#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/78/4027838.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_4027838
loop_
_publ_author_name
'Aviran Amir'
'Alon H. Sayer'
'Rostislav Zagalsky'
'Linda J. W. Shimon'
'Bilha Fischer'
_publ_section_title
;
 O,O'-Diester Methylenediphosphonotetrathioate: Synthesis,
 Characterization, and Potential Applications
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              270
_journal_page_last               277
_journal_paper_doi               10.1021/jo301786m
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C5 H10 P2 S6'
_chemical_formula_sum            'C5 H10 P2 S6'
_chemical_formula_weight         324.43
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.8996(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1901(2)
_cell_length_b                   13.8414(2)
_cell_length_c                   10.0300(2)
_cell_measurement_reflns_used    2670
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     1232.96(4)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Collect package (Bruker Nonius)'
_computing_data_reduction        HKL2000
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11012
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0361
_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)+(0.0517P)²+1.6038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2496
_reflns_number_total             2810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301786m_si_002.cif
_cod_data_source_block           aa68
_cod_database_code               4027838
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
S1 S 0.57254(7) 0.28075(4) 0.11113(7) 0.01815(16) Uani 1 1 d .
S2 S 0.58766(7) 0.53081(4) 0.17795(6) 0.01550(15) Uani 1 1 d .
S3 S 0.40648(7) 0.39013(4) 0.33185(7) 0.01679(16) Uani 1 1 d .
S4 S 0.94048(7) 0.44323(5) 0.17327(6) 0.01868(16) Uani 1 1 d .
S5 S 1.10753(7) 0.38062(4) 0.49974(6) 0.01681(16) Uani 1 1 d .
S6 S 0.94428(7) 0.20883(4) 0.30123(7) 0.01770(16) Uani 1 1 d .
P1 P 0.58833(7) 0.38669(4) 0.24176(6) 0.01234(15) Uani 1 1 d .
P2 P 0.92959(6) 0.35873(4) 0.32514(6) 0.01241(15) Uani 1 1 d .
C1 C 0.3889(3) 0.55161(19) 0.1699(3) 0.0184(5) Uani 1 1 d .
H1A H 0.3656 0.6213 0.1565 0.022 Uiso 1 1 calc R
H1B H 0.3248 0.5160 0.0906 0.022 Uiso 1 1 calc R
C2 C 0.3559(3) 0.51749(18) 0.3024(3) 0.0176(5) Uani 1 1 d .
H2A H 0.2476 0.5261 0.2966 0.021 Uiso 1 1 calc R
H2B H 0.4142 0.5566 0.3806 0.021 Uiso 1 1 calc R
C3 C 0.7580(3) 0.37602(18) 0.3831(2) 0.0150(5) Uani 1 1 d .
H3A H 0.7462 0.3207 0.4420 0.018 Uiso 1 1 calc R
H3B H 0.7690 0.4352 0.4404 0.018 Uiso 1 1 calc R
C4 C 1.1568(3) 0.2546(2) 0.5402(3) 0.0210(5) Uani 1 1 d .
H4A H 1.2626 0.2501 0.5957 0.025 Uiso 1 1 calc R
H4B H 1.0914 0.2273 0.5953 0.025 Uiso 1 1 calc R
C5 C 1.1376(3) 0.19744(19) 0.4088(3) 0.0217(5) Uani 1 1 d .
H5A H 1.1606 0.1286 0.4313 0.026 Uiso 1 1 calc R
H5B H 1.2088 0.2215 0.3573 0.026 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'
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
C1 S2 P1 95.04(9)
C2 S3 P1 98.62(8)
C4 S5 P2 98.29(9)
C5 S6 P2 95.68(9)
C3 P1 S1 111.30(9)
C3 P1 S2 104.45(8)
S1 P1 S2 121.19(4)
C3 P1 S3 106.48(8)
S1 P1 S3 112.20(4)
S2 P1 S3 99.79(3)
C3 P2 S4 113.11(8)
C3 P2 S5 105.50(8)
S4 P2 S5 112.52(4)
C3 P2 S6 104.57(8)
S4 P2 S6 119.21(4)
S5 P2 S6 100.36(3)
C2 C1 S2 109.57(17)
C2 C1 H1A 109.8
S2 C1 H1A 109.8
C2 C1 H1B 109.8
S2 C1 H1B 109.8
H1A C1 H1B 108.2
C1 C2 S3 110.08(17)
C1 C2 H2A 109.6
S3 C2 H2A 109.6
C1 C2 H2B 109.6
S3 C2 H2B 109.6
H2A C2 H2B 108.2
P1 C3 P2 113.40(13)
P1 C3 H3A 108.9
P2 C3 H3A 108.9
P1 C3 H3B 108.9
P2 C3 H3B 108.9
H3A C3 H3B 107.7
C5 C4 S5 109.93(18)
C5 C4 H4A 109.7
S5 C4 H4A 109.7
C5 C4 H4B 109.7
S5 C4 H4B 109.7
H4A C4 H4B 108.2
C4 C5 S6 110.35(18)
C4 C5 H5A 109.6
S6 C5 H5A 109.6
C4 C5 H5B 109.6
S6 C5 H5B 109.6
H5A C5 H5B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 P1 1.9468(9)
S2 C1 1.830(2)
S2 P1 2.0946(8)
S3 C2 1.828(3)
S3 P1 2.0949(8)
S4 P2 1.9433(9)
S5 C4 1.822(3)
S5 P2 2.0881(8)
S6 C5 1.832(3)
S6 P2 2.0970(9)
P1 C3 1.824(2)
P2 C3 1.832(2)
C1 C2 1.513(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.508(4)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
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
C1 S2 P1 C3 -133.91(12)
C1 S2 P1 S1 99.61(9)
C1 S2 P1 S3 -23.93(9)
C2 S3 P1 C3 107.95(12)
C2 S3 P1 S1 -130.06(9)
C2 S3 P1 S2 -0.41(9)
C4 S5 P2 C3 102.17(12)
C4 S5 P2 S4 -134.05(9)
C4 S5 P2 S6 -6.25(10)
C5 S6 P2 C3 -127.24(12)
C5 S6 P2 S4 105.18(10)
C5 S6 P2 S5 -18.08(10)
P1 S2 C1 C2 49.49(18)
S2 C1 C2 S3 -56.9(2)
P1 S3 C2 C1 32.23(18)
S1 P1 C3 P2 51.25(14)
S2 P1 C3 P2 -81.16(13)
S3 P1 C3 P2 173.81(10)
S4 P2 C3 P1 43.91(15)
S5 P2 C3 P1 167.31(10)
S6 P2 C3 P1 -87.33(13)
P2 S5 C4 C5 36.37(19)
S5 C4 C5 S6 -57.0(2)
P2 S6 C5 C4 45.28(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71527760
