#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:58:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180282 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/68/7116896.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_7116896
loop_
_publ_author_name
'Hai-Bin Yang'
'Yu-Chao Yuan'
'Yin Wei'
'Min Shi'
_publ_section_title
;
 Amine-catalyzed tunable reactions of allenoates with dithioesters: formal
 [4+2] and [2+2] cycloadditions for the synthesis of
 2,3-dihydro-1,4-oxathiines and enantioenriched thietanes
;
_journal_name_full               Chem.Commun.
_journal_page_first              6430
_journal_paper_doi               10.1039/C5cc01313E
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C22 H27 N O4 S'
_chemical_formula_weight         401.50
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-10-17 deposited with the CCDC.
2015-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.427(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.687(3)
_cell_length_b                   6.2286(5)
_cell_length_c                   23.0782(19)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.486
_cell_measurement_theta_min      5.129
_cell_volume                     4368.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12101
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.840
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0693
_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)+(0.0766P)²+0.8909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1746
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2630
_reflns_number_total             4064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc01313e2.cif
_cod_data_source_block           cd214587
_cod_original_cell_volume        4368.9(6)
_cod_database_code               7116896
#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. 
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18701(3) 0.35873(14) 1.03803(4) 0.0702(3) Uani 1 1 d . . . . .
H1A H 0.1682 0.3500 1.0764 0.105 Uiso 1 1 calc R U . . .
N1 N 0.10575(10) 0.9658(5) 1.04752(13) 0.0643(8) Uani 1 1 d . . . . .
O1 O 0.10633(9) 0.6100(4) 1.05818(11) 0.0847(8) Uani 1 1 d . . . . .
O2 O 0.25953(10) 0.4833(6) 0.81233(13) 0.1090(10) Uani 1 1 d . . . . .
O3 O 0.09995(7) 0.2661(3) 0.94764(10) 0.0688(7) Uani 1 1 d . . . . .
O4 O 0.08657(6) 0.6047(3) 0.91470(9) 0.0510(5) Uani 1 1 d . . . . .
C1 C 0.11956(10) 0.7703(5) 1.03883(13) 0.0538(8) Uani 1 1 d . . . . .
C2 C 0.15246(9) 0.7626(5) 1.00225(12) 0.0490(7) Uani 1 1 d . . . . .
H2A H 0.1809 0.8088 1.0276 0.059 Uiso 1 1 calc R U . . .
H2B H 0.1433 0.8628 0.9688 0.059 Uiso 1 1 calc R U . . .
C3 C 0.15710(9) 0.5392(4) 0.97729(12) 0.0475(7) Uani 1 1 d . . . . .
C4 C 0.18343(9) 0.5389(5) 0.93146(13) 0.0497(7) Uani 1 1 d . . . . .
C5 C 0.18346(11) 0.3561(5) 0.89679(16) 0.0682(9) Uani 1 1 d . . . . .
H5 H 0.1659 0.2399 0.9002 0.082 Uiso 1 1 calc R U . . .
C6 C 0.20878(13) 0.3439(6) 0.85795(18) 0.0811(11) Uani 1 1 d . . . . .
H6 H 0.2085 0.2191 0.8357 0.097 Uiso 1 1 calc R U . . .
C7 C 0.23491(11) 0.5151(7) 0.85121(16) 0.0715(10) Uani 1 1 d . . . . .
C8 C 0.23501(10) 0.6962(6) 0.88426(15) 0.0640(9) Uani 1 1 d . . . . .
H8 H 0.2521 0.8130 0.8799 0.077 Uiso 1 1 calc R U . . .
C9 C 0.20983(10) 0.7077(5) 0.92424(14) 0.0565(8) Uani 1 1 d . . . . .
H9 H 0.2107 0.8320 0.9468 0.068 Uiso 1 1 calc R U . . .
C10 C 0.28941(15) 0.6452(9) 0.8077(2) 0.1152(17) Uani 1 1 d . . . . .
H10A H 0.2735 0.7710 0.7898 0.173 Uiso 1 1 calc R U . . .
H10B H 0.3071 0.5954 0.7828 0.173 Uiso 1 1 calc R U . . .
H10C H 0.3081 0.6795 0.8472 0.173 Uiso 1 1 calc R U . . .
C11 C 0.07320(11) 1.0062(6) 1.07940(15) 0.0744(10) Uani 1 1 d . . . . .
H11A H 0.0538 0.8829 1.0743 0.089 Uiso 1 1 calc R U . . .
H11B H 0.0555 1.1286 1.0609 0.089 Uiso 1 1 calc R U . . .
C12 C 0.09187(10) 1.0495(5) 1.14576(14) 0.0572(8) Uani 1 1 d . . . . .
C13 C 0.11010(14) 1.2446(6) 1.16581(19) 0.0834(11) Uani 1 1 d . . . . .
H13 H 0.1111 1.3507 1.1379 0.100 Uiso 1 1 calc R U . . .
C14 C 0.12699(16) 1.2867(8) 1.2264(2) 0.1023(14) Uani 1 1 d . . . . .
H14 H 0.1397 1.4195 1.2390 0.123 Uiso 1 1 calc R U . . .
C15 C 0.12519(15) 1.1370(9) 1.26742(19) 0.0964(14) Uani 1 1 d . . . . .
H15 H 0.1364 1.1658 1.3085 0.116 Uiso 1 1 calc R U . . .
C16 C 0.10688(14) 0.9433(9) 1.24862(19) 0.0942(13) Uani 1 1 d . . . . .
H16 H 0.1055 0.8392 1.2769 0.113 Uiso 1 1 calc R U . . .
C17 C 0.09022(12) 0.8991(6) 1.18770(17) 0.0748(10) Uani 1 1 d . . . . .
H17 H 0.0778 0.7655 1.1753 0.090 Uiso 1 1 calc R U . . .
C18 C 0.11121(10) 0.4486(5) 0.94589(13) 0.0490(7) Uani 1 1 d . . . . .
C19 C 0.03973(10) 0.5720(5) 0.88145(14) 0.0582(8) Uani 1 1 d . . . . .
C20 C 0.02606(12) 0.7947(6) 0.8574(2) 0.0900(13) Uani 1 1 d . . . . .
H20A H 0.0293 0.8923 0.8906 0.135 Uiso 1 1 calc R U . . .
H20B H -0.0041 0.7924 0.8334 0.135 Uiso 1 1 calc R U . . .
H20C H 0.0443 0.8410 0.8330 0.135 Uiso 1 1 calc R U . . .
C21 C 0.01519(12) 0.5004(7) 0.92559(18) 0.0882(12) Uani 1 1 d . . . . .
H21A H 0.0243 0.3578 0.9394 0.132 Uiso 1 1 calc R U . . .
H21B H -0.0159 0.5012 0.9059 0.132 Uiso 1 1 calc R U . . .
H21C H 0.0216 0.5967 0.9594 0.132 Uiso 1 1 calc R U . . .
C22 C 0.03631(13) 0.4160(7) 0.83155(16) 0.0880(12) Uani 1 1 d . . . . .
H22A H 0.0533 0.4666 0.8059 0.132 Uiso 1 1 calc R U . . .
H22B H 0.0061 0.4017 0.8084 0.132 Uiso 1 1 calc R U . . .
H22C H 0.0474 0.2790 0.8481 0.132 Uiso 1 1 calc R U . . .
H1 H 0.1151(9) 1.065(5) 1.0298(12) 0.045(8) Uiso 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'
N N 0.0061 0.0033 '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
C3 S1 H1A 109.5 . .
C1 N1 C11 123.3(3) . .
C1 N1 H1 115(2) . .
C11 N1 H1 121(2) . .
C7 O2 C10 118.0(4) . .
C18 O4 C19 122.1(2) . .
O1 C1 N1 122.3(3) . .
O1 C1 C2 122.8(3) . .
N1 C1 C2 114.9(3) . .
C1 C2 C3 113.2(2) . .
C1 C2 H2A 108.9 . .
C3 C2 H2A 108.9 . .
C1 C2 H2B 108.9 . .
C3 C2 H2B 108.9 . .
H2A C2 H2B 107.8 . .
C4 C3 C2 113.2(2) . .
C4 C3 C18 107.7(2) . .
C2 C3 C18 109.4(2) . .
C4 C3 S1 105.27(19) . .
C2 C3 S1 110.69(19) . .
C18 C3 S1 110.49(19) . .
C9 C4 C5 117.0(3) . .
C9 C4 C3 123.5(3) . .
C5 C4 C3 119.4(3) . .
C6 C5 C4 121.3(3) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
C5 C6 C7 120.8(4) . .
C5 C6 H6 119.6 . .
C7 C6 H6 119.6 . .
O2 C7 C8 125.4(4) . .
O2 C7 C6 115.8(4) . .
C8 C7 C6 118.8(3) . .
C7 C8 C9 120.5(3) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C8 C9 C4 121.6(3) . .
C8 C9 H9 119.2 . .
C4 C9 H9 119.2 . .
O2 C10 H10A 109.5 . .
O2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
O2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C11 C12 114.7(3) . .
N1 C11 H11A 108.6 . .
C12 C11 H11A 108.6 . .
N1 C11 H11B 108.6 . .
C12 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
C17 C12 C13 118.0(3) . .
C17 C12 C11 121.3(3) . .
C13 C12 C11 120.7(3) . .
C12 C13 C14 121.3(4) . .
C12 C13 H13 119.4 . .
C14 C13 H13 119.4 . .
C15 C14 C13 120.2(4) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C14 C15 C16 119.5(4) . .
C14 C15 H15 120.2 . .
C16 C15 H15 120.2 . .
C15 C16 C17 120.6(4) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C12 C17 C16 120.5(4) . .
C12 C17 H17 119.8 . .
C16 C17 H17 119.8 . .
O3 C18 O4 125.5(3) . .
O3 C18 C3 125.8(3) . .
O4 C18 C3 108.7(2) . .
O4 C19 C22 109.5(3) . .
O4 C19 C20 101.9(2) . .
C22 C19 C20 111.4(3) . .
O4 C19 C21 108.8(2) . .
C22 C19 C21 112.9(3) . .
C20 C19 C21 111.7(3) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C19 C21 H21A 109.5 . .
C19 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C19 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C19 C22 H22A 109.5 . .
C19 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C19 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.837(3) .
S1 H1A 1.2000 .
N1 C1 1.328(4) .
N1 C11 1.448(4) .
N1 H1 0.84(3) .
O1 C1 1.216(3) .
O2 C7 1.360(4) .
O2 C10 1.408(5) .
O3 C18 1.195(3) .
O4 C18 1.325(3) .
O4 C19 1.479(3) .
C1 C2 1.516(4) .
C2 C3 1.529(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.521(4) .
C3 C18 1.537(4) .
C4 C9 1.383(4) .
C4 C5 1.392(4) .
C5 C6 1.364(5) .
C5 H5 0.9300 .
C6 C7 1.386(5) .
C6 H6 0.9300 .
C7 C8 1.361(5) .
C8 C9 1.382(4) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.502(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C17 1.359(4) .
C12 C13 1.369(5) .
C13 C14 1.374(6) .
C13 H13 0.9300 .
C14 C15 1.341(6) .
C14 H14 0.9300 .
C15 C16 1.356(6) .
C15 H15 0.9300 .
C16 C17 1.382(5) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C19 C22 1.487(5) .
C19 C20 1.511(5) .
C19 C21 1.513(5) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C11 N1 C1 O1 -1.4(5) . . . .
C11 N1 C1 C2 177.7(3) . . . .
O1 C1 C2 C3 16.3(4) . . . .
N1 C1 C2 C3 -162.8(3) . . . .
C1 C2 C3 C4 169.5(2) . . . .
C1 C2 C3 C18 49.4(3) . . . .
C1 C2 C3 S1 -72.6(3) . . . .
C2 C3 C4 C9 15.7(4) . . . .
C18 C3 C4 C9 136.8(3) . . . .
S1 C3 C4 C9 -105.3(3) . . . .
C2 C3 C4 C5 -168.1(3) . . . .
C18 C3 C4 C5 -47.0(3) . . . .
S1 C3 C4 C5 70.9(3) . . . .
C9 C4 C5 C6 0.6(5) . . . .
C3 C4 C5 C6 -175.8(3) . . . .
C4 C5 C6 C7 -0.9(6) . . . .
C10 O2 C7 C8 3.5(5) . . . .
C10 O2 C7 C6 -174.7(4) . . . .
C5 C6 C7 O2 178.5(3) . . . .
C5 C6 C7 C8 0.2(6) . . . .
O2 C7 C8 C9 -177.5(3) . . . .
C6 C7 C8 C9 0.7(5) . . . .
C7 C8 C9 C4 -0.9(5) . . . .
C5 C4 C9 C8 0.2(4) . . . .
C3 C4 C9 C8 176.5(3) . . . .
C1 N1 C11 C12 92.8(4) . . . .
N1 C11 C12 C17 -105.0(4) . . . .
N1 C11 C12 C13 76.7(4) . . . .
C17 C12 C13 C14 1.1(6) . . . .
C11 C12 C13 C14 179.5(4) . . . .
C12 C13 C14 C15 -1.1(7) . . . .
C13 C14 C15 C16 0.5(7) . . . .
C14 C15 C16 C17 0.2(7) . . . .
C13 C12 C17 C16 -0.5(5) . . . .
C11 C12 C17 C16 -178.8(3) . . . .
C15 C16 C17 C12 -0.1(6) . . . .
C19 O4 C18 O3 5.1(4) . . . .
C19 O4 C18 C3 -177.1(2) . . . .
C4 C3 C18 O3 95.4(3) . . . .
C2 C3 C18 O3 -141.2(3) . . . .
S1 C3 C18 O3 -19.1(4) . . . .
C4 C3 C18 O4 -82.4(3) . . . .
C2 C3 C18 O4 41.0(3) . . . .
S1 C3 C18 O4 163.11(19) . . . .
C18 O4 C19 C22 -65.3(3) . . . .
C18 O4 C19 C20 176.7(3) . . . .
C18 O4 C19 C21 58.6(4) . . . .
