#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:11:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178804 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/58/4105873.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_4105873
loop_
_publ_author_name
'Jørn H. Hansen'
'Timothy M. Gregg'
'Stephanie R. Ovalles'
'Yajing Lian'
'Jochen Autschbach'
'Huw M. L. Davies'
_publ_section_title
;
 On the Mechanism and Selectivity of the Combined C-H Activation/Cope
 Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5076
_journal_page_last               5085
_journal_paper_doi               10.1021/ja111408v
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 O2'
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.735(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2525(4)
_cell_length_b                   7.5766(3)
_cell_length_c                   11.1876(4)
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.60
_cell_measurement_theta_min      4.07
_cell_volume                     761.85(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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5184
_diffrn_reflns_theta_full        68.02
_diffrn_reflns_theta_max         68.02
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.9275
_exptl_absorpt_correction_T_min  0.8479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       irreg
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0292
_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)+(0.0420P)²+0.1010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                2365
_reflns_number_total             2380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja111408v_si_002.cif
_cod_data_source_block           yl_v_84cope
_cod_database_code               4105873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C1 C 0.18831(17) 0.3424(2) 0.44552(13) 0.0422(4) Uani 1 1 d .
H1A H 0.2670 0.3710 0.5142 0.051 Uiso 1 1 calc R
C2 C 0.07643(19) 0.2504(2) 0.46748(15) 0.0492(4) Uani 1 1 d .
H2A H 0.0795 0.2179 0.5501 0.059 Uiso 1 1 calc R
C3 C -0.05379(19) 0.1952(3) 0.37003(17) 0.0566(5) Uani 1 1 d .
H3A H -0.1455 0.2342 0.3933 0.068 Uiso 1 1 calc R
H3B H -0.0559 0.0646 0.3659 0.068 Uiso 1 1 calc R
C4 C -0.05543(16) 0.26668(19) 0.24409(14) 0.0377(3) Uani 1 1 d .
C5 C -0.18054(16) 0.2377(2) 0.14809(16) 0.0454(4) Uani 1 1 d .
H5A H -0.2627 0.1751 0.1645 0.054 Uiso 1 1 calc R
C6 C -0.18831(16) 0.2968(2) 0.03138(15) 0.0473(4) Uani 1 1 d .
H6A H -0.2752 0.2766 -0.0320 0.057 Uiso 1 1 calc R
C7 C -0.06877(17) 0.3860(2) 0.00643(13) 0.0442(4) Uani 1 1 d .
H7A H -0.0721 0.4258 -0.0747 0.053 Uiso 1 1 calc R
C8 C 0.05597(16) 0.4172(2) 0.10039(13) 0.0371(3) Uani 1 1 d .
H8A H 0.1377 0.4791 0.0827 0.045 Uiso 1 1 calc R
C9 C 0.06462(14) 0.36014(19) 0.22058(12) 0.0309(3) Uani 1 1 d .
C10 C 0.20255(15) 0.40627(18) 0.32118(12) 0.0326(3) Uani 1 1 d .
C11 C 0.34275(14) 0.31880(19) 0.28740(12) 0.0317(3) Uani 1 1 d .
H11A H 0.3419 0.3523 0.2008 0.038 Uiso 1 1 calc R
C12 C 0.48565(15) 0.3847(2) 0.36879(12) 0.0366(3) Uani 1 1 d .
H12A H 0.5039 0.3498 0.4526 0.044 Uiso 1 1 calc R
C13 C 0.59028(15) 0.4851(2) 0.33973(13) 0.0373(3) Uani 1 1 d .
H13A H 0.6755 0.5100 0.4038 0.045 Uiso 1 1 calc R
C14 C 0.58711(14) 0.56183(19) 0.21767(13) 0.0350(3) Uani 1 1 d .
C15 C 0.7189(2) 0.7494(2) 0.11260(16) 0.0529(4) Uani 1 1 d .
H15A H 0.8089 0.8224 0.1282 0.079 Uiso 1 1 calc R
H15B H 0.6314 0.8239 0.0817 0.079 Uiso 1 1 calc R
H15C H 0.7247 0.6591 0.0512 0.079 Uiso 1 1 calc R
C16 C 0.33691(15) 0.1168(2) 0.29394(13) 0.0367(3) Uani 1 1 d .
H16A H 0.3458 0.0808 0.3805 0.044 Uiso 1 1 calc R
H16B H 0.2390 0.0757 0.2451 0.044 Uiso 1 1 calc R
C17 C 0.45954(16) 0.0270(2) 0.24601(15) 0.0450(4) Uani 1 1 d .
H17A H 0.4506 -0.1013 0.2525 0.067 Uiso 1 1 calc R
H17B H 0.5569 0.0651 0.2950 0.067 Uiso 1 1 calc R
H17C H 0.4499 0.0595 0.1597 0.067 Uiso 1 1 calc R
C18 C 0.22097(17) 0.6087(2) 0.32604(15) 0.0434(4) Uani 1 1 d .
H18A H 0.1340 0.6627 0.3471 0.065 Uiso 1 1 calc R
H18B H 0.2298 0.6520 0.2456 0.065 Uiso 1 1 calc R
H18C H 0.3108 0.6399 0.3886 0.065 Uiso 1 1 calc R
O1 O 0.49384(11) 0.54052(16) 0.12342(9) 0.0464(3) Uani 1 1 d .
O2 O 0.70669(11) 0.66518(15) 0.22558(10) 0.0437(3) 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C2 C1 C10 125.87(14)
C2 C1 H1A 117.1
C10 C1 H1A 117.1
C1 C2 C3 123.36(14)
C1 C2 H2A 118.3
C3 C2 H2A 118.3
C2 C3 C4 114.38(14)
C2 C3 H3A 108.7
C4 C3 H3A 108.7
C2 C3 H3B 108.7
C4 C3 H3B 108.7
H3A C3 H3B 107.6
C9 C4 C5 119.13(14)
C9 C4 C3 121.85(13)
C5 C4 C3 119.02(14)
C6 C5 C4 121.97(14)
C6 C5 H5A 119.0
C4 C5 H5A 119.0
C5 C6 C7 119.41(13)
C5 C6 H6A 120.3
C7 C6 H6A 120.3
C6 C7 C8 119.58(15)
C6 C7 H7A 120.2
C8 C7 H7A 120.2
C7 C8 C9 121.67(14)
C7 C8 H8A 119.2
C9 C8 H8A 119.2
C4 C9 C8 118.22(13)
C4 C9 C10 122.73(12)
C8 C9 C10 119.03(12)
C1 C10 C9 111.44(12)
C1 C10 C18 108.64(13)
C9 C10 C18 108.62(12)
C1 C10 C11 110.03(11)
C9 C10 C11 108.50(10)
C18 C10 C11 109.59(12)
C12 C11 C16 109.79(12)
C12 C11 C10 111.73(11)
C16 C11 C10 111.52(11)
C12 C11 H11A 107.9
C16 C11 H11A 107.9
C10 C11 H11A 107.9
C13 C12 C11 128.95(12)
C13 C12 H12A 115.5
C11 C12 H12A 115.5
C12 C13 C14 126.48(12)
C12 C13 H13A 116.8
C14 C13 H13A 116.8
O1 C14 O2 122.99(13)
O1 C14 C13 127.53(13)
O2 C14 C13 109.48(11)
O2 C15 H15A 109.5
O2 C15 H15B 109.5
H15A C15 H15B 109.5
O2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C17 C16 C11 112.99(12)
C17 C16 H16A 109.0
C11 C16 H16A 109.0
C17 C16 H16B 109.0
C11 C16 H16B 109.0
H16A C16 H16B 107.8
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C10 C18 H18A 109.5
C10 C18 H18B 109.5
H18A C18 H18B 109.5
C10 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C14 O2 C15 115.79(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.319(2)
C1 C10 1.5079(19)
C1 H1A 0.9500
C2 C3 1.480(3)
C2 H2A 0.9500
C3 C4 1.506(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C9 1.394(2)
C4 C5 1.397(2)
C5 C6 1.366(2)
C5 H5A 0.9500
C6 C7 1.380(2)
C6 H6A 0.9500
C7 C8 1.385(2)
C7 H7A 0.9500
C8 C9 1.3966(19)
C8 H8A 0.9500
C9 C10 1.5282(18)
C10 C18 1.542(2)
C10 C11 1.5804(18)
C11 C12 1.5015(19)
C11 C16 1.534(2)
C11 H11A 1.0000
C12 C13 1.331(2)
C12 H12A 0.9500
C13 C14 1.478(2)
C13 H13A 0.9500
C14 O1 1.2044(17)
C14 O2 1.3411(17)
C15 O2 1.444(2)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 C17 1.525(2)
C16 H16A 0.9900
C16 H16B 0.9900
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
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
C10 C1 C2 C3 0.3(3)
C1 C2 C3 C4 -5.3(3)
C2 C3 C4 C9 6.8(2)
C2 C3 C4 C5 -173.49(15)
C9 C4 C5 C6 0.6(2)
C3 C4 C5 C6 -179.05(16)
C4 C5 C6 C7 0.8(2)
C5 C6 C7 C8 -1.2(2)
C6 C7 C8 C9 0.2(2)
C5 C4 C9 C8 -1.6(2)
C3 C4 C9 C8 178.07(15)
C5 C4 C9 C10 176.76(13)
C3 C4 C9 C10 -3.6(2)
C7 C8 C9 C4 1.2(2)
C7 C8 C9 C10 -177.22(14)
C2 C1 C10 C9 3.2(2)
C2 C1 C10 C18 122.88(18)
C2 C1 C10 C11 -117.16(17)
C4 C9 C10 C1 -1.48(19)
C8 C9 C10 C1 176.89(13)
C4 C9 C10 C18 -121.12(15)
C8 C9 C10 C18 57.25(17)
C4 C9 C10 C11 119.81(14)
C8 C9 C10 C11 -61.82(16)
C1 C10 C11 C12 -68.32(15)
C9 C10 C11 C12 169.53(12)
C18 C10 C11 C12 51.08(15)
C1 C10 C11 C16 54.98(15)
C9 C10 C11 C16 -67.18(14)
C18 C10 C11 C16 174.37(11)
C16 C11 C12 C13 123.64(17)
C10 C11 C12 C13 -112.10(17)
C11 C12 C13 C14 2.2(3)
C12 C13 C14 O1 -3.6(3)
C12 C13 C14 O2 175.72(14)
C12 C11 C16 C17 -63.07(15)
C10 C11 C16 C17 172.54(11)
O1 C14 O2 C15 -0.8(2)
C13 C14 O2 C15 179.87(12)
