#------------------------------------------------------------------------------
#$Date: 2021-02-04 02:39:27 +0200 (Thu, 04 Feb 2021) $
#$Revision: 261453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/55/4135575.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_4135575
loop_
_publ_author_name
'Haut, Franz-Lucas'
'Habiger, Christoph'
'Wein, Lukas A.'
'Wurst, Klaus'
'Podewitz, Maren'
'Magauer, Thomas'
_publ_section_title
;
 Rapid Assembly of Tetrasubstituted Furans via Pummerer-Type
 Rearrangement.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1216
_journal_page_last               1223
_journal_paper_doi               10.1021/jacs.0c12194
_journal_volume                  143
_journal_year                    2021
_chemical_formula_sum            'C15 H15 Cl O S'
_chemical_formula_weight         278.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.251(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2500(7)
_cell_length_b                   15.3411(10)
_cell_length_c                   8.6672(5)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.7
_cell_volume                     1362.87(15)
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL-XT-2014/4 (Bruker AXS, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            29960
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'Incoatec Microfocus'
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS-2014/5)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0357
_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)+(0.0221P)²+1.2095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2228
_reflns_number_total             2372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c12194_si_002.cif
_cod_data_source_block           7l
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4135575
_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   0.948
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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 0.50800(7) 0.28739(4) 0.13188(7) 0.03167(17) Uani 1 1 d . . . . .
Cl1 Cl 1.07062(6) 0.23373(5) 0.42521(9) 0.0426(2) Uani 1 1 d . . . . .
O1 O 0.64734(16) 0.16509(11) 0.2742(2) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.7859(3) 0.06387(18) 0.4106(3) 0.0359(7) Uani 1 1 d D . . . .
H1 H 0.859(2) 0.0599(19) 0.481(3) 0.035(8) Uiso 1 1 d D . . . .
C2 C 0.6819(3) -0.0055(2) 0.4237(4) 0.0420(7) Uani 1 1 d D . . . .
H2A H 0.592(2) 0.0132(19) 0.399(4) 0.044(9) Uiso 1 1 d D . . . .
H2B H 0.699(3) -0.0475(18) 0.505(3) 0.052(10) Uiso 1 1 d D . . . .
C3 C 0.7743(3) -0.0079(2) 0.2922(4) 0.0430(8) Uani 1 1 d D . . . .
H3A H 0.742(3) 0.010(2) 0.190(3) 0.069(12) Uiso 1 1 d D . . . .
H3B H 0.841(3) -0.0528(17) 0.293(4) 0.053(10) Uiso 1 1 d D . . . .
C4 C 0.7510(2) 0.15344(17) 0.3723(3) 0.0281(6) Uani 1 1 d . . . . .
C5 C 0.8025(2) 0.23148(16) 0.4137(3) 0.0247(5) Uani 1 1 d . . . . .
C6 C 0.7249(2) 0.29788(17) 0.3386(3) 0.0245(5) Uani 1 1 d . . . . .
C7 C 0.6312(2) 0.25430(17) 0.2562(3) 0.0259(5) Uani 1 1 d . . . . .
C8 C 0.9138(2) 0.24298(19) 0.5226(3) 0.0286(6) Uani 1 1 d . . . . .
H8A H 0.9085 0.1983 0.6047 0.034 Uiso 1 1 calc R U . . .
H8B H 0.9075 0.3010 0.5720 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7415(2) 0.39320(16) 0.3484(3) 0.0255(5) Uani 1 1 d . . . . .
C10 C 0.6339(3) 0.44887(18) 0.3587(3) 0.0319(6) Uani 1 1 d . . . . .
H10 H 0.5484 0.4249 0.3617 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6499(3) 0.53840(18) 0.3646(3) 0.0363(6) Uani 1 1 d . . . . .
H11 H 0.5757 0.5754 0.3705 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7742(3) 0.57425(18) 0.3619(3) 0.0372(7) Uani 1 1 d . . . . .
H12 H 0.7853 0.6357 0.3669 0.045 Uiso 1 1 calc R U . . .
C13 C 0.8818(3) 0.52013(18) 0.3518(3) 0.0362(6) Uani 1 1 d . . . . .
H13 H 0.9669 0.5446 0.3482 0.043 Uiso 1 1 calc R U . . .
C14 C 0.8660(3) 0.43037(17) 0.3468(3) 0.0295(6) Uani 1 1 d . . . . .
H14 H 0.9406 0.3938 0.3423 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3667(3) 0.28232(18) 0.2572(3) 0.0345(6) Uani 1 1 d . . . . .
H15A H 0.2887 0.2999 0.1994 0.052 Uiso 1 1 calc R U . . .
H15B H 0.3556 0.2226 0.2950 0.052 Uiso 1 1 calc R U . . .
H15C H 0.3795 0.3217 0.3450 0.052 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'
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C7 S1 C15 101.34(12) . . ?
C4 O1 C7 106.89(19) . . ?
C4 C1 C3 121.0(3) . . ?
C4 C1 C2 120.5(3) . . ?
C3 C1 C2 58.9(2) . . ?
C4 C1 H1 113.1(18) . . ?
C3 C1 H1 116.2(17) . . ?
C2 C1 H1 117.0(18) . . ?
C3 C2 C1 60.5(2) . . ?
C3 C2 H2A 116.1(19) . . ?
C1 C2 H2A 116.0(18) . . ?
C3 C2 H2B 115(2) . . ?
C1 C2 H2B 113(2) . . ?
H2A C2 H2B 121(3) . . ?
C2 C3 C1 60.6(2) . . ?
C2 C3 H3A 118(2) . . ?
C1 C3 H3A 116(2) . . ?
C2 C3 H3B 118(2) . . ?
C1 C3 H3B 118(2) . . ?
H3A C3 H3B 116(3) . . ?
C5 C4 O1 110.4(2) . . ?
C5 C4 C1 132.6(2) . . ?
O1 C4 C1 117.0(2) . . ?
C4 C5 C6 106.8(2) . . ?
C4 C5 C8 124.7(2) . . ?
C6 C5 C8 128.4(2) . . ?
C7 C6 C5 105.9(2) . . ?
C7 C6 C9 126.5(2) . . ?
C5 C6 C9 127.5(2) . . ?
C6 C7 O1 109.9(2) . . ?
C6 C7 S1 133.6(2) . . ?
O1 C7 S1 116.45(17) . . ?
C5 C8 Cl1 111.86(17) . . ?
C5 C8 H8A 109.2 . . ?
Cl1 C8 H8A 109.2 . . ?
C5 C8 H8B 109.2 . . ?
Cl1 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.2(2) . . ?
C14 C9 C6 120.6(2) . . ?
C10 C9 C6 121.2(2) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.732(3) . ?
S1 C15 1.816(3) . ?
Cl1 C8 1.824(2) . ?
O1 C4 1.370(3) . ?
O1 C7 1.387(3) . ?
C1 C4 1.458(4) . ?
C1 C3 1.510(4) . ?
C1 C2 1.511(4) . ?
C1 H1 0.963(17) . ?
C2 C3 1.486(4) . ?
C2 H2A 0.987(17) . ?
C2 H2B 0.971(18) . ?
C3 H3A 0.982(18) . ?
C3 H3B 0.970(18) . ?
C4 C5 1.356(4) . ?
C5 C6 1.446(3) . ?
C5 C8 1.487(3) . ?
C6 C7 1.369(3) . ?
C6 C9 1.475(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.398(3) . ?
C9 C10 1.398(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
_geom_torsion_publ_flag
C4 C1 C2 C3 110.0(3) . . . . ?
C4 C1 C3 C2 -109.3(3) . . . . ?
C7 O1 C4 C5 -1.5(3) . . . . ?
C7 O1 C4 C1 179.3(2) . . . . ?
C3 C1 C4 C5 -143.1(3) . . . . ?
C2 C1 C4 C5 147.0(3) . . . . ?
C3 C1 C4 O1 35.9(4) . . . . ?
C2 C1 C4 O1 -33.9(4) . . . . ?
O1 C4 C5 C6 1.0(3) . . . . ?
C1 C4 C5 C6 -179.9(3) . . . . ?
O1 C4 C5 C8 178.2(2) . . . . ?
C1 C4 C5 C8 -2.6(5) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C8 C5 C6 C7 -177.2(2) . . . . ?
C4 C5 C6 C9 179.6(2) . . . . ?
C8 C5 C6 C9 2.4(4) . . . . ?
C5 C6 C7 O1 -0.8(3) . . . . ?
C9 C6 C7 O1 179.5(2) . . . . ?
C5 C6 C7 S1 -176.9(2) . . . . ?
C9 C6 C7 S1 3.4(4) . . . . ?
C4 O1 C7 C6 1.4(3) . . . . ?
C4 O1 C7 S1 178.25(17) . . . . ?
C15 S1 C7 C6 -100.8(3) . . . . ?
C15 S1 C7 O1 83.3(2) . . . . ?
C4 C5 C8 Cl1 85.5(3) . . . . ?
C6 C5 C8 Cl1 -97.9(3) . . . . ?
C7 C6 C9 C14 -140.0(3) . . . . ?
C5 C6 C9 C14 40.5(4) . . . . ?
C7 C6 C9 C10 39.7(4) . . . . ?
C5 C6 C9 C10 -139.9(3) . . . . ?
C14 C9 C10 C11 1.1(4) . . . . ?
C6 C9 C10 C11 -178.6(2) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C9 1.5(4) . . . . ?
C10 C9 C14 C13 -1.5(4) . . . . ?
C6 C9 C14 C13 178.2(2) . . . . ?
