#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/07/2010748.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_2010748
loop_
_publ_author_name
'Brewer, A. David'
'Ferguson, George'
'Znotins, Andrew A.'
_publ_section_title
;7,7-Dichloro-1,6-dimethyl-2-oxa-5-thiabicyclo[4.1.0]heptane 5,5-dioxide and
 6-chloro-2,3-dihydro-7-methyl-5-methylene-2H,3H,5H-1,4-dithiepine
 1,1,4,4-tetraoxide
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e109
_journal_page_last               e110
_journal_paper_doi               10.1107/S0108270100002286
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C7 H10 Cl2 O3 S'
_chemical_formula_sum            'C7 H10 Cl2 O3 S'
_chemical_formula_weight         245.11
_chemical_name_systematic
;
7,7-Dichloro-1,6-dimethyl-2-oxa-5-thiabicyclo[4.1.0]heptane 5,5-dioxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 97.307(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2341(17)
_cell_length_b                   6.8536(11)
_cell_length_c                   13.0566(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      15.75
_cell_measurement_theta_min      9.45
_cell_volume                     997.1(2)
_computing_cell_refinement
'SET4 & CELDIM in CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'DATRD2 in NRCVAX96 (Gabe et al., 1989)'
_computing_publication_material
;
NRCVAX96, SHELXL97, PLATON (Spek, 2000) and WordPerfect macro PREP8
(Ferguson, 1998)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .008
_diffrn_reflns_av_sigmaI/netI    .0209
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2267
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        'no decay, variation 1.3'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .831
_exptl_absorpt_correction_T_max  .931
_exptl_absorpt_correction_T_min  .762
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .08
_refine_diff_density_max         .295
_refine_diff_density_min         -.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          .042
_refine_ls_R_factor_gt           .029
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0354P)²+0.3140P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .075
_reflns_number_gt                1718
_reflns_number_total             2166
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0222.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' tag value 'ues' was replaced with 'yes' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2010748
_cod_database_fobs_code          2010748
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .78475(15) .4669(3) .31075(12) .0282(4) Uani d . 1 . . C
C11 .90023(17) .3928(3) .36724(16) .0428(5) Uani d . 1 . . C
H11A .8852 .2762 .4042 .064 Uiso calc R 1 . . H
H11B .9343 .4903 .4151 .064 Uiso calc R 1 . . H
H11C .9552 .3645 .3187 .064 Uiso calc R 1 . . H
O2 .79899(12) .64577(18) .26284(9) .0366(3) Uani d . 1 . . O
C3 .7938(2) .6358(3) .15283(15) .0452(5) Uani d . 1 . . C
H3A .8423 .5277 .1340 .054 Uiso calc R 1 . . H
H3B .8257 .7552 .1271 .054 Uiso calc R 1 . . H
C4 .6653(2) .6083(3) .10517(16) .0498(5) Uani d . 1 . . C
H4A .6596 .6239 .0309 .060 Uiso calc R 1 . . H
H4B .6150 .7065 .1316 .060 Uiso calc R 1 . . H
S5 .61460(4) .37282(8) .13479(3) .03993(14) Uani d . 1 . . S
O51 .66289(16) .2379(3) .06725(11) .0632(5) Uani d . 1 . . O
O52 .48735(13) .3710(3) .13761(12) .0579(5) Uani d . 1 . . O
C6 .69069(15) .3203(3) .26106(13) .0280(4) Uani d . 1 . . C
C61 .7149(2) .1032(3) .27185(18) .0460(5) Uani d . 1 . . C
H61A .7811 .0692 .2355 .069 Uiso calc R 1 . . H
H61B .6449 .0321 .2433 .069 Uiso calc R 1 . . H
H61C .7342 .0708 .3436 .069 Uiso calc R 1 . . H
C7 .66683(15) .4430(3) .35355(12) .0276(4) Uani d . 1 . . C
Cl71 .56164(4) .63113(7) .33907(4) .04246(14) Uani d . 1 . . Cl
Cl72 .66578(5) .32905(8) .47344(3) .04365(15) Uani d . 1 . . Cl
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
C1 .0298(9) .0300(9) .0250(8) -.0026(7) .0042(7) -.0018(7)
C11 .0284(9) .0541(13) .0447(11) .0016(9) -.0008(8) -.0001(10)
O2 .0452(8) .0347(7) .0304(6) -.0091(6) .0072(6) .0016(5)
C3 .0537(12) .0529(13) .0308(9) -.0110(10) .0123(9) .0070(9)
C4 .0574(13) .0621(14) .0290(10) -.0012(11) .0022(9) .0129(10)
S5 .0388(3) .0564(3) .0237(2) -.0055(2) .00078(18) -.0065(2)
O51 .0757(12) .0783(12) .0370(8) -.0074(10) .0122(8) -.0258(8)
O52 .0369(8) .0938(13) .0402(8) -.0088(8) -.0061(6) -.0002(8)
C6 .0289(8) .0292(9) .0259(8) -.0002(7) .0039(7) -.0024(7)
C61 .0530(13) .0299(10) .0551(13) .0011(9) .0071(10) -.0075(9)
C7 .0293(9) .0295(9) .0242(8) .0013(7) .0049(6) .0009(7)
Cl71 .0417(3) .0421(3) .0451(3) .0131(2) .0117(2) -.0038(2)
Cl72 .0501(3) .0541(3) .0271(2) -.0100(2) .00634(19) .0076(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -2 -6
-1 1 -6
-1 3 -6
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
O2 C1 C11 112.18(15) ?
O2 C1 C7 114.66(14) ?
C11 C1 C7 121.77(15) ?
O2 C1 C6 119.74(14) ?
C11 C1 C6 119.43(15) ?
C7 C1 C6 59.88(11) ?
C1 C11 H11A 109.5 ?
C1 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C1 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C1 O2 C3 114.58(14) yes
O2 C3 C4 109.52(16) ?
O2 C3 H3A 109.8 ?
C4 C3 H3A 109.8 ?
O2 C3 H3B 109.8 ?
C4 C3 H3B 109.8 ?
H3A C3 H3B 108.2 ?
C3 C4 S5 109.96(15) ?
C3 C4 H4A 109.7 ?
S5 C4 H4A 109.7 ?
C3 C4 H4B 109.7 ?
S5 C4 H4B 109.7 ?
H4A C4 H4B 108.2 ?
O51 S5 O52 117.84(10) yes
O51 S5 C4 107.26(11) yes
O51 S5 C6 105.25(9) yes
O52 S5 C4 111.28(11) yes
O52 S5 C6 109.54(9) yes
C4 S5 C6 104.75(9) yes
C61 C6 C7 121.05(16) ?
C61 C6 C1 119.70(16) ?
C7 C6 C1 59.10(11) ?
C61 C6 S5 109.94(13) ?
C7 C6 S5 120.44(12) ?
C1 C6 S5 118.52(12) ?
C6 C61 H61A 109.5 ?
C6 C61 H61B 109.5 ?
H61A C61 H61B 109.5 ?
C6 C61 H61C 109.5 ?
H61A C61 H61C 109.5 ?
H61B C61 H61C 109.5 ?
C1 C7 C6 61.02(11) ?
C1 C7 Cl71 119.61(13) ?
C6 C7 Cl71 120.51(12) ?
C1 C7 Cl72 119.01(12) ?
C6 C7 Cl72 118.98(13) ?
Cl71 C7 Cl72 110.21(9) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.394(2) yes
C1 C6 . 1.540(2) ?
C1 C7 . 1.511(2) ?
C1 C11 . 1.497(2) ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .9600 ?
O2 C3 . 1.432(2) yes
C3 C4 . 1.510(3) ?
C3 H3A . .9700 ?
C3 H3B . .9700 ?
C4 S5 . 1.770(2) yes
C4 H4A . .9700 ?
C4 H4B . .9700 ?
S5 O51 . 1.4313(16) yes
S5 O52 . 1.4347(16) yes
S5 C6 . 1.7943(17) yes
C6 C61 . 1.516(3) ?
C6 C7 . 1.523(2) ?
C61 H61A . .9600 ?
C61 H61B . .9600 ?
C61 H61C . .9600 ?
C7 Cl71 . 1.7428(18) yes
C7 Cl72 . 1.7509(17) yes
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
C11 C1 O2 C3 106.79(18)
C7 C1 O2 C3 -108.83(17)
C6 C1 O2 C3 -40.8(2)
C1 O2 C3 C4 75.0(2)
O2 C3 C4 S5 -69.0(2)
C3 C4 S5 O51 -78.17(17)
C3 C4 S5 O52 151.60(15)
C3 C4 S5 C6 33.33(17)
O2 C1 C6 C61 146.52(17)
C11 C1 C6 C61 1.3(2)
C7 C1 C6 C61 -110.53(19)
O2 C1 C6 C7 -102.95(17)
C11 C1 C6 C7 111.82(17)
O2 C1 C6 S5 7.3(2)
C11 C1 C6 S5 -137.90(15)
C7 C1 C6 S5 110.28(14)
O51 S5 C6 C61 -34.86(16)
O52 S5 C6 C61 92.76(16)
C4 S5 C6 C61 -147.79(15)
O51 S5 C6 C7 176.97(14)
O52 S5 C6 C7 -55.41(16)
C4 S5 C6 C7 64.04(16)
O51 S5 C6 C1 107.99(14)
O52 S5 C6 C1 -124.39(14)
C4 S5 C6 C1 -4.95(16)
O2 C1 C7 C6 111.39(16)
C11 C1 C7 C6 -107.99(19)
O2 C1 C7 Cl71 .7(2)
C11 C1 C7 Cl71 141.36(15)
C6 C1 C7 Cl71 -110.66(15)
O2 C1 C7 Cl72 -139.58(13)
C11 C1 C7 Cl72 1.0(2)
C6 C1 C7 Cl72 109.03(15)
C61 C6 C7 C1 108.28(19)
S5 C6 C7 C1 -107.08(15)
C61 C6 C7 Cl71 -142.50(16)
C1 C6 C7 Cl71 109.22(15)
S5 C6 C7 Cl71 2.1(2)
C61 C6 C7 Cl72 -.8(2)
C1 C6 C7 Cl72 -109.09(14)
S5 C6 C7 Cl72 143.83(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8952047
