#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024933.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_4024933
loop_
_publ_author_name
'Young Tak Lee'
'Youn Kyung Kang'
'Young Keun Chung'
_publ_section_title
;
Au(I)-Catalyzed Cycloisomerization Reaction of Amide- or Ester-Tethered
1,6-Enynes to Bicyclo[3.2.0]hept-6-en-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7922
_journal_page_last               7934
_journal_paper_doi               10.1021/jo901771p
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C20.5 H20 Cl N O3 S'
_chemical_formula_weight         389.898
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 110.146(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.8036(7)
_cell_length_b                   6.1821(2)
_cell_length_c                   24.8527(8)
_cell_measurement_reflns_used    4481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3866.2(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP32
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K-alpha'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7514
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.9377
_exptl_absorpt_correction_T_min  0.9085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Blessing, R. H. Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0466
_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)+(0.0524P)²+2.2270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                2973
_reflns_number_total             4360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901771p_si_003.cif
_cod_data_source_block           14
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C20.50 H20 Cl N O3 S'
_cod_database_code               4024933
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.01091(3) 0.02655(15) 0.18833(3) 0.0862(3) Uani 1 1 d . . .
C21 C 0.0000 -0.1287(7) 0.2500 0.0789(11) Uani 1 2 d S . .
H21A H -0.0306 -0.2212 0.2446 0.095 Uiso 0.50 1 calc PR . .
H21B H 0.0306 -0.2212 0.2554 0.095 Uiso 0.50 1 calc PR . .
S1 S 0.09421(2) 0.40840(9) 0.10499(2) 0.04702(16) Uani 1 1 d . . .
O3 O 0.07792(6) 0.5696(3) 0.21202(6) 0.0600(4) Uani 1 1 d . . .
N1 N 0.11455(6) 0.3074(3) 0.17132(7) 0.0447(4) Uani 1 1 d . . .
C11 C 0.10149(8) 0.3999(4) 0.21582(8) 0.0448(5) Uani 1 1 d . . .
C5 C 0.02480(8) 0.3812(3) 0.08066(8) 0.0437(5) Uani 1 1 d . . .
O1 O 0.11528(6) 0.2625(3) 0.07366(6) 0.0610(4) Uani 1 1 d . . .
O2 O 0.10779(6) 0.6311(3) 0.10833(6) 0.0604(4) Uani 1 1 d . . .
C15 C 0.19421(8) 0.4928(4) 0.34822(8) 0.0459(5) Uani 1 1 d . . .
C10 C 0.12272(8) 0.2557(4) 0.26730(8) 0.0488(5) Uani 1 1 d . . .
H10 H 0.0974 0.2164 0.2862 0.059 Uiso 1 1 calc R . .
C14 C 0.17842(8) 0.3160(4) 0.30706(8) 0.0447(5) Uani 1 1 d . . .
C4 C 0.00200(9) 0.1873(4) 0.05670(9) 0.0543(5) Uani 1 1 d . . .
H4 H 0.0232 0.0719 0.0539 0.065 Uiso 1 1 calc R . .
C13 C 0.20182(9) 0.1547(4) 0.28813(9) 0.0507(5) Uani 1 1 d . . .
C19 C 0.17043(10) 0.8147(4) 0.38902(10) 0.0645(7) Uani 1 1 d . . .
H19 H 0.1447 0.9136 0.3902 0.077 Uiso 1 1 calc R . .
C6 C -0.00663(9) 0.5519(4) 0.08530(10) 0.0552(6) Uani 1 1 d . . .
H6 H 0.0087 0.6818 0.1017 0.066 Uiso 1 1 calc R . .
C2 C -0.08501(9) 0.3367(4) 0.04051(9) 0.0552(6) Uani 1 1 d . . .
C8 C 0.13718(10) 0.0874(4) 0.18347(10) 0.0577(6) Uani 1 1 d . . .
H8A H 0.1691 0.0744 0.1737 0.069 Uiso 1 1 calc R . .
H8B H 0.1117 -0.0207 0.1624 0.069 Uiso 1 1 calc R . .
C16 C 0.24638(9) 0.5205(4) 0.38521(9) 0.0592(6) Uani 1 1 d . . .
H16 H 0.2723 0.4216 0.3847 0.071 Uiso 1 1 calc R . .
C18 C 0.22205(11) 0.8410(5) 0.42463(10) 0.0717(7) Uani 1 1 d . . .
H18 H 0.2314 0.9573 0.4499 0.086 Uiso 1 1 calc R . .
C20 C 0.15645(9) 0.6428(4) 0.35153(9) 0.0552(6) Uani 1 1 d . . .
H20 H 0.1212 0.6263 0.3280 0.066 Uiso 1 1 calc R . .
C9 C 0.14975(9) 0.0640(4) 0.24792(10) 0.0552(6) Uani 1 1 d . . .
H9 H 0.1406 -0.0781 0.2594 0.066 Uiso 1 1 calc R . .
C12 C 0.25711(10) 0.0779(5) 0.29903(12) 0.0745(7) Uani 1 1 d . . .
H12A H 0.2817 0.1746 0.3253 0.112 Uiso 1 1 calc R . .
H12B H 0.2640 0.0743 0.2636 0.112 Uiso 1 1 calc R . .
H12C H 0.2613 -0.0647 0.3153 0.112 Uiso 1 1 calc R . .
C3 C -0.05269(9) 0.1671(4) 0.03696(10) 0.0608(6) Uani 1 1 d . . .
H3 H -0.0681 0.0368 0.0210 0.073 Uiso 1 1 calc R . .
C17 C 0.25987(10) 0.6937(5) 0.42267(10) 0.0719(8) Uani 1 1 d . . .
H17 H 0.2949 0.7107 0.4468 0.086 Uiso 1 1 calc R . .
C7 C -0.06129(9) 0.5273(4) 0.06522(10) 0.0623(6) Uani 1 1 d . . .
H7 H -0.0825 0.6420 0.0685 0.075 Uiso 1 1 calc R . .
C1 C -0.14473(9) 0.3147(5) 0.01734(12) 0.0785(8) Uani 1 1 d . . .
H1A H -0.1588 0.3943 -0.0178 0.118 Uiso 1 1 calc R . .
H1B H -0.1593 0.3711 0.0448 0.118 Uiso 1 1 calc R . .
H1C H -0.1541 0.1649 0.0103 0.118 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C21 Cl1 113.3(2) 2 . ?
O2 S1 O1 120.17(10) . . ?
O2 S1 N1 108.37(9) . . ?
O1 S1 N1 104.25(9) . . ?
O2 S1 C5 109.48(10) . . ?
O1 S1 C5 108.83(9) . . ?
N1 S1 C5 104.55(9) . . ?
C11 N1 C8 114.40(17) . . ?
C11 N1 S1 123.03(15) . . ?
C8 N1 S1 121.18(14) . . ?
O3 C11 N1 124.1(2) . . ?
O3 C11 C10 127.96(19) . . ?
N1 C11 C10 107.95(18) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 S1 120.20(16) . . ?
C4 C5 S1 119.35(17) . . ?
C16 C15 C20 117.5(2) . . ?
C16 C15 C14 122.6(2) . . ?
C20 C15 C14 119.90(19) . . ?
C11 C10 C14 113.97(17) . . ?
C11 C10 C9 105.65(16) . . ?
C14 C10 C9 86.01(16) . . ?
C13 C14 C15 138.0(2) . . ?
C13 C14 C10 93.58(18) . . ?
C15 C14 C10 128.39(19) . . ?
C3 C4 C5 119.2(2) . . ?
C14 C13 C12 136.6(2) . . ?
C14 C13 C9 94.04(18) . . ?
C12 C13 C9 129.3(2) . . ?
C18 C19 C20 120.5(2) . . ?
C5 C6 C7 119.1(2) . . ?
C7 C2 C3 118.3(2) . . ?
C7 C2 C1 120.8(2) . . ?
C3 C2 C1 120.9(2) . . ?
N1 C8 C9 103.22(17) . . ?
C17 C16 C15 120.6(2) . . ?
C19 C18 C17 119.4(2) . . ?
C19 C20 C15 121.2(2) . . ?
C13 C9 C8 118.48(19) . . ?
C13 C9 C10 86.26(16) . . ?
C8 C9 C10 107.20(17) . . ?
C4 C3 C2 121.4(2) . . ?
C18 C17 C16 120.7(2) . . ?
C2 C7 C6 121.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C21 1.746(2) . ?
C21 Cl1 1.746(2) 2 ?
S1 O2 1.4193(16) . ?
S1 O1 1.4287(15) . ?
S1 N1 1.6688(17) . ?
S1 C5 1.755(2) . ?
O3 C11 1.212(3) . ?
N1 C11 1.393(2) . ?
N1 C8 1.478(3) . ?
C11 C10 1.501(3) . ?
C5 C6 1.380(3) . ?
C5 C4 1.383(3) . ?
C15 C16 1.394(3) . ?
C15 C20 1.396(3) . ?
C15 C14 1.456(3) . ?
C10 C14 1.526(3) . ?
C10 C9 1.550(3) . ?
C14 C13 1.346(3) . ?
C4 C3 1.382(3) . ?
C13 C12 1.489(3) . ?
C13 C9 1.517(3) . ?
C19 C18 1.371(3) . ?
C19 C20 1.378(3) . ?
C6 C7 1.384(3) . ?
C2 C7 1.379(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.509(3) . ?
C8 C9 1.526(3) . ?
C16 C17 1.382(4) . ?
C18 C17 1.376(4) . ?
