#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:51:06 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238425 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/52/1555251.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_1555251
loop_
_publ_author_name
'Zhao, Peng'
'Liu, Yu'
'Xi, Chanjuan'
_publ_section_title
;
 MeOTf-Induced Carboannulation of Isothiocyanates and Aryl Alkynes with
 C═S Bond Cleavage: Access to Indenones.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4388
_journal_page_last               4391
_journal_paper_doi               10.1021/acs.orglett.5b02201
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C18 H16 O S'
_chemical_formula_weight         280.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.57(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3543(11)
_cell_length_b                   15.615(3)
_cell_length_c                   17.226(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1437.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7422
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.9533
_exptl_absorpt_correction_T_min  0.9090
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0768P)²+0.7368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                2422
_reflns_number_total             2502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02201_si_002.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1555251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 -0.00273(10) 0.34934(3) 0.30320(3) 0.0362(2) Uani 1 1 d .
O1 O -0.1223(3) 0.03426(9) 0.38529(9) 0.0406(4) Uani 1 1 d .
C16 C -0.2496(3) 0.16610(13) 0.17865(11) 0.0302(4) Uani 1 1 d .
H16A H -0.1093 0.2007 0.1686 0.036 Uiso 1 1 calc R
C12 C -0.5101(3) 0.09718(12) 0.26793(11) 0.0295(4) Uani 1 1 d .
H12A H -0.5499 0.0842 0.3196 0.035 Uiso 1 1 calc R
C11 C -0.3010(3) 0.14795(11) 0.25547(11) 0.0259(4) Uani 1 1 d .
C3 C 0.0072(3) 0.24545(12) 0.33804(10) 0.0255(4) Uani 1 1 d .
C13 C -0.6603(3) 0.06554(12) 0.20587(12) 0.0328(4) Uani 1 1 d .
H13A H -0.8024 0.0317 0.2158 0.039 Uiso 1 1 calc R
C8 C 0.5448(4) 0.24327(14) 0.49686(12) 0.0343(5) Uani 1 1 d .
H8A H 0.6806 0.2763 0.5187 0.041 Uiso 1 1 calc R
C4 C 0.1961(3) 0.22961(12) 0.40421(10) 0.0265(4) Uani 1 1 d .
C1 C -0.0442(3) 0.10699(12) 0.38105(11) 0.0290(4) Uani 1 1 d .
C2 C -0.1263(3) 0.17279(12) 0.32143(10) 0.0259(4) Uani 1 1 d .
C14 C -0.6060(3) 0.08254(13) 0.12915(12) 0.0330(4) Uani 1 1 d .
C9 C 0.3902(4) 0.27895(13) 0.43677(11) 0.0322(4) Uani 1 1 d .
H9A H 0.4178 0.3355 0.4188 0.039 Uiso 1 1 calc R
C7 C 0.5076(4) 0.16157(13) 0.52587(11) 0.0324(5) Uani 1 1 d .
C15 C -0.4000(4) 0.13438(14) 0.11696(12) 0.0341(5) Uani 1 1 d .
H15A H -0.3621 0.1482 0.0653 0.041 Uiso 1 1 calc R
C5 C 0.1605(3) 0.14705(12) 0.43184(11) 0.0280(4) Uani 1 1 d .
C6 C 0.3087(4) 0.11231(13) 0.49231(11) 0.0314(4) Uani 1 1 d .
H6A H 0.2771 0.0563 0.5109 0.038 Uiso 1 1 calc R
C18 C -0.2908(4) 0.36065(14) 0.24445(14) 0.0410(5) Uani 1 1 d .
H18A H -0.3034 0.4190 0.2237 0.062 Uiso 1 1 calc R
H18B H -0.4325 0.3494 0.2763 0.062 Uiso 1 1 calc R
H18C H -0.2933 0.3197 0.2013 0.062 Uiso 1 1 calc R
C17 C -0.7611(4) 0.04323(15) 0.06229(13) 0.0439(5) Uani 1 1 d .
H17A H -0.6975 0.0623 0.0130 0.066 Uiso 1 1 calc R
H17B H -0.9358 0.0612 0.0647 0.066 Uiso 1 1 calc R
H17C H -0.7508 -0.0193 0.0657 0.066 Uiso 1 1 calc R
C10 C 0.6796(4) 0.12609(16) 0.59066(13) 0.0438(5) Uani 1 1 d .
H10A H 0.6259 0.0681 0.6036 0.066 Uiso 1 1 calc R
H10B H 0.6736 0.1629 0.6366 0.066 Uiso 1 1 calc R
H10C H 0.8511 0.1243 0.5739 0.066 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
C3 S1 C18 107.09(10)
C15 C16 C11 120.99(18)
C13 C12 C11 120.95(18)
C16 C11 C12 117.83(17)
C16 C11 C2 121.48(16)
C12 C11 C2 120.33(17)
C2 C3 C4 110.07(16)
C2 C3 S1 134.77(15)
C4 C3 S1 115.09(13)
C12 C13 C14 121.10(18)
C7 C8 C9 122.70(18)
C9 C4 C5 119.51(17)
C9 C4 C3 132.18(18)
C5 C4 C3 108.25(16)
O1 C1 C5 126.77(17)
O1 C1 C2 126.51(17)
C5 C1 C2 106.67(16)
C3 C2 C11 132.76(17)
C3 C2 C1 107.43(16)
C11 C2 C1 119.43(16)
C15 C14 C13 117.79(18)
C15 C14 C17 121.63(19)
C13 C14 C17 120.55(19)
C4 C9 C8 118.20(19)
C8 C7 C6 118.39(18)
C8 C7 C10 120.62(19)
C6 C7 C10 121.0(2)
C16 C15 C14 121.32(19)
C6 C5 C4 122.52(18)
C6 C5 C1 129.98(18)
C4 C5 C1 107.37(16)
C5 C6 C7 118.66(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C3 1.7292(19)
S1 C18 1.800(2)
O1 C1 1.214(2)
C16 C15 1.385(3)
C16 C11 1.397(3)
C12 C13 1.388(3)
C12 C11 1.400(3)
C11 C2 1.478(3)
C3 C2 1.362(3)
C3 C4 1.497(2)
C13 C14 1.396(3)
C8 C7 1.389(3)
C8 C9 1.400(3)
C4 C9 1.384(3)
C4 C5 1.391(3)
C1 C5 1.496(3)
C1 C2 1.499(3)
C14 C15 1.394(3)
C14 C17 1.508(3)
C7 C6 1.408(3)
C7 C10 1.507(3)
C5 C6 1.381(3)
