#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:28:02 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178470 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/91/4029176.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_4029176
loop_
_publ_author_name
'Subba Reddy, B. V.'
'Venkateswarlu, A.'
'Borkar, Prashant'
'Yadav, J. S.'
'Sridhar, B.'
'Grée, René'
_publ_section_title
;
 Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in
 Prins Cyclization: Oxa- versus Thia-Selectivity.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2716
_journal_page_last               2722
_journal_paper_doi               10.1021/jo402832t
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C15 H20 O3 S'
_chemical_formula_sum            'C15 H20 O3 S'
_chemical_formula_weight         280.37
_chemical_name_systematic
; 
(3aS*,4R*,7aS*)-4-(2,5-Dimethoxyphenyl)hexahydro-2H-thieno[3,2-c]pyran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.916(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4466(11)
_cell_length_b                   9.6937(10)
_cell_length_c                   14.9923(16)
_cell_measurement_reflns_used    7532
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.53
_cell_volume                     1460.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'ω scan'
_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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13637
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0415
_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)+(0.0547P)²+0.5313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                2321
_reflns_number_total             2570
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo402832t_si_001.cif
_cod_data_source_block           ao61m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029176
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.03091(16) 0.64197(18) 0.28871(11) 0.0443(4) Uani 1 1 d .
H1 H -0.0425 0.7285 0.2536 0.053 Uiso 1 1 calc R
C2 C -0.1670(2) 0.7265(2) 0.38091(15) 0.0634(5) Uani 1 1 d .
H2A H -0.1785 0.8136 0.3477 0.076 Uiso 1 1 calc R
H2B H -0.1674 0.7453 0.4444 0.076 Uiso 1 1 calc R
C3 C -0.28207(19) 0.6323(2) 0.33655(15) 0.0635(5) Uani 1 1 d .
H3A H -0.2763 0.5480 0.3723 0.076 Uiso 1 1 calc R
H3B H -0.3659 0.6773 0.3342 0.076 Uiso 1 1 calc R
C4 C -0.27437(17) 0.6000(2) 0.23990(13) 0.0516(4) Uani 1 1 d .
H4 H -0.2869 0.6861 0.2043 0.062 Uiso 1 1 calc R
C5 C -0.28204(19) 0.4232(2) 0.10527(15) 0.0652(5) Uani 1 1 d .
H5A H -0.2649 0.3248 0.1110 0.078 Uiso 1 1 calc R
H5B H -0.3230 0.4442 0.0405 0.078 Uiso 1 1 calc R
C6 C -0.15109(18) 0.5036(2) 0.14037(13) 0.0560(5) Uani 1 1 d .
H6A H -0.0762 0.4472 0.1362 0.067 Uiso 1 1 calc R
H6B H -0.1528 0.5864 0.1037 0.067 Uiso 1 1 calc R
C7 C -0.13932(16) 0.54071(17) 0.24095(11) 0.0442(4) Uani 1 1 d .
H7 H -0.1263 0.4553 0.2773 0.053 Uiso 1 1 calc R
C8 C 0.10723(15) 0.58608(17) 0.29852(11) 0.0437(4) Uani 1 1 d .
C9 C 0.17526(17) 0.61686(18) 0.23267(12) 0.0481(4) Uani 1 1 d .
C10 C 0.30115(18) 0.5637(2) 0.24316(14) 0.0572(5) Uani 1 1 d .
H10 H 0.3469 0.5848 0.1997 0.069 Uiso 1 1 calc R
C11 C 0.36009(18) 0.4795(2) 0.31761(14) 0.0590(5) Uani 1 1 d .
H11 H 0.4451 0.4445 0.3241 0.071 Uiso 1 1 calc R
C12 C 0.29317(17) 0.4476(2) 0.38171(13) 0.0537(4) Uani 1 1 d .
C13 C 0.16703(17) 0.50134(19) 0.37205(12) 0.0492(4) Uani 1 1 d .
H13 H 0.1220 0.4799 0.4159 0.059 Uiso 1 1 calc R
C14 C 0.1699(3) 0.7256(3) 0.08935(17) 0.0913(8) Uani 1 1 d .
H14A H 0.2549 0.7687 0.1147 0.137 Uiso 1 1 calc R
H14B H 0.1142 0.7856 0.0440 0.137 Uiso 1 1 calc R
H14C H 0.1819 0.6400 0.0605 0.137 Uiso 1 1 calc R
C15 C 0.4705(2) 0.3080(3) 0.47304(17) 0.0846(8) Uani 1 1 d .
H15A H 0.4720 0.2463 0.4232 0.127 Uiso 1 1 calc R
H15B H 0.4937 0.2583 0.5306 0.127 Uiso 1 1 calc R
H15C H 0.5334 0.3810 0.4756 0.127 Uiso 1 1 calc R
O1 O -0.04154(12) 0.66800(14) 0.38054(8) 0.0546(3) Uani 1 1 d .
O2 O 0.10927(13) 0.70027(15) 0.16101(9) 0.0612(4) Uani 1 1 d .
O3 O 0.34087(14) 0.36461(18) 0.45777(10) 0.0770(5) Uani 1 1 d .
S1 S -0.39279(5) 0.47369(6) 0.17522(4) 0.0691(2) Uani 1 1 d .
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
O1 C1 C8 107.05(13)
O1 C1 C7 108.78(13)
C8 C1 C7 112.49(13)
O1 C1 H1 109.5
C8 C1 H1 109.5
C7 C1 H1 109.5
O1 C2 C3 112.20(16)
O1 C2 H2A 109.2
C3 C2 H2A 109.2
O1 C2 H2B 109.2
C3 C2 H2B 109.2
H2A C2 H2B 107.9
C4 C3 C2 107.65(16)
C4 C3 H3A 110.2
C2 C3 H3A 110.2
C4 C3 H3B 110.2
C2 C3 H3B 110.2
H3A C3 H3B 108.5
C3 C4 C7 111.30(15)
C3 C4 S1 116.41(14)
C7 C4 S1 104.17(12)
C3 C4 H4 108.2
C7 C4 H4 108.2
S1 C4 H4 108.2
C6 C5 S1 108.14(13)
C6 C5 H5A 110.1
S1 C5 H5A 110.1
C6 C5 H5B 110.1
S1 C5 H5B 110.1
H5A C5 H5B 108.4
C7 C6 C5 106.36(15)
C7 C6 H6A 110.5
C5 C6 H6A 110.5
C7 C6 H6B 110.5
C5 C6 H6B 110.5
H6A C6 H6B 108.6
C4 C7 C1 109.28(14)
C4 C7 C6 104.87(14)
C1 C7 C6 117.79(14)
C4 C7 H7 108.2
C1 C7 H7 108.2
C6 C7 H7 108.2
C13 C8 C9 119.02(15)
C13 C8 C1 120.17(15)
C9 C8 C1 120.80(15)
O2 C9 C10 124.63(16)
O2 C9 C8 115.84(15)
C10 C9 C8 119.53(17)
C9 C10 C11 120.75(17)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 119.93(17)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 O3 125.17(17)
C11 C12 C13 119.69(18)
O3 C12 C13 115.14(17)
C8 C13 C12 121.07(17)
C8 C13 H13 119.5
C12 C13 H13 119.5
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C2 O1 C1 112.71(13)
C9 O2 C14 117.77(17)
C12 O3 C15 118.25(18)
C4 S1 C5 92.36(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4337(19)
C1 C8 1.510(2)
C1 C7 1.521(2)
C1 H1 0.9800
C2 O1 1.430(2)
C2 C3 1.511(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.506(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C7 1.519(2)
C4 S1 1.8197(19)
C4 H4 0.9800
C5 C6 1.537(3)
C5 S1 1.829(2)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.522(2)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7 0.9800
C8 C13 1.379(2)
C8 C9 1.398(2)
C9 O2 1.370(2)
C9 C10 1.381(3)
C10 C11 1.384(3)
C10 H10 0.9300
C11 C12 1.370(3)
C11 H11 0.9300
C12 O3 1.373(2)
C12 C13 1.387(2)
C13 H13 0.9300
C14 O2 1.410(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 O3 1.421(2)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 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
O1 C2 C3 C4 -56.1(2)
C2 C3 C4 C7 54.9(2)
C2 C3 C4 S1 174.05(14)
S1 C5 C6 C7 24.9(2)
C3 C4 C7 C1 -57.1(2)
S1 C4 C7 C1 176.69(11)
C3 C4 C7 C6 175.75(16)
S1 C4 C7 C6 49.54(16)
O1 C1 C7 C4 57.57(17)
C8 C1 C7 C4 175.99(14)
O1 C1 C7 C6 177.03(14)
C8 C1 C7 C6 -64.6(2)
C5 C6 C7 C4 -48.0(2)
C5 C6 C7 C1 -169.73(16)
O1 C1 C8 C13 35.5(2)
C7 C1 C8 C13 -83.91(19)
O1 C1 C8 C9 -145.76(15)
C7 C1 C8 C9 94.81(18)
C13 C8 C9 O2 179.27(15)
C1 C8 C9 O2 0.5(2)
C13 C8 C9 C10 -0.9(3)
C1 C8 C9 C10 -179.65(16)
O2 C9 C10 C11 -179.64(17)
C8 C9 C10 C11 0.6(3)
C9 C10 C11 C12 0.2(3)
C10 C11 C12 O3 179.48(18)
C10 C11 C12 C13 -0.7(3)
C9 C8 C13 C12 0.5(3)
C1 C8 C13 C12 179.23(16)
C11 C12 C13 C8 0.3(3)
O3 C12 C13 C8 -179.83(16)
C3 C2 O1 C1 61.1(2)
C8 C1 O1 C2 177.80(15)
C7 C1 O1 C2 -60.40(19)
C10 C9 O2 C14 4.8(3)
C8 C9 O2 C14 -175.37(19)
C11 C12 O3 C15 1.0(3)
C13 C12 O3 C15 -178.87(18)
C3 C4 S1 C5 -153.14(16)
C7 C4 S1 C5 -30.20(14)
C6 C5 S1 C4 3.21(16)
