#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2000804.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2000804
loop_
_publ_author_name
'Beckwith, A. L. J.'
'Chai, C. L. L.'
'Willis, A. C.'
_publ_contact_author
;
      Dr Anthony C. Willis
      Research School of Chemistry
      Austalian National University
      GPO Box 4
      Canberra, A.C.T.
      Australia    2601
;
_publ_section_title
;
 2-(<i>tert</i>-Butyl)-<i>cis</i>-5-(<i>p</i>-chlorophenylthio)-<i>trans</i>-5-methyl-1,3-dioxolan-4-one
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1362
_journal_page_last               1364
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C14 H17 Cl O3 S'
_chemical_formula_sum            'C14 H17 Cl O3 S'
_chemical_formula_weight         300.80
_chemical_name_systematic
;
2-(tert-butyl)-cis-5-(p-chlorophenylthio)-trans-5-methyl-1,3-dioxolan-4-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           from_xtal_archive_file_using_CIFIO
_cell_angle_alpha                90.00000
_cell_angle_beta                 103.170(10)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            8
_cell_length_a                   28.795(3)
_cell_length_b                   8.8870(10)
_cell_length_c                   12.1390(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      22
_cell_measurement_theta_min      18
_cell_volume                     3024.7(5)
_computing_cell_refinement       'Philips PW1100/20 software 1976'
_computing_data_collection       'Philips PW1100/20 software 1976'
_computing_data_reduction
;
 xtal ADDREF, ABSORB, SORTRF (Hall & Stewart, 1990)
;
_computing_molecular_graphics
;
xtal (Hall & Stewart, 1990)
;
_computing_publication_material
;
xtal BONDLA, CIFIO (Hall & Stewart, 1990)
;
_computing_structure_refinement
;
xtal CRYLSQ (Hall & Stewart, 1990)
;
_computing_structure_solution
;
xtal SIMPEL (Hall & Stewart, 1990)
;
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Philips PW1100/20 diffractometer'
_diffrn_measurement_method       '\q/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           'molybdenum K\a'
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .012
_diffrn_reflns_av_sigmaI/netI    .014
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2831
_diffrn_reflns_reduction_process perpendicular_monochr_Lp
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.39
_exptl_absorpt_correction_T_max  .9379
_exptl_absorpt_correction_T_min  .9167
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1263.89
_exptl_crystal_size_max          .29
_exptl_crystal_size_mid          .23
_exptl_crystal_size_min          .20
_refine_diff_density_max         .155
_refine_diff_density_min         -.211
_refine_ls_extinction_coef       1.4E4(1)
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_all   1.258
_refine_ls_goodness_of_fit_obs   1.311
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     224
_refine_ls_number_reflns         1780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .061
_refine_ls_R_factor_obs          .031
_refine_ls_shift/esd_max         .013
_refine_ls_shift/esd_mean        .002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'calc w=1/[\s^2^(F)+0.0004F^2^]'
_refine_ls_wR_factor_all         .047
_refine_ls_wR_factor_obs         .039
_reflns_number_observed          1780
_reflns_number_total             2687
_reflns_observed_criterion       'refl observed if Inet > 3.00\s(Inet)'
_[local]_cod_data_source_file    hl1010.cif
_[local]_cod_data_source_block   CC2
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_[local]_cod_cif_authors_sg_Hall -C_2yc
_cod_database_code               2000804
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,+y,1/2-z
-x,-y,-z
+x,-y,1/2+z
1/2+x,1/2+y,+z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl .0651(5) .0899(6) .0882(6) -.0207(4) .0319(4) -.0006(5)
S .0475(4) .0378(3) .0548(4) .0043(3) .0134(3) -.0004(3)
O1 .0460(9) .0363(8) .0339(8) .0073(7) .0034(7) .0039(7)
C2 .0440(10) .0450(10) .0370(10) .0110(10) .0120(10) .0090(10)
O3 .0530(10) .0435(9) .0381(8) .0081(8) .0061(7) .0099(8)
C4 .0310(10) .0470(10) .0410(10) .0010(10) .0080(10) .0040(10)
C5 .0360(10) .0390(10) .0380(10) .0010(10) .0060(10) .0010(10)
C21 .0580(10) .0400(10) .0440(10) .0040(10) .0140(10) -.0020(10)
C22 .067(2) .069(2) .082(2) -.017(2) .022(2) -.016(2)
C23 .096(3) .041(2) .077(2) .009(2) .020(2) .002(2)
C24 .108(3) .064(2) .047(2) -.001(2) .011(2) -.004(2)
O41 .0520(10) .0730(10) .0350(10) .0016(9) .0039(8) .0019(9)
C51 .0460(10) .052(2) .059(2) -.0050(10) .0130(10) .0080(10)
C52 .0370(10) .0410(10) .0440(10) .0080(10) .0090(10) -.0030(10)
C53 .0440(10) .058(2) .0430(10) -.0010(10) .0040(10) -.0090(10)
C54 .050(2) .067(2) .0420(10) .0010(10) .0130(10) .0010(10)
C55 .0400(10) .054(2) .056(2) .0020(10) .0160(10) -.0010(10)
C56 .0440(10) .077(2) .052(2) -.0090(10) .0010(10) -.011(2)
C57 .0430(10) .070(2) .0400(10) -.0020(10) .0050(10) .0000(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Cl -.02232(3) .16553(9) .58320(7) .0787(5) Uani
S .12984(2) .57086(7) .43145(5) .0464(3) Uani
O1 .15402(5) .3421(2) .31270(10) .0396(8) Uani
C2 .17879(8) .2036(3) .3331(2) .0410(10) Uani
O3 .18959(5) .1880(2) .45580(10) .0455(8) Uani
C4 .18986(7) .3252(3) .5021(2) .0400(10) Uani
C5 .17392(8) .4379(2) .4064(2) .0380(10) Uani
C21 .14997(9) .0721(3) .2749(2) .0470(10) Uani
C22 .10230(10) .0592(4) .3078(3) .072(2) Uani
C23 .17960(10) -.0704(3) .3086(3) .071(2) Uani
C24 .14280(10) .0967(4) .1480(3) .074(2) Uani
O41 .20213(6) .3479(2) .60130(10) .0540(10) Uani
C51 .21630(10) .5277(3) .3859(3) .0520(10) Uani
C52 .08744(7) .4531(2) .4744(2) .0410(10) Uani
C53 .09069(9) .4234(3) .5882(2) .0490(10) Uani
C54 .05714(9) .3352(3) .6215(2) .0530(10) Uani
C55 .02014(8) .2766(3) .5413(2) .0490(10) Uani
C56 .01597(9) .3066(3) .4283(2) .060(2) Uani
C57 .04937(9) .3951(3) .3951(2) .0520(10) Uani
H2 .2099(8) .213(3) .313(2) .05100 Uiso
H22A .1050(10) .056(4) .387(3) .09000 Uiso
H22B .0850(10) -.029(4) .270(3) .09000 Uiso
H22C .0840(10) .143(4) .282(3) .09000 Uiso
H23A .2120(10) -.061(3) .290(3) .09000 Uiso
H23B .1790(10) -.095(4) .387(3) .09000 Uiso
H23C .1630(10) -.154(4) .270(3) .09000 Uiso
H24A .1230(10) .190(4) .124(2) .09000 Uiso
H24B .1270(10) .014(4) .110(3) .09000 Uiso
H24C .1750(10) .118(3) .128(3) .09000 Uiso
H51A .2293(9) .584(3) .450(2) .06500 Uiso
H51B .2410(10) .462(3) .373(2) .06500 Uiso
H51C .2070(10) .590(3) .321(2) .06500 Uiso
H53 .1160(10) .469(3) .642(2) .06300 Uiso
H54 .0599(9) .315(3) .699(2) .06300 Uiso
H56 -.0080(10) .265(3) .375(2) .06300 Uiso
H57 .0478(9) .417(3) .318(2) .06300 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl .132 .159 International_Tables_Vol_IV_Table_2.2B
S .11 .124 International_Tables_Vol_IV_Table_2.2B
O .008 .006 International_Tables_Vol_IV_Table_2.2B
C .002 .002 International_Tables_Vol_IV_Table_2.2B
H 0 0 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 S C52 102.70(10) yes
C2 O1 C5 106.50(10) yes
O1 C2 O3 104.1(2) yes
O1 C2 C21 112.9(2) yes
O1 C2 H2 109.0(10) ?
O3 C2 C21 111.8(2) yes
O3 C2 H2 106.0(10) ?
C21 C2 H2 113.0(10) ?
C2 O3 C4 108.8(2) yes
O3 C4 C5 107.8(2) yes
O3 C4 O41 123.3(2) yes
C5 C4 O41 128.9(2) yes
S C5 O1 110.70(10) yes
S C5 C4 113.7(2) yes
S C5 C51 107.6(2) yes
O1 C5 C4 102.2(2) yes
O1 C5 C51 111.9(2) yes
C4 C5 C51 110.8(2) yes
C2 C21 C22 111.6(2) yes
C2 C21 C23 107.6(2) yes
C2 C21 C24 107.2(2) yes
C22 C21 C23 110.4(3) yes
C22 C21 C24 110.7(3) yes
C23 C21 C24 109.2(3) yes
C21 C22 H22A 113(2) ?
C21 C22 H22B 109(2) ?
C21 C22 H22C 109(2) ?
H22A C22 H22B 112(3) ?
H22A C22 H22C 106(3) ?
H22B C22 H22C 108(3) ?
C21 C23 H23A 111(2) ?
C21 C23 H23B 109(2) ?
C21 C23 H23C 109(2) ?
H23A C23 H23B 117(3) ?
H23A C23 H23C 111(3) ?
H23B C23 H23C 101(3) ?
C21 C24 H24A 110(2) ?
C21 C24 H24B 109(2) ?
C21 C24 H24C 110(2) ?
H24A C24 H24B 110(3) ?
H24A C24 H24C 105(3) ?
H24B C24 H24C 113(3) ?
C5 C51 H51A 109(2) ?
C5 C51 H51B 110(2) ?
C5 C51 H51C 111(2) ?
H51A C51 H51B 107(2) ?
H51A C51 H51C 111(2) ?
H51B C51 H51C 108(2) ?
S C52 C53 120.6(2) yes
S C52 C57 120.3(2) yes
C53 C52 C57 119.0(2) yes
C52 C53 C54 120.5(2) yes
C52 C53 H53 118(2) ?
C54 C53 H53 121(2) ?
C53 C54 C55 119.5(2) yes
C53 C54 H54 120(2) ?
C55 C54 H54 121(2) ?
Cl C55 C54 119.6(2) yes
Cl C55 C56 119.7(2) yes
C54 C55 C56 120.7(3) yes
C55 C56 C57 119.8(2) yes
C55 C56 H56 120(2) ?
C57 C56 H56 120(2) ?
C52 C57 C56 120.4(2) yes
C52 C57 H57 117.0(10) ?
C56 C57 H57 122.0(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C55 1.735(3) yes
S C5 1.810(2) yes
S C52 1.775(2) yes
O1 C2 1.416(3) yes
O1 C5 1.432(2) yes
C2 O3 1.457(3) yes
C2 C21 1.512(3) yes
C2 H2 .99(3) ?
O3 C4 1.341(3) yes
C4 C5 1.524(3) yes
C4 O41 1.192(3) yes
C5 C51 1.524(4) yes
C21 C22 1.519(5) yes
C21 C23 1.530(4) yes
C21 C24 1.522(4) yes
C22 H22A .94(4) ?
C22 H22B .98(3) ?
C22 H22C .92(3) ?
C23 H23A 1.02(4) ?
C23 H23B .98(3) ?
C23 H23C .95(3) ?
C24 H24A 1.01(3) ?
C24 H24B .93(3) ?
C24 H24C 1.04(4) ?
C51 H51A .93(3) ?
C51 H51B .95(3) ?
C51 H51C .95(3) ?
C52 C53 1.389(3) yes
C52 C57 1.383(3) yes
C53 C54 1.374(4) yes
C53 H53 .95(2) ?
C54 C55 1.371(3) yes
C54 H54 .95(3) ?
C55 C56 1.375(4) yes
C56 C57 1.373(4) yes
C56 H56 .91(2) ?
C57 H57 .95(3) ?
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_publ_flag
C52 S C5 O1 65.9(2) ?
C52 S C5 C4 -48.4(2) ?
C52 S C5 C51 -171.6(2) ?
C5 S C52 C53 92.8(2) ?
C5 S C52 C57 -90.3(2) ?
C5 O1 C2 O3 33.2(2) yes
C5 O1 C2 C21 154.7(2) ?
C5 O1 C2 H2 -79.0(10) ?
C2 O1 C5 S -150.7(2) ?
C2 O1 C5 C4 -29.3(2) yes
C2 O1 C5 C51 89.3(2) ?
O1 C2 O3 C4 -23.8(2) yes
C21 C2 O3 C4 -146.0(2) ?
H2 C2 O3 C4 91.0(10) ?
O1 C2 C21 C22 -55.9(3) ?
O1 C2 C21 C23 -177.1(2) ?
O1 C2 C21 C24 65.5(3) ?
O3 C2 C21 C22 61.1(3) ?
O3 C2 C21 C23 -60.2(3) ?
O3 C2 C21 C24 -177.5(2) ?
H2 C2 C21 C22 180.0(10) ?
H2 C2 C21 C23 59.0(10) ?
H2 C2 C21 C24 -59.0(10) ?
C2 O3 C4 C5 5.5(2) yes
C2 O3 C4 O41 -172.6(2) ?
O3 C4 C5 S 133.8(2) ?
O3 C4 C5 O1 14.5(2) yes
O3 C4 C5 C51 -104.8(2) ?
O41 C4 C5 S -48.3(3) ?
O41 C4 C5 O1 -167.5(2) ?
O41 C4 C5 C51 73.1(3) ?
S C5 C51 H51A 62(2) ?
S C5 C51 H51B 179(2) ?
S C5 C51 H51C -61(2) ?
O1 C5 C51 H51A -177(2) ?
O1 C5 C51 H51B -59(2) ?
O1 C5 C51 H51C 60(2) ?
C4 C5 C51 H51A -63(2) ?
C4 C5 C51 H51B 54(2) ?
C4 C5 C51 H51C 174(2) ?
C2 C21 C22 H22A -53(2) ?
C2 C21 C22 H22B -178(2) ?
C2 C21 C22 H22C 64(2) ?
C23 C21 C22 H22A 66(2) ?
C23 C21 C22 H22B -59(2) ?
C23 C21 C22 H22C -176(2) ?
C24 C21 C22 H22A -173(2) ?
C24 C21 C22 H22B 62(2) ?
C24 C21 C22 H22C -55(2) ?
C2 C21 C23 H23A -56(2) ?
C2 C21 C23 H23B 74(2) ?
C2 C21 C23 H23C -178(2) ?
C22 C21 C23 H23A -178(2) ?
C22 C21 C23 H23B -48(2) ?
C22 C21 C23 H23C 60(2) ?
C24 C21 C23 H23A 60(2) ?
C24 C21 C23 H23B -170(2) ?
C24 C21 C23 H23C -62(2) ?
C2 C21 C24 H24A -64(2) ?
C2 C21 C24 H24B 176(2) ?
C2 C21 C24 H24C 52(2) ?
C22 C21 C24 H24A 58(2) ?
C22 C21 C24 H24B -63(2) ?
C22 C21 C24 H24C 174(2) ?
C23 C21 C24 H24A 180(2) ?
C23 C21 C24 H24B 59(2) ?
C23 C21 C24 H24C -65(2) ?
S C52 C53 C54 178.4(2) ?
S C52 C53 H53 0(2) ?
C57 C52 C53 C54 1.3(4) ?
C57 C52 C53 H53 -176(2) ?
S C52 C57 C56 -178.6(2) ?
S C52 C57 H57 3(2) ?
C53 C52 C57 C56 -1.6(4) ?
C53 C52 C57 H57 180(2) ?
C52 C53 C54 C55 -.2(4) ?
C52 C53 C54 H54 179(2) ?
H53 C53 C54 C55 177(2) ?
H53 C53 C54 H54 -4(3) ?
C53 C54 C55 Cl -179.9(2) ?
C53 C54 C55 C56 -.8(4) ?
H54 C54 C55 Cl 0(2) ?
H54 C54 C55 C56 180(2) ?
Cl C55 C56 C57 179.6(2) ?
Cl C55 C56 H56 -2(2) ?
C54 C55 C56 C57 .5(4) ?
C54 C55 C56 H56 178(2) ?
C55 C56 C57 C52 .7(4) ?
C55 C56 C57 H57 179(2) ?
H56 C56 C57 C52 -177(2) ?
H56 C56 C57 H57 1(3) ?