#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/11/4031136.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_4031136
loop_
_publ_author_name
'Tata, Rama Rao'
'Harmata, Michael'
_publ_section_title
;
 A Synthesis of Dihydrofuran-3(2H)-ones.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6839
_journal_page_last               6845
_journal_paper_doi               10.1021/acs.joc.5b01076
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H20 O4 S'
_chemical_formula_sum            'C19 H20 O4 S'
_chemical_formula_weight         344.41
_space_group_crystal_system      monoclinic
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.595(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.547(3)
_cell_length_b                   10.075(2)
_cell_length_c                   14.611(3)
_cell_measurement_reflns_used    5609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.2
_cell_volume                     1699.7(7)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19375
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.237
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       Prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0432P)²+0.7348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3304
_reflns_number_total             3895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b01076_si_003.cif
_cod_data_source_block           TRXI134A1
_cod_depositor_comments
'Adding full bibliography for 4031136--4031138.cif.'
_cod_original_cell_volume        1699.6(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4031136
#BEGIN Tags that were not found in dictionaries:
_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   0.921
_shelx_estimated_absorpt_t_max   0.949
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.33954(3) 0.66046(3) 0.06055(2) 0.01565(10) Uani 1 1 d . .
O1 O 0.24210(8) 0.45469(9) -0.15275(6) 0.0167(2) Uani 1 1 d . .
O2 O 0.49031(8) 0.64328(10) -0.11557(7) 0.0190(2) Uani 1 1 d . .
O3 O 0.45242(8) 0.66754(10) 0.10344(7) 0.0206(2) Uani 1 1 d . .
O4 O 0.29360(9) 0.77636(10) 0.01477(7) 0.0211(2) Uani 1 1 d . .
C1 C 0.22677(11) 0.47500(13) -0.05574(9) 0.0153(3) Uani 1 1 d . .
H1 H 0.1648 0.5425 -0.0452 0.018 Uiso 1 1 calc R U
C2 C 0.34502(11) 0.52954(13) -0.02263(9) 0.0145(3) Uani 1 1 d . .
H2 H 0.3940 0.4551 0.0013 0.017 Uiso 1 1 calc R U
C3 C 0.39885(11) 0.58633(12) -0.11017(9) 0.0148(3) Uani 1 1 d . .
C4 C 0.31458(12) 0.55796(13) -0.18880(9) 0.0167(3) Uani 1 1 d . .
C5 C 0.19233(12) 0.34396(13) -0.01437(9) 0.0160(3) Uani 1 1 d . .
C6 C 0.25932(13) 0.23136(14) -0.02942(10) 0.0204(3) Uani 1 1 d . .
H6 H 0.3284 0.2380 -0.0638 0.025 Uiso 1 1 calc R U
C7 C 0.22553(14) 0.10940(15) 0.00566(10) 0.0242(3) Uani 1 1 d . .
H7 H 0.2714 0.0328 -0.0050 0.029 Uiso 1 1 calc R U
C8 C 0.12495(14) 0.09932(16) 0.05620(11) 0.0285(4) Uani 1 1 d . .
H8 H 0.1012 0.0156 0.0793 0.034 Uiso 1 1 calc R U
C9 C 0.05928(14) 0.21132(18) 0.07294(12) 0.0322(4) Uani 1 1 d . .
H9 H -0.0090 0.2048 0.1084 0.039 Uiso 1 1 calc R U
C10 C 0.09305(12) 0.33370(15) 0.03790(10) 0.0237(3) Uani 1 1 d . .
H10 H 0.0479 0.4105 0.0498 0.028 Uiso 1 1 calc R U
C11 C 0.23752(12) 0.60996(14) 0.14209(9) 0.0166(3) Uani 1 1 d . .
C12 C 0.26697(12) 0.51428(14) 0.20721(10) 0.0197(3) Uani 1 1 d . .
H12 H 0.3405 0.4721 0.2061 0.024 Uiso 1 1 calc R U
C13 C 0.18687(13) 0.48199(15) 0.27355(10) 0.0209(3) Uani 1 1 d . .
H13 H 0.2060 0.4165 0.3180 0.025 Uiso 1 1 calc R U
C14 C 0.07878(12) 0.54356(14) 0.27654(10) 0.0194(3) Uani 1 1 d . .
C15 C 0.05000(12) 0.63581(14) 0.20838(10) 0.0213(3) Uani 1 1 d . .
H15 H -0.0245 0.6759 0.2081 0.026 Uiso 1 1 calc R U
C16 C 0.12870(12) 0.66950(14) 0.14132(10) 0.0196(3) Uani 1 1 d . .
H16 H 0.1087 0.7324 0.0954 0.023 Uiso 1 1 calc R U
C17 C -0.00414(13) 0.51530(16) 0.35319(11) 0.0257(3) Uani 1 1 d . .
H17A H 0.0022 0.4218 0.3711 0.038 Uiso 1 1 calc R U
H17B H -0.0835 0.5339 0.3325 0.038 Uiso 1 1 calc R U
H17C H 0.0150 0.5718 0.4058 0.038 Uiso 1 1 calc R U
C18 C 0.24351(12) 0.68283(14) -0.20905(10) 0.0205(3) Uani 1 1 d . .
H18A H 0.1790 0.6605 -0.2504 0.031 Uiso 1 1 calc R U
H18B H 0.2929 0.7495 -0.2380 0.031 Uiso 1 1 calc R U
H18C H 0.2130 0.7185 -0.1517 0.031 Uiso 1 1 calc R U
C19 C 0.37684(13) 0.50453(14) -0.27209(10) 0.0207(3) Uani 1 1 d . .
H19A H 0.4202 0.4245 -0.2551 0.031 Uiso 1 1 calc R U
H19B H 0.4305 0.5719 -0.2949 0.031 Uiso 1 1 calc R U
H19C H 0.3200 0.4826 -0.3200 0.031 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 O4 119.17(6)
O3 S1 C11 109.18(6)
O4 S1 C11 107.59(6)
O3 S1 C2 107.00(6)
O4 S1 C2 107.21(6)
C11 S1 C2 105.93(6)
C4 O1 C1 109.54(10)
O1 C1 C5 107.75(10)
O1 C1 C2 103.93(10)
C5 C1 C2 114.96(11)
O1 C1 H1 110.0
C5 C1 H1 110.0
C2 C1 H1 110.0
C3 C2 C1 103.62(10)
C3 C2 S1 107.88(9)
C1 C2 S1 115.86(9)
C3 C2 H2 109.7
C1 C2 H2 109.7
S1 C2 H2 109.7
O2 C3 C4 126.34(12)
O2 C3 C2 126.41(12)
C4 C3 C2 107.25(11)
O1 C4 C19 108.61(11)
O1 C4 C3 103.23(10)
C19 C4 C3 111.50(11)
O1 C4 C18 110.65(11)
C19 C4 C18 113.22(11)
C3 C4 C18 109.17(11)
C10 C5 C6 119.33(13)
C10 C5 C1 120.58(12)
C6 C5 C1 120.08(12)
C7 C6 C5 120.26(14)
C7 C6 H6 119.9
C5 C6 H6 119.9
C8 C7 C6 120.10(14)
C8 C7 H7 119.9
C6 C7 H7 119.9
C9 C8 C7 119.89(14)
C9 C8 H8 120.1
C7 C8 H8 120.1
C8 C9 C10 120.10(15)
C8 C9 H9 120.0
C10 C9 H9 120.0
C5 C10 C9 120.29(14)
C5 C10 H10 119.9
C9 C10 H10 119.9
C16 C11 C12 121.14(13)
C16 C11 S1 118.72(11)
C12 C11 S1 120.12(11)
C13 C12 C11 118.69(13)
C13 C12 H12 120.7
C11 C12 H12 120.7
C12 C13 C14 121.44(13)
C12 C13 H13 119.3
C14 C13 H13 119.3
C13 C14 C15 118.62(13)
C13 C14 C17 120.97(13)
C15 C14 C17 120.38(13)
C16 C15 C14 120.87(13)
C16 C15 H15 119.6
C14 C15 H15 119.6
C15 C16 C11 119.16(13)
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
C4 C18 H18A 109.5
C4 C18 H18B 109.5
H18A C18 H18B 109.5
C4 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C4 C19 H19A 109.5
C4 C19 H19B 109.5
H19A C19 H19B 109.5
C4 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4420(11)
S1 O4 1.4438(10)
S1 C11 1.7593(14)
S1 C2 1.7951(14)
O1 C4 1.4385(16)
O1 C1 1.4448(16)
O2 C3 1.2052(16)
C1 C5 1.5071(18)
C1 C2 1.5448(18)
C1 H1 1.0000
C2 C3 1.5382(18)
C2 H2 1.0000
C3 C4 1.5249(19)
C4 C19 1.5183(19)
C4 C18 1.5292(19)
C5 C10 1.388(2)
C5 C6 1.392(2)
C6 C7 1.389(2)
C6 H6 0.9500
C7 C8 1.387(2)
C7 H7 0.9500
C8 C9 1.383(2)
C8 H8 0.9500
C9 C10 1.392(2)
C9 H9 0.9500
C10 H10 0.9500
C11 C16 1.3923(19)
C11 C12 1.394(2)
C12 C13 1.385(2)
C12 H12 0.9500
C13 C14 1.395(2)
C13 H13 0.9500
C14 C15 1.400(2)
C14 C17 1.508(2)
C15 C16 1.385(2)
C15 H15 0.9500
C16 H16 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 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
C4 O1 C1 C5 -158.54(10)
C4 O1 C1 C2 -36.13(13)
O1 C1 C2 C3 22.04(12)
C5 C1 C2 C3 139.56(11)
O1 C1 C2 S1 139.97(9)
C5 C1 C2 S1 -102.52(12)
O3 S1 C2 C3 -82.55(10)
O4 S1 C2 C3 46.38(10)
C11 S1 C2 C3 161.05(9)
O3 S1 C2 C1 161.91(9)
O4 S1 C2 C1 -69.16(11)
C11 S1 C2 C1 45.51(11)
C1 C2 C3 O2 177.31(13)
S1 C2 C3 O2 53.97(16)
C1 C2 C3 C4 -2.34(13)
S1 C2 C3 C4 -125.68(9)
C1 O1 C4 C19 152.68(11)
C1 O1 C4 C3 34.22(13)
C1 O1 C4 C18 -82.47(13)
O2 C3 C4 O1 162.12(12)
C2 C3 C4 O1 -18.23(13)
O2 C3 C4 C19 45.69(18)
C2 C3 C4 C19 -134.66(11)
O2 C3 C4 C18 -80.15(16)
C2 C3 C4 C18 99.50(12)
O1 C1 C5 C10 -126.21(13)
C2 C1 C5 C10 118.46(14)
O1 C1 C5 C6 52.89(16)
C2 C1 C5 C6 -62.44(17)
C10 C5 C6 C7 1.6(2)
C1 C5 C6 C7 -177.55(13)
C5 C6 C7 C8 -0.2(2)
C6 C7 C8 C9 -1.1(2)
C7 C8 C9 C10 1.0(3)
C6 C5 C10 C9 -1.6(2)
C1 C5 C10 C9 177.49(14)
C8 C9 C10 C5 0.3(3)
O3 S1 C11 C16 140.15(11)
O4 S1 C11 C16 9.48(13)
C2 S1 C11 C16 -104.94(12)
O3 S1 C11 C12 -38.40(13)
O4 S1 C11 C12 -169.06(11)
C2 S1 C11 C12 76.52(13)
C16 C11 C12 C13 -2.0(2)
S1 C11 C12 C13 176.50(11)
C11 C12 C13 C14 -0.4(2)
C12 C13 C14 C15 2.6(2)
C12 C13 C14 C17 -175.29(14)
C13 C14 C15 C16 -2.5(2)
C17 C14 C15 C16 175.40(14)
C14 C15 C16 C11 0.2(2)
C12 C11 C16 C15 2.1(2)
S1 C11 C16 C15 -176.43(11)
