#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/82/2018286.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_2018286
loop_
_publ_author_name
'Arumugam, Kuppuswamy'
'Clark, Daniel Seth'
'Mague, Joel T.'
'Donahue, James P.'
_publ_section_title
;
 The dithiolene ligand and tetrathiafulvalene precursor molecules
 4,5-bis(bromomethyl)-1,3-dithiol-2-one and
 4,5-bis[(dihydroxyphosphoryl)methyl]-1,3-dithiol-2-one
;
_journal_coeditor_code           FN3090
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o446
_journal_page_last               o449
_journal_paper_doi               10.1107/S0108270111040431
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H8 O7 P2 S2'
_chemical_formula_moiety         'C5 H8 O7 P2 S2'
_chemical_formula_sum            'C5 H8 O7 P2 S2'
_chemical_formula_weight         306.17
_chemical_name_systematic
;
4,5-bis[(dihydroxyphosphoryl)methyl]-1,3-dithiol-2-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.188(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.078(3)
_cell_length_b                   8.1736(14)
_cell_length_c                   8.3628(15)
_cell_measurement_reflns_used    6382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.74
_cell_volume                     1017.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008a)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008a)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXI CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8625
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_correction_T_min  0.8290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick 2008b)'
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0335P)²+1.4614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0686
_reflns_number_gt                1196
_reflns_number_total             1269
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL II in C2/c
CELL 0.71073  15.0777   8.1736   8.3628  90.000  99.188  90.000
ZERR    4.00   0.0026   0.0014   0.0015   0.000   0.002   0.000
LATT 7
SYMM -X, Y, 0.5-Z
SFAC C  H  O  P  S
UNIT 20  32  28  8  8
L.S. 6
BOND $H
ACTA
EQIV $1 x, -y, 0.5+z
EQIV $2 0.5-x, 0.5+y, 1.5-z
HTAB O1 O3_$1
HTAB O2 O3_$2
FMAP 2
PLAN 5
SIZE 0.055 0.222 0.228
TEMP -173
WGHT    0.033500    1.461400
FVAR       0.15786
MOLE 1
P1    4    0.324030    0.139637    0.708022    11.00000    0.01292    0.01361 =
         0.01207   -0.00057    0.00219   -0.00119
S1    5    0.417301    0.552573    0.630651    11.00000    0.01629    0.01379 =
         0.02070    0.00322    0.00258    0.00286
O1    3    0.363478    0.119391    0.889249    11.00000    0.01939    0.02096 =
         0.01203    0.00190    0.00182   -0.00266
AFIX   3
H1O   2    0.332835    0.081567    0.959145    11.00000   -1.20000
AFIX   0
O2    3    0.248444    0.268620    0.686761    11.00000    0.01739    0.02356 =
         0.01771   -0.00341    0.00162    0.00556
AFIX   3
H2O   2    0.246091    0.334334    0.763972    11.00000   -1.20000
AFIX   0
O3    3    0.288739   -0.015735    0.623263    11.00000    0.02041    0.01584 =
         0.01623   -0.00336    0.00473   -0.00602
O4    3    0.500000    0.821562    0.750000    10.50000    0.03463    0.01283 =
         0.03375    0.00000    0.00856    0.00000
C1    1    0.416380    0.212555    0.616698    11.00000    0.01376    0.01525 =
         0.01249   -0.00102    0.00235   -0.00167
AFIX  23
H1A   2    0.461276    0.123708    0.620226    11.00000   -1.20000
H1B   2    0.394153    0.237047    0.501321    11.00000   -1.20000
AFIX   0
C2    1    0.462507    0.362195    0.694180    11.00000    0.01373    0.01201 =
         0.01385    0.00107    0.00474    0.00045
C3    1    0.500000    0.673920    0.750000    10.50000    0.02013    0.01568 =
         0.02136    0.00000    0.00764    0.00000
HKLF 4
REM  JPD225_0m in C2/c
REM R1 =  0.0240 for   1196 Fo > 4sig(Fo)  and  0.0254 for all   1269 data
REM     74 parameters refined using      0 restraints
END
WGHT      0.0337      1.4472
REM Highest difference peak  0.484,  deepest hole -0.338,  1-sigma level  0.065
Q1    1   0.3751  0.1789  0.6645  11.00000  0.05    0.48
Q2    1   0.3018  0.0578  0.6480  11.00000  0.05    0.43
Q3    1   0.3402  0.1340  0.8030  11.00000  0.05    0.42
Q4    1   0.4393  0.2805  0.6570  11.00000  0.05    0.39
Q5    1   0.5478  0.6245  0.8061  11.00000  0.05    0.38
;
_cod_data_source_file            fn3090.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018286
_cod_database_fobs_code          2018286
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
P P1 0.32403(2) 0.13964(4) 0.70802(4) 0.01285(12) Uani d . 1 1
S S1 0.41730(3) 0.55257(4) 0.63065(5) 0.01697(12) Uani d . 1 1
O O1 0.36348(8) 0.11939(13) 0.88925(13) 0.0175(2) Uani d . 1 1
H H1O 0.3328 0.0816 0.9591 0.021 Uiso d R 1 1
O O2 0.24844(7) 0.26862(14) 0.68676(13) 0.0197(2) Uani d . 1 1
H H2O 0.2461 0.3343 0.7640 0.024 Uiso d R 1 1
O O3 0.28874(8) -0.01573(13) 0.62326(13) 0.0173(2) Uani d . 1 1
O O4 0.5000 0.8216(2) 0.7500 0.0267(4) Uani d S 1 2
C C1 0.41638(9) 0.21256(18) 0.61670(16) 0.0138(3) Uani d . 1 1
H H1A 0.4613 0.1237 0.6202 0.017 Uiso calc R 1 1
H H1B 0.3942 0.2370 0.5013 0.017 Uiso calc R 1 1
C C2 0.46251(10) 0.36220(17) 0.69418(17) 0.0129(3) Uani d . 1 1
C C3 0.5000 0.6739(3) 0.7500 0.0186(4) Uani d S 1 2
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
P1 0.0129(2) 0.0136(2) 0.01207(19) -0.00119(12) 0.00219(14) -0.00057(12)
S1 0.0163(2) 0.01379(19) 0.0207(2) 0.00286(13) 0.00258(14) 0.00322(13)
O1 0.0194(6) 0.0210(6) 0.0120(5) -0.0027(4) 0.0018(4) 0.0019(4)
O2 0.0174(5) 0.0236(6) 0.0177(5) 0.0056(4) 0.0016(4) -0.0034(4)
O3 0.0204(5) 0.0158(5) 0.0162(5) -0.0060(4) 0.0047(4) -0.0034(4)
O4 0.0346(10) 0.0128(7) 0.0337(9) 0.000 0.0086(8) 0.000
C1 0.0138(6) 0.0152(7) 0.0125(6) -0.0017(5) 0.0023(5) -0.0010(5)
C2 0.0137(7) 0.0120(6) 0.0139(6) 0.0005(5) 0.0047(5) 0.0011(5)
C3 0.0201(10) 0.0157(10) 0.0214(10) 0.000 0.0076(8) 0.000
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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O3 P1 O2 . . 108.82(7)
O3 P1 O1 . . 114.96(6)
O2 P1 O1 . . 110.35(6)
O3 P1 C1 . . 108.61(7)
O2 P1 C1 . . 109.48(7)
O1 P1 C1 . . 104.46(7)
C2 S1 C3 . . 97.01(8)
P1 O1 H1O . . 122.8
P1 O2 H2O . . 117.8
C2 C1 P1 . . 115.11(10)
C2 C1 H1A . . 108.5
P1 C1 H1A . . 108.5
C2 C1 H1B . . 108.5
P1 C1 H1B . . 108.5
H1A C1 H1B . . 107.5
C2 C2 C1 2_656 . 125.37(8)
C2 C2 S1 2_656 . 117.03(5)
C1 C2 S1 . . 117.57(10)
O4 C3 S1 . . 124.05(6)
S1 C3 S1 . 2_656 111.89(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
P1 O3 . 1.5093(11)
P1 O2 . 1.5418(12)
P1 O1 . 1.5460(11)
P1 C1 . 1.7936(15)
S1 C2 . 1.7472(15)
S1 C3 . 1.7712(13)
O1 H1O . 0.8585
O2 H2O . 0.8450
O4 C3 . 1.207(3)
C1 C2 . 1.5019(19)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 C2 2_656 1.346(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O O3 6_556 0.86 1.70 2.5538(16) 170
O2 H2O O3 4_556 0.84 1.68 2.4959(16) 161
