#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/96/2009693.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_2009693
loop_
_publ_author_name
'Kelkar, Shripad V.'
'Kilburn, Jeremy D.'
'Webster, Michael'
_publ_section_title
;Diethyl
 5,6-dihydro-2H-1,3-dithiolo[4,5-b][1,4]dithiin-2-ylphosphonate,
 C₉H₁₅O₃PS₄
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              724
_journal_page_last               726
_journal_paper_doi               10.1107/S0108270193011941
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C9 H15 O3 P1 S4'
_chemical_formula_sum            'C9 H15 O3 P S4'
_chemical_formula_weight         330.43
_chemical_name_systematic
;
2-Diethoxyphosphoryl-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiin
;
_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                90.00
_cell_angle_beta                 99.280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.197(6)
_cell_length_b                   9.141(2)
_cell_length_c                   19.5400(10)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     2855.2(12)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 software'
_computing_molecular_graphics    'ORTEPII  (Johnson, 1976)'
_computing_structure_refinement  'SHELX76  (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86  (Sheldrick, 1985)'
_diffrn_ambient_temperature      150
_diffrn_measurement_device
;                                 Enraf-Nonius FAST area
                                  detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14911
_diffrn_reflns_theta_max         30.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.74
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       'air-stable blocks'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.27
_refine_ls_goodness_of_fit_obs   0.31
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0265
_refine_ls_shift/esd_max         0.1
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0015F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0367
_reflns_number_observed          3607
_reflns_number_total             7339
_reflns_observed_criterion       F>3\s(F)
_cod_data_source_file            ha1077.cif
_cod_data_source_block           NUM_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F) + 0.0015F^2^]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^(F) +
0.0015F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2855.2(1.2)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_original_formula_sum        'C9 H15 O3 P1 S4'
_cod_database_code               2009693
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2+x,1/2-y,z
1/2-x,1/2+y,-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_thermal_displace_type
_atom_site_calc_flag
S1A 0.12926(4) 0.59609(6) 0.03763(4) 0.0195(3) Uani d
S2A 0.18492(4) 0.32845(7) 0.16330(4) 0.0227(3) Uani d
S3A 0.34226(4) 0.30766(6) 0.10434(4) 0.0187(3) Uani d
S4A 0.29113(4) 0.52483(6) -0.00605(3) 0.0171(3) Uani d
P1A 0.44751(4) 0.58225(6) 0.09249(4) 0.0147(3) Uani d
O1A 0.48190(10) 0.6772(2) 0.04350(10) 0.0203(8) Uani d
O2A 0.51100(10) 0.4880(2) 0.14340(10) 0.0230(9) Uani d
O3A 0.39710(10) 0.6660(2) 0.14280(10) 0.0188(8) Uani d
C1A 0.06470(10) 0.5128(3) 0.0949(2) 0.0225(13) Uani d
C2A 0.08330(10) 0.3531(3) 0.11120(10) 0.0220(12) Uani d
C3A 0.24500(10) 0.3957(2) 0.10400(10) 0.0171(12) Uani d
C4A 0.22240(10) 0.4951(2) 0.05450(10) 0.0150(11) Uani d
C5A 0.38100(10) 0.4411(2) 0.04810(10) 0.0155(11) Uani d
C6A 0.5659(2) 0.5493(3) 0.2030(2) 0.0293(14) Uani d
C7A 0.6482(2) 0.5910(3) 0.1851(2) 0.0313(15) Uani d
C8A 0.3511(2) 0.8007(2) 0.12170(10) 0.0213(12) Uani d
C9A 0.3711(2) 0.9109(3) 0.1789(2) 0.0271(14) Uani d
S1B 0.86313(4) 0.58945(7) 0.46053(4) 0.0212(3) Uani d
S2B 0.79525(4) 0.36666(8) 0.32297(4) 0.0267(3) Uani d
S3B 0.64058(4) 0.32970(6) 0.38656(4) 0.0223(3) Uani d
S4B 0.70227(4) 0.51688(7) 0.50683(4) 0.0215(3) Uani d
P1B 0.54712(4) 0.60806(6) 0.41364(4) 0.0164(3) Uani d
O1B 0.52410(10) 0.7059(2) 0.46710(10) 0.0226(9) Uani d
O2B 0.47260(10) 0.5288(2) 0.36660(10) 0.0225(9) Uani d
O3B 0.59420(10) 0.6850(2) 0.35940(10) 0.0192(8) Uani d
C1B 0.9293(2) 0.4909(3) 0.4086(2) 0.0285(14) Uani d
C2B 0.8955(2) 0.3468(3) 0.3790(2) 0.0264(14) Uani d
C3B 0.73810(10) 0.4159(2) 0.38740(10) 0.0183(12) Uani d
C4B 0.76660(10) 0.4994(2) 0.44240(10) 0.0169(12) Uani d
C5B 0.60840(10) 0.4533(2) 0.45010(10) 0.0185(12) Uani d
C6B 0.4064(2) 0.6175(3) 0.3270(2) 0.0268(13) Uani d
C7B 0.3455(2) 0.5194(3) 0.2857(2) 0.0357(16) Uani d
C8B 0.6462(2) 0.8150(3) 0.3766(2) 0.0259(13) Uani d
C9B 0.6251(2) 0.9239(3) 0.3197(2) 0.0342(15) Uani d
H1A 0.0079 0.5207 0.0736 0.035(2) Uiso calc
H2A 0.0729 0.5657 0.1373 0.035(2) Uiso calc
H3A 0.0419 0.3154 0.1357 0.035(2) Uiso calc
H4A 0.0816 0.3010 0.0689 0.035(2) Uiso calc
H5A 0.4158 0.3892 0.0217 0.035(2) Uiso calc
H6A 0.5401 0.6337 0.2186 0.035(2) Uiso calc
H7A 0.5742 0.4784 0.2390 0.035(2) Uiso calc
H8A 0.6841 0.6246 0.2253 0.035(2) Uiso calc
H9A 0.6420 0.6655 0.1507 0.035(2) Uiso calc
H10A 0.6718 0.5063 0.1676 0.035(2) Uiso calc
H11A 0.3676 0.8376 0.0804 0.035(2) Uiso calc
H12A 0.2927 0.7813 0.1136 0.035(2) Uiso calc
H13A 0.3415 0.9978 0.1637 0.035(2) Uiso calc
H14A 0.4294 0.9305 0.1872 0.035(2) Uiso calc
H15A 0.3540 0.8779 0.2206 0.035(2) Uiso calc
H1B 0.9816 0.4728 0.4371 0.035(2) Uiso calc
H2B 0.9375 0.5522 0.3710 0.035(2) Uiso calc
H3B 0.9344 0.3054 0.3530 0.035(2) Uiso calc
H4B 0.8888 0.2832 0.4162 0.035(2) Uiso calc
H5B 0.5723 0.3997 0.4747 0.035(2) Uiso calc
H6B 0.3792 0.6731 0.3579 0.035(2) Uiso calc
H7B 0.4299 0.6816 0.2971 0.035(2) Uiso calc
H8B 0.3028 0.5763 0.2592 0.035(2) Uiso calc
H9B 0.3212 0.4528 0.3140 0.035(2) Uiso calc
H10B 0.3748 0.4663 0.2553 0.035(2) Uiso calc
H11B 0.6354 0.8556 0.4190 0.035(2) Uiso calc
H12B 0.7036 0.7891 0.3810 0.035(2) Uiso calc
H13B 0.6603 1.0066 0.3306 0.035(2) Uiso calc
H14B 0.5684 0.9523 0.3178 0.035(2) Uiso calc
H15B 0.6329 0.8855 0.2760 0.035(2) Uiso calc
loop_
_atom_type_symbol
_atom_type_scat_source
C 'SHELX76 (Sheldrick, 1976)'
H 'SHELX76 (Sheldrick, 1976)'
O 'SHELX76 (Sheldrick, 1976)'
P 'SHELX76 (Sheldrick, 1976)'
S 'SHELX76 (Sheldrick, 1976)'
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
S1A C1A C2A 114.8(2) no
C1A C2A S2A 111.8(2) no
C2A S2A C3A 97.90(10) yes
S2A C3A C4A 127.2(2) no
C3A C4A S1A 128.5(2) no
C4A S1A C1A 103.10(10) yes
S1A C4A S4A 114.10(10) no
S2A C3A S3A 115.50(10) no
S4A C4A C3A 117.3(2) yes
C4A C3A S3A 117.0(2) yes
C3A S3A C5A 95.00(10) yes
S3A C5A S4A 108.10(10) yes
C5A S4A C4A 94.40(10) yes
P1A C5A S3A 115.20(10) no
P1A C5A S4A 109.70(10) no
C5A P1A O1A 111.60(10) no
C5A P1A O2A 101.00(10) no
C5A P1A O3A 108.50(10) no
O1A P1A O2A 117.40(10) no
O1A P1A O3A 114.20(10) no
O2A P1A O3A 102.90(10) no
P1A O2A C6A 123.2(2) no
P1A O3A C8A 121.6(2) no
O2A C6A C7A 111.4(2) no
O3A C8A C9A 108.4(2) no
S1B C1B C2B 115.7(2) no
C1B C2B S2B 112.2(2) no
C2B S2B C3B 96.80(10) yes
S2B C3B C4B 125.0(2) no
C3B C4B S1B 127.7(2) no
C4B S1B C1B 103.90(10) yes
S1B C4B S4B 115.00(10) no
S2B C3B S3B 117.40(10) no
S4B C4B C3B 117.2(2) yes
C4B C3B S3B 117.0(2) yes
C3B S3B C5B 94.10(10) yes
S3B C5B S4B 108.10(10) yes
C5B S4B C4B 93.90(10) yes
P1B C5B S3B 114.70(10) no
P1B C5B S4B 109.90(10) no
C5B P1B O1B 112.50(10) no
C5B P1B O2B 101.00(10) no
C5B P1B O3B 108.70(10) no
O1B P1B O2B 116.00(10) no
O1B P1B O3B 114.40(10) no
O2B P1B O3B 102.90(10) no
P1B O2B C6B 118.8(2) no
P1B O3B C8B 122.3(2) no
O2B C6B C7B 108.8(2) no
O3B C8B C9B 108.5(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1A C1A . . 1.817(3) yes
S1A C4A . . 1.753(2) yes
S2A C2A . . 1.805(3) yes
S2A C3A . . 1.742(3) yes
S3A C3A . . 1.767(2) yes
S3A C5A . . 1.820(2) yes
S4A C4A . . 1.772(3) yes
S4A C5A . . 1.825(2) yes
C1A C2A . . 1.514(3) yes
C3A C4A . . 1.334(3) yes
P1A C5A . . 1.810(2) yes
P1A O1A . . 1.466(2) yes
P1A O2A . . 1.568(2) no
P1A O3A . . 1.574(2) no
O2A C6A . . 1.458(3) no
C6A C7A . . 1.483(4) no
O3A C8A . . 1.464(3) no
C8A C9A . . 1.502(4) no
S1B C1B . . 1.828(3) yes
S1B C4B . . 1.752(2) yes
S2B C2B . . 1.815(3) yes
S2B C3B . . 1.737(3) yes
S3B C3B . . 1.762(2) yes
S3B C5B . . 1.816(3) yes
S4B C4B . . 1.766(3) yes
S4B C5B . . 1.827(2) yes
C1B C2B . . 1.506(4) yes
C3B C4B . . 1.339(4) yes
P1B C5B . . 1.807(2) yes
P1B O1B . . 1.468(2) yes
P1B O2B . . 1.570(2) no
P1B O3B . . 1.568(2) no
O2B C6B . . 1.463(3) no
C6B C7B . . 1.474(4) no
O3B C8B . . 1.463(3) no
C8B C9B . . 1.490(4) no
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
P1A O2A C6A C7A -92.3(3) yes
P1A O3A C8A C9A -133.4(2) yes
O1A P1A C5A S4A -62.9(2) no
O1A P1A C5A S3A 175.00(10) no
S1A C1A C2A S2A 67.8(2) no
P1B O2B C6B C7B 178.3(2) yes
P1B O3B C8B C9B -133.9(2) yes
O1B P1B C5B S4B -56.9(2) no
O1B P1B C5B S3B -178.9(2) no
S1B C1B C2B S2B 59.3(2) no
