#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/21/4022130.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_4022130
loop_
_publ_author_name
'Sang Ick Lee'
'Soo Min Kim'
'Mi Ra Choi'
'Sun Young Kim'
'Young Keun Chung'
'Won-Sik Han'
'Sang Ook Kang'
_publ_section_title
;
 Au(I)-Catalyzed Cyclization of Enynes Bearing an Olefinic Cycle
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9366
_journal_page_last               9372
_journal_paper_doi               10.1021/jo061254r
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C27 H30 N2 O4 S2'
_chemical_formula_weight         510.16
_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                 97.708(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5935(4)
_cell_length_b                   9.6906(6)
_cell_length_c                   19.9797(12)
_cell_measurement_temperature    293(2)
_cell_volume                     2608.1(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '95mm CCD camera on κ-goniostat'
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9776
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.060
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    0.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1109P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.2152
_reflns_number_gt                3508
_reflns_number_total             5816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061254rsi20060620_095210.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022130
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
S1 S 0.68340(6) 0.86714(9) 0.17530(4) 0.0508(3) Uani 1 1 d .
S2 S 0.14247(6) 0.61486(10) -0.02697(4) 0.0534(3) Uani 1 1 d .
N1 N 0.62619(18) 0.8582(3) 0.09833(13) 0.0463(6) Uani 1 1 d .
N2 N 0.23737(17) 0.7189(3) -0.02720(13) 0.0496(7) Uani 1 1 d .
O1 O 0.62237(17) 0.9477(3) 0.21277(13) 0.0684(7) Uani 1 1 d .
O2 O 0.78293(17) 0.9098(3) 0.16963(13) 0.0655(7) Uani 1 1 d .
O3 O 0.17992(18) 0.4784(3) -0.03256(15) 0.0765(8) Uani 1 1 d .
O4 O 0.06740(16) 0.6674(3) -0.07671(12) 0.0748(8) Uani 1 1 d .
C1 C 0.6883(4) 0.2783(5) 0.2758(3) 0.0940(14) Uani 1 1 d .
H1A H 0.6229 0.2533 0.2846 0.141 Uiso 1 1 calc R
H1B H 0.7343 0.2683 0.3164 0.141 Uiso 1 1 calc R
H1C H 0.7080 0.2192 0.2414 0.141 Uiso 1 1 calc R
C2 C 0.6881(3) 0.4266(4) 0.25224(18) 0.0594(9) Uani 1 1 d .
C3 C 0.7588(2) 0.4728(4) 0.21237(17) 0.0566(9) Uani 1 1 d .
H3 H 0.8062 0.4115 0.2006 0.068 Uiso 1 1 calc R
C4 C 0.7593(2) 0.6071(4) 0.19026(16) 0.0486(8) Uani 1 1 d .
H4 H 0.8068 0.6364 0.1639 0.058 Uiso 1 1 calc R
C5 C 0.6885(2) 0.6985(3) 0.20757(14) 0.0443(7) Uani 1 1 d .
C6 C 0.6175(2) 0.6543(4) 0.24623(17) 0.0547(9) Uani 1 1 d .
H6 H 0.5695 0.7152 0.2576 0.066 Uiso 1 1 calc R
C7 C 0.6185(3) 0.5187(4) 0.26779(17) 0.0630(10) Uani 1 1 d .
H7 H 0.5705 0.4894 0.2936 0.076 Uiso 1 1 calc R
C8 C 0.6724(2) 0.7818(4) 0.04722(16) 0.0517(8) Uani 1 1 d .
H8A H 0.6837 0.6860 0.0601 0.078 Uiso 1 1 calc R
H8B H 0.7347 0.8235 0.0395 0.078 Uiso 1 1 calc R
C9 C 0.5946(2) 0.7948(4) -0.01432(16) 0.0552(9) Uani 1 1 d .
H9 H 0.5968 0.8898 -0.0309 0.083 Uiso 1 1 calc R
C10 C 0.5000(2) 0.7782(4) 0.01641(15) 0.0496(8) Uani 1 1 d .
C11 C 0.5177(2) 0.8288(4) 0.08886(16) 0.0531(8) Uani 1 1 d .
H11A H 0.4795 0.9115 0.0947 0.080 Uiso 1 1 calc R
H11B H 0.5011 0.7584 0.1200 0.080 Uiso 1 1 calc R
C12 C 0.6000(2) 0.7023(4) -0.07169(18) 0.0611(10) Uani 1 1 d .
H12 H 0.6614 0.6867 -0.0861 0.073 Uiso 1 1 calc R
C13 C 0.5209(3) 0.6402(5) -0.10371(19) 0.0695(11) Uani 1 1 d .
H13 H 0.5284 0.5863 -0.1412 0.083 Uiso 1 1 calc R
C14 C 0.4200(3) 0.6523(5) -0.08270(19) 0.0727(12) Uani 1 1 d .
H14A H 0.3904 0.5612 -0.0832 0.109 Uiso 1 1 calc R
H14B H 0.3789 0.7086 -0.1155 0.109 Uiso 1 1 calc R
C15 C 0.4200(2) 0.7141(4) -0.01415(16) 0.0526(8) Uani 1 1 d .
C16 C 0.3280(2) 0.6876(4) 0.01996(16) 0.0571(9) Uani 1 1 d .
H16A H 0.3268 0.5919 0.0340 0.086 Uiso 1 1 calc R
H16B H 0.3300 0.7452 0.0599 0.086 Uiso 1 1 calc R
C17 C 0.2194(3) 0.8646(4) -0.04261(18) 0.0619(10) Uani 1 1 d .
H17A H 0.1661 0.8716 -0.0799 0.093 Uiso 1 1 calc R
H17B H 0.2786 0.9031 -0.0577 0.093 Uiso 1 1 calc R
C18 C 0.1934(3) 0.9495(4) 0.0135(2) 0.0616(9) Uani 1 1 d .
C19 C 0.1705(3) 1.0197(4) 0.0572(2) 0.0662(10) Uani 1 1 d .
C20 C 0.1397(4) 1.1044(5) 0.1117(2) 0.0930(14) Uani 1 1 d .
H20A H 0.1026 1.0487 0.1391 0.139 Uiso 1 1 calc R
H20B H 0.0990 1.1792 0.0925 0.139 Uiso 1 1 calc R
H20C H 0.1974 1.1407 0.1389 0.139 Uiso 1 1 calc R
C21 C 0.1007(2) 0.6271(3) 0.05282(17) 0.0486(8) Uani 1 1 d .
C22 C 0.0337(2) 0.7266(4) 0.06549(18) 0.0582(9) Uani 1 1 d .
H22 H 0.0070 0.7857 0.0311 0.070 Uiso 1 1 calc R
C23 C 0.0061(3) 0.7390(5) 0.1287(2) 0.0686(11) Uani 1 1 d .
H23 H -0.0399 0.8060 0.1367 0.082 Uiso 1 1 calc R
C24 C 0.0459(3) 0.6526(5) 0.18143(19) 0.0713(12) Uani 1 1 d .
C25 C 0.0186(3) 0.6684(7) 0.2508(2) 0.112(2) Uani 1 1 d .
H25A H -0.0182 0.5889 0.2618 0.168 Uiso 1 1 calc R
H25B H -0.0214 0.7495 0.2527 0.168 Uiso 1 1 calc R
H25C H 0.0778 0.6769 0.2826 0.168 Uiso 1 1 calc R
C26 C 0.1116(3) 0.5506(5) 0.1671(2) 0.0796(13) Uani 1 1 d .
H26 H 0.1375 0.4897 0.2009 0.096 Uiso 1 1 calc R
C27 C 0.1392(3) 0.5381(4) 0.1036(2) 0.0660(10) Uani 1 1 d .
H27 H 0.1837 0.4697 0.0949 0.079 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'
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
O1 S1 O2 120.42(16)
O1 S1 N1 106.71(15)
O2 S1 N1 106.07(14)
O1 S1 C5 108.36(16)
O2 S1 C5 107.82(15)
N1 S1 C5 106.70(13)
O4 S2 O3 120.54(18)
O4 S2 N2 105.64(16)
O3 S2 N2 106.31(14)
O4 S2 C21 108.64(16)
O3 S2 C21 107.11(17)
N2 S2 C21 108.05(14)
C8 N1 C11 108.9(2)
C8 N1 S1 119.3(2)
C11 N1 S1 118.0(2)
C17 N2 C16 115.7(3)
C17 N2 S2 119.1(2)
C16 N2 S2 117.5(2)
C7 C2 C3 117.9(4)
C7 C2 C1 121.5(4)
C3 C2 C1 120.5(4)
C4 C3 C2 121.3(3)
C3 C4 C5 119.4(3)
C6 C5 C4 120.1(3)
C6 C5 S1 119.8(3)
C4 C5 S1 119.9(2)
C7 C6 C5 119.3(3)
C2 C7 C6 121.9(3)
N1 C8 C9 101.9(3)
C12 C9 C10 112.9(3)
C12 C9 C8 118.8(3)
C10 C9 C8 101.6(2)
C15 C10 C9 123.6(3)
C15 C10 C11 127.3(3)
C9 C10 C11 108.6(2)
N1 C11 C10 102.2(2)
C13 C12 C9 122.3(3)
C12 C13 C14 123.2(3)
C13 C14 C15 113.8(3)
C10 C15 C14 120.5(3)
C10 C15 C16 122.9(3)
C14 C15 C16 116.3(3)
N2 C16 C15 110.1(3)
N2 C17 C18 115.5(3)
C19 C18 C17 178.0(4)
C18 C19 C20 178.4(4)
C22 C21 C27 119.9(3)
C22 C21 S2 121.0(3)
C27 C21 S2 119.0(3)
C23 C22 C21 120.1(4)
C22 C23 C24 121.1(4)
C26 C24 C23 117.8(4)
C26 C24 C25 120.9(5)
C23 C24 C25 121.3(5)
C27 C26 C24 121.1(4)
C26 C27 C21 120.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.423(2)
S1 O2 1.434(2)
S1 N1 1.630(3)
S1 C5 1.755(3)
S2 O4 1.420(3)
S2 O3 1.427(3)
S2 N2 1.638(3)
S2 C21 1.767(3)
N1 C8 1.469(4)
N1 C11 1.489(4)
N2 C17 1.459(5)
N2 C16 1.478(4)
C1 C2 1.511(6)
C2 C7 1.366(5)
C2 C3 1.401(5)
C3 C4 1.375(5)
C4 C5 1.385(4)
C5 C6 1.383(4)
C6 C7 1.382(5)
C8 C9 1.515(4)
C9 C12 1.465(5)
C9 C10 1.507(4)
C10 C15 1.328(4)
C10 C11 1.517(4)
C12 C13 1.320(5)
C13 C14 1.491(5)
C14 C15 1.495(5)
C15 C16 1.524(4)
C17 C18 1.471(6)
C18 C19 1.181(5)
C19 C20 1.468(6)
C21 C22 1.373(5)
C21 C27 1.380(5)
C22 C23 1.371(5)
C23 C24 1.396(6)
C24 C26 1.388(6)
C24 C25 1.490(5)
C26 C27 1.375(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17253735
