#------------------------------------------------------------------------------
#$Date: 2018-01-30 09:15:35 +0200 (Tue, 30 Jan 2018) $
#$Revision: 205881 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242361.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_2242361
loop_
_publ_author_name
'Przychodzeń, Witold'
'Chojnacki, Jarosław'
_publ_section_title
;
 Crystal structures of eight- and ten-membered cyclic
 bisanisylphosphonothioyl disulfanes and comparison with their
 P-ferrocenyl analogues
;
_journal_coeditor_code           ZP2026
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              212
_journal_page_last               216
_journal_paper_doi               10.1107/S2056989018001068
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C16 H18 O4 P2 S4'
_chemical_formula_moiety         'C16 H18 O4 P2 S4'
_chemical_formula_sum            'C16 H18 O4 P2 S4'
_chemical_formula_weight         464.48
_chemical_name_systematic
2,5-Bis(4-methoxyphenyl)-1,6,3,4,2λ⁵,5λ⁵-dioxadithiadiphosphocane-2,5-dithione
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2415(3)
_cell_length_b                   7.2415(3)
_cell_length_c                   39.516(2)
_cell_measurement_reflns_used    6759
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.4367
_cell_measurement_theta_min      2.0556
_cell_volume                     2072.19(16)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.1883
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '4-axis κ geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction KM-4 CCD'
_diffrn_measurement_method       'ω scans, 0.40 deg width'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            14211
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         2.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.216
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.45(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0514P)²+0.5163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                1839
_reflns_number_total             2019
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zp2026sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        2072.2(2)
_cod_database_code               2242361
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-x+1/2, y+1/2, -z+3/4'
'-y, -x, -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_occupancy
P P1 0.93887(12) 0.21832(13) 0.04117(2) 0.0424(2) Uani d 1
S S1 0.84270(13) 0.04364(17) 0.00256(2) 0.0584(3) Uani d 1
S S2 0.79007(17) 0.43697(17) 0.03709(3) 0.0715(4) Uani d 1
O O1 1.1556(3) 0.2344(3) 0.03669(5) 0.0424(6) Uani d 1
O O2 0.8974(4) -0.1523(4) 0.17469(6) 0.0552(7) Uani d 1
C C1 1.2424(5) 0.3553(5) 0.01202(8) 0.0450(8) Uani d 1
H H1A 1.3209 0.4439 0.0235 0.054 Uiso calc 1
H H1B 1.1485 0.4228 -0.0004 0.054 Uiso calc 1
C C10 0.9277(5) 0.1007(5) 0.08087(8) 0.0412(7) Uani d 1
C C11 1.0238(5) -0.0610(6) 0.08670(9) 0.0576(10) Uani d 1
H H11 1.0949 -0.1113 0.0694 0.069 Uiso calc 1
C C12 1.0170(6) -0.1496(6) 0.11749(9) 0.0584(10) Uani d 1
H H12 1.082 -0.2589 0.1207 0.07 Uiso calc 1
C C13 0.9144(5) -0.0768(5) 0.14352(7) 0.0434(8) Uani d 1
C C14 0.8206(6) 0.0864(6) 0.13813(9) 0.0555(10) Uani d 1
H H14 0.7529 0.1384 0.1557 0.067 Uiso calc 1
C C15 0.8252(6) 0.1736(5) 0.10720(9) 0.0526(9) Uani d 1
H H15 0.759 0.2823 0.104 0.063 Uiso calc 1
C C16 1.0028(6) -0.3130(6) 0.18232(11) 0.0672(12) Uani d 1
H H16A 0.9613 -0.4138 0.1685 0.101 Uiso calc 1
H H16B 0.9871 -0.3442 0.2058 0.101 Uiso calc 1
H H16C 1.1309 -0.2894 0.1779 0.101 Uiso calc 1
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O1 P1 C10 . . 100.26(14)
O1 P1 S2 . . 119.05(11)
C10 P1 S2 . . 116.15(13)
O1 P1 S1 . . 106.97(9)
C10 P1 S1 . . 109.61(12)
S2 P1 S1 . . 104.44(6)
S1 S1 P1 6_645 . 105.17(6)
C1 O1 P1 . . 123.2(2)
C13 O2 C16 . . 118.3(3)
O1 C1 C1 . 6_645 109.5(3)
O1 C1 H1A . . 109.8
C1 C1 H1A 6_645 . 109.8
O1 C1 H1B . . 109.8
C1 C1 H1B 6_645 . 109.8
H1A C1 H1B . . 108.2
C11 C10 C15 . . 117.9(3)
C11 C10 P1 . . 121.8(3)
C15 C10 P1 . . 120.2(3)
C12 C11 C10 . . 121.6(3)
C12 C11 H11 . . 119.2
C10 C11 H11 . . 119.2
C13 C12 C11 . . 120.2(4)
C13 C12 H12 . . 119.9
C11 C12 H12 . . 119.9
O2 C13 C12 . . 125.1(3)
O2 C13 C14 . . 116.2(3)
C12 C13 C14 . . 118.6(3)
C15 C14 C13 . . 121.2(3)
C15 C14 H14 . . 119.4
C13 C14 H14 . . 119.4
C14 C15 C10 . . 120.4(3)
C14 C15 H15 . . 119.8
C10 C15 H15 . . 119.8
O2 C16 H16A . . 109.5
O2 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
O2 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
P1 O1 . 1.584(2)
P1 C10 . 1.787(3)
P1 S2 . 1.9220(14)
P1 S1 . 2.1006(13)
S1 S1 6_645 2.068(2)
O1 C1 . 1.453(4)
O2 C13 . 1.353(4)
O2 C16 . 1.424(5)
C1 C1 6_645 1.496(7)
C1 H1A . 0.97
C1 H1B . 0.97
C10 C11 . 1.382(5)
C10 C15 . 1.383(5)
C11 C12 . 1.376(5)
C11 H11 . 0.93
C12 C13 . 1.374(5)
C12 H12 . 0.93
C13 C14 . 1.380(5)
C14 C15 . 1.376(5)
C14 H14 . 0.93
C15 H15 . 0.93
C16 H16A . 0.96
C16 H16B . 0.96
C16 H16C . 0.96
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
_geom_hbond_publ_flag
C1 H1A O2 5_555 0.970 2.603 3.4843(2) 151 yes
C14 H14 O1 5_455 0.930 2.550 3.4548(2) 163 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_site_symmetry_4
_geom_torsion
C10 P1 O1 C1 . -165.8(2)
S2 P1 O1 C1 . -38.0(3)
S1 P1 O1 C1 . 79.8(2)
P1 O1 C1 C1 6_645 -119.6(3)
O1 P1 C10 C11 . -52.2(3)
S2 P1 C10 C11 . 178.1(3)
S1 P1 C10 C11 . 60.1(3)
O1 P1 C10 C15 . 125.9(3)
S2 P1 C10 C15 . -3.8(4)
S1 P1 C10 C15 . -121.9(3)
C15 C10 C11 C12 . 0.9(6)
P1 C10 C11 C12 . 179.0(3)
C10 C11 C12 C13 . -0.6(7)
C16 O2 C13 C12 . 4.4(6)
C16 O2 C13 C14 . -175.3(4)
C11 C12 C13 O2 . 179.8(4)
C11 C12 C13 C14 . -0.5(6)
O2 C13 C14 C15 . -178.8(4)
C12 C13 C14 C15 . 1.5(6)
C13 C14 C15 C10 . -1.2(7)
C11 C10 C15 C14 . 0.1(6)
P1 C10 C15 C14 . -178.1(3)

_cod_database_fobs_code 2242361
