#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:47:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178824 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/78/4107856.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_4107856
loop_
_publ_author_name
'Guotao Li'
'Xiaogen Huang'
'Liming Zhang'
_publ_section_title
;
 Au(I)-Catalyzed Efficient Synthesis of Functionalized
 Bicyclo[3.2.0]heptanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6944
_journal_page_last               6945
_journal_paper_doi               10.1021/ja802294t
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.8550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7982(3)
_cell_length_b                   9.9351(2)
_cell_length_c                   10.1855(2)
_cell_measurement_reflns_used    4297
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.87
_cell_volume                     1394.56(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      99(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11330
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       brick
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.916
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0676
_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)+(0.0899P)²+1.6896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1873
_reflns_number_gt                3217
_reflns_number_total             4038
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802294t-file001.cif
_cod_data_source_block           zhang5
_cod_database_code               4107856
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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 0.75217(9) 1.13980(15) 0.31789(14) 0.0243(3) Uani 1 1 d .
H1A H 0.7373 1.1980 0.2605 0.036 Uiso 1 1 calc R
O2 O 0.69686(10) 1.16718(14) 0.62658(13) 0.0240(3) Uani 1 1 d .
O3 O 0.98922(9) 0.80934(15) 0.96775(13) 0.0246(3) Uani 1 1 d .
C1 C 0.69237(12) 0.98973(17) 0.47529(15) 0.0151(3) Uani 1 1 d .
C2 C 0.67899(14) 0.85746(18) 0.45367(18) 0.0218(4) Uani 1 1 d .
H2A H 0.6919 0.7904 0.5187 0.026 Uiso 1 1 calc R
C3 C 0.64164(15) 0.82660(19) 0.31629(19) 0.0247(4) Uani 1 1 d .
H3A H 0.5832 0.7687 0.3163 0.030 Uiso 1 1 calc R
H3B H 0.6918 0.7813 0.2659 0.030 Uiso 1 1 calc R
C4 C 0.61735(12) 0.96465(17) 0.25972(17) 0.0176(3) Uani 1 1 d .
C5 C 0.51842(13) 1.0242(2) 0.3022(2) 0.0234(4) Uani 1 1 d .
H5A H 0.4716 1.0424 0.2275 0.028 Uiso 1 1 calc R
H5B H 0.4878 0.9708 0.3709 0.028 Uiso 1 1 calc R
C6 C 0.57193(13) 1.15213(19) 0.35580(19) 0.0221(4) Uani 1 1 d .
H6A H 0.5684 1.2296 0.2946 0.027 Uiso 1 1 calc R
H6B H 0.5539 1.1790 0.4449 0.027 Uiso 1 1 calc R
C7 C 0.66787(11) 1.07215(16) 0.35368(16) 0.0148(3) Uani 1 1 d .
C8 C 0.63230(16) 0.9842(2) 0.11465(19) 0.0278(4) Uani 1 1 d .
H8A H 0.5889 0.9239 0.0633 0.042 Uiso 1 1 calc R
H8B H 0.6998 0.9637 0.0966 0.042 Uiso 1 1 calc R
H8C H 0.6178 1.0778 0.0903 0.042 Uiso 1 1 calc R
C9 C 0.72529(12) 1.05309(17) 0.60097(16) 0.0155(3) Uani 1 1 d .
C10 C 0.79244(12) 0.98018(17) 0.69447(16) 0.0155(3) Uani 1 1 d .
C11 C 0.79501(13) 1.01541(18) 0.82829(17) 0.0189(3) Uani 1 1 d .
H11A H 0.7511 1.0810 0.8583 0.023 Uiso 1 1 calc R
C12 C 0.85778(13) 0.88394(18) 0.65334(17) 0.0190(3) Uani 1 1 d .
H12A H 0.8564 0.8589 0.5633 0.023 Uiso 1 1 calc R
C13 C 0.86073(13) 0.95545(19) 0.91615(17) 0.0206(4) Uani 1 1 d .
H13A H 0.8614 0.9791 1.0066 0.025 Uiso 1 1 calc R
C14 C 0.92642(12) 0.86002(19) 0.87310(17) 0.0190(3) Uani 1 1 d .
C15 C 0.92510(13) 0.82355(19) 0.74135(18) 0.0210(4) Uani 1 1 d .
H15A H 0.9694 0.7584 0.7117 0.025 Uiso 1 1 calc R
C16 C 1.05975(16) 0.7141(3) 0.9283(2) 0.0379(6) Uani 1 1 d .
H16A H 1.1006 0.6865 1.0051 0.057 Uiso 1 1 calc R
H16B H 1.1003 0.7554 0.8631 0.057 Uiso 1 1 calc R
H16C H 1.0267 0.6351 0.8897 0.057 Uiso 1 1 calc R
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
C7 O1 H1A 109.5
C14 O3 C16 117.68(15)
C2 C1 C9 126.33(15)
C2 C1 C7 111.89(15)
C9 C1 C7 121.77(14)
C1 C2 C3 113.03(16)
C1 C2 H2A 123.5
C3 C2 H2A 123.5
C2 C3 C4 103.22(14)
C2 C3 H3A 111.1
C4 C3 H3A 111.1
C2 C3 H3B 111.1
C4 C3 H3B 111.1
H3A C3 H3B 109.1
C8 C4 C3 116.61(16)
C8 C4 C5 112.53(15)
C3 C4 C5 114.52(16)
C8 C4 C7 115.36(15)
C3 C4 C7 107.43(14)
C5 C4 C7 86.65(12)
C6 C5 C4 90.04(13)
C6 C5 H5A 113.6
C4 C5 H5A 113.6
C6 C5 H5B 113.6
C4 C5 H5B 113.6
H5A C5 H5B 110.9
C7 C6 C5 88.11(13)
C7 C6 H6A 114.0
C5 C6 H6A 114.0
C7 C6 H6B 114.0
C5 C6 H6B 114.0
H6A C6 H6B 111.2
O1 C7 C1 108.52(13)
O1 C7 C6 118.55(14)
C1 C7 C6 115.13(14)
O1 C7 C4 120.90(14)
C1 C7 C4 101.84(13)
C6 C7 C4 90.21(12)
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O2 C9 C1 119.21(15)
O2 C9 C10 120.57(15)
C1 C9 C10 120.21(14)
C12 C10 C11 118.50(15)
C12 C10 C9 122.33(15)
C11 C10 C9 119.04(15)
C13 C11 C10 120.41(16)
C13 C11 H11A 119.8
C10 C11 H11A 119.8
C10 C12 C15 121.50(16)
C10 C12 H12A 119.3
C15 C12 H12A 119.3
C11 C13 C14 120.39(16)
C11 C13 H13A 119.8
C14 C13 H13A 119.8
O3 C14 C15 124.42(16)
O3 C14 C13 115.41(15)
C15 C14 C13 120.17(16)
C14 C15 C12 119.03(16)
C14 C15 H15A 120.5
C12 C15 H15A 120.5
O3 C16 H16A 109.5
O3 C16 H16B 109.5
H16A C16 H16B 109.5
O3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.407(2)
O1 H1A 0.8400
O2 C9 1.232(2)
O3 C14 1.360(2)
O3 C16 1.429(2)
C1 C2 1.344(2)
C1 C9 1.478(2)
C1 C7 1.509(2)
C2 C3 1.499(3)
C2 H2A 0.9500
C3 C4 1.519(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C8 1.515(3)
C4 C5 1.568(3)
C4 C7 1.574(2)
C5 C6 1.555(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.545(2)
C6 H6A 0.9900
C6 H6B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.484(2)
C10 C12 1.393(2)
C10 C11 1.406(2)
C11 C13 1.377(2)
C11 H11A 0.9500
C12 C15 1.394(2)
C12 H12A 0.9500
C13 C14 1.397(2)
C13 H13A 0.9500
C14 C15 1.389(2)
C15 H15A 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 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
C9 C1 C2 C3 177.90(16)
C7 C1 C2 C3 -1.1(2)
C1 C2 C3 C4 -9.1(2)
C2 C3 C4 C8 146.41(17)
C2 C3 C4 C5 -79.21(18)
C2 C3 C4 C7 15.15(19)
C8 C4 C5 C6 -99.48(17)
C3 C4 C5 C6 124.28(15)
C7 C4 C5 C6 16.64(13)
C4 C5 C6 C7 -16.94(13)
C2 C1 C7 O1 -118.14(17)
C9 C1 C7 O1 62.78(19)
C2 C1 C7 C6 106.32(18)
C9 C1 C7 C6 -72.8(2)
C2 C1 C7 C4 10.44(19)
C9 C1 C7 C4 -168.64(14)
C5 C6 C7 O1 142.79(15)
C5 C6 C7 C1 -86.33(16)
C5 C6 C7 C4 16.88(13)
C8 C4 C7 O1 -27.4(2)
C3 C4 C7 O1 104.59(18)
C5 C4 C7 O1 -140.75(16)
C8 C4 C7 C1 -147.60(15)
C3 C4 C7 C1 -15.66(17)
C5 C4 C7 C1 99.01(14)
C8 C4 C7 C6 96.64(17)
C3 C4 C7 C6 -131.42(15)
C5 C4 C7 C6 -16.75(13)
C2 C1 C9 O2 -149.04(19)
C7 C1 C9 O2 29.9(2)
C2 C1 C9 C10 31.4(3)
C7 C1 C9 C10 -149.62(15)
O2 C9 C10 C12 -151.80(18)
C1 C9 C10 C12 27.7(2)
O2 C9 C10 C11 23.9(2)
C1 C9 C10 C11 -156.62(16)
C12 C10 C11 C13 -0.1(3)
C9 C10 C11 C13 -175.98(16)
C11 C10 C12 C15 -0.4(3)
C9 C10 C12 C15 175.28(16)
C10 C11 C13 C14 0.8(3)
C16 O3 C14 C15 1.3(3)
C16 O3 C14 C13 -178.30(18)
C11 C13 C14 O3 178.75(17)
C11 C13 C14 C15 -0.8(3)
O3 C14 C15 C12 -179.25(17)
C13 C14 C15 C12 0.3(3)
C10 C12 C15 C14 0.3(3)
