##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-03-23
_journal_date_accepted     2007-04-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2407
_journal_page_last     o2409
_journal_paper_category     EO
_journal_coeditor_code     RZ2131
_publ_contact_author_name     'Prof. M.Krishaniah'
_publ_contact_author_address
;   Department of Physics
    S.V. University,
    Tirupati-517502,
    India.
;
_publ_contact_author_email     'mkphysvu@gmail.com'
_publ_contact_author_fax     '91 877 2248428'
_publ_contact_author_phone     '91 877 2248485'
_publ_section_title
;
6-Bromo-3-(4-chlorophenyl)-2-(4-methoxyphenyl)-
3,4-dihydro-1,3,2-benzoxazaphosphinine 2-sulfide
;
loop_
    _publ_author_name
    _publ_author_address
    'Radha Krishna, J.'
;     Department of Physics
      S. V. University,
      Tirupati 517 502,
      India
;
    ' Krishnaiah, M.'
;     Department of Physics
      S. V. University,
      Tirupati 517 502,
      India
;
    'Syam Prasad, G.'
;     Department of Chemistry
      S. V. University,
      Tirupati 517 502,
      India
;
    'Suresh Reddy, C.'
;     Department of Chemistry
      S. V. University,
      Tirupati 517 502,
      India
;
    'Vedavati G. Puranik.'
;     Centre of Material Characterization
      National Chemical Laboratory
      Pune 411 008
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6-Bromo-3-(4-chlorophenyl)-2-(4-methoxyphenyl)-
3,4-dihydro-1,3,2-benzoxazaphosphinine 2-sulfide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H16 Br Cl N O2 P S'
_chemical_formula_sum     'C20 H16 Br Cl N O2 P S'
_chemical_formula_iupac     'C20 H16 Br Cl N O2 P S'
_chemical_formula_weight     480.73
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     8.7765(10)
_cell_length_b     10.1549(12)
_cell_length_c     22.707(3)
_cell_angle_alpha     90.00
_cell_angle_beta     95.885(2)
_cell_angle_gamma     90.00
_cell_volume     2013.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     898
_cell_measurement_theta_min     2.20
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'white'
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.586
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     968
_exptl_absorpt_coefficient_mu     2.373
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.588
_exptl_absorpt_correction_T_max     0.731
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Siemens SMART CCD area-detector
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18958
_diffrn_reflns_av_R_equivalents     0.0331
_diffrn_reflns_av_sigmaI/netI     0.0238
_diffrn_reflns_theta_min     2.20
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
Weighted least-squares planes through the starred atoms
 (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II-A),807).
 Equation of the plane: m1*X+m2*Y+m3*Z=d
Plane  1
 m1 =   0.94956(0.00059)
 m2 =   0.31103(0.00178)
 m3 =  -0.03982(0.00098)
 D  =   2.01109(0.00459)
 Atom              d          s           d/s      (d/s)**2
 P1    *        -0.0013     0.0009      -1.415        2.002
 N5    *         0.0149     0.0030       4.974       24.738
 C17   *        -0.0252     0.0035      -7.101       50.421
 C12   *         0.0231     0.0035       6.686       44.697
 C18             0.5165     0.0038     135.962    18485.555
 O3              0.5914     0.0025     240.524    57851.988
                                                ============
               Sum((d/s)**2) for starred atoms      121.858
 Chi-squared at 95% for  1 degrees of freedom:  3.84
 The group of atoms deviates significantly from planarity
 Plane  2
 m1 =   0.96646(0.00033)
 m2 =   0.22178(0.00132)
 m3 =  -0.12946(0.00089)
 D  =   1.69026(0.00428)
 Atom              d          s           d/s      (d/s)**2
 P1    *        -0.0320     0.0009     -36.095     1302.868
 N5    *         0.0345     0.0030      11.514      132.582
 C17   *        -0.3090     0.0035     -87.328     7626.171
 C12   *        -0.3133     0.0034     -90.913     8265.249
 C18   *         0.4031     0.0038     106.262    11291.619
 O3    *         0.3641     0.0025     147.683    21810.215
                                                ============
               Sum((d/s)**2) for starred atoms    50428.703
 Chi-squared at 95% for  3 degrees of freedom:  7.81
 The group of atoms deviates significantly from planarity
 Plane  3
 m1 =  -0.82271(0.00080)
 m2 =  -0.43779(0.00153)
 m3 =  -0.36261(0.00048)
 D  =  -4.54452(0.00475)
 Atom              d          s           d/s      (d/s)**2
 C12   *         0.0242     0.0035       7.001       49.015
 C13   *         0.0092     0.0039       2.351        5.526
 C14   *        -0.0333     0.0043      -7.812       61.029
 C15   *        -0.0418     0.0041     -10.162      103.269
 C16   *        -0.0274     0.0040      -6.834       46.705
 C17   *         0.0066     0.0036       1.858        3.454
 Br26  *         0.0010     0.0006       1.717        2.947
                                                ============
               Sum((d/s)**2) for starred atoms      271.944
 Chi-squared at 95% for  4 degrees of freedom:  9.49
 The group of atoms deviates significantly from planarity
 Plane  4
 m1 =  -0.09860(0.00137)
 m2 =  -0.88456(0.00082)
 m3 =  -0.45588(0.00142)
 D  =  -2.27969(0.00734)
 Atom              d          s           d/s      (d/s)**2
 C6    *         0.0021     0.0036       0.576        0.332
 C7    *         0.0006     0.0044       0.144        0.021
 C8    *        -0.0027     0.0048      -0.560        0.313
 C9    *        -0.0027     0.0041      -0.660        0.436
 C10   *        -0.0021     0.0050      -0.417        0.174
 C11   *        -0.0012     0.0048      -0.255        0.065
 O4    *         0.0028     0.0033       0.842        0.708
 C25   *        -0.0012     0.0062      -0.201        0.040
                                                ============
               Sum((d/s)**2) for starred atoms        2.090
 Chi-squared at 95% for  5 degrees of freedom: 11.10
 The group of atoms does not deviate significantly from planarity
 Plane  5
 m1 =  -0.77601(0.00086)
 m2 =   0.44397(0.00050)
 m3 =  -0.44800(0.00135)
 D  =  -4.68147(0.00513)
 Atom              d          s           d/s      (d/s)**2
 C19   *        -0.0183     0.0034      -5.328       28.392
 C20   *        -0.0046     0.0040      -1.158        1.341
 C21   *         0.0189     0.0042       4.503       20.275
 C22   *         0.0305     0.0040       7.619       58.055
 C23   *         0.0099     0.0041       2.427        5.891
 C24   *         0.0028     0.0038       0.744        0.554
 Cl27  *        -0.0032     0.0013      -2.494        6.220
                                                ============
               Sum((d/s)**2) for starred atoms      120.728
 Chi-squared at 95% for  4 degrees of freedom:  9.49
 The group of atoms deviates significantly from planarity
 Dihedral angles formed by LSQ-planes
 Plane - plane            angle (s.u.)             angle (s.u.)
   1       2               7.32( 0.10)             172.68( 0.10)
   1       3              25.45( 0.07)             154.55( 0.07)
   1       4              69.48( 0.11)             110.52( 0.11)
   1       5              54.48( 0.09)             125.52( 0.09)
   2       3              32.30( 0.07)             147.70( 0.07)
   2       4              76.56( 0.11)             103.44( 0.11)
   2       5              53.59( 0.09)             126.41( 0.09)
   3       4              50.68( 0.11)             129.32( 0.11)
   3       5              52.66( 0.09)             127.34( 0.09)
   4       5              83.57( 0.09)              96.43( 0.09)
;
_reflns_number_total     3543
_reflns_number_gt     2775
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0618
_refine_ls_R_factor_gt     0.0468
_refine_ls_wR_factor_gt     0.1211
_refine_ls_wR_factor_ref     0.1312
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_restrained_S_all     1.035
_refine_ls_number_reflns     3543
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0704P)²+1.7985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.403
_refine_diff_density_min     -0.730
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'N' 'N' 0.0061 0.0033
                         '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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ZORTEPII (Zsolnai, 1998)'
_computing_publication_material
;
enCIFer (Allen et al.,  2004) and PARST (Nardelli, 1995)
;
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
    Br Br26 0.17792(7) 0.06566(6) 0.47281(2) 0.0836(2) Uani d . 1 . .
    P P1 0.29439(10) 0.03359(9) 0.17673(4) 0.0410(2) Uani d . 1 . .
    S S2 0.08073(10) 0.02314(10) 0.14719(5) 0.0537(3) Uani d . 1 . .
    Cl Cl27 0.09865(15) -0.62080(11) 0.14604(6) 0.0812(4) Uani d . 1 . .
    O O3 0.3399(3) 0.1485(2) 0.22477(11) 0.0458(6) Uani d . 1 . .
    O O4 0.7010(3) 0.1901(3) -0.00369(13) 0.0716(9) Uani d . 1 . .
    N N5 0.3610(3) -0.0990(3) 0.21532(13) 0.0456(7) Uani d . 1 . .
    C C12 0.3000(4) 0.1307(3) 0.28257(15) 0.0424(8) Uani d . 1 . .
    C C6 0.4183(4) 0.0763(3) 0.12219(16) 0.0444(8) Uani d . 1 . .
    C C7 0.5731(4) 0.0508(4) 0.13178(18) 0.0586(11) Uani d . 1 . .
    H H7 0.6123 0.0082 0.1663 0.070 Uiso calc R 1 . .
    C C17 0.3485(4) 0.0157(4) 0.31110(16) 0.0440(8) Uani d . 1 . .
    C C9 0.6162(4) 0.1504(4) 0.03956(17) 0.0525(9) Uani d . 1 . .
    C C21 0.2625(5) -0.4005(4) 0.12862(18) 0.0564(10) Uani d . 1 . .
    H H21 0.2811 -0.4372 0.0925 0.068 Uiso calc R 1 . .
    C C13 0.2199(4) 0.2272(4) 0.30874(18) 0.0525(9) Uani d . 1 . .
    H H13 0.1884 0.3034 0.2882 0.063 Uiso calc R 1 . .
    C C8 0.6712(5) 0.0880(5) 0.09050(19) 0.0650(12) Uani d . 1 . .
    H H8 0.7754 0.0702 0.0977 0.078 Uiso calc R 1 . .
    C C22 0.1720(4) -0.4658(4) 0.16594(19) 0.0529(10) Uani d . 1 . .
    C C19 0.2982(4) -0.2242(3) 0.19944(15) 0.0413(8) Uani d . 1 . .
    C C23 0.1447(5) -0.4132(4) 0.21936(19) 0.0550(10) Uani d . 1 . .
    H H23 0.0855 -0.4586 0.2443 0.066 Uiso calc R 1 . .
    C C16 0.3144(5) -0.0026(4) 0.36873(17) 0.0523(9) Uani d . 1 . .
    H H16 0.3452 -0.0789 0.3893 0.063 Uiso calc R 1 . .
    C C15 0.2336(5) 0.0942(4) 0.39528(17) 0.0538(10) Uani d . 1 . .
    C C24 0.2066(4) -0.2911(4) 0.23573(17) 0.0505(9) Uani d . 1 . .
    H H24 0.1863 -0.2537 0.2715 0.061 Uiso calc R 1 . .
    C C20 0.3245(5) -0.2795(4) 0.14623(17) 0.0532(9) Uani d . 1 . .
    H H20 0.3852 -0.2349 0.1215 0.064 Uiso calc R 1 . .
    C C18 0.4364(4) -0.0790(4) 0.27644(16) 0.0494(9) Uani d . 1 . .
    H H18A 0.5392 -0.0454 0.2744 0.059 Uiso calc R 1 . .
    H H18B 0.4447 -0.1630 0.2968 0.059 Uiso calc R 1 . .
    C C14 0.1876(5) 0.2076(4) 0.36653(18) 0.0586(10) Uani d . 1 . .
    H H14 0.1348 0.2714 0.3857 0.070 Uiso calc R 1 . .
    C C10 0.4605(5) 0.1763(5) 0.02979(19) 0.0703(13) Uani d . 1 . .
    H H10 0.4215 0.2188 -0.0048 0.084 Uiso calc R 1 . .
    C C11 0.3633(5) 0.1397(5) 0.07065(19) 0.0652(12) Uani d . 1 . .
    H H11 0.2593 0.1580 0.0635 0.078 Uiso calc R 1 . .
    C C25 0.8597(5) 0.1672(6) 0.0035(2) 0.0861(16) Uani d . 1 . .
    H H25A 0.9046 0.2000 -0.0305 0.129 Uiso calc R 1 . .
    H H25B 0.8786 0.0744 0.0074 0.129 Uiso calc R 1 . .
    H H25C 0.9043 0.2117 0.0384 0.129 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Br26 C15 . 1.897(4) ?
    P1 O3 . 1.619(3) y
    P1 N5 . 1.678(3) y
    P1 C6 . 1.784(4) ?
    P1 S2 . 1.9287(13) ?
    Cl27 C22 . 1.743(4) ?
    O3 C12 . 1.404(4) y
    O4 C9 . 1.353(5) ?
    O4 C25 . 1.405(5) ?
    N5 C19 . 1.417(5) ?
    N5 C18 . 1.489(5) y
    C12 C13 . 1.376(5) ?
    C12 C17 . 1.381(5) y
    C6 C7 . 1.378(5) ?
    C6 C11 . 1.379(5) ?
    C7 C8 . 1.388(6) ?
    C7 H7 . 0.9300 ?
    C17 C16 . 1.384(5) ?
    C17 C18 . 1.505(5) y
    C9 C8 . 1.363(6) ?
    C9 C10 . 1.387(6) ?
    C21 C20 . 1.386(6) ?
    C21 C22 . 1.388(6) ?
    C21 H21 . 0.9300 ?
    C13 C14 . 1.385(6) ?
    C13 H13 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C22 C23 . 1.369(6) ?
    C19 C20 . 1.373(5) ?
    C19 C24 . 1.387(5) ?
    C23 C24 . 1.389(5) ?
    C23 H23 . 0.9300 ?
    C16 C15 . 1.386(6) ?
    C16 H16 . 0.9300 ?
    C15 C14 . 1.364(6) ?
    C24 H24 . 0.9300 ?
    C20 H20 . 0.9300 ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C14 H14 . 0.9300 ?
    C10 C11 . 1.374(6) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C25 H25A . 0.9600 ?
    C25 H25B . 0.9600 ?
    C25 H25C . 0.9600 ?
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
    O3 P1 N5 . . 100.24(14) y
    O3 P1 C6 . . 99.60(15) ?
    N5 P1 C6 . . 110.68(16) ?
    O3 P1 S2 . . 115.96(11) ?
    N5 P1 S2 . . 114.30(12) ?
    C6 P1 S2 . . 114.34(13) ?
    C12 O3 P1 . . 118.0(2) y
    C9 O4 C25 . . 118.7(3) ?
    C19 N5 C18 . . 118.9(3) ?
    C19 N5 P1 . . 118.8(2) ?
    C18 N5 P1 . . 118.4(2) y
    C13 C12 C17 . . 123.1(3) ?
    C13 C12 O3 . . 119.9(3) ?
    C17 C12 O3 . . 117.0(3) y
    C7 C6 C11 . . 118.4(4) ?
    C7 C6 P1 . . 120.4(3) ?
    C11 C6 P1 . . 121.2(3) ?
    C6 C7 C8 . . 120.8(4) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C12 C17 C16 . . 118.1(3) ?
    C12 C17 C18 . . 116.4(3) y
    C16 C17 C18 . . 125.5(3) ?
    O4 C9 C8 . . 125.5(4) ?
    O4 C9 C10 . . 115.7(3) ?
    C8 C9 C10 . . 118.8(4) ?
    C20 C21 C22 . . 118.7(4) ?
    C20 C21 H21 . . 120.7 ?
    C22 C21 H21 . . 120.7 ?
    C12 C13 C14 . . 118.0(4) ?
    C12 C13 H13 . . 121.0 ?
    C14 C13 H13 . . 121.0 ?
    C9 C8 C7 . . 120.6(4) ?
    C9 C8 H8 . . 119.7 ?
    C7 C8 H8 . . 119.7 ?
    C23 C22 C21 . . 121.2(4) ?
    C23 C22 Cl27 . . 119.2(3) ?
    C21 C22 Cl27 . . 119.5(3) ?
    C20 C19 C24 . . 118.8(3) ?
    C20 C19 N5 . . 119.7(3) ?
    C24 C19 N5 . . 121.5(3) ?
    C22 C23 C24 . . 119.1(4) ?
    C22 C23 H23 . . 120.5 ?
    C24 C23 H23 . . 120.5 ?
    C17 C16 C15 . . 119.1(4) ?
    C17 C16 H16 . . 120.5 ?
    C15 C16 H16 . . 120.5 ?
    C14 C15 C16 . . 122.0(4) ?
    C14 C15 Br26 . . 118.8(3) ?
    C16 C15 Br26 . . 119.2(3) ?
    C19 C24 C23 . . 120.9(4) ?
    C19 C24 H24 . . 119.6 ?
    C23 C24 H24 . . 119.6 ?
    C19 C20 C21 . . 121.3(4) ?
    C19 C20 H20 . . 119.3 ?
    C21 C20 H20 . . 119.3 ?
    N5 C18 C17 . . 111.8(3) y
    N5 C18 H18A . . 109.3 ?
    C17 C18 H18A . . 109.3 ?
    N5 C18 H18B . . 109.3 ?
    C17 C18 H18B . . 109.3 ?
    H18A C18 H18B . . 107.9 ?
    C15 C14 C13 . . 119.7(4) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C11 C10 C9 . . 120.7(4) ?
    C11 C10 H10 . . 119.7 ?
    C9 C10 H10 . . 119.7 ?
    C10 C11 C6 . . 120.8(4) ?
    C10 C11 H11 . . 119.6 ?
    C6 C11 H11 . . 119.6 ?
    O4 C25 H25A . . 109.5 ?
    O4 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    O4 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N5 P1 O3 C12 . . . . -49.2(3) y
    C6 P1 O3 C12 . . . . -162.4(2) ?
    S2 P1 O3 C12 . . . . 74.4(2) ?
    O3 P1 N5 C19 . . . . 157.1(3) ?
    C6 P1 N5 C19 . . . . -98.4(3) ?
    S2 P1 N5 C19 . . . . 32.4(3) ?
    O3 P1 N5 C18 . . . . -0.2(3) y
    C6 P1 N5 C18 . . . . 104.2(3) ?
    S2 P1 N5 C18 . . . . -125.0(3) ?
    P1 O3 C12 C13 . . . . -127.8(3) ?
    P1 O3 C12 C17 . . . . 54.0(4) y
    O3 P1 C6 C7 . . . . 74.6(3) ?
    N5 P1 C6 C7 . . . . -30.3(4) ?
    S2 P1 C6 C7 . . . . -161.1(3) ?
    O3 P1 C6 C11 . . . . -103.0(4) ?
    N5 P1 C6 C11 . . . . 152.2(3) ?
    S2 P1 C6 C11 . . . . 21.3(4) ?
    C11 C6 C7 C8 . . . . -0.1(7) ?
    P1 C6 C7 C8 . . . . -177.7(3) ?
    C13 C12 C17 C16 . . . . 0.0(5) ?
    O3 C12 C17 C16 . . . . 178.2(3) ?
    C13 C12 C17 C18 . . . . -179.3(3) ?
    O3 C12 C17 C18 . . . . -1.1(5) y
    C25 O4 C9 C8 . . . . -0.5(7) ?
    C25 O4 C9 C10 . . . . 179.8(5) ?
    C17 C12 C13 C14 . . . . 0.4(6) ?
    O3 C12 C13 C14 . . . . -177.8(3) ?
    O4 C9 C8 C7 . . . . -179.6(4) ?
    C10 C9 C8 C7 . . . . 0.1(7) ?
    C6 C7 C8 C9 . . . . -0.1(7) ?
    C20 C21 C22 C23 . . . . -0.4(6) ?
    C20 C21 C22 Cl27 . . . . -177.6(3) ?
    C18 N5 C19 C20 . . . . -135.0(4) ?
    P1 N5 C19 C20 . . . . 67.7(4) ?
    C18 N5 C19 C24 . . . . 47.0(5) ?
    P1 N5 C19 C24 . . . . -110.3(3) ?
    C21 C22 C23 C24 . . . . 1.2(6) ?
    Cl27 C22 C23 C24 . . . . 178.4(3) ?
    C12 C17 C16 C15 . . . . 0.0(5) ?
    C18 C17 C16 C15 . . . . 179.3(4) ?
    C17 C16 C15 C14 . . . . -0.5(6) ?
    C17 C16 C15 Br26 . . . . 176.9(3) ?
    C20 C19 C24 C23 . . . . 1.3(6) ?
    N5 C19 C24 C23 . . . . 179.4(3) ?
    C22 C23 C24 C19 . . . . -1.7(6) ?
    C24 C19 C20 C21 . . . . -0.5(6) ?
    N5 C19 C20 C21 . . . . -178.6(3) ?
    C22 C21 C20 C19 . . . . 0.1(6) ?
    C19 N5 C18 C17 . . . . -113.2(4) ?
    P1 N5 C18 C17 . . . . 44.2(4) y
    C12 C17 C18 N5 . . . . -46.4(4) y
    C16 C17 C18 N5 . . . . 134.4(4) ?
    C16 C15 C14 C13 . . . . 0.9(6) ?
    Br26 C15 C14 C13 . . . . -176.5(3) ?
    C12 C13 C14 C15 . . . . -0.8(6) ?
    O4 C9 C10 C11 . . . . 179.7(4) ?
    C8 C9 C10 C11 . . . . 0.0(7) ?
    C9 C10 C11 C6 . . . . -0.1(8) ?
    C7 C6 C11 C10 . . . . 0.2(7) ?
    P1 C6 C11 C10 . . . . 177.8(4) ?
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
    C8 H8 S2 1_655 0.93 2.84 3.750(5) 167.0
