#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/71/1507170.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_1507170
loop_
_publ_author_name
'Wang, Qiaoyi'
'Aparaj, Siddhita'
'Akhmedov, Novruz G.'
'Petersen, Jeffrey L.'
'Shi, Xiaodong'
_publ_section_title
;
 Ambient schmittel cyclization promoted by chemoselective triazole-gold
 catalyst.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1334
_journal_page_last               1337
_journal_paper_doi               10.1021/ol300227a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C32 H26 O3 S'
_chemical_formula_weight         490.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.929(2)
_cell_angle_beta                 84.678(2)
_cell_angle_gamma                75.454(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3720(7)
_cell_length_b                   13.1046(14)
_cell_length_c                   13.6194(14)
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.21
_cell_volume                     1268.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9013
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9330
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0812P)²+0.2323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1922
_reflns_number_gt                3595
_reflns_number_total             5638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300227a_si_002.cif
_cod_data_source_block           xs38ccd
_cod_original_sg_symbol_H-M      'P (-1)'
_cod_database_code               1507170
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.28174(9) 0.27443(6) -0.01935(5) 0.0659(2) Uani 1 1 d .
O1 O 0.4593(2) 0.20733(15) 0.03165(14) 0.0643(5) Uani 1 1 d .
O2 O 0.1386(3) 0.21825(17) -0.00868(17) 0.0807(6) Uani 1 1 d .
O3 O 0.3575(3) 0.29941(19) -0.11442(15) 0.0868(7) Uani 1 1 d .
C1 C 0.7825(3) 0.12931(19) 0.14707(18) 0.0530(6) Uani 1 1 d .
H1 H 0.8070 0.1583 0.0813 0.064 Uiso 1 1 calc R
C2 C 0.7657(3) 0.21348(19) 0.22316(17) 0.0502(5) Uani 1 1 d .
C3 C 0.6490(3) 0.3122(2) 0.22925(19) 0.0573(6) Uani 1 1 d .
H3 H 0.5576 0.3336 0.1849 0.069 Uiso 1 1 calc R
C4 C 0.6657(3) 0.3825(2) 0.3024(2) 0.0584(6) Uani 1 1 d .
C5 C 0.5572(4) 0.4882(2) 0.3055(3) 0.0751(8) Uani 1 1 d .
H5 H 0.4680 0.5116 0.2604 0.090 Uiso 1 1 calc R
C6 C 0.5816(4) 0.5564(3) 0.3737(3) 0.0844(9) Uani 1 1 d .
H6 H 0.5102 0.6259 0.3742 0.101 Uiso 1 1 calc R
C7 C 0.7122(4) 0.5226(3) 0.4422(3) 0.0800(9) Uani 1 1 d .
H7 H 0.7266 0.5698 0.4885 0.096 Uiso 1 1 calc R
C8 C 0.8203(4) 0.4214(2) 0.4431(2) 0.0679(7) Uani 1 1 d .
H8 H 0.9056 0.4002 0.4905 0.082 Uiso 1 1 calc R
C9 C 0.8034(3) 0.3481(2) 0.37192(19) 0.0549(6) Uani 1 1 d .
C10 C 0.9255(3) 0.24477(19) 0.36481(18) 0.0511(5) Uani 1 1 d .
C11 C 0.9078(3) 0.18014(18) 0.29085(17) 0.0482(5) Uani 1 1 d .
C12 C 1.0260(3) 0.07623(18) 0.25846(17) 0.0494(5) Uani 1 1 d .
C13 C 1.1868(3) 0.0099(2) 0.2935(2) 0.0586(6) Uani 1 1 d .
H13 H 1.2332 0.0266 0.3505 0.070 Uiso 1 1 calc R
C14 C 1.2765(4) -0.0810(2) 0.2426(2) 0.0659(7) Uani 1 1 d .
H14 H 1.3857 -0.1243 0.2647 0.079 Uiso 1 1 calc R
C15 C 1.2063(4) -0.1084(2) 0.1594(2) 0.0647(7) Uani 1 1 d .
H15 H 1.2686 -0.1698 0.1261 0.078 Uiso 1 1 calc R
C16 C 1.0448(4) -0.0452(2) 0.12549(19) 0.0605(6) Uani 1 1 d .
H16 H 0.9956 -0.0648 0.0707 0.073 Uiso 1 1 calc R
C17 C 0.9562(3) 0.04762(19) 0.17353(18) 0.0517(5) Uani 1 1 d .
C18 C 0.6144(3) 0.0794(2) 0.1470(2) 0.0654(7) Uani 1 1 d .
H18A H 0.6459 0.0235 0.0988 0.078 Uiso 1 1 calc R
H18B H 0.5965 0.0471 0.2113 0.078 Uiso 1 1 calc R
C19 C 0.4305(4) 0.1540(2) 0.1245(2) 0.0659(7) Uani 1 1 d .
H19A H 0.3356 0.1152 0.1203 0.079 Uiso 1 1 calc R
H19B H 0.3874 0.2052 0.1767 0.079 Uiso 1 1 calc R
C20 C 0.2091(3) 0.3885(2) 0.0514(2) 0.0572(6) Uani 1 1 d .
C21 C 0.0942(4) 0.3895(2) 0.1379(2) 0.0697(7) Uani 1 1 d .
H21 H 0.0493 0.3308 0.1566 0.084 Uiso 1 1 calc R
C22 C 0.0466(4) 0.4774(2) 0.1959(2) 0.0724(8) Uani 1 1 d .
H22 H -0.0293 0.4769 0.2543 0.087 Uiso 1 1 calc R
C23 C 0.1086(4) 0.5664(2) 0.1699(2) 0.0652(7) Uani 1 1 d .
C24 C 0.2187(4) 0.5655(2) 0.0824(3) 0.0753(8) Uani 1 1 d .
H24 H 0.2598 0.6252 0.0629 0.090 Uiso 1 1 calc R
C25 C 0.2693(4) 0.4783(2) 0.0230(2) 0.0686(7) Uani 1 1 d .
H25 H 0.3435 0.4796 -0.0359 0.082 Uiso 1 1 calc R
C26 C 0.0556(5) 0.6604(3) 0.2371(3) 0.0913(10) Uani 1 1 d .
H26A H 0.0070 0.7231 0.1995 0.137 Uiso 1 1 calc R
H26B H 0.1649 0.6673 0.2670 0.137 Uiso 1 1 calc R
H26C H -0.0386 0.6507 0.2876 0.137 Uiso 1 1 calc R
C27 C 1.0796(3) 0.2103(2) 0.43273(18) 0.0557(6) Uani 1 1 d .
C28 C 1.2527(3) 0.2324(2) 0.4092(2) 0.0664(7) Uani 1 1 d .
H28 H 1.2707 0.2730 0.3534 0.080 Uiso 1 1 calc R
C29 C 1.3986(4) 0.1945(3) 0.4678(3) 0.0874(10) Uani 1 1 d .
H29 H 1.5150 0.2089 0.4513 0.105 Uiso 1 1 calc R
C30 C 1.3714(6) 0.1354(4) 0.5508(3) 0.1110(14) Uani 1 1 d .
H30 H 1.4699 0.1088 0.5900 0.133 Uiso 1 1 calc R
C31 C 1.1999(7) 0.1158(4) 0.5753(3) 0.1116(13) Uani 1 1 d .
H31 H 1.1809 0.0778 0.6327 0.134 Uiso 1 1 calc R
C32 C 1.0544(5) 0.1513(3) 0.5163(2) 0.0817(9) Uani 1 1 d .
H32 H 0.9392 0.1355 0.5329 0.098 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'
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
O3 S1 O2 120.81(14)
O3 S1 O1 103.95(11)
O2 S1 O1 108.45(12)
O3 S1 C20 109.66(14)
O2 S1 C20 109.02(12)
O1 S1 C20 103.48(11)
C19 O1 S1 119.03(15)
C17 C1 C2 102.24(18)
C17 C1 C18 110.5(2)
C2 C1 C18 116.3(2)
C3 C2 C11 120.0(2)
C3 C2 C1 129.4(2)
C11 C2 C1 110.4(2)
C2 C3 C4 120.6(2)
C3 C4 C5 121.8(3)
C3 C4 C9 119.4(2)
C5 C4 C9 118.7(3)
C6 C5 C4 121.0(3)
C5 C6 C7 120.3(3)
C8 C7 C6 121.3(3)
C7 C8 C9 120.5(3)
C8 C9 C10 122.1(2)
C8 C9 C4 118.2(2)
C10 C9 C4 119.7(2)
C11 C10 C9 118.9(2)
C11 C10 C27 120.7(2)
C9 C10 C27 120.3(2)
C10 C11 C2 121.3(2)
C10 C11 C12 130.9(2)
C2 C11 C12 107.57(19)
C13 C12 C17 119.1(2)
C13 C12 C11 132.4(2)
C17 C12 C11 108.42(19)
C14 C13 C12 119.2(2)
C15 C14 C13 121.1(2)
C16 C15 C14 120.3(3)
C15 C16 C17 119.5(2)
C16 C17 C12 120.7(2)
C16 C17 C1 128.1(2)
C12 C17 C1 111.2(2)
C19 C18 C1 115.5(2)
O1 C19 C18 108.6(2)
C21 C20 C25 119.1(3)
C21 C20 S1 120.3(2)
C25 C20 S1 120.6(2)
C22 C21 C20 119.9(3)
C21 C22 C23 121.7(3)
C24 C23 C22 117.9(3)
C24 C23 C26 122.3(3)
C22 C23 C26 119.8(3)
C25 C24 C23 121.6(3)
C24 C25 C20 119.7(3)
C32 C27 C28 119.1(3)
C32 C27 C10 120.5(2)
C28 C27 C10 120.3(2)
C29 C28 C27 120.5(3)
C30 C29 C28 119.8(3)
C31 C30 C29 119.8(3)
C30 C31 C32 120.9(4)
C31 C32 C27 119.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.422(2)
S1 O2 1.425(2)
S1 O1 1.5861(18)
S1 C20 1.748(3)
O1 C19 1.447(3)
C1 C17 1.511(3)
C1 C2 1.515(3)
C1 C18 1.540(3)
C2 C3 1.363(3)
C2 C11 1.435(3)
C3 C4 1.414(4)
C4 C5 1.415(4)
C4 C9 1.431(4)
C5 C6 1.366(4)
C6 C7 1.383(4)
C7 C8 1.365(4)
C8 C9 1.424(4)
C9 C10 1.426(3)
C10 C11 1.375(3)
C10 C27 1.502(3)
C11 C12 1.478(3)
C12 C13 1.395(3)
C12 C17 1.408(3)
C13 C14 1.384(4)
C14 C15 1.383(4)
C15 C16 1.377(4)
C16 C17 1.383(3)
C18 C19 1.510(4)
C20 C21 1.383(4)
C20 C25 1.389(4)
C21 C22 1.373(4)
C22 C23 1.379(4)
C23 C24 1.377(4)
C23 C26 1.511(4)
C24 C25 1.376(4)
C27 C32 1.378(4)
C27 C28 1.385(4)
C28 C29 1.380(4)
C29 C30 1.375(5)
C30 C31 1.362(6)
C31 C32 1.377(5)
