#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/55/1505503.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_1505503
loop_
_publ_author_name
'Lim, Choongmin'
'Kang, Ji-Eun'
'Lee, Ji-Eun'
'Shin, Seunghoon'
_publ_section_title
;
 Gold-catalyzed tandem C-C and C-O bond formation: a highly
 diastereoselective formation of cyclohex-4-ene-1,2-diol derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3539
_journal_page_last               3542
_journal_paper_doi               10.1021/ol071402f
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C17 H18 O3'
_chemical_formula_weight         270.31
_chemical_name_systematic
; 
 ? 
;
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.0439(7)
_cell_length_b                   9.8777(7)
_cell_length_c                   27.4151(19)
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.23
_cell_volume                     2719.9(3)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15962
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0642
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1738
_reflns_number_gt                2382
_reflns_number_total             3227
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071402f-file003.cif
_cod_data_source_block           aaa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1505503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
O1 O 1.09554(13) 0.01711(14) 0.54589(5) 0.0234(3) Uani 1 1 d .
O2 O 0.97549(14) -0.15671(15) 0.57435(6) 0.0313(4) Uani 1 1 d .
O3 O 0.93500(13) 0.05592(13) 0.59953(5) 0.0200(3) Uani 1 1 d .
C1 C 0.99956(18) -0.0381(2) 0.57357(7) 0.0204(4) Uani 1 1 d .
C2 C 1.09983(17) 0.16362(19) 0.55286(7) 0.0178(4) Uani 1 1 d .
H2A H 1.0915 0.2099 0.5206 0.021 Uiso 1 1 calc R
C3 C 1.23190(18) 0.2022(2) 0.57655(7) 0.0215(4) Uani 1 1 d .
H3A H 1.3027 0.1421 0.5638 0.026 Uiso 1 1 calc R
H3B H 1.2546 0.2962 0.5671 0.026 Uiso 1 1 calc R
C4 C 1.22972(18) 0.1924(2) 0.63127(7) 0.0219(4) Uani 1 1 d .
H4A H 1.3076 0.1631 0.6479 0.026 Uiso 1 1 calc R
C5 C 1.12177(17) 0.22344(19) 0.65706(7) 0.0187(4) Uani 1 1 d .
C6 C 1.00026(16) 0.27592(19) 0.62988(6) 0.0168(4) Uani 1 1 d .
H6A H 0.9212 0.2671 0.6518 0.020 Uiso 1 1 calc R
C7 C 1.01687(19) 0.4266(2) 0.61665(7) 0.0217(4) Uani 1 1 d .
H7A H 1.0241 0.4800 0.6471 0.026 Uiso 1 1 calc R
H7B H 1.1009 0.4382 0.5982 0.026 Uiso 1 1 calc R
C8 C 0.9019(2) 0.4818(2) 0.58629(8) 0.0252(5) Uani 1 1 d .
H8A H 0.9212 0.5765 0.5768 0.030 Uiso 1 1 calc R
H8B H 0.8195 0.4816 0.6061 0.030 Uiso 1 1 calc R
C9 C 0.8809(2) 0.3963(2) 0.54055(7) 0.0249(5) Uani 1 1 d .
H9A H 0.8029 0.4309 0.5223 0.030 Uiso 1 1 calc R
H9B H 0.9600 0.4040 0.5192 0.030 Uiso 1 1 calc R
C10 C 0.85832(18) 0.2484(2) 0.55369(7) 0.0200(4) Uani 1 1 d .
H10A H 0.8487 0.1946 0.5234 0.024 Uiso 1 1 calc R
H10B H 0.7747 0.2399 0.5725 0.024 Uiso 1 1 calc R
C11 C 0.97402(17) 0.19197(19) 0.58383(6) 0.0156(4) Uani 1 1 d .
C12 C 1.11989(18) 0.2195(2) 0.71125(7) 0.0216(4) Uani 1 1 d .
C13 C 1.2000(2) 0.1289(2) 0.73711(7) 0.0295(5) Uani 1 1 d .
H13A H 1.2532 0.0656 0.7198 0.035 Uiso 1 1 calc R
C14 C 1.2030(2) 0.1299(3) 0.78768(8) 0.0369(6) Uani 1 1 d .
H14A H 1.2580 0.0673 0.8046 0.044 Uiso 1 1 calc R
C15 C 1.1264(2) 0.2214(3) 0.81369(8) 0.0362(6) Uani 1 1 d .
H15A H 1.1301 0.2232 0.8483 0.043 Uiso 1 1 calc R
C16 C 1.0446(2) 0.3101(3) 0.78891(8) 0.0352(6) Uani 1 1 d .
H16A H 0.9910 0.3723 0.8066 0.042 Uiso 1 1 calc R
C17 C 1.0401(2) 0.3090(2) 0.73818(7) 0.0296(5) Uani 1 1 d .
H17A H 0.9823 0.3696 0.7216 0.036 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
C1 O1 C2 110.47(14)
C1 O3 C11 110.54(14)
O2 C1 O3 124.91(18)
O2 C1 O1 123.57(18)
O3 C1 O1 111.52(16)
O1 C2 C3 109.21(15)
O1 C2 C11 103.12(14)
C3 C2 C11 115.53(15)
C4 C3 C2 113.32(15)
C5 C4 C3 121.82(17)
C4 C5 C12 122.39(17)
C4 C5 C6 118.17(17)
C12 C5 C6 119.25(15)
C5 C6 C11 110.92(15)
C5 C6 C7 110.95(15)
C11 C6 C7 110.32(15)
C8 C7 C6 113.10(16)
C7 C8 C9 110.80(17)
C10 C9 C8 110.94(16)
C9 C10 C11 111.36(15)
O3 C11 C10 106.84(14)
O3 C11 C6 107.48(14)
C10 C11 C6 112.20(15)
O3 C11 C2 102.34(14)
C10 C11 C2 112.91(15)
C6 C11 C2 114.16(14)
C13 C12 C17 117.74(18)
C13 C12 C5 121.15(18)
C17 C12 C5 121.09(18)
C14 C13 C12 121.0(2)
C15 C14 C13 120.5(2)
C16 C15 C14 119.5(2)
C15 C16 C17 120.4(2)
C16 C17 C12 120.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.343(2)
O1 C2 1.460(2)
O2 C1 1.197(2)
O3 C1 1.338(2)
O3 C11 1.464(2)
C2 C3 1.525(2)
C2 C11 1.548(2)
C3 C4 1.503(3)
C4 C5 1.330(3)
C5 C12 1.486(3)
C5 C6 1.521(2)
C6 C11 1.533(2)
C6 C7 1.541(3)
C7 C8 1.524(3)
C8 C9 1.526(3)
C9 C10 1.522(3)
C10 C11 1.531(2)
C12 C13 1.396(3)
C12 C17 1.404(3)
C13 C14 1.387(3)
C14 C15 1.385(4)
C15 C16 1.380(3)
C16 C17 1.391(3)
