#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/23/2212367.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_2212367
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 O,O-Bis(2-tert-butylphenyl) chlorothiophosphonate
;
_journal_coeditor_code           SJ2188
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o580
_journal_page_last               o581
_journal_paper_doi               10.1107/S1600536806055371
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H26 Cl O2 P S'
_chemical_formula_moiety         'C20 H26 Cl O2 P S'
_chemical_formula_sum            'C20 H26 Cl O2 P S'
_chemical_formula_weight         396.89
_chemical_name_systematic
;
O,O-Bis(2-tert-butylphenyl) chlorothiophosphonate
;
_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                 105.863(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.8761(16)
_cell_length_b                   8.2053(5)
_cell_length_c                   14.5700(14)
_cell_measurement_reflns_used    16049
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.37
_cell_volume                     2055.7(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16049
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  0.8136
_exptl_absorpt_correction_T_min  0.7708
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0329
_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)+(0.0459P)²+0.6643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                1796
_reflns_number_total             2010
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2188.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212367
_cod_database_fobs_code          2212367
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_disorder_assembly
_atom_site_disorder_group
C C1 0.41775(8) 0.49918(17) 0.36712(10) 0.0497(3) Uani d . 1 . .
C C2 0.41947(10) 0.6438(2) 0.41531(12) 0.0632(4) Uani d . 1 . .
H H2 0.4555 0.7240 0.4122 0.076 Uiso calc R 1 . .
C C3 0.36717(11) 0.6689(2) 0.46838(12) 0.0691(5) Uani d . 1 . .
H H3 0.3674 0.7662 0.5012 0.083 Uiso calc R 1 . .
C C4 0.31529(11) 0.5494(2) 0.47208(12) 0.0710(5) Uani d . 1 . .
H H4 0.2794 0.5659 0.5069 0.085 Uiso calc R 1 . .
C C5 0.31541(10) 0.4039(2) 0.42448(12) 0.0644(4) Uani d . 1 . .
H H5 0.2795 0.3242 0.4288 0.077 Uiso calc R 1 . .
C C6 0.36715(8) 0.37132(17) 0.37010(10) 0.0496(3) Uani d . 1 . .
C C7 0.36881(9) 0.20689(18) 0.32119(12) 0.0551(4) Uani d . 1 . .
C C8 0.30685(13) 0.0900(3) 0.33651(19) 0.0902(6) Uani d . 1 . .
H H8A 0.2563 0.1369 0.3107 0.108 Uiso calc R 1 . .
H H8B 0.3153 0.0709 0.4036 0.108 Uiso calc R 1 . .
H H8C 0.3101 -0.0114 0.3049 0.108 Uiso calc R 1 . .
C C9 0.35290(11) 0.2293(2) 0.21273(13) 0.0696(5) Uani d . 1 . .
H H9A 0.3917 0.2996 0.1998 0.083 Uiso calc R 1 . .
H H9B 0.3024 0.2772 0.1875 0.083 Uiso calc R 1 . .
H H9C 0.3546 0.1253 0.1833 0.083 Uiso calc R 1 . .
C C10 0.44805(10) 0.1250(2) 0.36165(14) 0.0694(5) Uani d . 1 . .
H H10A 0.4570 0.1084 0.4290 0.083 Uiso calc R 1 . .
H H10B 0.4882 0.1935 0.3505 0.083 Uiso calc R 1 . .
H H10C 0.4486 0.0218 0.3308 0.083 Uiso calc R 1 . .
O O1 0.47267(6) 0.47372(12) 0.31437(8) 0.0567(3) Uani d . 1 A .
P P1 0.5000 0.59996(6) 0.2500 0.05492(18) Uani d S 1 . .
S S1 0.5891(4) 0.7367(9) 0.3235(5) 0.0566(8) Uani d P 0.50 A 1
Cl Cl1 0.5847(4) 0.7217(9) 0.3244(5) 0.077(2) Uani d P 0.50 A 2
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 . . 123.91(13) ?
C2 C1 O1 . . 118.80(13) ?
C6 C1 O1 . . 117.22(12) ?
C1 C2 C3 . . 119.33(16) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
C4 C3 C2 . . 119.21(17) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 120.55(15) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C4 C5 C6 . . 122.81(16) ?
C4 C5 H5 . . 118.6 ?
C6 C5 H5 . . 118.6 ?
C1 C6 C5 . . 114.16(14) y
C1 C6 C7 . . 123.64(12) ?
C5 C6 C7 . . 122.18(14) ?
C8 C7 C6 . . 112.25(14) ?
C8 C7 C10 . . 107.42(15) ?
C6 C7 C10 . . 109.94(13) ?
C8 C7 C9 . . 106.71(16) ?
C6 C7 C9 . . 110.56(13) ?
C10 C7 C9 . . 109.85(14) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C1 O1 P1 . . 127.16(9) ?
O1 P1 O1 2_655 . 96.96(8) ?
O1 P1 Cl1 2_655 . 111.23(19) ?
O1 P1 Cl1 . . 109.8(2) ?
Cl1 P1 Cl1 . 2_655 116.1(4) ?
O1 P1 S1 2_655 . 111.05(15) ?
O1 P1 S1 . . 112.6(2) ?
Cl1 P1 S1 2_655 . 113.96(6) ?
S1 P1 S1 . 2_655 111.8(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.375(2) y
C1 C6 1.394(2) y
C1 O1 1.4180(16) y
C2 C3 1.382(2) y
C2 H2 0.9300 ?
C3 C4 1.360(3) y
C3 H3 0.9300 ?
C4 C5 1.381(3) y
C4 H4 0.9300 ?
C5 C6 1.398(2) y
C5 H5 0.9300 ?
C6 C7 1.530(2) ?
C7 C8 1.527(2) ?
C7 C10 1.533(2) ?
C7 C9 1.538(2) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
O1 P1 1.5626(10) y
P1 Cl1 1.889(9) y
P1 S1 2.002(8) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9A O1 0.96 2.37 3.011(2) 124
C10 H10B O1 0.96 2.36 3.0041(19) 124
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
C6 C1 C2 C3 . -1.8(3)
O1 C1 C2 C3 . -178.82(14)
C1 C2 C3 C4 . 0.3(3)
C2 C3 C4 C5 . 0.9(3)
C3 C4 C5 C6 . -0.6(3)
C2 C1 C6 C5 . 2.0(2)
O1 C1 C6 C5 . 179.08(12)
C2 C1 C6 C7 . -176.19(14)
O1 C1 C6 C7 . 0.9(2)
C4 C5 C6 C1 . -0.8(2)
C4 C5 C6 C7 . 177.40(15)
C1 C6 C7 C8 . 179.92(16)
C5 C6 C7 C8 . 1.9(2)
C1 C6 C7 C10 . 60.42(19)
C5 C6 C7 C10 . -117.64(16)
C1 C6 C7 C9 . -61.04(19)
C5 C6 C7 C9 . 120.90(16)
C2 C1 O1 P1 . -41.42(19)
C6 C1 O1 P1 . 141.35(12)
C1 O1 P1 O1 2_655 -156.62(14)
C1 O1 P1 Cl1 . 87.8(2)
C1 O1 P1 Cl1 2_655 -42.2(3)
C1 O1 P1 S1 . 87.11(19)
C1 O1 P1 S1 2_655 -39.2(3)
