#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117722.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_7117722
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_absolute_configuration ad
_chemical_formula_sum            'C17 H15 N O2 S'
_chemical_formula_weight         297.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-10-17 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2454(10)
_cell_length_b                   7.9709(13)
_cell_length_c                   30.185(5)
_cell_measurement_reflns_used    1091
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.659
_cell_measurement_theta_min      5.286
_cell_volume                     1502.7(4)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9020
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32061
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                1685
_reflns_number_total             2960
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05808b2.cif
_cod_data_source_block           cd213583
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7117722
loop_
_symmetry_equiv_pos_as_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'
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
S1 S 0.98472(16) 0.50440(13) 0.89675(3) 0.0731(3) Uani 1 1 d . . .
N1 N 0.9789(4) 0.5381(3) 0.84248(9) 0.0655(7) Uani 1 1 d . . .
O1 O 0.8548(5) 0.3615(3) 0.90426(8) 0.0873(8) Uani 1 1 d . . .
O2 O 1.2052(4) 0.5041(4) 0.90825(9) 0.0937(8) Uani 1 1 d . . .
C1 C 1.1288(6) 0.6290(5) 0.81920(14) 0.0768(11) Uani 1 1 d . . .
H1 H 1.2578 0.6699 0.8302 0.092 Uiso 1 1 calc R . .
C2 C 1.0554(6) 0.6478(5) 0.77791(14) 0.0756(11) Uani 1 1 d . . .
H2 H 1.1260 0.7037 0.7552 0.091 Uiso 1 1 calc R . .
C3 C 0.8522(5) 0.5688(4) 0.77427(11) 0.0576(9) Uani 1 1 d . . .
C4 C 0.8077(5) 0.5017(5) 0.81476(11) 0.0633(8) Uani 1 1 d . . .
H4 H 0.6850 0.4423 0.8224 0.076 Uiso 1 1 calc R . .
C5 C 0.7192(6) 0.5587(4) 0.73399(11) 0.0579(9) Uani 1 1 d . . .
C6 C 0.7797(7) 0.6416(5) 0.69604(13) 0.0879(13) Uani 1 1 d . . .
H6 H 0.9073 0.7017 0.6954 0.105 Uiso 1 1 calc R . .
C7 C 0.6499(8) 0.6357(7) 0.65840(14) 0.1043(15) Uani 1 1 d . . .
H7 H 0.6927 0.6913 0.6328 0.125 Uiso 1 1 calc R . .
C8 C 0.4639(7) 0.5508(6) 0.65858(14) 0.0910(13) Uani 1 1 d . . .
H8 H 0.3765 0.5505 0.6336 0.109 Uiso 1 1 calc R . .
C9 C 0.4048(6) 0.4654(5) 0.69559(15) 0.0849(12) Uani 1 1 d . . .
H9 H 0.2783 0.4039 0.6956 0.102 Uiso 1 1 calc R . .
C10 C 0.5304(6) 0.4689(5) 0.73326(11) 0.0703(10) Uani 1 1 d . . .
H10 H 0.4873 0.4101 0.7583 0.084 Uiso 1 1 calc R . .
C11 C 0.8621(6) 0.6793(5) 0.92090(10) 0.0589(9) Uani 1 1 d . . .
C12 C 0.6595(6) 0.6662(5) 0.93786(12) 0.0714(10) Uani 1 1 d . . .
H12 H 0.5864 0.5647 0.9364 0.086 Uiso 1 1 calc R . .
C13 C 0.5651(7) 0.8029(6) 0.95696(12) 0.0766(11) Uani 1 1 d . . .
H13 H 0.4278 0.7934 0.9686 0.092 Uiso 1 1 calc R . .
C14 C 0.6705(7) 0.9552(5) 0.95926(11) 0.0713(11) Uani 1 1 d . . .
C15 C 0.8754(6) 0.9647(5) 0.94216(12) 0.0719(10) Uani 1 1 d . . .
H15 H 0.9498 1.0656 0.9439 0.086 Uiso 1 1 calc R . .
C16 C 0.9711(6) 0.8295(5) 0.92286(11) 0.0667(9) Uani 1 1 d . . .
H16 H 1.1083 0.8384 0.9111 0.080 Uiso 1 1 calc R . .
C17 C 0.5618(8) 1.1071(6) 0.97841(15) 0.1052(15) Uani 1 1 d . . .
H17A H 0.4109 1.0861 0.9809 0.158 Uiso 1 1 calc R . .
H17B H 0.5853 1.2017 0.9593 0.158 Uiso 1 1 calc R . .
H17C H 0.6198 1.1304 1.0072 0.158 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 S1 O2 121.00(19) . .
O1 S1 N1 105.99(15) . .
O2 S1 N1 105.23(16) . .
O1 S1 C11 108.85(17) . .
O2 S1 C11 108.90(19) . .
N1 S1 C11 105.81(15) . .
C1 N1 C4 109.0(3) . .
C1 N1 S1 125.0(3) . .
C4 N1 S1 125.3(2) . .
C2 C1 N1 107.5(3) . .
C2 C1 H1 126.2 . .
N1 C1 H1 126.2 . .
C1 C2 C3 109.2(3) . .
C1 C2 H2 125.4 . .
C3 C2 H2 125.4 . .
C4 C3 C2 106.7(3) . .
C4 C3 C5 127.1(3) . .
C2 C3 C5 126.2(3) . .
C3 C4 N1 107.5(3) . .
C3 C4 H4 126.2 . .
N1 C4 H4 126.2 . .
C6 C5 C10 118.1(3) . .
C6 C5 C3 120.4(3) . .
C10 C5 C3 121.5(3) . .
C5 C6 C7 120.1(4) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C8 C7 C6 121.0(4) . .
C8 C7 H7 119.5 . .
C6 C7 H7 119.5 . .
C7 C8 C9 119.4(4) . .
C7 C8 H8 120.3 . .
C9 C8 H8 120.3 . .
C8 C9 C10 120.8(4) . .
C8 C9 H9 119.6 . .
C10 C9 H9 119.6 . .
C5 C10 C9 120.6(3) . .
C5 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C12 C11 C16 120.5(4) . .
C12 C11 S1 120.0(3) . .
C16 C11 S1 119.6(3) . .
C13 C12 C11 119.7(4) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C12 C13 C14 121.1(4) . .
C12 C13 H13 119.5 . .
C14 C13 H13 119.5 . .
C13 C14 C15 118.0(4) . .
C13 C14 C17 120.7(4) . .
C15 C14 C17 121.2(4) . .
C16 C15 C14 121.5(4) . .
C16 C15 H15 119.3 . .
C14 C15 H15 119.3 . .
C15 C16 C11 119.3(3) . .
C15 C16 H16 120.4 . .
C11 C16 H16 120.4 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.417(3) .
S1 O2 1.420(2) .
S1 N1 1.660(3) .
S1 C11 1.750(4) .
N1 C1 1.377(4) .
N1 C4 1.388(4) .
C1 C2 1.336(5) .
C1 H1 0.9300 .
C2 C3 1.421(5) .
C2 H2 0.9300 .
C3 C4 1.363(4) .
C3 C5 1.475(5) .
C4 H4 0.9300 .
C5 C6 1.375(5) .
C5 C10 1.380(4) .
C6 C7 1.397(6) .
C6 H6 0.9300 .
C7 C8 1.344(5) .
C7 H7 0.9300 .
C8 C9 1.359(5) .
C8 H8 0.9300 .
C9 C10 1.382(5) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C12 1.369(5) .
C11 C16 1.378(5) .
C12 C13 1.367(5) .
C12 H12 0.9300 .
C13 C14 1.383(5) .
C13 H13 0.9300 .
C14 C15 1.382(5) .
C14 C17 1.503(5) .
C15 C16 1.363(5) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 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
O1 S1 N1 C1 -159.2(3) . . . .
O2 S1 N1 C1 -30.0(3) . . . .
C11 S1 N1 C1 85.3(3) . . . .
O1 S1 N1 C4 31.1(3) . . . .
O2 S1 N1 C4 160.4(3) . . . .
C11 S1 N1 C4 -84.4(3) . . . .
C4 N1 C1 C2 -0.6(4) . . . .
S1 N1 C1 C2 -171.7(3) . . . .
N1 C1 C2 C3 0.5(4) . . . .
C1 C2 C3 C4 -0.3(4) . . . .
C1 C2 C3 C5 -179.0(3) . . . .
C2 C3 C4 N1 -0.1(4) . . . .
C5 C3 C4 N1 178.6(3) . . . .
C1 N1 C4 C3 0.4(4) . . . .
S1 N1 C4 C3 171.5(2) . . . .
C4 C3 C5 C6 176.2(4) . . . .
C2 C3 C5 C6 -5.4(5) . . . .
C4 C3 C5 C10 -3.0(5) . . . .
C2 C3 C5 C10 175.5(3) . . . .
C10 C5 C6 C7 1.0(6) . . . .
C3 C5 C6 C7 -178.1(4) . . . .
C5 C6 C7 C8 0.5(7) . . . .
C6 C7 C8 C9 -2.0(7) . . . .
C7 C8 C9 C10 1.9(7) . . . .
C6 C5 C10 C9 -1.2(5) . . . .
C3 C5 C10 C9 178.0(3) . . . .
C8 C9 C10 C5 -0.3(6) . . . .
O1 S1 C11 C12 -7.9(3) . . . .
O2 S1 C11 C12 -141.7(3) . . . .
N1 S1 C11 C12 105.7(3) . . . .
O1 S1 C11 C16 171.9(3) . . . .
O2 S1 C11 C16 38.1(3) . . . .
N1 S1 C11 C16 -74.6(3) . . . .
C16 C11 C12 C13 -0.2(5) . . . .
S1 C11 C12 C13 179.5(3) . . . .
C11 C12 C13 C14 0.4(5) . . . .
C12 C13 C14 C15 -0.8(6) . . . .
C12 C13 C14 C17 177.1(4) . . . .
C13 C14 C15 C16 1.1(5) . . . .
C17 C14 C15 C16 -176.8(4) . . . .
C14 C15 C16 C11 -0.9(5) . . . .
C12 C11 C16 C15 0.5(5) . . . .
S1 C11 C16 C15 -179.3(3) . . . .
