#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/48/4034877.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_4034877
loop_
_publ_author_name
'Gao, Yuzhen'
'Zhang, Pengbo'
'Li, Gang'
'Zhao, Yufen'
_publ_section_title
;
 Cascade Annulation of 2-Alkynylthioanisoles with Unsaturated
 α-Bromocarbonyls Leading to Thio-Benzobicyclic Skeletons.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13726
_journal_page_last               13733
_journal_paper_doi               10.1021/acs.joc.8b02001
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C16 H16 O4 S'
_chemical_formula_weight         304.35
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.866(2)
_cell_length_b                   9.4032(15)
_cell_length_c                   22.169(4)
_cell_measurement_reflns_used    6819
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      1
_cell_measurement_theta_min      0.875896
_cell_volume                     2890.5(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.2365
_diffrn_reflns_av_sigmaI/netI    0.0931
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21188
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colreless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.764
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.764
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0609
_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)+(0.1724P)²+2.9015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.1982
_reflns_number_gt                2474
_reflns_number_total             2846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02001_si_001.cif
_cod_data_source_block           gyz
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4034877
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'
'-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
S1 S 0.74449(5) 0.07190(8) 0.73976(3) 0.0489(3) Uani 1 1 d .
O4 O 0.87185(13) -0.07069(18) 1.03188(8) 0.0414(5) Uani 1 1 d .
C7 C 0.86163(14) 0.0381(2) 0.86110(10) 0.0281(5) Uani 1 1 d .
O2 O 0.91807(12) 0.23810(17) 1.03775(8) 0.0410(4) Uani 1 1 d .
C1 C 0.85368(17) -0.0181(3) 0.75127(11) 0.0361(5) Uani 1 1 d .
C6 C 0.90184(15) -0.0270(2) 0.80657(10) 0.0296(5) Uani 1 1 d .
C12 C 0.89405(15) 0.0257(2) 0.91687(10) 0.0294(5) Uani 1 1 d .
H12A H 0.9473 -0.0289 0.9275 0.035 Uiso 1 1 calc R
C5 C 0.98980(16) -0.0996(2) 0.80848(11) 0.0345(5) Uani 1 1 d .
H5A H 1.0224 -0.1067 0.8450 0.041 Uiso 1 1 calc R
C15 C 0.80575(16) 0.0249(2) 1.01688(10) 0.0330(5) Uani 1 1 d .
C11 C 0.83503(15) 0.1099(2) 0.96139(9) 0.0298(5) Uani 1 1 d .
C13 C 0.89221(16) 0.2412(2) 0.98031(10) 0.0325(5) Uani 1 1 d .
C10 C 0.74670(16) 0.1541(3) 0.92318(11) 0.0358(5) Uani 1 1 d .
H10A H 0.6924 0.0920 0.9314 0.043 Uiso 1 1 calc R
H10B H 0.7281 0.2512 0.9323 0.043 Uiso 1 1 calc R
C8 C 0.77757(18) 0.1409(3) 0.85756(12) 0.0421(6) Uani 1 1 d .
H8A H 0.8019 0.2334 0.8440 0.051 Uiso 1 1 calc R
C4 C 1.0297(2) -0.1608(3) 0.75779(12) 0.0450(6) Uani 1 1 d .
H4A H 1.0885 -0.2079 0.7601 0.054 Uiso 1 1 calc R
C9 C 0.7016(2) 0.0932(3) 0.81504(13) 0.0503(7) Uani 1 1 d .
H9A H 0.6495 0.1621 0.8151 0.060 Uiso 1 1 calc R
H9B H 0.6755 0.0032 0.8290 0.060 Uiso 1 1 calc R
C3 C 0.9809(2) -0.1513(3) 0.70354(13) 0.0512(7) Uani 1 1 d .
H3A H 1.0071 -0.1928 0.6691 0.061 Uiso 1 1 calc R
C2 C 0.8949(2) -0.0818(3) 0.70006(12) 0.0479(7) Uani 1 1 d .
H2A H 0.8630 -0.0764 0.6632 0.057 Uiso 1 1 calc R
O3 O 0.73186(14) 0.0415(2) 1.04338(9) 0.0517(5) Uani 1 1 d .
O1 O 0.91172(17) 0.33565(19) 0.94636(9) 0.0552(6) Uani 1 1 d .
C16 C 0.8533(2) -0.1516(3) 1.08599(12) 0.0528(7) Uani 1 1 d .
H16A H 0.9051 -0.2174 1.0926 0.079 Uiso 1 1 calc R
H16B H 0.7939 -0.2030 1.0816 0.079 Uiso 1 1 calc R
H16C H 0.8485 -0.0881 1.1198 0.079 Uiso 1 1 calc R
C14 C 0.9742(2) 0.3589(3) 1.05822(14) 0.0534(7) Uani 1 1 d .
H14A H 0.9894 0.3475 1.1002 0.080 Uiso 1 1 calc R
H14B H 0.9375 0.4446 1.0527 0.080 Uiso 1 1 calc R
H14C H 1.0328 0.3647 1.0353 0.080 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
C1 S1 C9 101.90(12)
C15 O4 C16 116.2(2)
C12 C7 C6 127.30(19)
C12 C7 C8 111.49(19)
C6 C7 C8 121.07(19)
C13 O2 C14 115.42(19)
C6 C1 C2 119.3(2)
C6 C1 S1 124.66(18)
C2 C1 S1 116.1(2)
C5 C6 C1 118.2(2)
C5 C6 C7 120.72(19)
C1 C6 C7 121.1(2)
C7 C12 C11 112.45(18)
C4 C5 C6 121.9(2)
O3 C15 O4 124.0(2)
O3 C15 C11 124.0(2)
O4 C15 C11 111.98(18)
C12 C11 C15 113.46(18)
C12 C11 C13 108.84(17)
C15 C11 C13 109.95(18)
C12 C11 C10 102.27(17)
C15 C11 C10 111.87(18)
C13 C11 C10 110.19(18)
O1 C13 O2 124.1(2)
O1 C13 C11 123.1(2)
O2 C13 C11 112.80(18)
C8 C10 C11 106.21(18)
C9 C8 C7 112.7(2)
C9 C8 C10 115.6(2)
C7 C8 C10 102.62(19)
C5 C4 C3 119.1(2)
C8 C9 S1 113.0(2)
C2 C3 C4 120.5(2)
C3 C2 C1 121.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.753(3)
S1 C9 1.783(3)
O4 C15 1.326(3)
O4 C16 1.444(3)
C7 C12 1.321(3)
C7 C6 1.465(3)
C7 C8 1.517(3)
O2 C13 1.323(3)
O2 C14 1.450(3)
C1 C6 1.398(3)
C1 C2 1.405(3)
C6 C5 1.398(3)
C12 C11 1.507(3)
C5 C4 1.378(3)
C15 O3 1.191(3)
C15 C11 1.522(3)
C11 C13 1.526(3)
C11 C10 1.546(3)
C13 O1 1.195(3)
C10 C8 1.521(4)
C8 C9 1.484(4)
C4 C3 1.382(4)
C3 C2 1.363(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328719
