#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151844.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_7151844
loop_
_publ_author_name
'Bondalapati, Somasekhar'
'Reddy, Udagandla C.'
'Saha, Pipas'
'Saikia, Anil K.'
_publ_section_title
;
 An efficient synthesis of dihydro- and tetrahydropyrans via
 oxonium-ene cyclization reaction.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3428
_journal_page_last               3438
_journal_paper_doi               10.1039/c1ob00033k
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C19 H20 O4 S'
_chemical_formula_sum            'C19 H20 O4 S'
_chemical_formula_weight         344.41
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.883(3)
_cell_angle_beta                 95.733(3)
_cell_angle_gamma                91.650(3)
_cell_formula_units_Z            4
_cell_length_a                   9.8247(5)
_cell_length_b                   11.1954(6)
_cell_length_c                   16.1562(9)
_cell_measurement_reflns_used    6956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.33
_cell_volume                     1728.04(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.1139
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18086
_diffrn_reflns_theta_full        29.66
_diffrn_reflns_theta_max         29.66
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.9501
_exptl_absorpt_correction_T_min  0.9219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         8244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0514
_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)+(0.0770P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                5131
_reflns_number_total             9793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob00033k.txt
_cod_data_source_block           ss-le
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151844
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.28461(5) 0.62319(4) 0.11906(3) 0.04944(15) Uani 1 1 d . . .
S1 S 0.94062(5) 0.88095(5) 0.87060(3) 0.05230(16) Uani 1 1 d . . .
C32 C 0.10569(19) 0.61406(16) 0.11421(10) 0.0433(4) Uani 1 1 d . . .
C37 C 0.0368(2) 0.50710(18) 0.11908(12) 0.0522(5) Uani 1 1 d . . .
H37 H 0.0852 0.4394 0.1270 0.063 Uiso 1 1 calc R . .
C35 C -0.1784(2) 0.6018(2) 0.10253(11) 0.0558(5) Uani 1 1 d . . .
C33 C 0.0335(2) 0.71420(18) 0.10186(13) 0.0547(5) Uani 1 1 d . . .
H33 H 0.0797 0.7855 0.0967 0.066 Uiso 1 1 calc R . .
C36 C -0.1040(2) 0.5012(2) 0.11217(12) 0.0581(5) Uani 1 1 d . . .
H36 H -0.1502 0.4283 0.1140 0.070 Uiso 1 1 calc R . .
C34 C -0.1072(2) 0.7075(2) 0.09730(13) 0.0597(5) Uani 1 1 d . . .
H34 H -0.1554 0.7758 0.0906 0.072 Uiso 1 1 calc R . .
C38 C -0.3322(2) 0.5960(3) 0.09895(15) 0.0811(7) Uani 1 1 d . . .
H38A H -0.3670 0.5139 0.0750 0.122 Uiso 1 1 calc R . .
H38B H -0.3693 0.6498 0.0641 0.122 Uiso 1 1 calc R . .
H38C H -0.3584 0.6208 0.1554 0.122 Uiso 1 1 calc R . .
O15 O 0.32680(15) 0.67712(14) 0.05318(9) 0.0658(4) Uani 1 1 d . . .
O13 O 0.33210(14) 0.72702(11) 0.20236(8) 0.0530(3) Uani 1 1 d . . .
C29 C 0.3174(2) 0.70553(17) 0.28415(12) 0.0501(5) Uani 1 1 d . . .
C30 C 0.2177(2) 0.76455(19) 0.32788(13) 0.0598(5) Uani 1 1 d . . .
H30 H 0.1563 0.8106 0.3017 0.072 Uiso 1 1 calc R . .
C26 C 0.2989(2) 0.6880(2) 0.45108(13) 0.0594(5) Uani 1 1 d . . .
C27 C 0.3974(2) 0.6281(2) 0.40550(14) 0.0682(6) Uani 1 1 d . . .
H27 H 0.4573 0.5802 0.4310 0.082 Uiso 1 1 calc R . .
C28 C 0.4087(2) 0.6383(2) 0.32156(13) 0.0637(6) Uani 1 1 d . . .
H28 H 0.4773 0.5999 0.2919 0.076 Uiso 1 1 calc R . .
C31 C 0.2090(2) 0.7552(2) 0.41109(14) 0.0652(6) Uani 1 1 d . . .
H31 H 0.1411 0.7951 0.4406 0.078 Uiso 1 1 calc R . .
C24 C 0.2841(2) 0.6793(2) 0.54226(13) 0.0660(6) Uani 1 1 d . . .
H24 H 0.2561 0.7584 0.5724 0.079 Uiso 1 1 calc R . .
C22 C 0.1812(2) 0.55757(18) 0.63616(13) 0.0584(5) Uani 1 1 d . . .
C23 C 0.1770(2) 0.58227(19) 0.54827(12) 0.0589(5) Uani 1 1 d . . .
H23A H 0.0869 0.6086 0.5318 0.071 Uiso 1 1 calc R . .
H23B H 0.1918 0.5072 0.5087 0.071 Uiso 1 1 calc R . .
C25 C 0.0624(3) 0.4868(2) 0.65452(15) 0.0758(7) Uani 1 1 d . . .
H25A H 0.0794 0.4707 0.7106 0.114 Uiso 1 1 calc R . .
H25B H 0.0486 0.4109 0.6136 0.114 Uiso 1 1 calc R . .
H25C H -0.0181 0.5331 0.6512 0.114 Uiso 1 1 calc R . .
C20 C 0.4088(3) 0.6649(3) 0.67061(14) 0.0889(8) Uani 1 1 d . . .
H20A H 0.4077 0.7502 0.6984 0.107 Uiso 1 1 calc R . .
H20B H 0.4920 0.6327 0.6931 0.107 Uiso 1 1 calc R . .
C21 C 0.2900(3) 0.5982(2) 0.69121(14) 0.0765(7) Uani 1 1 d . . .
H21 H 0.2913 0.5837 0.7459 0.092 Uiso 1 1 calc R . .
O12 O 0.41155(17) 0.65649(18) 0.58156(10) 0.0883(6) Uani 1 1 d . . .
C13 C 0.76382(19) 0.88569(17) 0.87877(11) 0.0468(4) Uani 1 1 d . . .
C16 C 0.4849(2) 0.8922(2) 0.89472(12) 0.0581(5) Uani 1 1 d . . .
C10 C 0.9055(2) 0.78978(18) 0.70753(12) 0.0514(5) Uani 1 1 d . . .
C14 C 0.6957(2) 0.98754(19) 0.86837(13) 0.0586(5) Uani 1 1 d . . .
H14 H 0.7417 1.0539 0.8553 0.070 Uiso 1 1 calc R . .
C18 C 0.6950(2) 0.78702(19) 0.89773(14) 0.0631(6) Uani 1 1 d . . .
H18 H 0.7416 0.7184 0.9055 0.076 Uiso 1 1 calc R . .
C9 C 0.7863(2) 0.7300(2) 0.66808(14) 0.0637(6) Uani 1 1 d . . .
H9 H 0.7341 0.6841 0.6964 0.076 Uiso 1 1 calc R . .
C4 C 0.6631(2) 0.9120(2) 0.45079(13) 0.0623(5) Uani 1 1 d . . .
H4A H 0.5791 0.8835 0.4689 0.075 Uiso 1 1 calc R . .
H4B H 0.6962 0.9869 0.4905 0.075 Uiso 1 1 calc R . .
C15 C 0.5572(2) 0.9898(2) 0.87762(14) 0.0663(6) Uani 1 1 d . . .
H15 H 0.5114 1.0598 0.8721 0.080 Uiso 1 1 calc R . .
C3 C 0.6335(2) 0.9383(2) 0.36389(14) 0.0628(5) Uani 1 1 d . . .
C7 C 0.8203(2) 0.8062(2) 0.54254(13) 0.0598(5) Uani 1 1 d . . .
C11 C 0.9853(2) 0.8560(2) 0.66717(13) 0.0641(6) Uani 1 1 d . . .
H11 H 1.0680 0.8939 0.6943 0.077 Uiso 1 1 calc R . .
C5 C 0.7693(2) 0.8162(2) 0.45300(13) 0.0646(6) Uani 1 1 d . . .
H5 H 0.7268 0.7368 0.4230 0.078 Uiso 1 1 calc R . .
C8 C 0.7437(2) 0.7385(2) 0.58506(14) 0.0686(6) Uani 1 1 d . . .
H8 H 0.6624 0.6981 0.5578 0.082 Uiso 1 1 calc R . .
C12 C 0.9399(3) 0.8658(2) 0.58386(13) 0.0685(6) Uani 1 1 d . . .
H12 H 0.9915 0.9132 0.5562 0.082 Uiso 1 1 calc R . .
C2 C 0.7166(3) 0.8992(2) 0.30542(14) 0.0770(7) Uani 1 1 d . . .
H2 H 0.6949 0.9134 0.2510 0.092 Uiso 1 1 calc R . .
C17 C 0.5568(2) 0.7912(2) 0.90493(15) 0.0693(6) Uani 1 1 d . . .
H17 H 0.5106 0.7242 0.9170 0.083 Uiso 1 1 calc R . .
C19 C 0.3338(2) 0.8935(3) 0.90056(16) 0.0862(8) Uani 1 1 d . . .
H19A H 0.3091 0.9757 0.9215 0.129 Uiso 1 1 calc R . .
H19B H 0.3097 0.8430 0.9387 0.129 Uiso 1 1 calc R . .
H19C H 0.2857 0.8627 0.8452 0.129 Uiso 1 1 calc R . .
C1 C 0.8414(3) 0.8344(3) 0.32210(14) 0.0883(8) Uani 1 1 d . . .
H1A H 0.8259 0.7489 0.2944 0.106 Uiso 1 1 calc R . .
H1B H 0.9156 0.8679 0.2971 0.106 Uiso 1 1 calc R . .
O4 O 0.88180(17) 0.84283(17) 0.41052(9) 0.0823(5) Uani 1 1 d . . .
O9 O 0.95155(14) 0.77212(11) 0.78988(8) 0.0552(3) Uani 1 1 d . . .
O11 O 1.00680(16) 0.83400(16) 0.93792(9) 0.0740(5) Uani 1 1 d . . .
O14 O 0.33573(14) 0.51059(12) 0.13146(9) 0.0631(4) Uani 1 1 d . . .
O10 O 0.98864(15) 0.99155(12) 0.85152(9) 0.0639(4) Uani 1 1 d . . .
C6 C 0.5095(3) 1.0074(2) 0.34951(16) 0.0802(7) Uani 1 1 d . . .
H6A H 0.5034 1.0238 0.2933 0.120 Uiso 1 1 calc R . .
H6B H 0.5155 1.0832 0.3906 0.120 Uiso 1 1 calc R . .
H6C H 0.4295 0.9599 0.3554 0.120 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O14 S2 O15 120.45(9) . . ?
O14 S2 O13 108.92(8) . . ?
O15 S2 O13 102.12(8) . . ?
O14 S2 C32 109.06(9) . . ?
O15 S2 C32 110.57(9) . . ?
O13 S2 C32 104.35(8) . . ?
O11 S1 O10 121.25(10) . . ?
O11 S1 O9 102.19(9) . . ?
O10 S1 O9 108.56(8) . . ?
O11 S1 C13 110.23(9) . . ?
O10 S1 C13 109.34(9) . . ?
O9 S1 C13 103.63(8) . . ?
C37 C32 C33 120.14(18) . . ?
C37 C32 S2 120.74(14) . . ?
C33 C32 S2 119.06(14) . . ?
C36 C37 C32 119.53(18) . . ?
C34 C35 C36 118.07(19) . . ?
C34 C35 C38 121.1(2) . . ?
C36 C35 C38 120.9(2) . . ?
C34 C33 C32 119.47(19) . . ?
C37 C36 C35 121.3(2) . . ?
C33 C34 C35 121.42(19) . . ?
C29 O13 S2 120.41(11) . . ?
C28 C29 C30 121.12(19) . . ?
C28 C29 O13 120.58(18) . . ?
C30 C29 O13 117.96(18) . . ?
C29 C30 C31 119.6(2) . . ?
C31 C26 C27 118.30(19) . . ?
C31 C26 C24 119.2(2) . . ?
C27 C26 C24 122.5(2) . . ?
C26 C27 C28 121.2(2) . . ?
C29 C28 C27 118.7(2) . . ?
C26 C31 C30 121.1(2) . . ?
O12 C24 C23 110.56(19) . . ?
O12 C24 C26 109.08(18) . . ?
C23 C24 C26 112.57(18) . . ?
C21 C22 C25 124.7(2) . . ?
C21 C22 C23 118.6(2) . . ?
C25 C22 C23 116.69(19) . . ?
C22 C23 C24 112.26(17) . . ?
O12 C20 C21 113.2(2) . . ?
C22 C21 C20 123.7(2) . . ?
C24 O12 C20 111.67(19) . . ?
C14 C13 C18 120.41(19) . . ?
C14 C13 S1 120.17(15) . . ?
C18 C13 S1 119.40(15) . . ?
C15 C16 C17 117.35(19) . . ?
C15 C16 C19 121.8(2) . . ?
C17 C16 C19 120.8(2) . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 O9 117.85(18) . . ?
C11 C10 O9 120.14(19) . . ?
C13 C14 C15 118.8(2) . . ?
C17 C18 C13 119.4(2) . . ?
C10 C9 C8 119.1(2) . . ?
C3 C4 C5 112.00(16) . . ?
C16 C15 C14 122.3(2) . . ?
C2 C3 C6 124.4(2) . . ?
C2 C3 C4 119.2(2) . . ?
C6 C3 C4 116.31(18) . . ?
C12 C7 C8 118.8(2) . . ?
C12 C7 C5 121.6(2) . . ?
C8 C7 C5 119.5(2) . . ?
C10 C11 C12 118.6(2) . . ?
O4 C5 C7 109.21(18) . . ?
O4 C5 C4 110.34(18) . . ?
C7 C5 C4 112.57(16) . . ?
C7 C8 C9 120.9(2) . . ?
C7 C12 C11 120.8(2) . . ?
C3 C2 C1 123.4(2) . . ?
C18 C17 C16 121.7(2) . . ?
O4 C1 C2 113.29(19) . . ?
C5 O4 C1 111.05(19) . . ?
C10 O9 S1 119.02(11) . . ?
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
S2 O14 1.4148(14) . ?
S2 O15 1.4169(14) . ?
S2 O13 1.6060(13) . ?
S2 C32 1.7508(19) . ?
S1 O11 1.4128(15) . ?
S1 O10 1.4154(14) . ?
S1 O9 1.6057(13) . ?
S1 C13 1.7566(19) . ?
C32 C37 1.379(3) . ?
C32 C33 1.382(3) . ?
C37 C36 1.375(3) . ?
C35 C34 1.379(3) . ?
C35 C36 1.387(3) . ?
C35 C38 1.506(3) . ?
C33 C34 1.377(3) . ?
O13 C29 1.411(2) . ?
C29 C28 1.362(3) . ?
C29 C30 1.371(3) . ?
C30 C31 1.380(3) . ?
C26 C31 1.375(3) . ?
C26 C27 1.380(3) . ?
C26 C24 1.517(3) . ?
C27 C28 1.399(3) . ?
C24 O12 1.401(3) . ?
C24 C23 1.514(3) . ?
C22 C21 1.325(3) . ?
C22 C25 1.480(3) . ?
C22 C23 1.498(3) . ?
C20 O12 1.425(3) . ?
C20 C21 1.470(4) . ?
C13 C14 1.370(3) . ?
C13 C18 1.382(3) . ?
C16 C15 1.377(3) . ?
C16 C17 1.380(3) . ?
C16 C19 1.497(3) . ?
C10 C9 1.362(3) . ?
C10 C11 1.363(3) . ?
C10 O9 1.417(2) . ?
C14 C15 1.384(3) . ?
C18 C17 1.375(3) . ?
C9 C8 1.388(3) . ?
C4 C3 1.495(3) . ?
C4 C5 1.521(3) . ?
C3 C2 1.324(3) . ?
C3 C6 1.486(3) . ?
C7 C12 1.373(3) . ?
C7 C8 1.377(3) . ?
C7 C5 1.510(3) . ?
C11 C12 1.402(3) . ?
C5 O4 1.414(3) . ?
C2 C1 1.473(4) . ?
C1 O4 1.427(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190656
