#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:35:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178486 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/07/4030779.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_4030779
loop_
_publ_author_name
'Mal, Kanchan'
'Das, Supriya'
'Maiti, Nakul C.'
'Natarajan, Ramalingam'
'Das, Indrajit'
_publ_section_title
;
 ZnI2-Catalyzed Diastereoselective [4 + 2] Cycloadditions of
 β,γ-Unsaturated α-Ketothioesters with Olefins.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2972
_journal_page_last               2988
_journal_paper_doi               10.1021/jo5024766
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H16 Cl2 O2 S'
_chemical_formula_sum            'C19 H16 Cl2 O2 S'
_chemical_formula_weight         379.28
_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'
_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
_audit_creation_date             2014-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.874(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8651(8)
_cell_length_b                   17.8961(12)
_cell_length_c                   8.7169(5)
_cell_measurement_reflns_used    7154
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.276
_cell_volume                     1796.9(2)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17267
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.359
_diffrn_reflns_theta_min         2.103
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.778190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0989 before and 0.0513 after correction. The Ratio of minimum to maximum transmission is 0.7782. The λ/2 correction factor is 0.0015.'
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0400
_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)+(0.0484P)²+0.6885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3204
_reflns_number_total             4055
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5024766_si_002.cif
_cod_data_source_block           kanchan
_cod_depositor_comments
'Adding full bibliography for 4030777--4030784.cif.'
_cod_database_code               4030779
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
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
C1 C 0.77327(15) 0.03327(9) 0.7299(2) 0.0374(4) Uani 1 1 d .
C2 C 0.85413(17) 0.06566(10) 0.8542(2) 0.0445(4) Uani 1 1 d .
H2 H 0.8948 0.1075 0.8342 0.053 Uiso 1 1 calc R
C3 C 0.87623(17) 0.03774(11) 1.0069(2) 0.0468(4) Uani 1 1 d .
H3 H 0.9302 0.0608 1.0882 0.056 Uiso 1 1 calc R
C4 C 0.81702(16) -0.02443(10) 1.0360(2) 0.0420(4) Uani 1 1 d .
C5 C 0.73611(17) -0.05854(10) 0.9171(2) 0.0452(4) Uani 1 1 d .
H5 H 0.6961 -0.1006 0.9375 0.054 Uiso 1 1 calc R
C6 C 0.71548(16) -0.02875(10) 0.7659(2) 0.0416(4) Uani 1 1 d .
C7 C 0.74975(16) 0.06718(9) 0.5656(2) 0.0401(4) Uani 1 1 d .
H7 H 0.7016 0.0320 0.4917 0.048 Uiso 1 1 calc R
C8 C 0.85876(17) 0.08079(10) 0.5122(2) 0.0423(4) Uani 1 1 d .
H8 H 0.9179 0.0455 0.5358 0.051 Uiso 1 1 calc R
C9 C 0.87408(15) 0.14160(10) 0.4321(2) 0.0396(4) Uani 1 1 d .
C10 C 0.67775(15) 0.17952(10) 0.3996(2) 0.0400(4) Uani 1 1 d .
H10 H 0.6420 0.1453 0.3141 0.048 Uiso 1 1 calc R
C11 C 0.68336(15) 0.14123(10) 0.5569(2) 0.0395(4) Uani 1 1 d .
H11A H 0.6053 0.1318 0.5685 0.047 Uiso 1 1 calc R
H11B H 0.7220 0.1736 0.6427 0.047 Uiso 1 1 calc R
C12 C 0.98329(16) 0.15416(10) 0.3821(2) 0.0435(4) Uani 1 1 d .
C13 C 1.1268(2) 0.22742(15) 0.2334(4) 0.0790(8) Uani 1 1 d .
H13A H 1.1830 0.2264 0.3330 0.118 Uiso 1 1 calc GR
H13B H 1.1415 0.2696 0.1730 0.118 Uiso 1 1 calc GR
H13C H 1.1325 0.1823 0.1762 0.118 Uiso 1 1 calc GR
C14 C 0.60920(15) 0.25123(11) 0.3798(2) 0.0416(4) Uani 1 1 d .
C15 C 0.50170(17) 0.25463(13) 0.2735(3) 0.0550(5) Uani 1 1 d .
H15 H 0.4731 0.2132 0.2119 0.066 Uiso 1 1 calc R
C16 C 0.43676(19) 0.31993(15) 0.2590(3) 0.0701(7) Uani 1 1 d .
H16 H 0.3642 0.3219 0.1887 0.084 Uiso 1 1 calc R
C17 C 0.4790(2) 0.38163(14) 0.3479(3) 0.0689(7) Uani 1 1 d .
H17 H 0.4354 0.4253 0.3372 0.083 Uiso 1 1 calc R
C18 C 0.5859(2) 0.37876(13) 0.4528(3) 0.0623(6) Uani 1 1 d .
H18 H 0.6147 0.4206 0.5127 0.075 Uiso 1 1 calc R
C19 C 0.65114(18) 0.31334(11) 0.4696(2) 0.0502(5) Uani 1 1 d .
H19 H 0.7231 0.3114 0.5414 0.060 Uiso 1 1 calc R
Cl1 Cl 0.84351(5) -0.06091(3) 1.22645(6) 0.06197(17) Uani 1 1 d .
Cl2 Cl 0.61132(6) -0.07329(4) 0.61987(7) 0.0827(2) Uani 1 1 d .
O1 O 1.06521(14) 0.11216(9) 0.4155(2) 0.0697(5) Uani 1 1 d .
O2 O 0.79442(11) 0.19760(7) 0.38553(15) 0.0449(3) Uani 1 1 d .
S1 S 0.98377(5) 0.23490(3) 0.26667(7) 0.05915(17) 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'
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
C2 C1 C7 120.33(15)
C6 C1 C2 116.48(16)
C6 C1 C7 123.17(16)
C1 C2 H2 118.9
C3 C2 C1 122.30(17)
C3 C2 H2 118.9
C2 C3 H3 120.6
C4 C3 C2 118.84(17)
C4 C3 H3 120.6
C3 C4 C5 121.11(17)
C3 C4 Cl1 119.81(14)
C5 C4 Cl1 119.08(14)
C4 C5 H5 120.7
C4 C5 C6 118.52(16)
C6 C5 H5 120.7
C1 C6 C5 122.75(16)
C1 C6 Cl2 120.43(14)
C5 C6 Cl2 116.82(14)
C1 C7 H7 108.1
C1 C7 C11 111.59(14)
C8 C7 C1 112.43(15)
C8 C7 H7 108.1
C8 C7 C11 108.42(14)
C11 C7 H7 108.1
C7 C8 H8 118.8
C9 C8 C7 122.30(16)
C9 C8 H8 118.8
C8 C9 C12 121.26(16)
C8 C9 O2 125.65(16)
O2 C9 C12 113.08(15)
C11 C10 H10 108.8
C14 C10 H10 108.8
C14 C10 C11 113.16(15)
O2 C10 H10 108.8
O2 C10 C11 109.85(13)
O2 C10 C14 107.40(14)
C7 C11 H11A 109.6
C7 C11 H11B 109.6
C10 C11 C7 110.17(14)
C10 C11 H11A 109.6
C10 C11 H11B 109.6
H11A C11 H11B 108.1
C9 C12 S1 114.57(13)
O1 C12 C9 123.05(17)
O1 C12 S1 122.38(15)
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
S1 C13 H13A 109.5
S1 C13 H13B 109.5
S1 C13 H13C 109.5
C15 C14 C10 119.93(18)
C19 C14 C10 120.59(16)
C19 C14 C15 119.46(19)
C14 C15 H15 120.0
C14 C15 C16 119.9(2)
C16 C15 H15 120.0
C15 C16 H16 119.8
C17 C16 C15 120.4(2)
C17 C16 H16 119.8
C16 C17 H17 120.0
C18 C17 C16 119.9(2)
C18 C17 H17 120.0
C17 C18 H18 119.9
C17 C18 C19 120.1(2)
C19 C18 H18 119.9
C14 C19 C18 120.1(2)
C14 C19 H19 119.9
C18 C19 H19 119.9
C9 O2 C10 114.51(13)
C12 S1 C13 99.44(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.390(3)
C1 C6 1.380(2)
C1 C7 1.518(2)
C2 H2 0.9300
C2 C3 1.387(3)
C3 H3 0.9300
C3 C4 1.372(3)
C4 C5 1.375(3)
C4 Cl1 1.7407(18)
C5 H5 0.9300
C5 C6 1.388(2)
C6 Cl2 1.7402(18)
C7 H7 0.9800
C7 C8 1.496(3)
C7 C11 1.534(2)
C8 H8 0.9300
C8 C9 1.329(2)
C9 C12 1.480(3)
C9 O2 1.371(2)
C10 H10 0.9800
C10 C11 1.520(2)
C10 C14 1.507(2)
C10 O2 1.455(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O1 1.208(2)
C12 S1 1.7615(19)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C13 S1 1.794(2)
C14 C15 1.386(3)
C14 C19 1.382(3)
C15 H15 0.9300
C15 C16 1.389(3)
C16 H16 0.9300
C16 C17 1.373(4)
C17 H17 0.9300
C17 C18 1.375(4)
C18 H18 0.9300
C18 C19 1.392(3)
C19 H19 0.9300
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
C1 C2 C3 C4 0.6(3)
C1 C7 C8 C9 -140.36(18)
C1 C7 C11 C10 171.20(14)
C2 C1 C6 C5 -0.4(3)
C2 C1 C6 Cl2 179.37(15)
C2 C1 C7 C8 50.8(2)
C2 C1 C7 C11 -71.3(2)
C2 C3 C4 C5 -0.6(3)
C2 C3 C4 Cl1 179.71(15)
C3 C4 C5 C6 0.1(3)
C4 C5 C6 C1 0.4(3)
C4 C5 C6 Cl2 -179.38(15)
C6 C1 C2 C3 -0.1(3)
C6 C1 C7 C8 -130.94(18)
C6 C1 C7 C11 106.99(19)
C7 C1 C2 C3 178.29(17)
C7 C1 C6 C5 -178.80(17)
C7 C1 C6 Cl2 1.0(3)
C7 C8 C9 C12 179.30(16)
C7 C8 C9 O2 -1.5(3)
C8 C7 C11 C10 46.84(19)
C8 C9 C12 O1 -2.8(3)
C8 C9 C12 S1 176.21(15)
C8 C9 O2 C10 -12.8(3)
C9 C12 S1 C13 -179.57(16)
C10 C14 C15 C16 177.82(19)
C10 C14 C19 C18 -178.56(18)
C11 C7 C8 C9 -16.5(2)
C11 C10 C14 C15 -109.10(19)
C11 C10 C14 C19 69.2(2)
C11 C10 O2 C9 44.00(19)
C12 C9 O2 C10 166.46(14)
C14 C10 C11 C7 177.54(15)
C14 C10 O2 C9 167.46(14)
C14 C15 C16 C17 0.9(3)
C15 C14 C19 C18 -0.2(3)
C15 C16 C17 C18 -0.5(4)
C16 C17 C18 C19 -0.3(3)
C17 C18 C19 C14 0.6(3)
C19 C14 C15 C16 -0.5(3)
Cl1 C4 C5 C6 179.77(15)
O1 C12 S1 C13 -0.5(2)
O2 C9 C12 O1 177.93(19)
O2 C9 C12 S1 -3.0(2)
O2 C10 C11 C7 -62.44(18)
O2 C10 C14 C15 129.49(17)
O2 C10 C14 C19 -52.2(2)
