 -84.03(14) .
C3 C2 O3 C4 154.61(11) .
