#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/23/2212340.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_2212340
loop_
_publ_author_name
' Krishnaiah, M.'
' Radha Krishna, J.'
'Jagadeesh Kumar, N.'
'Devandranath Reddy, C.'
'Rao, S. N.'
_publ_section_title
6-Chloro-2-(4-chlorophenoxy)-2-thioxo-4-trichloromethyl-4H-1,3,2-benzodioxaphosphorine
_journal_coeditor_code           RZ2105
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o731
_journal_page_last               o732
_journal_paper_doi               10.1107/S160053680700092X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H8 Cl5 O3 P S'
_chemical_formula_moiety         'C14 H8 Cl5 O3 P S'
_chemical_formula_sum            'C14 H8 Cl5 O3 P S'
_chemical_formula_weight         464.48
_chemical_name_systematic
;
6-Chloro-2-(4-chlorophenoxy)-2-thioxo-4-trichloromethyl-4H-1,3,2-
benzodioxaphosphorine
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.694(10)
_cell_angle_beta                 101.516(8)
_cell_angle_gamma                112.166(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4022(9)
_cell_length_b                   10.6065(10)
_cell_length_c                   10.6577(9)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.04
_cell_volume                     923.75(18)
_computing_cell_refinement       'SAINT (Bruker 2002)'
_computing_data_collection       'SMART (Bruker 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ZORTEPII (Zsolnai, 1997)'
_computing_publication_material
;
enCIFer (Allen et al.,  2004) and PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type
;
Siemens SMART CCD area-detector
;
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3412
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      1.67
_exptl_crystal_density_method    'KI flotation'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0489
_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)+(0.0386P)²+0.3459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                1981
_reflns_number_total             3192
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2105.cif
_cod_data_source_block           I
_cod_database_code               2212340
_cod_database_fobs_code          2212340
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
H H5 -0.247(5) 0.647(4) 0.091(4) 0.033(11) Uiso d 1
H H13 0.362(6) 0.364(5) 0.508(5) 0.059(17) Uiso d 1
H H17 0.109(5) 0.199(4) 0.137(4) 0.046(13) Uiso d 1
H H16 0.224(5) 0.038(5) 0.121(5) 0.050(14) Uiso d 1
H H14 0.487(6) 0.209(5) 0.506(5) 0.078(17) Uiso d 1
H H8 0.184(6) 0.858(5) 0.469(5) 0.061(17) Uiso d 1
H H7 0.052(6) 0.991(6) 0.413(5) 0.066(16) Uiso d 1
H H4 -0.168(5) 0.454(4) 0.045(4) 0.033(11) Uiso d 1
P P2 0.17031(15) 0.50431(14) 0.26326(11) 0.0413(3) Uani d 1
Cl Cl1 -0.43246(15) 0.38416(16) 0.13589(15) 0.0674(4) Uani d 1
Cl Cl2 -0.20095(17) 0.36383(16) 0.33999(12) 0.0641(4) Uani d 1
Cl Cl3 -0.3024(2) 0.18500(15) 0.06985(15) 0.0770(5) Uani d 1
Cl Cl4 -0.2156(2) 0.92839(18) 0.1963(2) 0.0987(6) Uani d 1
Cl Cl5 0.4520(2) -0.00887(16) 0.29591(16) 0.0767(5) Uani d 1
S S18 0.35925(15) 0.57791(15) 0.20949(12) 0.0518(4) Uani d 1
O O1 0.1418(4) 0.6116(3) 0.3689(3) 0.0465(8) Uani d 1
O O3 0.0107(3) 0.4354(3) 0.1415(3) 0.0447(8) Uani d 1
O O5 0.1585(4) 0.3910(4) 0.3419(3) 0.0532(9) Uani d 1
C C4 -0.1253(5) 0.4692(5) 0.1331(4) 0.0378(11) Uani d 1
C C5 -0.1589(6) 0.6959(6) 0.1714(5) 0.0498(12) Uani d 1
C C6 -0.1106(6) 0.8331(6) 0.2454(6) 0.0559(14) Uani d 1
C C7 0.0213(7) 0.8976(6) 0.3577(6) 0.0601(15) Uani d 1
C C8 0.1052(7) 0.8248(6) 0.3986(5) 0.0531(14) Uani d 1
C C9 0.0560(6) 0.6857(5) 0.3254(4) 0.0417(11) Uani d 1
C C10 -0.0760(5) 0.6188(5) 0.2114(4) 0.0402(11) Uani d 1
C C11 -0.2578(5) 0.3550(5) 0.1693(4) 0.0426(11) Uani d 1
C C12 0.2303(6) 0.2973(5) 0.3266(5) 0.0449(12) Uani d 1
C C13 0.3377(6) 0.3018(6) 0.4368(5) 0.0514(13) Uani d 1
C C14 0.4067(6) 0.2088(5) 0.4275(5) 0.0504(13) Uani d 1
C C15 0.3659(6) 0.1099(5) 0.3081(5) 0.0499(12) Uani d 1
C C16 0.2576(7) 0.1041(6) 0.1980(6) 0.0558(14) Uani d 1
C C17 0.1879(6) 0.1978(5) 0.2068(5) 0.0506(13) Uani d 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 0.0000 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
_geom_angle_publ_flag
O5 P2 O1 97.47(17) ?
O5 P2 O3 106.47(19) y
O1 P2 O3 104.42(16) y
O5 P2 S18 116.56(13) y
O1 P2 S18 117.45(15) y
O3 P2 S18 112.68(13) ?
C9 O1 P2 119.9(3) y
C4 O3 P2 125.9(3) ?
C12 O5 P2 124.6(3) y
O3 C4 C10 111.7(4) y
O3 C4 C11 109.3(3) y
C10 C4 C11 114.9(4) y
O3 C4 H4 105(2) ?
C10 C4 H4 112(2) ?
C11 C4 H4 104(3) ?
C6 C5 C10 119.7(5) ?
C6 C5 H5 125(2) ?
C10 C5 H5 116(2) ?
C5 C6 C7 121.1(5) ?
C5 C6 Cl4 119.6(4) ?
C7 C6 Cl4 119.3(4) ?
C8 C7 C6 120.4(5) ?
C8 C7 H7 118(3) ?
C6 C7 H7 122(3) ?
C7 C8 C9 118.8(5) ?
C7 C8 H8 124(4) ?
C9 C8 H8 117(4) ?
C8 C9 C10 121.8(4) ?
C8 C9 O1 118.4(4) ?
C10 C9 O1 119.8(4) y
C9 C10 C5 118.2(4) ?
C9 C10 C4 120.7(4) y
C5 C10 C4 121.1(4) ?
C4 C11 Cl3 109.7(3) ?
C4 C11 Cl1 108.5(3) ?
Cl3 C11 Cl1 108.7(2) ?
C4 C11 Cl2 112.0(3) ?
Cl3 C11 Cl2 109.8(3) ?
Cl1 C11 Cl2 108.0(2) ?
C13 C12 C17 120.5(5) ?
C13 C12 O5 118.1(4) ?
C17 C12 O5 121.3(4) ?
C12 C13 C14 120.1(5) ?
C12 C13 H13 118(3) ?
C14 C13 H13 122(4) ?
C15 C14 C13 119.8(5) ?
C15 C14 H14 117(3) ?
C13 C14 H14 123(3) ?
C16 C15 C14 120.4(5) ?
C16 C15 Cl5 119.7(4) ?
C14 C15 Cl5 120.0(4) ?
C15 C16 C17 120.1(5) ?
C15 C16 H16 122(3) ?
C17 C16 H16 117(3) ?
C12 C17 C16 119.2(5) ?
C12 C17 H17 115(3) ?
C16 C17 H17 126(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P2 O5 1.571(3) y
P2 O1 1.584(3) y
P2 O3 1.585(3) y
P2 S18 1.9025(18) y
Cl1 C11 1.764(5) ?
Cl2 C11 1.765(4) ?
Cl3 C11 1.758(5) ?
Cl4 C6 1.736(5) ?
Cl5 C15 1.735(5) ?
O1 C9 1.396(5) y
O3 C4 1.443(5) y
O5 C12 1.400(5) y
C4 C10 1.493(6) y
C4 C11 1.548(6) ?
C4 H4 0.90(4) ?
C5 C6 1.371(7) ?
C5 C10 1.391(6) ?
C5 H5 0.96(4) ?
C6 C7 1.379(8) ?
C7 C8 1.363(7) ?
C7 H7 0.95(5) ?
C8 C9 1.383(7) ?
C8 H8 0.84(5) ?
C9 C10 1.390(6) y
C12 C13 1.368(7) ?
C12 C17 1.371(7) ?
C13 C14 1.370(7) ?
C13 H13 0.83(5) ?
C14 C15 1.369(7) ?
C14 H14 1.00(5) ?
C15 C16 1.366(7) ?
C16 C17 1.381(7) ?
C16 H16 0.88(4) ?
C17 H17 0.95(4) ?
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
O5 P2 O1 C9 -144.6(3) ?
O3 P2 O1 C9 -35.4(4) y
S18 P2 O1 C9 90.2(3) ?
O5 P2 O3 C4 103.7(3) ?
O1 P2 O3 C4 1.2(4) y
S18 P2 O3 C4 -127.4(3) ?
O1 P2 O5 C12 -155.0(4) ?
O3 P2 O5 C12 97.5(4) ?
S18 P2 O5 C12 -29.1(4) ?
P2 O3 C4 C10 29.0(5) y
P2 O3 C4 C11 -99.3(4) ?
C10 C5 C6 C7 1.4(8) ?
C10 C5 C6 Cl4 -179.3(4) ?
C5 C6 C7 C8 -1.1(8) ?
Cl4 C6 C7 C8 179.7(4) ?
C6 C7 C8 C9 0.2(8) ?
C7 C8 C9 C10 0.2(8) ?
C7 C8 C9 O1 -179.4(4) ?
P2 O1 C9 C8 -142.7(4) ?
P2 O1 C9 C10 37.7(6) y
C8 C9 C10 C5 0.2(7) ?
O1 C9 C10 C5 179.7(4) ?
C8 C9 C10 C4 179.2(4) ?
O1 C9 C10 C4 -1.3(7) y
C6 C5 C10 C9 -1.0(7) ?
C6 C5 C10 C4 -180.0(4) ?
O3 C4 C10 C9 -30.3(6) y
C11 C4 C10 C9 94.9(5) ?
O3 C4 C10 C5 148.6(4) ?
C11 C4 C10 C5 -86.1(5) ?
O3 C4 C11 Cl3 -53.3(4) ?
C10 C4 C11 Cl3 -179.8(3) ?
O3 C4 C11 Cl1 -171.9(3) ?
C10 C4 C11 Cl1 61.6(4) ?
O3 C4 C11 Cl2 68.9(4) ?
C10 C4 C11 Cl2 -57.5(4) ?
P2 O5 C12 C13 121.3(4) ?
P2 O5 C12 C17 -62.5(6) ?
C17 C12 C13 C14 1.5(8) ?
O5 C12 C13 C14 177.8(4) ?
C12 C13 C14 C15 -1.0(8) ?
C13 C14 C15 C16 0.3(8) ?
C13 C14 C15 Cl5 -179.6(4) ?
C14 C15 C16 C17 -0.3(8) ?
Cl5 C15 C16 C17 179.7(4) ?
C13 C12 C17 C16 -1.4(8) ?
O5 C12 C17 C16 -177.6(5) ?
C15 C16 C17 C12 0.8(8) ?
