#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519269.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_1519269
loop_
_publ_author_name
'Gelbrich, Thomas'
'Lucas, Matthew'
'Hursthouse, Michael B.'
'Harrowven, David C.'
_publ_section_title
;
 6a-Methyl-2,3,3-trioxo-octahydro-1-oxa-3lamda*6*-thia-cyclopenta[cd]pentalene-
 6b-carboxylic acid ethyl ester
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              533
_journal_year                    2000
_chemical_formula_sum            'C12 H16 O6 S'
_chemical_formula_weight         288.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.078(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9623(4)
_cell_length_b                   10.1397(4)
_cell_length_c                   11.9175(5)
_cell_measurement_reflns_used    6502
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.97
_cell_measurement_theta_min      2.91
_cell_volume                     1323.81(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7489
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0109(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0001P)²+0.8020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                2051
_reflns_number_total             2572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-533.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
Citation :
Gelbrich, Thomas and Lucas, Matthew and Hursthouse, Michael B. and 
Harrowven, David C (2000) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/533)

More at:
http://ecrystals.chem.soton.ac.uk/533/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1519269
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51487(4) 0.13123(5) 0.15251(4) 0.03509(16) Uani 1 1 d . . .
O1 O 0.55341(13) 0.21369(14) 0.24524(12) 0.0492(4) Uani 1 1 d . . .
O3 O 0.42965(12) 0.00930(13) 0.39092(10) 0.0384(4) Uani 1 1 d . . .
O2 O 0.60365(12) 0.04477(16) 0.10522(12) 0.0489(4) Uani 1 1 d . . .
O4 O 0.25864(11) 0.11173(13) 0.33462(10) 0.0365(3) Uani 1 1 d . . .
O5 O 0.21852(11) -0.11637(11) 0.07154(10) 0.0292(3) Uani 1 1 d . . .
O6 O 0.13870(10) 0.05242(12) -0.02838(10) 0.0306(3) Uani 1 1 d . . .
C1 C 0.38224(15) 0.03537(17) 0.19151(13) 0.0237(4) Uani 1 1 d . . .
H1 H 0.3909 -0.0591 0.1690 0.033(5) Uiso 1 1 calc R . .
C3 C 0.30563(18) 0.23329(17) 0.08282(15) 0.0341(4) Uani 1 1 d . . .
H3 H 0.2518 0.2511 0.0150 0.031(5) Uiso 1 1 calc R . .
C2 C 0.26953(15) 0.09791(17) 0.13356(13) 0.0245(4) Uani 1 1 d . . .
C4 C 0.43726(18) 0.2267(2) 0.04759(16) 0.0399(5) Uani 1 1 d . . .
H4A H 0.4729 0.3163 0.0438 0.040(5) Uiso 1 1 calc R . .
H4B H 0.4424 0.1843 -0.0269 0.051(6) Uiso 1 1 calc R . .
C5 C 0.36394(16) 0.04730(17) 0.31581(14) 0.0288(4) Uani 1 1 d . . .
C6 C 0.18315(17) 0.1327(2) 0.23237(15) 0.0338(5) Uani 1 1 d . . .
C7 C 0.1605(2) 0.2801(2) 0.22130(18) 0.0520(6) Uani 1 1 d . . .
H7A H 0.0896 0.2980 0.1698 0.056(6) Uiso 1 1 calc R . .
H7B H 0.1453 0.3200 0.2953 0.074(8) Uiso 1 1 calc R . .
C8 C 0.2771(2) 0.33400(19) 0.17387(19) 0.0510(6) Uani 1 1 d . . .
H8A H 0.3436 0.3381 0.2322 0.054(6) Uiso 1 1 calc R . .
H8B H 0.2641 0.4230 0.1415 0.069(7) Uiso 1 1 calc R . .
C9 C 0.07093(18) 0.0482(3) 0.24392(17) 0.0479(6) Uani 1 1 d . . .
H9A H 0.0952 -0.0446 0.2508 0.049(6) Uiso 1 1 calc R . .
H9B H 0.0166 0.0594 0.1775 0.051(6) Uiso 1 1 calc R . .
H9C H 0.0281 0.0749 0.3111 0.073(8) Uiso 1 1 calc R . .
C10 C 0.20299(15) 0.01067(17) 0.04773(13) 0.0249(4) Uani 1 1 d . . .
C11 C 0.15521(18) -0.20898(18) -0.00314(16) 0.0360(5) Uani 1 1 d . . .
H11A H 0.1788 -0.1949 -0.0816 0.046(6) Uiso 1 1 calc R . .
H11B H 0.0657 -0.1978 0.0007 0.049(6) Uiso 1 1 calc R . .
C12 C 0.1925(2) -0.34367(19) 0.03614(19) 0.0434(5) Uani 1 1 d . . .
H12A H 0.1519 -0.4102 -0.0117 0.081(8) Uiso 1 1 calc R . .
H12B H 0.1689 -0.3559 0.1140 0.046(6) Uiso 1 1 calc R . .
H12C H 0.2812 -0.3531 0.0319 0.057(7) 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
O1 S1 O2 118.11(9) . .
O1 S1 C4 110.16(9) . .
O2 S1 C4 111.72(10) . .
O1 S1 C1 109.22(8) . .
O2 S1 C1 109.37(8) . .
C4 S1 C1 95.98(8) . .
C5 O4 C6 113.12(13) . .
C10 O5 C11 116.18(13) . .
C5 C1 C2 106.03(14) . .
C5 C1 S1 110.10(11) . .
C2 C1 S1 107.59(11) . .
C5 C1 H1 111.0 . .
C2 C1 H1 111.0 . .
S1 C1 H1 111.0 . .
C4 C3 C8 116.46(17) . .
C4 C3 C2 109.03(15) . .
C8 C3 C2 104.57(16) . .
C4 C3 H3 108.8 . .
C8 C3 H3 108.8 . .
C2 C3 H3 108.8 . .
C10 C2 C1 115.00(14) . .
C10 C2 C3 112.00(13) . .
C1 C2 C3 109.15(14) . .
C10 C2 C6 110.26(14) . .
C1 C2 C6 104.63(13) . .
C3 C2 C6 105.10(14) . .
C3 C4 S1 105.38(13) . .
C3 C4 H4A 110.7 . .
S1 C4 H4A 110.7 . .
C3 C4 H4B 110.7 . .
S1 C4 H4B 110.7 . .
H4A C4 H4B 108.8 . .
O3 C5 O4 121.86(16) . .
O3 C5 C1 127.85(17) . .
O4 C5 C1 110.28(14) . .
O4 C6 C9 106.23(16) . .
O4 C6 C7 107.51(15) . .
C9 C6 C7 115.80(18) . .
O4 C6 C2 104.61(13) . .
C9 C6 C2 117.01(16) . .
C7 C6 C2 104.82(17) . .
C8 C7 C6 104.43(16) . .
C8 C7 H7A 110.9 . .
C6 C7 H7A 110.9 . .
C8 C7 H7B 110.9 . .
C6 C7 H7B 110.9 . .
H7A C7 H7B 108.9 . .
C7 C8 C3 102.71(17) . .
C7 C8 H8A 111.2 . .
C3 C8 H8A 111.2 . .
C7 C8 H8B 111.2 . .
C3 C8 H8B 111.2 . .
H8A C8 H8B 109.1 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O6 C10 O5 124.63(15) . .
O6 C10 C2 123.76(16) . .
O5 C10 C2 111.48(13) . .
O5 C11 C12 106.23(15) . .
O5 C11 H11A 110.5 . .
C12 C11 H11A 110.5 . .
O5 C11 H11B 110.5 . .
C12 C11 H11B 110.5 . .
H11A C11 H11B 108.7 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4370(14) .
S1 O2 1.4399(15) .
S1 C4 1.7741(19) .
S1 C1 1.8230(17) .
O3 C5 1.192(2) .
O4 C5 1.352(2) .
O4 C6 1.464(2) .
O5 C10 1.329(2) .
O5 C11 1.453(2) .
O6 C10 1.2052(19) .
C1 C5 1.507(2) .
C1 C2 1.531(2) .
C1 H1 1.0000 .
C3 C4 1.519(3) .
C3 C8 1.530(3) .
C3 C2 1.557(2) .
C3 H3 1.0000 .
C2 C10 1.519(2) .
C2 C6 1.578(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C6 C9 1.510(3) .
C6 C7 1.520(3) .
C7 C8 1.518(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C11 C12 1.496(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
