#------------------------------------------------------------------------------
#$Date: 2017-03-04 13:55:23 +0100 (Sat 04 de Mar de 2017) $
#$Revision: 193367 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/54/1545445.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_1545445
loop_
_publ_author_name
'Zhang, Shuyao'
'Cheng, Beiming'
'Wang, Shen-An'
'Zhou, Ling'
'Tung, Chen-Ho'
'Wang, Jianwu'
'Xu, Zhenghu'
_publ_section_title
;
 Gold-Catalyzed Cycloisomerization/1,5-H Migration/Diels-Alder Reaction
 Cascade: Synthesis of Complex Nitrogen-Containing Heterocycles.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1072
_journal_page_last               1075
_journal_paper_doi               10.1021/acs.orglett.7b00090
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C28 H26 N2 O5 S'
_chemical_formula_weight         502.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                68.18(3)
_cell_angle_beta                 67.74(3)
_cell_angle_gamma                70.59(3)
_cell_formula_units_Z            2
_cell_length_a                   10.430(5)
_cell_length_b                   11.137(5)
_cell_length_c                   12.934(5)
_cell_measurement_reflns_used    1426
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      19.736
_cell_measurement_theta_min      2.611
_cell_volume                     1258.3(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11533
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.611
_exptl_absorpt_coefficient_mu    0.170
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0798P)²+0.7152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2465
_reflns_number_total             4395
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00090_si_002.cif
_cod_data_source_block           p
_cod_original_cell_volume        1258.4(10)
_cod_database_code               1545445
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.15944(12) 0.19213(10) 0.50112(9) 0.0507(4) Uani 1 1 d . .
N1 N 0.0560(4) 0.6836(3) 0.1511(3) 0.0482(9) Uani 1 1 d . .
O4 O 0.0322(3) 0.1455(3) 0.5654(2) 0.0630(8) Uani 1 1 d . .
N2 N 0.1092(3) 0.3436(3) 0.4215(2) 0.0422(8) Uani 1 1 d . .
O3 O 0.2423(3) 0.2054(3) 0.5612(3) 0.0666(9) Uani 1 1 d . .
O1 O 0.2563(3) 0.7096(3) 0.1705(3) 0.0647(9) Uani 1 1 d . .
O2 O -0.1503(3) 0.6238(3) 0.1849(3) 0.0683(9) Uani 1 1 d . .
C14 C 0.1382(4) 0.3629(3) 0.2272(3) 0.0381(9) Uani 1 1 d . .
C12 C 0.0225(4) 0.3796(4) 0.3390(3) 0.0402(9) Uani 1 1 d . .
C13 C 0.2174(4) 0.4245(3) 0.3419(3) 0.0412(9) Uani 1 1 d . .
H13 H 0.2956 0.4150 0.3707 0.049 Uiso 1 1 calc R U
C19 C 0.2586(4) 0.3878(3) 0.2300(3) 0.0398(9) Uani 1 1 d . .
C7 C 0.1544(5) 0.6597(4) 0.2098(4) 0.0476(10) Uani 1 1 d . .
C15 C 0.1388(5) 0.3362(4) 0.1316(3) 0.0519(11) Uani 1 1 d . .
H15 H 0.0575 0.3228 0.1278 0.062 Uiso 1 1 calc R U
C8 C -0.0516(5) 0.6157(4) 0.2164(4) 0.0473(10) Uani 1 1 d . .
C18 C 0.3820(4) 0.3828(4) 0.1400(3) 0.0509(11) Uani 1 1 d . .
H18 H 0.4621 0.3997 0.1425 0.061 Uiso 1 1 calc R U
C10 C 0.1121(4) 0.5625(4) 0.3260(3) 0.0442(10) Uani 1 1 d . .
H10 H 0.0929 0.6001 0.3893 0.053 Uiso 1 1 calc R U
C9 C -0.0217(4) 0.5318(4) 0.3288(3) 0.0437(10) Uani 1 1 d . .
H9 H -0.1018 0.5513 0.3954 0.052 Uiso 1 1 calc R U
C3 C 0.0704(6) 0.7597(4) 0.0322(4) 0.0698(12) Uani 1 1 d . U
C20 C 0.2702(4) 0.0904(4) 0.4105(3) 0.0472(10) Uani 1 1 d . .
C16 C 0.2631(6) 0.3299(4) 0.0410(4) 0.0637(13) Uani 1 1 d . .
H16 H 0.2657 0.3105 -0.0238 0.076 Uiso 1 1 calc R U
C23 C 0.4407(6) -0.0504(4) 0.2494(4) 0.0663(13) Uani 1 1 d . .
C17 C 0.3837(5) 0.3518(5) 0.0450(4) 0.0644(13) Uani 1 1 d . .
H17 H 0.4667 0.3456 -0.0164 0.077 Uiso 1 1 calc R U
C11 C -0.1008(5) 0.3155(5) 0.3770(4) 0.0665(13) Uani 1 1 d . .
H11A H -0.0656 0.2227 0.3823 0.100 Uiso 1 1 calc R U
H11B H -0.1535 0.3567 0.3211 0.100 Uiso 1 1 calc R U
H11C H -0.1617 0.3262 0.4517 0.100 Uiso 1 1 calc R U
C21 C 0.2128(5) 0.0237(4) 0.3749(4) 0.0614(12) Uani 1 1 d . .
H21 H 0.1161 0.0251 0.4048 0.074 Uiso 1 1 calc R U
C22 C 0.2983(6) -0.0455(5) 0.2950(4) 0.0679(13) Uani 1 1 d . .
H22 H 0.2580 -0.0902 0.2714 0.081 Uiso 1 1 calc R U
C26 C 0.4161(5) 0.0819(5) 0.3697(5) 0.0713(14) Uani 1 1 d . .
H26 H 0.4572 0.1237 0.3952 0.086 Uiso 1 1 calc R U
C2 C -0.0371(7) 0.8649(5) 0.0031(5) 0.0832(13) Uani 1 1 d . U
H2 H -0.1194 0.8895 0.0597 0.100 Uiso 1 1 calc R U
C25 C 0.4988(5) 0.0103(5) 0.2904(5) 0.0778(15) Uani 1 1 d . .
H25 H 0.5966 0.0030 0.2641 0.093 Uiso 1 1 calc R U
C4 C 0.1919(7) 0.7231(6) -0.0516(5) 0.0883(14) Uani 1 1 d . U
H4 H 0.2631 0.6514 -0.0299 0.106 Uiso 1 1 calc R U
C24 C 0.5324(6) -0.1205(6) 0.1577(5) 0.102(2) Uani 1 1 d . .
H24A H 0.6012 -0.1940 0.1880 0.153 Uiso 1 1 calc R U
H24B H 0.5806 -0.0599 0.0906 0.153 Uiso 1 1 calc R U
H24C H 0.4740 -0.1524 0.1361 0.153 Uiso 1 1 calc R U
C1 C -0.0174(8) 0.9350(5) -0.1175(5) 0.0962(14) Uani 1 1 d . U
H1 H -0.0875 1.0061 -0.1419 0.115 Uiso 1 1 calc R U
C6 C 0.1054(8) 0.8955(6) -0.1951(6) 0.1021(15) Uani 1 1 d . U
H6 H 0.1185 0.9438 -0.2730 0.122 Uiso 1 1 calc R U
C5 C 0.2091(8) 0.7922(6) -0.1680(5) 0.1055(16) Uani 1 1 d . U
H5 H 0.2904 0.7674 -0.2254 0.127 Uiso 1 1 calc R U
O5 O 0.3976(5) 0.4757(4) 0.4702(4) 0.1108(14) Uani 1 1 d . .
C28 C 0.4855(7) 0.5655(7) 0.3900(5) 0.107(2) Uani 1 1 d . .
H28A H 0.4344 0.6348 0.3382 0.128 Uiso 1 1 calc R U
H28B H 0.5699 0.5185 0.3431 0.128 Uiso 1 1 calc R U
C27 C 0.4733(7) 0.3753(7) 0.5463(6) 0.114(2) Uani 1 1 d . .
H27A H 0.5577 0.3260 0.5015 0.137 Uiso 1 1 calc R U
H27B H 0.4141 0.3139 0.6012 0.137 Uiso 1 1 calc R U
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
_geom_angle_site_symmetry_3
O4 S1 O3 119.88(19) .
O4 S1 N2 105.31(17) .
O3 S1 N2 104.87(17) .
O4 S1 C20 108.41(19) .
O3 S1 C20 108.2(2) .
N2 S1 C20 109.89(17) .
C8 N1 C7 113.1(3) .
C8 N1 C3 122.4(3) .
C7 N1 C3 124.2(4) .
C13 N2 C12 97.5(3) .
C13 N2 S1 120.1(2) .
C12 N2 S1 124.6(2) .
C15 C14 C19 120.4(4) .
C15 C14 C12 132.4(4) .
C19 C14 C12 107.1(3) .
C11 C12 N2 118.9(3) .
C11 C12 C14 117.5(3) .
N2 C12 C14 101.5(3) .
C11 C12 C9 114.3(3) .
N2 C12 C9 95.0(3) .
C14 C12 C9 106.6(3) .
N2 C13 C19 101.9(3) .
N2 C13 C10 97.1(3) .
C19 C13 C10 106.3(3) .
C18 C19 C14 121.5(4) .
C18 C19 C13 132.0(4) .
C14 C19 C13 106.4(3) .
O1 C7 N1 124.8(4) .
O1 C7 C10 127.1(4) .
N1 C7 C10 108.1(4) .
C14 C15 C16 118.3(4) .
O2 C8 N1 124.8(4) .
O2 C8 C9 127.3(4) .
N1 C8 C9 107.9(3) .
C19 C18 C17 118.0(4) .
C7 C10 C9 104.9(3) .
C7 C10 C13 114.6(3) .
C9 C10 C13 103.4(3) .
C8 C9 C10 106.0(3) .
C8 C9 C12 112.8(3) .
C10 C9 C12 103.8(3) .
C2 C3 C4 121.3(5) .
C2 C3 N1 120.2(5) .
C4 C3 N1 118.5(4) .
C21 C20 C26 119.4(4) .
C21 C20 S1 120.2(3) .
C26 C20 S1 120.3(4) .
C17 C16 C15 121.2(4) .
C22 C23 C25 117.9(5) .
C22 C23 C24 121.5(5) .
C25 C23 C24 120.6(5) .
C16 C17 C18 120.5(4) .
C20 C21 C22 120.0(4) .
C23 C22 C21 121.8(5) .
C25 C26 C20 118.9(5) .
C3 C2 C1 117.4(6) .
C23 C25 C26 121.9(5) .
C3 C4 C5 120.5(6) .
C6 C1 C2 118.4(6) .
C5 C6 C1 124.7(6) .
C6 C5 C4 117.7(7) .
C27 O5 C28 109.1(4) .
O5 C28 C27 109.8(5) 2_666
O5 C27 C28 110.5(5) 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O4 1.423(3) .
S1 O3 1.432(3) .
S1 N2 1.646(3) .
S1 C20 1.756(4) .
N1 C8 1.384(5) .
N1 C7 1.400(5) .
N1 C3 1.431(5) .
N2 C13 1.500(5) .
N2 C12 1.514(5) .
O1 C7 1.212(5) .
O2 C8 1.209(5) .
C14 C15 1.373(5) .
C14 C19 1.389(5) .
C14 C12 1.520(5) .
C12 C11 1.509(6) .
C12 C9 1.569(5) .
C13 C19 1.515(5) .
C13 C10 1.557(5) .
C19 C18 1.372(5) .
C7 C10 1.494(6) .
C15 C16 1.382(6) .
C8 C9 1.491(5) .
C18 C17 1.387(6) .
C10 C9 1.528(5) .
C3 C2 1.375(7) .
C3 C4 1.375(8) .
C20 C21 1.372(6) .
C20 C26 1.392(6) .
C16 C17 1.381(6) .
C23 C22 1.365(6) .
C23 C25 1.375(7) .
C23 C24 1.504(7) .
C21 C22 1.377(6) .
C26 C25 1.382(7) .
C2 C1 1.430(7) .
C4 C5 1.385(7) .
C1 C6 1.349(9) .
C6 C5 1.334(9) .
O5 C27 1.424(6) .
O5 C28 1.426(7) .
C28 C27 1.469(8) 2_666
C27 C28 1.469(8) 2_666
