#------------------------------------------------------------------------------
#$Date: 2015-08-31 12:02:20 +0300 (Mon, 31 Aug 2015) $
#$Revision: 153832 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117726.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_7117726
loop_
_publ_author_name
'Yin-Wei Sun'
'Xiang-Ying Tang'
'Min Shi'
_publ_section_title
;
 A gold-catalyzed 1,2-acyloxy migration/intramolecular
 cyclopropanation/ring enlargement cascade: syntheses of medium-sized
 heterocycles
;
_journal_name_full               Chem.Commun.
_journal_page_first              13937
_journal_paper_doi               10.1039/C5cc05808B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C24 H23 N O5 S'
_chemical_formula_weight         437.49
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-04-15 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5654(9)
_cell_length_b                   18.5476(13)
_cell_length_c                   18.7414(13)
_cell_measurement_reflns_used    4792
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.328
_cell_measurement_theta_min      4.478
_cell_volume                     4367.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.173
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0720P)²+0.6491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1315
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                3275
_reflns_number_total             4286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05808b2.cif
_cod_data_source_block           cd214205
_cod_database_code               7117726
_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. 
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.06010(4) 0.07676(3) 0.32554(2) 0.04282(17) Uani 1 1 d . . . . .
N1 N 0.09310(13) 0.15662(8) 0.35449(8) 0.0413(4) Uani 1 1 d . . . . .
O1 O 0.20656(11) 0.35542(7) 0.40192(7) 0.0498(4) Uani 1 1 d . . . . .
O2 O 0.39236(14) 0.28930(9) 0.29984(8) 0.0666(5) Uani 1 1 d . . . . .
O3 O 0.39183(10) 0.26252(7) 0.41700(6) 0.0450(3) Uani 1 1 d . . . . .
O4 O 0.13651(11) 0.02799(7) 0.35478(8) 0.0556(4) Uani 1 1 d . . . . .
O5 O 0.04864(12) 0.08196(8) 0.25008(7) 0.0578(4) Uani 1 1 d . . . . .
C1 C 0.1488(2) 0.39627(12) 0.35529(12) 0.0608(6) Uani 1 1 d . . . . .
H1 H 0.1599 0.4452 0.3475 0.073 Uiso 1 1 calc R U . . .
C2 C 0.0748(2) 0.35738(12) 0.32244(11) 0.0567(6) Uani 1 1 d . . . . .
H2 H 0.0254 0.3737 0.2892 0.068 Uiso 1 1 calc R U . . .
C3 C 0.08602(16) 0.28559(10) 0.34837(10) 0.0438(5) Uani 1 1 d . . . . .
C4 C 0.16542(15) 0.28755(10) 0.39619(9) 0.0398(4) Uani 1 1 d . . . . .
C5 C 0.21093(14) 0.22563(10) 0.43765(9) 0.0377(4) Uani 1 1 d . . . . .
C6 C 0.12760(15) 0.16491(10) 0.42888(10) 0.0399(4) Uani 1 1 d . . . . .
H6A H 0.1579 0.1198 0.4454 0.048 Uiso 1 1 calc R U . . .
H6B H 0.0662 0.1756 0.4584 0.048 Uiso 1 1 calc R U . . .
C7 C 0.02894(18) 0.21789(10) 0.32800(11) 0.0500(5) Uani 1 1 d . . . . .
H7A H -0.0414 0.2170 0.3493 0.060 Uiso 1 1 calc R U . . .
H7B H 0.0213 0.2151 0.2766 0.060 Uiso 1 1 calc R U . . .
C8 C 0.31882(15) 0.20557(11) 0.40727(10) 0.0433(5) Uani 1 1 d . . . . .
C9 C 0.34910(18) 0.14539(13) 0.37792(14) 0.0646(6) Uani 1 1 d . . . . .
H9A H 0.4193 0.1397 0.3632 0.078 Uiso 1 1 calc R U . . .
H9B H 0.3006 0.1081 0.3717 0.078 Uiso 1 1 calc R U . . .
C10 C 0.42074(15) 0.30265(11) 0.35901(10) 0.0436(5) Uani 1 1 d . . . . .
C11 C 0.48924(17) 0.36361(11) 0.38055(11) 0.0524(5) Uani 1 1 d . . . . .
H11A H 0.5100 0.3904 0.3390 0.079 Uiso 1 1 calc R U . . .
H11B H 0.5515 0.3455 0.4042 0.079 Uiso 1 1 calc R U . . .
H11C H 0.4507 0.3945 0.4125 0.079 Uiso 1 1 calc R U . . .
C12 C 0.21853(14) 0.23937(10) 0.51861(9) 0.0393(4) Uani 1 1 d . . . . .
C13 C 0.27952(16) 0.19356(12) 0.56069(11) 0.0522(5) Uani 1 1 d . . . . .
H13 H 0.3202 0.1577 0.5392 0.063 Uiso 1 1 calc R U . . .
C14 C 0.28045(19) 0.20067(14) 0.63422(12) 0.0620(6) Uani 1 1 d . . . . .
H14 H 0.3210 0.1692 0.6617 0.074 Uiso 1 1 calc R U . . .
C15 C 0.22194(18) 0.25380(14) 0.66676(11) 0.0595(6) Uani 1 1 d . . . . .
H15 H 0.2229 0.2587 0.7161 0.071 Uiso 1 1 calc R U . . .
C16 C 0.16214(19) 0.29948(13) 0.62580(12) 0.0584(6) Uani 1 1 d . . . . .
H16 H 0.1231 0.3360 0.6475 0.070 Uiso 1 1 calc R U . . .
C17 C 0.15923(17) 0.29178(11) 0.55210(11) 0.0497(5) Uani 1 1 d . . . . .
H17 H 0.1167 0.3224 0.5251 0.060 Uiso 1 1 calc R U . . .
C18 C -0.06607(15) 0.05401(10) 0.36032(10) 0.0412(4) Uani 1 1 d . . . . .
C19 C -0.14985(18) 0.04013(13) 0.31480(12) 0.0607(6) Uani 1 1 d . . . . .
H19 H -0.1407 0.0437 0.2657 0.073 Uiso 1 1 calc R U . . .
C20 C -0.2473(2) 0.02086(14) 0.34269(15) 0.0711(7) Uani 1 1 d . . . . .
H20 H -0.3029 0.0101 0.3117 0.085 Uiso 1 1 calc R U . . .
C21 C -0.26440(18) 0.01708(12) 0.41525(14) 0.0591(6) Uani 1 1 d . . . . .
C22 C -0.17974(19) 0.03081(13) 0.45993(12) 0.0625(6) Uani 1 1 d . . . . .
H22 H -0.1895 0.0282 0.5091 0.075 Uiso 1 1 calc R U . . .
C23 C -0.08101(17) 0.04828(12) 0.43317(11) 0.0546(5) Uani 1 1 d . . . . .
H23 H -0.0244 0.0562 0.4641 0.066 Uiso 1 1 calc R U . . .
C24 C -0.3736(2) 0.00094(16) 0.4449(2) 0.0933(10) Uani 1 1 d . . . . .
H24A H -0.4116 0.0453 0.4519 0.140 Uiso 1 1 calc R U . . .
H24B H -0.3666 -0.0237 0.4897 0.140 Uiso 1 1 calc R U . . .
H24C H -0.4119 -0.0290 0.4119 0.140 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_1
_geom_angle_site_symmetry_3
O5 S1 O4 119.44(9) . .
O5 S1 N1 107.12(8) . .
O4 S1 N1 106.06(8) . .
O5 S1 C18 106.98(9) . .
O4 S1 C18 108.10(9) . .
N1 S1 C18 108.82(9) . .
C6 N1 C7 113.53(15) . .
C6 N1 S1 119.07(11) . .
C7 N1 S1 116.58(13) . .
C4 O1 C1 105.08(16) . .
C10 O3 C8 118.55(14) . .
C2 C1 O1 111.56(19) . .
C2 C1 H1 124.2 . .
O1 C1 H1 124.2 . .
C1 C2 C3 106.26(19) . .
C1 C2 H2 126.9 . .
C3 C2 H2 126.9 . .
C4 C3 C2 106.05(18) . .
C4 C3 C7 123.36(17) . .
C2 C3 C7 130.55(19) . .
C3 C4 O1 111.05(16) . .
C3 C4 C5 127.51(17) . .
O1 C4 C5 121.39(16) . .
C4 C5 C8 109.52(15) . .
C4 C5 C12 114.02(15) . .
C8 C5 C12 110.77(15) . .
C4 C5 C6 104.15(14) . .
C8 C5 C6 112.74(15) . .
C12 C5 C6 105.48(14) . .
N1 C6 C5 112.14(14) . .
N1 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
N1 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
N1 C7 C3 107.33(16) . .
N1 C7 H7A 110.2 . .
C3 C7 H7A 110.2 . .
N1 C7 H7B 110.2 . .
C3 C7 H7B 110.2 . .
H7A C7 H7B 108.5 . .
C9 C8 O3 120.44(18) . .
C9 C8 C5 129.08(19) . .
O3 C8 C5 110.43(15) . .
C8 C9 H9A 120.0 . .
C8 C9 H9B 120.0 . .
H9A C9 H9B 120.0 . .
O2 C10 O3 123.21(19) . .
O2 C10 C11 126.03(19) . .
O3 C10 C11 110.76(16) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C17 C12 C13 118.14(18) . .
C17 C12 C5 122.15(17) . .
C13 C12 C5 119.45(17) . .
C14 C13 C12 120.7(2) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C15 C14 C13 120.4(2) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C16 C15 C14 119.31(19) . .
C16 C15 H15 120.3 . .
C14 C15 H15 120.3 . .
C15 C16 C17 120.6(2) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C12 C17 C16 120.8(2) . .
C12 C17 H17 119.6 . .
C16 C17 H17 119.6 . .
C19 C18 C23 119.53(19) . .
C19 C18 S1 120.11(16) . .
C23 C18 S1 120.34(15) . .
C20 C19 C18 119.4(2) . .
C20 C19 H19 120.3 . .
C18 C19 H19 120.3 . .
C19 C20 C21 121.7(2) . .
C19 C20 H20 119.1 . .
C21 C20 H20 119.1 . .
C22 C21 C20 118.0(2) . .
C22 C21 C24 121.0(2) . .
C20 C21 C24 121.0(2) . .
C23 C22 C21 121.2(2) . .
C23 C22 H22 119.4 . .
C21 C22 H22 119.4 . .
C22 C23 C18 120.0(2) . .
C22 C23 H23 120.0 . .
C18 C23 H23 120.0 . .
C21 C24 H24A 109.5 . .
C21 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C21 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O5 1.4248(15) .
S1 O4 1.4284(15) .
S1 N1 1.6311(16) .
S1 C18 1.765(2) .
N1 C6 1.468(2) .
N1 C7 1.479(2) .
O1 C4 1.365(2) .
O1 C1 1.365(2) .
O2 C10 1.191(2) .
O3 C10 1.366(2) .
O3 C8 1.411(2) .
C1 C2 1.328(3) .
C1 H1 0.9300 .
C2 C3 1.424(3) .
C2 H2 0.9300 .
C3 C4 1.342(3) .
C3 C7 1.496(3) .
C4 C5 1.500(3) .
C5 C8 1.517(3) .
C5 C12 1.542(2) .
C5 C6 1.547(2) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.301(3) .
C9 H9A 0.9300 .
C9 H9B 0.9300 .
C10 C11 1.477(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C17 1.376(3) .
C12 C13 1.390(3) .
C13 C14 1.384(3) .
C13 H13 0.9300 .
C14 C15 1.372(3) .
C14 H14 0.9300 .
C15 C16 1.368(3) .
C15 H15 0.9300 .
C16 C17 1.389(3) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C19 1.379(3) .
C18 C23 1.382(3) .
C19 C20 1.378(3) .
C19 H19 0.9300 .
C20 C21 1.379(3) .
C20 H20 0.9300 .
C21 C22 1.378(3) .
C21 C24 1.510(3) .
C22 C23 1.377(3) .
C22 H22 0.9300 .
C23 H23 0.9300 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O5 S1 N1 C6 -169.90(14) . . . .
O4 S1 N1 C6 -41.30(16) . . . .
C18 S1 N1 C6 74.77(15) . . . .
O5 S1 N1 C7 48.00(17) . . . .
O4 S1 N1 C7 176.60(14) . . . .
C18 S1 N1 C7 -67.33(16) . . . .
C4 O1 C1 C2 0.7(2) . . . .
O1 C1 C2 C3 -1.2(3) . . . .
C1 C2 C3 C4 1.2(3) . . . .
C1 C2 C3 C7 -176.4(2) . . . .
C2 C3 C4 O1 -0.8(2) . . . .
C7 C3 C4 O1 176.97(18) . . . .
C2 C3 C4 C5 -178.23(19) . . . .
C7 C3 C4 C5 -0.5(3) . . . .
C1 O1 C4 C3 0.1(2) . . . .
C1 O1 C4 C5 177.73(17) . . . .
C3 C4 C5 C8 105.8(2) . . . .
O1 C4 C5 C8 -71.4(2) . . . .
C3 C4 C5 C12 -129.4(2) . . . .
O1 C4 C5 C12 53.3(2) . . . .
C3 C4 C5 C6 -15.0(2) . . . .
O1 C4 C5 C6 167.78(16) . . . .
C7 N1 C6 C5 -68.9(2) . . . .
S1 N1 C6 C5 147.88(13) . . . .
C4 C5 C6 N1 46.64(19) . . . .
C8 C5 C6 N1 -72.00(19) . . . .
C12 C5 C6 N1 167.00(14) . . . .
C6 N1 C7 C3 47.5(2) . . . .
S1 N1 C7 C3 -168.31(13) . . . .
C4 C3 C7 N1 -14.3(3) . . . .
C2 C3 C7 N1 162.8(2) . . . .
C10 O3 C8 C9 75.6(3) . . . .
C10 O3 C8 C5 -106.64(18) . . . .
C4 C5 C8 C9 -117.6(2) . . . .
C12 C5 C8 C9 115.8(2) . . . .
C6 C5 C8 C9 -2.1(3) . . . .
C4 C5 C8 O3 64.88(19) . . . .
C12 C5 C8 O3 -61.73(19) . . . .
C6 C5 C8 O3 -179.66(14) . . . .
C8 O3 C10 O2 -4.7(3) . . . .
C8 O3 C10 C11 174.65(16) . . . .
C4 C5 C12 C17 19.8(2) . . . .
C8 C5 C12 C17 143.91(18) . . . .
C6 C5 C12 C17 -93.8(2) . . . .
C4 C5 C12 C13 -166.16(17) . . . .
C8 C5 C12 C13 -42.1(2) . . . .
C6 C5 C12 C13 80.2(2) . . . .
C17 C12 C13 C14 -0.1(3) . . . .
C5 C12 C13 C14 -174.31(19) . . . .
C12 C13 C14 C15 -0.8(3) . . . .
C13 C14 C15 C16 0.4(4) . . . .
C14 C15 C16 C17 0.9(3) . . . .
C13 C12 C17 C16 1.3(3) . . . .
C5 C12 C17 C16 175.39(18) . . . .
C15 C16 C17 C12 -1.7(3) . . . .
O5 S1 C18 C19 4.4(2) . . . .
O4 S1 C18 C19 -125.39(18) . . . .
N1 S1 C18 C19 119.85(18) . . . .
O5 S1 C18 C23 -177.13(16) . . . .
O4 S1 C18 C23 53.04(19) . . . .
N1 S1 C18 C23 -61.72(18) . . . .
C23 C18 C19 C20 0.1(3) . . . .
S1 C18 C19 C20 178.55(19) . . . .
C18 C19 C20 C21 1.9(4) . . . .
C19 C20 C21 C22 -2.2(4) . . . .
C19 C20 C21 C24 175.7(3) . . . .
C20 C21 C22 C23 0.4(3) . . . .
C24 C21 C22 C23 -177.5(2) . . . .
C21 C22 C23 C18 1.6(3) . . . .
C19 C18 C23 C22 -1.8(3) . . . .
S1 C18 C23 C22 179.73(18) . . . .
