#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206879.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_2206879
loop_
_publ_author_name
'Wieczorek, Wanda'
'Trzesowska, Agata'
'Kruszynski, Rafal'
_publ_section_title
;4-Phenyl-14,18-dithia-4-phosphatricyclo[18.4.0.0^7,12^]tetracosa-2,5-dien-4-one
 benzene hemisolvate
;
_journal_coeditor_code           BT6735
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3304
_journal_page_last               o3306
_journal_paper_doi               10.1107/S1600536805029181
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C27 H27 O P S2, 0.5C6 H6'
_chemical_formula_moiety         'C27 H27 O P S2, 0.5C6 H6'
_chemical_formula_sum            'C30 H30 O P S2'
_chemical_formula_weight         501.67
_chemical_name_systematic
;
4-Phenyl-14,18-dithia-4-phosphatricyclo[18.4.0.0^7,12^]tetracosa-2,5-
dien-4-one benzene solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.920(10)
_cell_angle_beta                 91.520(10)
_cell_angle_gamma                100.830(10)
_cell_formula_units_Z            2
_cell_length_a                   5.4920(10)
_cell_length_b                   14.0980(10)
_cell_length_c                   18.0560(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291.3(3)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      5.0
_cell_volume                     1340.4(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics
;
MERCURY (Version 1.4; Bruno et al., 2002) and ORTEP-3 (Windows Version
1.062;  Farrugia 1997)
;
_computing_publication_material  'SHELXL97  and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291.3(3)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6116
_diffrn_reflns_theta_full        74.95
_diffrn_reflns_theta_max         74.95
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        11.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.513
_exptl_absorpt_correction_T_max  0.507
_exptl_absorpt_correction_T_min  0.473
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 1999)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.564
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1002P)²+0.714P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                5155
_reflns_number_total             5512
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6735.cif
_cod_data_source_block           I
_cod_database_code               2206879
_cod_database_fobs_code          2206879
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
P1 0.44869(9) 0.25594(4) 0.83092(3) 0.04345(18) Uani d . 1 P
S1 0.31456(17) 0.33957(6) 0.50919(4) 0.0727(2) Uani d . 1 S
S2 -0.16347(15) 0.04734(5) 0.58578(4) 0.0663(2) Uani d . 1 S
O1 0.7059(3) 0.26417(15) 0.80580(12) 0.0623(5) Uani d . 1 O
C1 0.2688(4) 0.32519(17) 0.78772(12) 0.0438(5) Uani d . 1 C
H1 0.1014 0.3215 0.8031 0.053 Uiso d R 1 H
C2 0.3731(4) 0.38156(17) 0.74235(12) 0.0459(5) Uani d . 1 C
H2 0.5433 0.3846 0.7296 0.055 Uiso d R 1 H
C3 0.2556(4) 0.45207(17) 0.71133(13) 0.0459(5) Uani d . 1 C
C4 0.0814(5) 0.49724(19) 0.75230(14) 0.0530(5) Uani d . 1 C
H4 0.0351 0.4795 0.7975 0.064 Uiso calc R 1 H
C5 -0.0240(6) 0.5673(2) 0.72771(17) 0.0625(6) Uani d . 1 C
H5 -0.1406 0.5962 0.7559 0.075 Uiso calc R 1 H
C6 0.0447(6) 0.5945(2) 0.66077(18) 0.0682(7) Uani d . 1 C
H6 -0.0219 0.6432 0.6444 0.082 Uiso calc R 1 H
C7 0.2107(6) 0.5496(2) 0.61873(16) 0.0646(7) Uani d . 1 C
H7 0.2523 0.5672 0.5731 0.078 Uiso calc R 1 H
C8 0.3200(5) 0.47791(19) 0.64224(14) 0.0524(5) Uani d . 1 C
C9 0.4848(5) 0.4263(2) 0.59060(15) 0.0612(6) Uani d . 1 C
H9A 0.5760 0.3912 0.6188 0.073 Uiso calc R 1 H
H9B 0.6047 0.4753 0.5730 0.073 Uiso calc R 1 H
C10 0.1007(6) 0.2622(3) 0.55788(18) 0.0751(8) Uani d . 1 C
H10A 0.1917 0.2228 0.5820 0.090 Uiso calc R 1 H
H10B 0.0285 0.3041 0.5973 0.090 Uiso calc R 1 H
C11 -0.1018(7) 0.1955(3) 0.5048(2) 0.0793(9) Uani d . 1 C
H11A -0.0307 0.1498 0.4680 0.095 Uiso calc R 1 H
H11B -0.1839 0.2345 0.4776 0.095 Uiso calc R 1 H
C12 -0.2915(6) 0.1375(3) 0.5465(2) 0.0818(9) Uani d . 1 C
H12A -0.4338 0.1037 0.5118 0.098 Uiso calc R 1 H
H12B -0.3485 0.1829 0.5872 0.098 Uiso calc R 1 H
C13 -0.3635(5) 0.0334(2) 0.66203(16) 0.0637(7) Uani d . 1 C
H13A -0.3577 0.0971 0.6957 0.076 Uiso calc R 1 H
H13B -0.5337 0.0071 0.6418 0.076 Uiso calc R 1 H
C14 -0.2756(5) -0.0360(2) 0.70469(16) 0.0601(6) Uani d . 1 C
C15 -0.4017(7) -0.1339(3) 0.6910(2) 0.0816(10) Uani d . 1 C
H15 -0.5429 -0.1541 0.6577 0.098 Uiso calc R 1 H
C16 -0.3202(9) -0.2017(3) 0.7263(3) 0.0979(13) Uani d . 1 C
H16 -0.4071 -0.2668 0.7170 0.118 Uiso calc R 1 H
C17 -0.1119(9) -0.1728(3) 0.7748(3) 0.0964(12) Uani d . 1 C
H17 -0.0565 -0.2187 0.7979 0.116 Uiso calc R 1 H
C18 0.0172(7) -0.0763(2) 0.7898(2) 0.0762(8) Uani d . 1 C
H18 0.1583 -0.0576 0.8231 0.091 Uiso calc R 1 H
C19 -0.0623(5) -0.00640(19) 0.75526(15) 0.0573(6) Uani d . 1 C
C20 0.0754(5) 0.09650(18) 0.77219(14) 0.0513(5) Uani d . 1 C
H20 -0.0068 0.1452 0.7467 0.062 Uiso d R 1 H
C21 0.2804(5) 0.13211(18) 0.81524(15) 0.0525(5) Uani d . 1 C
H21 0.3534 0.0977 0.8460 0.063 Uiso d R 1 H
C22 0.4458(4) 0.30653(18) 0.93115(14) 0.0511(5) Uani d . 1 C
C23 0.2419(6) 0.2866(3) 0.97138(18) 0.0800(9) Uani d . 1 C
H23 0.0980 0.2446 0.9471 0.096 Uiso calc R 1 H
C24 0.2487(9) 0.3284(4) 1.0477(2) 0.1027(14) Uani d . 1 C
H24 0.1103 0.3132 1.0748 0.123 Uiso calc R 1 H
C25 0.4538(9) 0.3911(4) 1.0835(2) 0.0980(12) Uani d . 1 C
H25 0.4583 0.4175 1.1352 0.118 Uiso calc R 1 H
C26 0.6530(9) 0.4153(4) 1.0439(2) 0.1137(16) Uani d . 1 C
H26 0.7911 0.4613 1.0678 0.136 Uiso calc R 1 H
C27 0.6518(7) 0.3719(3) 0.96815(19) 0.0845(10) Uani d . 1 C
H27 0.7919 0.3871 0.9417 0.101 Uiso calc R 1 H
C51 0.3077(13) -0.0315(7) 0.0375(5) 0.165(3) Uani d . 1 C
H51 0.1691 -0.0524 0.0628 0.198 Uiso calc R 1 H
C52 0.4245(16) 0.0639(7) 0.0547(5) 0.163(3) Uani d . 1 C
H52 0.3736 0.1074 0.0945 0.196 Uiso calc R 1 H
C53 0.6097(13) 0.0964(5) 0.0159(4) 0.134(2) Uani d . 1 C
H53 0.6819 0.1633 0.0255 0.161 Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
O1 P1 C21 . . 113.51(12) yes
O1 P1 C1 . . 113.10(11) yes
C21 P1 C1 . . 107.95(11) yes
O1 P1 C22 . . 111.75(12) yes
C21 P1 C22 . . 106.03(12) yes
C1 P1 C22 . . 103.80(11) yes
C9 S1 C10 . . 99.52(13) yes
C13 S2 C12 . . 100.59(17) yes
C2 C1 P1 . . 119.89(17) no
C2 C1 H1 . . 125.0 no
P1 C1 H1 . . 114.9 no
C1 C2 C3 . . 125.2(2) no
C1 C2 H2 . . 122.3 no
C3 C2 H2 . . 112.3 no
C4 C3 C8 . . 118.6(2) no
C4 C3 C2 . . 119.6(2) no
C8 C3 C2 . . 121.8(2) no
C5 C4 C3 . . 121.8(2) no
C5 C4 H4 . . 119.1 no
C3 C4 H4 . . 119.1 no
C4 C5 C6 . . 119.5(3) no
C4 C5 H5 . . 120.2 no
C6 C5 H5 . . 120.2 no
C7 C6 C5 . . 119.8(3) no
C7 C6 H6 . . 120.1 no
C5 C6 H6 . . 120.1 no
C6 C7 C8 . . 121.9(3) no
C6 C7 H7 . . 119.1 no
C8 C7 H7 . . 119.1 no
C7 C8 C3 . . 118.4(2) no
C7 C8 C9 . . 118.9(2) no
C3 C8 C9 . . 122.5(2) no
C8 C9 S1 . . 112.82(19) no
C8 C9 H9A . . 109.0 no
S1 C9 H9A . . 109.0 no
C8 C9 H9B . . 109.0 no
S1 C9 H9B . . 109.0 no
H9A C9 H9B . . 107.8 no
C11 C10 S1 . . 111.8(2) no
C11 C10 H10A . . 109.3 no
S1 C10 H10A . . 109.3 no
C11 C10 H10B . . 109.3 no
S1 C10 H10B . . 109.3 no
H10A C10 H10B . . 107.9 no
C10 C11 C12 . . 111.6(3) no
C10 C11 H11A . . 109.3 no
C12 C11 H11A . . 109.3 no
C10 C11 H11B . . 109.3 no
C12 C11 H11B . . 109.3 no
H11A C11 H11B . . 108.0 no
C11 C12 S2 . . 111.8(3) no
C11 C12 H12A . . 109.3 no
S2 C12 H12A . . 109.3 no
C11 C12 H12B . . 109.3 no
S2 C12 H12B . . 109.3 no
H12A C12 H12B . . 107.9 no
C14 C13 S2 . . 108.35(19) no
C14 C13 H13A . . 110.0 no
S2 C13 H13A . . 110.0 no
C14 C13 H13B . . 110.0 no
S2 C13 H13B . . 110.0 no
H13A C13 H13B . . 108.4 no
C15 C14 C19 . . 119.0(3) no
C15 C14 C13 . . 118.9(3) no
C19 C14 C13 . . 122.0(2) no
C16 C15 C14 . . 120.9(3) no
C16 C15 H15 . . 119.5 no
C14 C15 H15 . . 119.5 no
C17 C16 C15 . . 119.9(3) no
C17 C16 H16 . . 120.1 no
C15 C16 H16 . . 120.1 no
C16 C17 C18 . . 120.7(4) no
C16 C17 H17 . . 119.6 no
C18 C17 H17 . . 119.6 no
C17 C18 C19 . . 120.5(3) no
C17 C18 H18 . . 119.8 no
C19 C18 H18 . . 119.8 no
C18 C19 C14 . . 119.0(3) no
C18 C19 C20 . . 120.1(3) no
C14 C19 C20 . . 120.9(2) no
C21 C20 C19 . . 126.8(2) no
C21 C20 H20 . . 118.7 no
C19 C20 H20 . . 114.5 no
C20 C21 P1 . . 125.4(2) no
C20 C21 H21 . . 124.9 no
P1 C21 H21 . . 109.5 no
C23 C22 C27 . . 118.2(3) no
C23 C22 P1 . . 122.7(2) no
C27 C22 P1 . . 119.0(2) no
C22 C23 C24 . . 120.3(3) no
C22 C23 H23 . . 119.8 no
C24 C23 H23 . . 119.8 no
C25 C24 C23 . . 120.7(4) no
C25 C24 H24 . . 119.6 no
C23 C24 H24 . . 119.6 no
C24 C25 C26 . . 119.8(3) no
C24 C25 H25 . . 120.1 no
C26 C25 H25 . . 120.1 no
C25 C26 C27 . . 120.1(4) no
C25 C26 H26 . . 119.9 no
C27 C26 H26 . . 119.9 no
C22 C27 C26 . . 120.7(4) no
C22 C27 H27 . . 119.6 no
C26 C27 H27 . . 119.6 no
C53 C51 C52 2_655 . 120.2(6) no
C53 C51 H51 2_655 . 119.9 no
C52 C51 H51 . . 119.9 no
C53 C52 C51 . . 120.9(7) no
C53 C52 H52 . . 119.6 no
C51 C52 H52 . . 119.6 no
C52 C53 C51 . 2_655 118.8(7) no
C52 C53 H53 . . 120.6 no
C51 C53 H53 2_655 . 120.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . 1.4859(17) yes
P1 C21 . 1.777(3) yes
P1 C1 . 1.781(2) yes
P1 C22 . 1.805(3) yes
S1 C9 . 1.813(3) yes
S1 C10 . 1.819(3) yes
S2 C13 . 1.803(3) yes
S2 C12 . 1.814(4) yes
C1 C2 . 1.324(3) no
C1 H1 . 0.9628 no
C2 C3 . 1.473(3) no
C2 H2 . 0.9637 no
C3 C4 . 1.393(3) no
C3 C8 . 1.406(3) no
C4 C5 . 1.374(4) no
C4 H4 . 0.9300 no
C5 C6 . 1.383(4) no
C5 H5 . 0.9300 no
C6 C7 . 1.365(4) no
C6 H6 . 0.9300 no
C7 C8 . 1.398(4) no
C7 H7 . 0.9300 no
C8 C9 . 1.493(4) no
C9 H9A . 0.9700 no
C9 H9B . 0.9700 no
C10 C11 . 1.490(4) no
C10 H10A . 0.9700 no
C10 H10B . 0.9700 no
C11 C12 . 1.516(5) no
C11 H11A . 0.9700 no
C11 H11B . 0.9700 no
C12 H12A . 0.9700 no
C12 H12B . 0.9700 no
C13 C14 . 1.502(4) no
C13 H13A . 0.9700 no
C13 H13B . 0.9700 no
C14 C15 . 1.392(4) no
C14 C19 . 1.408(4) no
C15 C16 . 1.384(6) no
C15 H15 . 0.9300 no
C16 C17 . 1.366(6) no
C16 H16 . 0.9300 no
C17 C18 . 1.379(5) no
C17 H17 . 0.9300 no
C18 C19 . 1.397(4) no
C18 H18 . 0.9300 no
C19 C20 . 1.470(3) no
C20 C21 . 1.305(4) no
C20 H20 . 1.0596 no
C21 H21 . 0.9360 no
C22 C23 . 1.367(4) no
C22 C27 . 1.375(4) no
C23 C24 . 1.379(5) no
C23 H23 . 0.9300 no
C24 C25 . 1.349(6) no
C24 H24 . 0.9300 no
C25 C26 . 1.351(6) no
C25 H25 . 0.9300 no
C26 C27 . 1.377(5) no
C26 H26 . 0.9300 no
C27 H27 . 0.9300 no
C51 C53 2_655 1.337(10) no
C51 C52 . 1.345(10) no
C51 H51 . 0.9300 no
C52 C53 . 1.315(9) no
C52 H52 . 0.9300 no
C53 C51 2_655 1.337(10) no
C53 H53 . 0.9300 no
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
C1 H1 O1 1_455 0.96 2.18 3.094(3) 159
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
P1 C1 C2 C3 -171.50(17) yes
C1 C2 C3 C8 -152.8(2) yes
C2 C3 C8 C9 8.4(4) yes
C3 C8 C9 S1 103.1(3) yes
C8 C9 S1 C10 -56.4(2) yes
C9 S1 C10 C11 168.0(3) yes
S1 C10 C11 C12 -175.2(3) yes
C10 C11 C12 S2 -68.6(4) yes
C11 C12 S2 C13 155.6(2) yes
C12 S2 C13 C14 -177.01(19) yes
S2 C13 C14 C19 75.7(3) yes
C13 C14 C19 C20 3.9(4) yes
C14 C19 C20 C21 -176.9(3) yes
C19 C20 C21 P1 177.0(2) yes
C20 C21 P1 C1 7.2(3) yes
C21 P1 C1 C2 -130.6(2) yes
