data_General
_audit_creation_date                  'Wed Feb  9 19:53:12 2005'
_audit_creation_method                'by teXsan'
_audit_update_record                   ?
#------------------------------------------------------------------------------
# PROCESSING SUMMARY (IUCr Office Use Only)
_journal_date_recd_electronic          ?
_journal_date_from_coeditor            ?
_journal_date_accepted                 ?
_journal_coeditor_code                 ?
#------------------------------------------------------------------------------
# SUBMISSION DETAILS
_publ_contact_author_name             ' Toshihiro Murafuji'
_publ_contact_author_address
;
    Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753-8512, Japan
;
_publ_contact_author_email            ' murafuji@yamaguchi-u.ac.jp '
_publ_contact_author_fax              ' +81-83-933-5738 '
_publ_contact_author_phone            ' +81-83-933-5738 '
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal               ' Organometallics'
_publ_requested_category              ' CHOOSE FI FM FO CI CM CO or AD'

_publ_requested_coeditor_name          ?
#------------------------------------------------------------------------------
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;

_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
  ENTER SYNOPSIS
;
#------------------------------------------------------------------------------
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;

_publ_section_comment
;
    ENTER TEXT
;

_publ_section_acknowledgements
;
    ENTER ACKNOWLEDGEMENTS
;

_publ_section_references
;
    ENTER OTHER REFERENCES
Molecular Structure Corporation, Rigaku Corporation. (2004). teXsan.
Single Crystal Structure Analysis Software. Version 2.0.
MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA.
Rigaku, 3-9-12 Akishima, Tokyo, Japan.
North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968).
Acta Cryst. A24, 351-359.
Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564.
;

_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;

_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;

_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;
#------------------------------------------------------------------------------
data_[azulene-PO-ph2 Compound 3b]
#------------------------------------------------------------------------------
# CHEMICAL DATA
_chemical_formula_sum                  'C22 H15 Br2 O P '
_chemical_formula_moiety               'C22 H15 Br2 O P '
_chemical_formula_weight               486.14
_chemical_melting_point                ?
#------------------------------------------------------------------------------
# CRYSTAL DATA
_symmetry_cell_setting                 monoclinic
_symmetry_space_group_name_H-M        'P 21/n       '
_symmetry_Int_Tables_number            14
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
_cell_length_a                         6.707(6)
_cell_length_b                         31.633(7)
_cell_length_c                         9.144(3)
_cell_angle_alpha                      90
_cell_angle_beta                       101.34(4)
_cell_angle_gamma                      90
_cell_volume                           1902(1)
_cell_formula_units_Z                  4
_cell_measurement_reflns_used          24
_cell_measurement_theta_min            10.1
_cell_measurement_theta_max            12.5
_cell_measurement_temperature          298.2
#------------------------------------------------------------------------------
_exptl_crystal_description            'prismatic'
_exptl_crystal_colour                 'brown'
_exptl_crystal_size_max                0.250
_exptl_crystal_size_mid                0.250
_exptl_crystal_size_min                0.130
_exptl_crystal_size_rad                ?
_exptl_crystal_density_diffrn          1.697
_exptl_crystal_density_meas            ?
_exptl_crystal_density_method         'not measured'
_exptl_crystal_F_000                   960.00
_exptl_absorpt_coefficient_mu          4.367
_exptl_absorpt_correction_type         psi-scan
_exptl_absorpt_process_details        '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min        0.646
_exptl_absorpt_correction_T_max        0.999
#------------------------------------------------------------------------------
# EXPERIMENTAL DATA
_diffrn_radiation_type                'Mo K\a'
_diffrn_radiation_wavelength           0.7107
_diffrn_measurement_device_type       'Rigaku AFC5R'
_diffrn_measurement_method             ω
_diffrn_reflns_number                  4822
_diffrn_reflns_av_R_equivalents        0.049
_diffrn_reflns_theta_max               27.50
_diffrn_measured_fraction_theta_max    0.9993
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.9993
_diffrn_reflns_limit_h_min             0
_diffrn_reflns_limit_h_max             8
_diffrn_reflns_limit_k_min             0
_diffrn_reflns_limit_k_max             41
_diffrn_reflns_limit_l_min             -11
_diffrn_reflns_limit_l_max             11
_diffrn_standards_number              3
_diffrn_standards_interval_count      150
_diffrn_standards_decay_%             0.64
#------------------------------------------------------------------------------
# REFINEMENT DATA
_refine_special_details
;
Refinement was carried out using all reflections. The weighted
R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are
based on F. The threshold expression of F² > 2.0 sigma(F²) is used only
for calculating R-factor (gt).
;
_reflns_number_total                   4720
_reflns_number_gt                      2292
_reflns_threshold_expression           F²>2.0σ(F²)
_refine_ls_structure_factor_coef       Fsqd
_refine_ls_R_factor_gt                 0.0598
_refine_ls_wR_factor_ref               0.1964
_refine_ls_hydrogen_treatment          noref
_refine_ls_number_reflns               4365
_refine_ls_number_parameters           236
_refine_ls_goodness_of_fit_ref         0.951
_refine_ls_weighting_scheme            calc
_refine_ls_weighting_details
   'w = 1/[σ²(Fo²) + (0.10000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_shift/su_max                0.0001
_refine_diff_density_max               1.14
_refine_diff_density_min               -1.61
_refine_ls_extinction_method
   'Zachariasen(1967) type 2 Gaussian isotropic'
_refine_ls_extinction_coef             0.017(2)
_refine_ls_abs_structure_details       ?
_refine_ls_abs_structure_Flack         ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
  'H' 'H'  0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
  'Br' 'Br'  -0.290 2.459
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
  'O' 'O'  0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
  'P' 'P'  0.102 0.094
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
#------------------------------------------------------------------------------
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Br(1) Br 0.7679(1) 0.10984(3) 0.65821(8) 0.0489(2) Uani 1.00 1 d . . .
 Br(2) Br 0.7435(2) 0.05171(3) 0.04711(10) 0.0664(3) Uani 1.00 1 d . . .
 P P 0.7825(3) 0.14281(6) 0.2708(2) 0.0379(5) Uani 1.00 1 d . . .
 O O 0.9939(8) 0.1481(2) 0.2488(6) 0.054(2) Uani 1.00 1 d . . .
 C(1) C 0.7429(10) 0.0905(2) 0.3390(8) 0.034(2) Uani 1.00 1 d . . .
 C(2) C 0.7508(10) 0.0763(2) 0.4858(7) 0.034(2) Uani 1.00 1 d . . .
 C(3) C 0.7476(10) 0.0317(2) 0.4925(8) 0.039(2) Uani 1.00 1 d . . .
 C(4) C 0.759(1) 0.0074(3) 0.6202(9) 0.048(2) Uani 1.00 1 d . . .
 C(5) C 0.763(1) -0.0365(3) 0.631(1) 0.056(3) Uani 1.00 1 d . . .
 C(6) C 0.750(1) -0.0671(3) 0.521(1) 0.065(3) Uani 1.00 1 d . . .
 C(7) C 0.728(1) -0.0612(3) 0.369(1) 0.066(3) Uani 1.00 1 d . . .
 C(8) C 0.724(1) -0.0245(3) 0.288(1) 0.052(2) Uani 1.00 1 d . . .
 C(9) C 0.731(1) 0.0173(2) 0.3380(8) 0.038(2) Uani 1.00 1 d . . .
 C(10) C 0.734(1) 0.0535(2) 0.2523(8) 0.037(2) Uani 1.00 1 d . . .
 C(11) C 0.592(1) 0.1482(2) 0.1031(7) 0.038(2) Uani 1.00 1 d . . .
 C(12) C 0.393(1) 0.1345(3) 0.0910(9) 0.050(2) Uani 1.00 1 d . . .
 C(13) C 0.248(1) 0.1423(3) -0.0371(9) 0.060(3) Uani 1.00 1 d . . .
 C(14) C 0.303(2) 0.1635(3) -0.1521(10) 0.069(3) Uani 1.00 1 d . . .
 C(15) C 0.498(2) 0.1775(3) -0.1434(9) 0.069(3) Uani 1.00 1 d . . .
 C(16) C 0.646(1) 0.1703(3) -0.0140(9) 0.053(3) Uani 1.00 1 d . . .
 C(17) C 0.717(1) 0.1831(2) 0.3955(8) 0.040(2) Uani 1.00 1 d . . .
 C(18) C 0.520(1) 0.1940(2) 0.4047(9) 0.049(2) Uani 1.00 1 d . . .
 C(19) C 0.485(1) 0.2272(3) 0.4942(10) 0.056(3) Uani 1.00 1 d . . .
 C(20) C 0.644(2) 0.2497(3) 0.5743(10) 0.061(3) Uani 1.00 1 d . . .
 C(21) C 0.841(1) 0.2382(3) 0.568(1) 0.062(3) Uani 1.00 1 d . . .
 C(22) C 0.879(1) 0.2060(3) 0.4775(10) 0.055(3) Uani 1.00 1 d . . .
 H(1) H 0.7638 0.0225 0.7107 0.0572 Uiso 1.00 1 calc . . .
 H(2) H 0.7775 -0.0472 0.7299 0.0666 Uiso 1.00 1 calc . . .
 H(3) H 0.7573 -0.0957 0.5542 0.0783 Uiso 1.00 1 calc . . .
 H(4) H 0.7139 -0.0865 0.3111 0.0788 Uiso 1.00 1 calc . . .
 H(5) H 0.7160 -0.0280 0.1833 0.0619 Uiso 1.00 1 calc . . .
 H(6) H 0.3552 0.1194 0.1714 0.0600 Uiso 1.00 1 calc . . .
 H(7) H 0.1114 0.1330 -0.0441 0.0719 Uiso 1.00 1 calc . . .
 H(8) H 0.2044 0.1688 -0.2401 0.0826 Uiso 1.00 1 calc . . .
 H(9) H 0.5342 0.1921 -0.2253 0.0831 Uiso 1.00 1 calc . . .
 H(10) H 0.7809 0.1804 -0.0067 0.0633 Uiso 1.00 1 calc . . .
 H(11) H 0.4085 0.1787 0.3492 0.0589 Uiso 1.00 1 calc . . .
 H(12) H 0.3497 0.2345 0.5004 0.0675 Uiso 1.00 1 calc . . .
 H(13) H 0.6197 0.2730 0.6337 0.0731 Uiso 1.00 1 calc . . .
 H(14) H 0.9511 0.2530 0.6272 0.0746 Uiso 1.00 1 calc . . .
 H(15) H 1.0153 0.1992 0.4706 0.0663 Uiso 1.00 1 calc . . .

#------------------------------------------------------------------------------
_computing_data_collection            'MSC/AFC Diffractometer Control'
_computing_cell_refinement            'MSC/AFC Diffractometer Control'
_computing_data_reduction             'teXsan Ver. 2.0'
_computing_structure_solution          SHELXS97
_computing_structure_refinement       'teXsan Ver. 2.0'
_computing_publication_material       'teXsan Ver. 2.0'
_computing_molecular_graphics          ?
#------------------------------------------------------------------------------
_geom_special_details
;
 ?
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
 Br(1)     C(2)      1.886(7)   . . yes
 Br(2)     C(10)     1.890(7)   . . yes
 P         O         1.480(5)   . . yes
 P         C(1)      1.806(7)   . . yes
 P         C(11)     1.802(7)   . . yes
 P         C(17)     1.821(8)   . . yes
 C(1)      C(2)      1.407(9)   . . yes
 C(1)      C(10)     1.410(9)   . . yes
 C(2)      C(3)      1.412(10)  . . yes
 C(3)      C(4)      1.39(1)    . . yes
 C(3)      C(9)      1.47(1)    . . yes
 C(4)      C(5)      1.39(1)    . . yes
 C(5)      C(6)      1.39(1)    . . yes
 C(6)      C(7)      1.38(1)    . . yes
 C(7)      C(8)      1.38(1)    . . yes
 C(8)      C(9)      1.40(1)    . . yes
 C(9)      C(10)     1.389(10)  . . yes
 C(11)     C(12)     1.39(1)    . . yes
 C(11)     C(16)     1.39(1)    . . yes
 C(12)     C(13)     1.39(1)    . . yes
 C(13)     C(14)     1.36(1)    . . yes
 C(14)     C(15)     1.37(1)    . . yes
 C(15)     C(16)     1.40(1)    . . yes
 C(17)     C(18)     1.39(1)    . . yes
 C(17)     C(22)     1.39(1)    . . yes
 C(18)     C(19)     1.38(1)    . . yes
 C(19)     C(20)     1.37(1)    . . yes
 C(20)     C(21)     1.38(1)    . . yes
 C(21)     C(22)     1.37(1)    . . yes
#------------------------------------------------------------------------------
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
   O         P         C(1)      111.2(3)   . . . yes
   O         P         C(11)     114.4(3)   . . . yes
   O         P         C(17)     111.1(3)   . . . yes
   C(1)      P         C(11)     104.6(3)   . . . yes
   C(1)      P         C(17)     110.8(3)   . . . yes
   C(11)     P         C(17)     104.3(3)   . . . yes
   P         C(1)      C(2)      130.0(5)   . . . yes
   P         C(1)      C(10)     124.0(5)   . . . yes
   C(2)      C(1)      C(10)     105.1(6)   . . . yes
   Br(1)     C(2)      C(1)      127.0(5)   . . . yes
   Br(1)     C(2)      C(3)      121.7(5)   . . . yes
   C(1)      C(2)      C(3)      111.3(6)   . . . yes
   C(2)      C(3)      C(4)      126.2(7)   . . . yes
   C(2)      C(3)      C(9)      105.4(6)   . . . yes
   C(4)      C(3)      C(9)      128.4(7)   . . . yes
   C(3)      C(4)      C(5)      127.6(8)   . . . yes
   C(4)      C(5)      C(6)      130.2(8)   . . . yes
   C(5)      C(6)      C(7)      128.0(8)   . . . yes
   C(6)      C(7)      C(8)      130.0(9)   . . . yes
   C(7)      C(8)      C(9)      128.7(9)   . . . yes
   C(3)      C(9)      C(8)      127.0(7)   . . . yes
   C(3)      C(9)      C(10)     106.3(6)   . . . yes
   C(8)      C(9)      C(10)     126.6(7)   . . . yes
   Br(2)     C(10)     C(1)      125.3(5)   . . . yes
   Br(2)     C(10)     C(9)      122.9(5)   . . . yes
   C(1)      C(10)     C(9)      111.8(6)   . . . yes
   P         C(11)     C(12)     123.4(6)   . . . yes
   P         C(11)     C(16)     117.0(6)   . . . yes
   C(12)     C(11)     C(16)     119.5(7)   . . . yes
   C(11)     C(12)     C(13)     121.0(8)   . . . yes
   C(12)     C(13)     C(14)     119.2(9)   . . . yes
   C(13)     C(14)     C(15)     121.2(8)   . . . yes
   C(14)     C(15)     C(16)     120.2(8)   . . . yes
   C(11)     C(16)     C(15)     119.0(8)   . . . yes
   P         C(17)     C(18)     124.2(6)   . . . yes
   P         C(17)     C(22)     116.2(6)   . . . yes
   C(18)     C(17)     C(22)     119.5(7)   . . . yes
   C(17)     C(18)     C(19)     120.0(8)   . . . yes
   C(18)     C(19)     C(20)     120.6(8)   . . . yes
   C(19)     C(20)     C(21)     119.4(8)   . . . yes
   C(20)     C(21)     C(22)     121.2(8)   . . . yes
   C(17)     C(22)     C(21)     119.3(8)   . . . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
 Br(1)     C(2)      C(1)      P         10.0(10)   . . . . yes
 Br(1)     C(2)      C(1)      C(10)     179.2(5)   . . . . yes
 Br(1)     C(2)      C(3)      C(4)      0(1)       . . . . yes
 Br(1)     C(2)      C(3)      C(9)      179.3(5)   . . . . yes
 Br(2)     C(10)     C(1)      P         -4.6(9)    . . . . yes
 Br(2)     C(10)     C(1)      C(2)      -174.5(5)  . . . . yes
 Br(2)     C(10)     C(9)      C(3)      173.7(5)   . . . . yes
 Br(2)     C(10)     C(9)      C(8)      -3(1)      . . . . yes
 P         C(1)      C(2)      C(3)      -169.0(5)  . . . . yes
 P         C(1)      C(10)     C(9)      171.6(5)   . . . . yes
 P         C(11)     C(12)     C(13)     175.0(6)   . . . . yes
 P         C(11)     C(16)     C(15)     -176.2(6)  . . . . yes
 P         C(17)     C(18)     C(19)     -175.1(6)  . . . . yes
 P         C(17)     C(22)     C(21)     176.7(7)   . . . . yes
 O         P         C(1)      C(2)      96.1(7)    . . . . yes
 O         P         C(1)      C(10)     -71.2(7)   . . . . yes
 O         P         C(11)     C(12)     163.5(6)   . . . . yes
 O         P         C(11)     C(16)     -21.6(7)   . . . . yes
 O         P         C(17)     C(18)     160.9(6)   . . . . yes
 O         P         C(17)     C(22)     -14.3(7)   . . . . yes
 C(1)      P         C(11)     C(12)     41.6(7)    . . . . yes
 C(1)      P         C(11)     C(16)     -143.5(6)  . . . . yes
 C(1)      P         C(17)     C(18)     -75.0(7)   . . . . yes
 C(1)      P         C(17)     C(22)     109.8(6)   . . . . yes
 C(1)      C(2)      C(3)      C(4)      178.3(7)   . . . . yes
 C(1)      C(2)      C(3)      C(9)      -1.6(8)    . . . . yes
 C(1)      C(10)     C(9)      C(3)      -2.6(8)    . . . . yes
 C(1)      C(10)     C(9)      C(8)      -179.4(7)  . . . . yes
 C(2)      C(1)      P         C(11)     -139.9(7)  . . . . yes
 C(2)      C(1)      P         C(17)     -27.9(8)   . . . . yes
 C(2)      C(1)      C(10)     C(9)      1.6(8)     . . . . yes
 C(2)      C(3)      C(4)      C(5)      -177.5(7)  . . . . yes
 C(2)      C(3)      C(9)      C(8)      179.3(7)   . . . . yes
 C(2)      C(3)      C(9)      C(10)     2.5(8)     . . . . yes
 C(3)      C(2)      C(1)      C(10)     0.1(8)     . . . . yes
 C(3)      C(4)      C(5)      C(6)      -2(1)      . . . . yes
 C(3)      C(9)      C(8)      C(7)      1(1)       . . . . yes
 C(4)      C(3)      C(9)      C(8)      0(1)       . . . . yes
 C(4)      C(3)      C(9)      C(10)     -177.4(7)  . . . . yes
 C(4)      C(5)      C(6)      C(7)      0(1)       . . . . yes
 C(5)      C(4)      C(3)      C(9)      2(1)       . . . . yes
 C(5)      C(6)      C(7)      C(8)      3(1)       . . . . yes
 C(6)      C(7)      C(8)      C(9)      -3(1)      . . . . yes
 C(7)      C(8)      C(9)      C(10)     177.4(8)   . . . . yes
 C(10)     C(1)      P         C(11)     52.8(7)    . . . . yes
 C(10)     C(1)      P         C(17)     164.7(6)   . . . . yes
 C(11)     P         C(17)     C(18)     37.1(7)    . . . . yes
 C(11)     P         C(17)     C(22)     -138.1(6)  . . . . yes
 C(11)     C(12)     C(13)     C(14)     0(1)       . . . . yes
 C(11)     C(16)     C(15)     C(14)     1(1)       . . . . yes
 C(12)     C(11)     P         C(17)     -74.8(7)   . . . . yes
 C(12)     C(11)     C(16)     C(15)     -1(1)      . . . . yes
 C(12)     C(13)     C(14)     C(15)     0(1)       . . . . yes
 C(13)     C(12)     C(11)     C(16)     0(1)       . . . . yes
 C(13)     C(14)     C(15)     C(16)     0(1)       . . . . yes
 C(16)     C(11)     P         C(17)     100.1(6)   . . . . yes
 C(17)     C(18)     C(19)     C(20)     0(1)       . . . . yes
 C(17)     C(22)     C(21)     C(20)     -2(1)      . . . . yes
 C(18)     C(17)     C(22)     C(21)     1(1)       . . . . yes
 C(18)     C(19)     C(20)     C(21)     -1(1)      . . . . yes
 C(19)     C(18)     C(17)     C(22)     0(1)       . . . . yes
 C(19)     C(20)     C(21)     C(22)     3(1)       . . . . yes
 C(19)     C(20)     C(21)     C(22)     3(1)       . . . . yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
 Br(1)     C(15)     3.525(9)   . 1_556 ?
 O         C(12)     3.308(10)  . 1_655 ?
 O         C(13)     3.39(1)    . 1_655 ?
 O         C(6)      3.54(1)    . 3_756 ?
 C(1)      C(6)      3.47(1)    . 3_756 ?
 C(2)      C(6)      3.36(1)    . 3_656 ?
 C(2)      C(6)      3.37(1)    . 3_756 ?
 C(2)      C(7)      3.52(1)    . 3_756 ?
 C(3)      C(5)      3.39(1)    . 3_656 ?
 C(3)      C(6)      3.50(1)    . 3_656 ?
 C(3)      C(4)      3.570(10)  . 3_656 ?
 C(3)      C(6)      3.57(1)    . 3_756 ?
 C(4)      C(8)      3.45(1)    . 3_756 ?
 C(4)      C(9)      3.46(1)    . 3_756 ?
 C(4)      C(9)      3.47(1)    . 3_656 ?
 C(4)      C(8)      3.55(1)    . 3_656 ?
 C(5)      C(10)     3.37(1)    . 3_756 ?
 C(5)      C(9)      3.40(1)    . 3_756 ?
 C(5)      C(9)      3.44(1)    . 3_656 ?
 C(15)     C(21)     3.57(1)    . 4_454 ?
 Br(2)     P         3.513(2)   . . ?
#------------------------------------------------------------------------------
#------------------------------------------------------------------------------




#= = = END




data_General
_audit_creation_date                  '2005-05-24'
_audit_creation_method                'by CrystalStructure 3.6.0'
_audit_update_record                   ?

#==============================================================================

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic     ?
_journal_date_from_coeditor       ?
_journal_date_accepted            ?
_journal_coeditor_code            ?

#==============================================================================

# SUBMISSION DETAILS

_publ_contact_author_name             'ENTER NAME'
_publ_contact_author_email            'ENTER EMAIL ADDRESS'
_publ_contact_author_fax              'ENTER FAX NUMBER'
_publ_contact_author_phone            'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal               'ENTER JOURNAL NAME HERE'
_publ_requested_category              'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name          ?

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
  ENTER SYNOPSIS
;

#==============================================================================

# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku/MSC and Rigaku Corporation. (2004).
    CrystalStructure 3.6.0.
    Single Crystal Structure Analysis Software.
    Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381-5209.
    Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan.

    Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996)
    CRYSTALS Issue 10, Chemical Crystallography Laboratory, Oxford, UK.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================

data___AzureneCT-050520    Compound 9

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum                  'C22 H16 Br O P '
_chemical_formula_moiety               'C22 H16 Br O P '
_chemical_formula_weight               407.25
_chemical_melting_point                ?

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting                 monoclinic
_symmetry_space_group_name_H-M        'P 1 21/n 1'
_symmetry_space_group_name_Hall       '-P 2yn'
_symmetry_Int_Tables_number            14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '1/2-X,1/2+Y,1/2-Z'
3   '-X,-Y,-Z'
4   '1/2+X,1/2-Y,1/2+Z'

#------------------------------------------------------------------------------

_cell_length_a                         9.984(5)
_cell_length_b                         9.519(5)
_cell_length_c                         18.881(10)
_cell_angle_alpha                      90
_cell_angle_beta                       95.740(2)
_cell_angle_gamma                      90
_cell_volume                           1785.5(16)
_cell_formula_units_Z                  4
_cell_measurement_reflns_used          3018
_cell_measurement_theta_min            2.1
_cell_measurement_theta_max            28.7
_cell_measurement_temperature          173.1

#------------------------------------------------------------------------------

_exptl_crystal_description            'unknown'
_exptl_crystal_colour                 'green'
_exptl_crystal_size_max                0.20
_exptl_crystal_size_mid                0.18
_exptl_crystal_size_min                0.08
_exptl_crystal_density_diffrn          1.515
_exptl_crystal_density_meas            ?
_exptl_crystal_density_method         'not measured'
_exptl_crystal_F_000                   824.00
_exptl_absorpt_coefficient_mu          2.405
_exptl_absorpt_correction_type         multi-scan
_exptl_absorpt_process_details
'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min        0.586
_exptl_absorpt_correction_T_max        0.825

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type                'Mo Kalpha'
_diffrn_radiation_wavelength           0.7107
_diffrn_measurement_device_type       'Rigaku Mercury'
_diffrn_measurement_method             omega
_diffrn_detector_area_resol_mean       7.31
_diffrn_reflns_number                  15194
_diffrn_reflns_av_R_equivalents        0.050
_diffrn_reflns_theta_max               28.70
_diffrn_measured_fraction_theta_max    0.9816
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.9904
_diffrn_reflns_limit_h_min             -13
_diffrn_reflns_limit_h_max             12
_diffrn_reflns_limit_k_min             -12
_diffrn_reflns_limit_k_max             12
_diffrn_reflns_limit_l_min             -25
_diffrn_reflns_limit_l_max             24

#==============================================================================

# REFINEMENT DATA

_refine_special_details
;
    Refinement using all reflections. The weighted R-factor
(wR), goodness of fit (S) and R-factor (gt) are
    based on F, with F set to zero for negative F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                   4546
_reflns_number_gt                      1765
_reflns_threshold_expression           F²>2.0sigma(F²)
_refine_ls_structure_factor_coef       Fsqd
_refine_ls_R_factor_gt                 0.0460
_refine_ls_wR_factor_ref               0.1100
_refine_ls_hydrogen_treatment          refall
_refine_ls_number_reflns               4072
_refine_ls_number_parameters           227
_refine_ls_goodness_of_fit_ref         0.955
_refine_ls_weighting_scheme            calc
_refine_ls_weighting_details
   'w = 1/[sigma²(Fo²)+(0.0418P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max                0.0000
_refine_diff_density_max               0.79
_refine_diff_density_min               -0.49
_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'  0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
  'Br' 'Br'  -0.290 2.459
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'P' 'P'  0.102 0.094
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================

# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Br(1)  Br 0.20603(4)  0.90907(4)  0.10240(2)  0.0414(2)   Uani 1.00 1 d . . .
 P(1)   P  0.40759(9)  0.61274(10) 0.16229(5)  0.0247(2)   Uani 1.00 1 d . . .
 O(1)   O  0.3525(2)   0.6567(3)   0.22888(13) 0.0311(6)   Uani 1.00 1 d . . .
 C(1)   C  0.2088(4)   0.7321(4)   0.0584(2)   0.0279(9)   Uani 1.00 1 d . . .
 C(2)   C  0.2897(3)   0.6180(4)   0.0846(2)   0.0228(8)   Uani 1.00 1 d . . .
 C(3)   C  0.2610(3)   0.5066(4)   0.0375(2)   0.0255(9)   Uani 1.00 1 d . . .
 C(4)   C  0.1213(4)   0.4643(4)   -0.0747(2)  0.0293(9)   Uani 1.00 1 d . . .
 C(5)   C  0.0362(4)   0.4987(4)   -0.1349(2)  0.0342(10)  Uani 1.00 1 d . . .
 C(6)   C  -0.0247(4)  0.6257(4)   -0.1517(2)  0.0340(10)  Uani 1.00 1 d . . .
 C(7)   C  -0.0217(4)  0.7509(4)   -0.1131(2)  0.0342(10)  Uani 1.00 1 d . . .
 C(8)   C  0.0457(4)   0.7819(4)   -0.0478(2)  0.0307(9)   Uani 1.00 1 d . . .
 C(9)   C  0.1322(3)   0.6957(4)   -0.0047(2)  0.0245(8)   Uani 1.00 1 d . . .
 C(10)  C  0.1669(3)   0.5476(4)   -0.0179(2)  0.0236(8)   Uani 1.00 1 d . . .
 C(11)  C  0.5482(4)   0.7198(4)   0.1411(2)   0.0275(9)   Uani 1.00 1 d . . .
 C(12)  C  0.5587(4)   0.7760(4)   0.0745(2)   0.0327(9)   Uani 1.00 1 d . . .
 C(13)  C  0.6684(4)   0.8607(4)   0.0619(3)   0.0428(11)  Uani 1.00 1 d . . .
 C(14)  C  0.7664(4)   0.8876(4)   0.1174(3)   0.0452(12)  Uani 1.00 1 d . . .
 C(15)  C  0.7573(4)   0.8311(4)   0.1831(3)   0.0435(12)  Uani 1.00 1 d . . .
 C(16)  C  0.6490(4)   0.7481(4)   0.1958(2)   0.0353(10)  Uani 1.00 1 d . . .
 C(17)  C  0.4624(4)   0.4330(4)   0.1646(2)   0.0244(8)   Uani 1.00 1 d . . .
 C(18)  C  0.5665(4)   0.3853(4)   0.1270(2)   0.0320(9)   Uani 1.00 1 d . . .
 C(19)  C  0.5953(4)   0.2426(4)   0.1260(2)   0.0372(10)  Uani 1.00 1 d . . .
 C(20)  C  0.5211(4)   0.1483(4)   0.1615(2)   0.0359(10)  Uani 1.00 1 d . . .
 C(21)  C  0.4187(4)   0.1954(4)   0.1985(2)   0.0334(10)  Uani 1.00 1 d . . .
 C(22)  C  0.3897(4)   0.3371(4)   0.2013(2)   0.0272(9)   Uani 1.00 1 d . . .
 H(1)   H  0.2993      0.4176      0.0425      0.031       Uiso 1.00 1 c R . .
 H(2)   H  0.1517      0.3719      -0.0725     0.035       Uiso 1.00 1 c R . .
 H(3)   H  0.0181      0.4270      -0.1679     0.041       Uiso 1.00 1 c R . .
 H(4)   H  -0.0758     0.6285      -0.1956     0.041       Uiso 1.00 1 c R . .
 H(5)   H  -0.0726     0.8239      -0.1346     0.041       Uiso 1.00 1 c R . .
 H(6)   H  0.0318      0.8715      -0.0303     0.037       Uiso 1.00 1 c R . .
 H(7)   H  0.4922      0.7574      0.0376      0.039       Uiso 1.00 1 c R . .
 H(8)   H  0.6753      0.8983      0.0170      0.051       Uiso 1.00 1 c R . .
 H(9)   H  0.8391      0.9447      0.1098      0.054       Uiso 1.00 1 c R . .
 H(10)  H  0.8247      0.8487      0.2196      0.052       Uiso 1.00 1 c R . .
 H(11)  H  0.6432      0.7110      0.2410      0.042       Uiso 1.00 1 c R . .
 H(12)  H  0.3217      0.3684      0.2277      0.033       Uiso 1.00 1 c R . .
 H(13)  H  0.3682      0.1314      0.2218      0.040       Uiso 1.00 1 c R . .
 H(14)  H  0.5406      0.0528      0.1603      0.043       Uiso 1.00 1 c R . .
 H(15)  H  0.6652      0.2104      0.1013      0.045       Uiso 1.00 1 c R . .
 H(16)  H  0.6163      0.4484      0.1027      0.038       Uiso 1.00 1 c R . .



#==============================================================================

_computing_data_collection            'CrystalClear'
_computing_cell_refinement            'CrystalClear'
_computing_data_reduction             'CrystalStructure'
_computing_structure_solution         'SHELXS97'
_computing_structure_refinement       'SHELXL'
_computing_publication_material       'CrystalStructure 3.6.0'
_computing_molecular_graphics          ?

#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br(1)     C(1)      1.880(4)    ?     . .
P(1)      O(1)      1.482(3)    ?     . .
P(1)      C(2)      1.787(3)    ?     . .
P(1)      C(11)     1.812(4)    ?     . .
P(1)      C(17)     1.796(4)    ?     . .
C(1)      C(2)      1.413(5)    ?     . .
C(1)      C(9)      1.394(5)    ?     . .
C(2)      C(3)      1.395(5)    ?     . .
C(3)      C(10)     1.390(5)    ?     . .
C(4)      C(5)      1.388(5)    ?     . .
C(4)      C(10)     1.374(5)    ?     . .
C(5)      C(6)      1.376(6)    ?     . .
C(6)      C(7)      1.396(6)    ?     . .
C(7)      C(8)      1.376(5)    ?     . .
C(8)      C(9)      1.393(5)    ?     . .
C(9)      C(10)     1.479(5)    ?     . .
C(11)     C(12)     1.381(6)    ?     . .
C(11)     C(16)     1.394(5)    ?     . .
C(12)     C(13)     1.399(6)    ?     . .
C(13)     C(14)     1.384(6)    ?     . .
C(14)     C(15)     1.363(7)    ?     . .
C(15)     C(16)     1.380(6)    ?     . .
C(17)     C(18)     1.392(5)    ?     . .
C(17)     C(22)     1.394(5)    ?     . .
C(18)     C(19)     1.389(5)    ?     . .
C(19)     C(20)     1.380(6)    ?     . .
C(20)     C(21)     1.370(6)    ?     . .
C(21)     C(22)     1.382(5)    ?     . .
C(3)      H(1)      0.9300      ?     . .
C(4)      H(2)      0.9300      ?     . .
C(5)      H(3)      0.9300      ?     . .
C(6)      H(4)      0.9299      ?     . .
C(7)      H(5)      0.9300      ?     . .
C(8)      H(6)      0.9300      ?     . .
C(12)     H(7)      0.9300      ?     . .
C(13)     H(8)      0.9301      ?     . .
C(14)     H(9)      0.9300      ?     . .
C(15)     H(10)     0.9300      ?     . .
C(16)     H(11)     0.9298      ?     . .
C(18)     H(16)     0.9299      ?     . .
C(19)     H(15)     0.9299      ?     . .
C(20)     H(14)     0.9300      ?     . .
C(21)     H(13)     0.9300      ?     . .
C(22)     H(12)     0.9300      ?     . .

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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
Br(1)     C(1)      C(2)      124.6(3)    ?     . . .
Br(1)     C(1)      C(9)      124.7(3)    ?     . . .
C(2)      P(1)      O(1)      114.8(2)    ?     . . .
C(11)     P(1)      O(1)      113.0(2)    ?     . . .
C(17)     P(1)      O(1)      112.8(2)    ?     . . .
P(1)      C(2)      C(1)      127.9(3)    ?     . . .
P(1)      C(2)      C(3)      125.3(3)    ?     . . .
C(11)     P(1)      C(2)      105.3(2)    ?     . . .
C(17)     P(1)      C(2)      102.7(2)    ?     . . .
P(1)      C(11)     C(12)     123.4(3)    ?     . . .
P(1)      C(11)     C(16)     117.6(3)    ?     . . .
C(17)     P(1)      C(11)     107.4(2)    ?     . . .
P(1)      C(17)     C(18)     122.7(3)    ?     . . .
P(1)      C(17)     C(22)     117.6(3)    ?     . . .
C(9)      C(1)      C(2)      110.7(3)    ?     . . .
C(1)      C(2)      C(3)      106.7(3)    ?     . . .
C(1)      C(9)      C(8)      127.4(3)    ?     . . .
C(1)      C(9)      C(10)     105.3(3)    ?     . . .
C(2)      C(3)      C(10)     110.3(3)    ?     . . .
C(3)      C(10)     C(9)      107.0(3)    ?     . . .
C(3)      C(10)     C(4)      124.9(3)    ?     . . .
C(10)     C(4)      C(5)      129.1(4)    ?     . . .
C(4)      C(5)      C(6)      128.1(4)    ?     . . .
C(4)      C(10)     C(9)      128.1(3)    ?     . . .
C(5)      C(6)      C(7)      130.0(4)    ?     . . .
C(6)      C(7)      C(8)      129.4(4)    ?     . . .
C(7)      C(8)      C(9)      128.0(4)    ?     . . .
C(8)      C(9)      C(10)     127.3(3)    ?     . . .
C(16)     C(11)     C(12)     119.1(3)    ?     . . .
C(11)     C(12)     C(13)     120.6(4)    ?     . . .
C(11)     C(16)     C(15)     120.1(4)    ?     . . .
C(12)     C(13)     C(14)     119.0(4)    ?     . . .
C(13)     C(14)     C(15)     120.6(4)    ?     . . .
C(14)     C(15)     C(16)     120.6(4)    ?     . . .
C(22)     C(17)     C(18)     119.5(3)    ?     . . .
C(17)     C(18)     C(19)     119.5(4)    ?     . . .
C(17)     C(22)     C(21)     119.9(4)    ?     . . .
C(18)     C(19)     C(20)     120.5(4)    ?     . . .
C(19)     C(20)     C(21)     119.9(4)    ?     . . .
C(20)     C(21)     C(22)     120.7(4)    ?     . . .
C(2)      C(3)      H(1)      124.8580    ?     . . .
H(1)      C(3)      C(10)     124.8632    ?     . . .
H(2)      C(4)      C(5)      115.4431    ?     . . .
C(4)      C(5)      H(3)      115.9698    ?     . . .
H(2)      C(4)      C(10)     115.4474    ?     . . .
H(3)      C(5)      C(6)      115.9668    ?     . . .
C(5)      C(6)      H(4)      114.9924    ?     . . .
H(4)      C(6)      C(7)      114.9897    ?     . . .
C(6)      C(7)      H(5)      115.3013    ?     . . .
C(7)      C(8)      H(6)      116.0175    ?     . . .
H(5)      C(7)      C(8)      115.3058    ?     . . .
H(6)      C(8)      C(9)      116.0105    ?     . . .
C(11)     C(12)     H(7)      119.6916    ?     . . .
C(11)     C(16)     H(11)     119.9693    ?     . . .
H(7)      C(12)     C(13)     119.6964    ?     . . .
C(12)     C(13)     H(8)      120.4921    ?     . . .
H(8)      C(13)     C(14)     120.4968    ?     . . .
C(13)     C(14)     H(9)      119.7071    ?     . . .
C(14)     C(15)     H(10)     119.6702    ?     . . .
H(9)      C(14)     C(15)     119.6986    ?     . . .
C(15)     C(16)     H(11)     119.9666    ?     . . .
H(10)     C(15)     C(16)     119.6827    ?     . . .
C(17)     C(18)     H(16)     120.2472    ?     . . .
C(17)     C(22)     H(12)     120.0673    ?     . . .
H(16)     C(18)     C(19)     120.2456    ?     . . .
C(18)     C(19)     H(15)     119.7457    ?     . . .
H(15)     C(19)     C(20)     119.7474    ?     . . .
C(19)     C(20)     H(14)     120.0296    ?     . . .
C(20)     C(21)     H(13)     119.6668    ?     . . .
H(14)     C(20)     C(21)     120.0411    ?     . . .
C(21)     C(22)     H(12)     120.0521    ?     . . .
H(13)     C(21)     C(22)     119.6827    ?     . . .

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O(1)      P(1)      C(2)      C(1)      53.5(4)     ?     . . . .
O(1)      P(1)      C(2)      C(3)      -126.7(3)   ?     . . . .
C(11)     P(1)      C(2)      C(1)      -71.4(4)    ?     . . . .
C(11)     P(1)      C(2)      C(3)      108.4(3)    ?     . . . .
C(17)     P(1)      C(2)      C(1)      176.3(3)    ?     . . . .
C(17)     P(1)      C(2)      C(3)      -4.0(3)     ?     . . . .
O(1)      P(1)      C(11)     C(12)     -132.3(3)   ?     . . . .
O(1)      P(1)      C(11)     C(16)     46.4(3)     ?     . . . .
C(2)      P(1)      C(11)     C(12)     -6.3(3)     ?     . . . .
C(2)      P(1)      C(11)     C(16)     172.4(3)    ?     . . . .
C(17)     P(1)      C(11)     C(12)     102.8(3)    ?     . . . .
C(17)     P(1)      C(11)     C(16)     -78.5(3)    ?     . . . .
O(1)      P(1)      C(17)     C(18)     -150.5(3)   ?     . . . .
O(1)      P(1)      C(17)     C(22)     34.7(3)     ?     . . . .
C(2)      P(1)      C(17)     C(18)     85.5(3)     ?     . . . .
C(2)      P(1)      C(17)     C(22)     -89.4(3)    ?     . . . .
C(11)     P(1)      C(17)     C(18)     -25.3(3)    ?     . . . .
C(11)     P(1)      C(17)     C(22)     159.8(2)    ?     . . . .
Br(1)     C(1)      C(2)      P(1)      -1.0(5)     ?     . . . .
Br(1)     C(1)      C(2)      C(3)      179.2(3)    ?     . . . .
C(9)      C(1)      C(2)      P(1)      178.5(3)    ?     . . . .
C(9)      C(1)      C(2)      C(3)      -1.3(4)     ?     . . . .
Br(1)     C(1)      C(9)      C(8)      2.8(6)      ?     . . . .
Br(1)     C(1)      C(9)      C(10)     -179.6(3)   ?     . . . .
C(2)      C(1)      C(9)      C(8)      -176.7(4)   ?     . . . .
C(2)      C(1)      C(9)      C(10)     0.9(4)      ?     . . . .
P(1)      C(2)      C(3)      C(10)     -178.7(3)   ?     . . . .
C(1)      C(2)      C(3)      C(10)     1.1(4)      ?     . . . .
C(2)      C(3)      C(10)     C(4)      177.2(4)    ?     . . . .
C(2)      C(3)      C(10)     C(9)      -0.6(4)     ?     . . . .
C(10)     C(4)      C(5)      C(6)      -0.9(7)     ?     . . . .
C(5)      C(4)      C(10)     C(3)      -174.6(4)   ?     . . . .
C(5)      C(4)      C(10)     C(9)      2.8(7)      ?     . . . .
C(4)      C(5)      C(6)      C(7)      -2.3(7)     ?     . . . .
C(5)      C(6)      C(7)      C(8)      1.4(7)      ?     . . . .
C(6)      C(7)      C(8)      C(9)      2.3(7)      ?     . . . .
C(7)      C(8)      C(9)      C(1)      174.1(4)    ?     . . . .
C(7)      C(8)      C(9)      C(10)     -3.0(7)     ?     . . . .
C(1)      C(9)      C(10)     C(3)      -0.2(4)     ?     . . . .
C(1)      C(9)      C(10)     C(4)      -177.9(4)   ?     . . . .
C(8)      C(9)      C(10)     C(3)      177.4(4)    ?     . . . .
C(8)      C(9)      C(10)     C(4)      -0.3(6)     ?     . . . .
P(1)      C(11)     C(12)     C(13)     178.4(3)    ?     . . . .
C(16)     C(11)     C(12)     C(13)     -0.2(5)     ?     . . . .
P(1)      C(11)     C(16)     C(15)     -178.9(3)   ?     . . . .
C(12)     C(11)     C(16)     C(15)     -0.1(4)     ?     . . . .
C(11)     C(12)     C(13)     C(14)     -0.1(5)     ?     . . . .
C(12)     C(13)     C(14)     C(15)     0.8(6)      ?     . . . .
C(13)     C(14)     C(15)     C(16)     -1.2(7)     ?     . . . .
C(14)     C(15)     C(16)     C(11)     0.8(6)      ?     . . . .
P(1)      C(17)     C(18)     C(19)     -174.1(3)   ?     . . . .
C(22)     C(17)     C(18)     C(19)     0.7(5)      ?     . . . .
P(1)      C(17)     C(22)     C(21)     173.2(3)    ?     . . . .
C(18)     C(17)     C(22)     C(21)     -1.9(5)     ?     . . . .
C(17)     C(18)     C(19)     C(20)     0.5(6)      ?     . . . .
C(18)     C(19)     C(20)     C(21)     -0.4(6)     ?     . . . .
C(19)     C(20)     C(21)     C(22)     -0.8(6)     ?     . . . .
C(20)     C(21)     C(22)     C(17)     1.9(6)      ?     . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Br(1)     P(1)      3.582(1)    ?     . .
Br(1)     O(1)      3.594(2)    ?     . .
Br(1)     C(2)      2.923(3)    ?     . .
Br(1)     C(8)      3.341(4)    ?     . .
Br(1)     C(9)      2.909(4)    ?     . .
P(1)      C(1)      2.880(4)    ?     . .
P(1)      C(3)      2.833(4)    ?     . .
P(1)      C(12)     2.818(4)    ?     . .
P(1)      C(16)     2.750(4)    ?     . .
P(1)      C(18)     2.804(4)    ?     . .
P(1)      C(22)     2.737(4)    ?     . .
O(1)      C(1)      3.465(4)    ?     . .
O(1)      C(2)      2.758(4)    ?     . .
O(1)      C(6)      3.213(5)    ?     . 56504
O(1)      C(7)      3.242(4)    ?     . 56504
O(1)      C(11)     2.752(5)    ?     . .
O(1)      C(16)     3.206(5)    ?     . .
O(1)      C(17)     2.735(4)    ?     . .
O(1)      C(21)     3.177(5)    ?     . 55502
O(1)      C(22)     3.115(5)    ?     . .
O(1)      C(22)     3.342(5)    ?     . 55502
C(1)      C(3)      2.253(5)    ?     . .
C(1)      C(8)      2.499(5)    ?     . .
C(1)      C(10)     2.284(5)    ?     . .
C(1)      C(11)     3.589(5)    ?     . .
C(1)      C(12)     3.501(5)    ?     . .
C(2)      C(9)      2.309(5)    ?     . .
C(2)      C(10)     2.285(5)    ?     . .
C(2)      C(11)     2.861(5)    ?     . .
C(2)      C(12)     3.100(5)    ?     . .
C(2)      C(17)     2.799(5)    ?     . .
C(2)      C(18)     3.569(5)    ?     . .
C(2)      C(22)     3.545(5)    ?     . .
C(3)      C(4)      2.450(5)    ?     . .
C(3)      C(6)      3.580(5)    ?     . 56503
C(3)      C(9)      2.307(5)    ?     . .
C(3)      C(17)     3.054(5)    ?     . .
C(3)      C(18)     3.530(5)    ?     . .
C(4)      C(6)      2.485(5)    ?     . .
C(4)      C(7)      3.130(5)    ?     . .
C(4)      C(8)      3.169(5)    ?     . .
C(4)      C(9)      2.565(5)    ?     . .
C(4)      C(9)      3.425(5)    ?     . 56503
C(4)      C(10)     3.515(5)    ?     . 56503
C(5)      C(7)      2.513(6)    ?     . .
C(5)      C(8)      3.154(6)    ?     . .
C(5)      C(9)      3.163(5)    ?     . .
C(5)      C(10)     2.494(5)    ?     . .
C(6)      O(1)      3.213(5)    ?     . 46404
C(6)      C(3)      3.580(5)    ?     . 56503
C(6)      C(8)      2.506(6)    ?     . .
C(6)      C(9)      3.120(5)    ?     . .
C(6)      C(10)     3.103(5)    ?     . .
C(7)      O(1)      3.242(4)    ?     . 46404
C(7)      C(9)      2.489(5)    ?     . .
C(7)      C(10)     3.137(5)    ?     . .
C(8)      C(10)     2.573(5)    ?     . .
C(9)      C(4)      3.425(5)    ?     . 56503
C(10)     C(4)      3.515(5)    ?     . 56503
C(10)     C(10)     3.583(5)    ?     . 56503
C(10)     C(18)     3.582(5)    ?     . 66503
C(11)     C(13)     2.415(6)    ?     . .
C(11)     C(14)     2.773(6)    ?     . .
C(11)     C(15)     2.403(5)    ?     . .
C(11)     C(17)     2.908(5)    ?     . .
C(11)     C(18)     3.202(5)    ?     . .
C(12)     C(14)     2.398(6)    ?     . .
C(12)     C(15)     2.757(6)    ?     . .
C(12)     C(16)     2.392(6)    ?     . .
C(13)     C(15)     2.386(7)    ?     . .
C(13)     C(16)     2.771(6)    ?     . .
C(14)     C(16)     2.383(6)    ?     . .
C(16)     C(17)     3.548(5)    ?     . .
C(17)     C(19)     2.402(5)    ?     . .
C(17)     C(20)     2.775(5)    ?     . .
C(17)     C(21)     2.403(5)    ?     . .
C(18)     C(10)     3.582(5)    ?     . 66503
C(18)     C(20)     2.404(6)    ?     . .
C(18)     C(21)     2.768(6)    ?     . .
C(18)     C(22)     2.407(6)    ?     . .
C(19)     C(21)     2.380(6)    ?     . .
C(19)     C(22)     2.762(6)    ?     . .
C(20)     C(22)     2.391(6)    ?     . .
C(21)     O(1)      3.177(5)    ?     . 54502
C(22)     O(1)      3.342(5)    ?     . 54502
Br(1)     H(6)      2.9251      ?     . .
Br(1)     H(7)      3.5275      ?     . .
Br(1)     H(12)     3.2697      ?     . 55502
Br(1)     H(13)     3.3843      ?     . 56501
P(1)      H(1)      3.0411      ?     . .
P(1)      H(7)      2.9246      ?     . .
P(1)      H(11)     2.8134      ?     . .
P(1)      H(12)     2.8081      ?     . .
P(1)      H(16)     2.9194      ?     . .
O(1)      H(4)      2.5530      ?     . 56504
O(1)      H(5)      2.6183      ?     . 56504
O(1)      H(11)     2.9339      ?     . .
O(1)      H(12)     2.7619      ?     . .
O(1)      H(12)     2.8357      ?     . 55502
O(1)      H(13)     2.4877      ?     . 55502
C(1)      H(1)      3.1498      ?     . .
C(1)      H(3)      3.5539      ?     . 56503
C(1)      H(6)      2.6640      ?     . .
C(1)      H(7)      2.9053      ?     . .
C(1)      H(15)     3.4252      ?     . 66503
C(2)      H(1)      2.0723      ?     . .
C(2)      H(7)      2.6446      ?     . .
C(2)      H(12)     3.5888      ?     . .
C(3)      H(2)      2.5873      ?     . .
C(3)      H(7)      3.3210      ?     . .
C(3)      H(16)     3.0566      ?     . 66503
C(4)      H(1)      2.7317      ?     . .
C(4)      H(3)      1.9804      ?     . .
C(4)      H(4)      3.2608      ?     . .
C(4)      H(16)     2.8481      ?     . 66503
C(5)      H(2)      1.9750      ?     . .
C(5)      H(4)      1.9593      ?     . .
C(5)      H(5)      3.2807      ?     . .
C(5)      H(13)     3.2803      ?     . 45404
C(5)      H(16)     3.4984      ?     . 66503
C(6)      H(2)      3.2627      ?     . .
C(6)      H(3)      1.9693      ?     . .
C(6)      H(5)      1.9812      ?     . .
C(6)      H(6)      3.2855      ?     . .
C(6)      H(11)     3.1641      ?     . 46404
C(6)      H(12)     3.1630      ?     . 56503
C(6)      H(13)     3.5100      ?     . 45404
C(7)      H(1)      3.5732      ?     . 56503
C(7)      H(3)      3.2889      ?     . .
C(7)      H(4)      1.9778      ?     . .
C(7)      H(6)      1.9699      ?     . .
C(7)      H(11)     3.3677      ?     . 46404
C(7)      H(15)     3.5630      ?     . 66503
C(8)      H(2)      3.4759      ?     . 56503
C(8)      H(4)      3.2744      ?     . .
C(8)      H(5)      1.9626      ?     . .
C(8)      H(15)     3.1524      ?     . 66503
C(9)      H(1)      3.2069      ?     . .
C(9)      H(2)      3.3501      ?     . .
C(9)      H(2)      3.3760      ?     . 56503
C(9)      H(5)      3.2679      ?     . .
C(9)      H(6)      1.9856      ?     . .
C(9)      H(15)     2.9920      ?     . 66503
C(9)      H(16)     3.5412      ?     . 66503
C(10)     H(1)      2.0676      ?     . .
C(10)     H(2)      1.9623      ?     . .
C(10)     H(3)      3.2717      ?     . .
C(10)     H(6)      3.3643      ?     . .
C(10)     H(15)     3.3350      ?     . 66503
C(10)     H(16)     2.8183      ?     . 66503
C(11)     H(2)      3.4919      ?     . 66503
C(11)     H(7)      2.0111      ?     . .
C(11)     H(8)      3.2536      ?     . .
C(11)     H(10)     3.2412      ?     . .
C(11)     H(11)     2.0260      ?     . .
C(11)     H(14)     3.1930      ?     . 56501
C(11)     H(16)     2.7851      ?     . .
C(12)     H(1)      3.3029      ?     . 66503
C(12)     H(2)      3.2202      ?     . 66503
C(12)     H(8)      2.0352      ?     . .
C(12)     H(9)      3.2390      ?     . .
C(12)     H(11)     3.2328      ?     . .
C(12)     H(14)     3.1087      ?     . 56501
C(12)     H(16)     3.2061      ?     . .
C(13)     H(1)      3.3370      ?     . 66503
C(13)     H(2)      2.8462      ?     . 66503
C(13)     H(7)      2.0275      ?     . .
C(13)     H(9)      2.0139      ?     . .
C(13)     H(10)     3.2229      ?     . .
C(13)     H(14)     2.9832      ?     . 56501
C(13)     H(15)     3.4113      ?     . 56501
C(14)     H(2)      2.7623      ?     . 66503
C(14)     H(7)      3.2369      ?     . .
C(14)     H(8)      2.0216      ?     . .
C(14)     H(10)     1.9945      ?     . .
C(14)     H(11)     3.2186      ?     . .
C(14)     H(14)     2.9290      ?     . 56501
C(14)     H(15)     3.2391      ?     . 56501
C(15)     H(2)      3.0495      ?     . 66503
C(15)     H(3)      3.3584      ?     . 66503
C(15)     H(8)      3.2249      ?     . .
C(15)     H(9)      1.9947      ?     . .
C(15)     H(11)     2.0124      ?     . .
C(15)     H(14)     3.0222      ?     . 56501
C(16)     H(2)      3.4085      ?     . 66503
C(16)     H(4)      3.3963      ?     . 56504
C(16)     H(7)      3.2333      ?     . .
C(16)     H(9)      3.2195      ?     . .
C(16)     H(10)     2.0098      ?     . .
C(16)     H(14)     3.1448      ?     . 56501
C(16)     H(16)     3.3496      ?     . .
C(17)     H(1)      2.6909      ?     . .
C(17)     H(10)     3.0018      ?     . 64502
C(17)     H(11)     3.4377      ?     . .
C(17)     H(12)     2.0271      ?     . .
C(17)     H(13)     3.2408      ?     . .
C(17)     H(15)     3.2412      ?     . .
C(17)     H(16)     2.0261      ?     . .
C(18)     H(1)      2.9847      ?     . .
C(18)     H(7)      3.3878      ?     . 66503
C(18)     H(10)     3.0096      ?     . 64502
C(18)     H(12)     3.2471      ?     . .
C(18)     H(14)     3.2423      ?     . .
C(18)     H(15)     2.0190      ?     . .
C(19)     H(7)      3.1244      ?     . 66503
C(19)     H(10)     3.1120      ?     . 64502
C(19)     H(11)     3.4498      ?     . 64502
C(19)     H(13)     3.2182      ?     . .
C(19)     H(14)     2.0131      ?     . .
C(19)     H(16)     2.0239      ?     . .
C(20)     H(3)      3.3029      ?     . 55504
C(20)     H(10)     3.2178      ?     . 64502
C(20)     H(12)     3.2269      ?     . .
C(20)     H(13)     2.0004      ?     . .
C(20)     H(15)     2.0103      ?     . .
C(20)     H(16)     3.2421      ?     . .
C(21)     H(3)      2.8650      ?     . 55504
C(21)     H(5)      3.5487      ?     . 56503
C(21)     H(10)     3.2081      ?     . 64502
C(21)     H(12)     2.0152      ?     . .
C(21)     H(14)     2.0041      ?     . .
C(21)     H(15)     3.2172      ?     . .
C(22)     H(1)      3.1397      ?     . .
C(22)     H(4)      3.1414      ?     . 56503
C(22)     H(10)     3.0855      ?     . 64502
C(22)     H(13)     2.0116      ?     . .
C(22)     H(14)     3.2287      ?     . .
C(22)     H(16)     3.2486      ?     . .
H(1)      C(7)      3.5732      ?     . 56503
H(1)      C(12)     3.3029      ?     . 66503
H(1)      C(13)     3.3370      ?     . 66503
H(2)      C(8)      3.4759      ?     . 56503
H(2)      C(9)      3.3760      ?     . 56503
H(2)      C(11)     3.4919      ?     . 66503
H(2)      C(12)     3.2202      ?     . 66503
H(2)      C(13)     2.8462      ?     . 66503
H(2)      C(14)     2.7623      ?     . 66503
H(2)      C(15)     3.0495      ?     . 66503
H(2)      C(16)     3.4085      ?     . 66503
H(3)      C(1)      3.5539      ?     . 56503
H(3)      C(15)     3.3584      ?     . 66503
H(3)      C(20)     3.3029      ?     . 45404
H(3)      C(21)     2.8650      ?     . 45404
H(4)      O(1)      2.5530      ?     . 46404
H(4)      C(16)     3.3963      ?     . 46404
H(4)      C(22)     3.1414      ?     . 56503
H(5)      O(1)      2.6183      ?     . 46404
H(5)      C(21)     3.5487      ?     . 56503
H(7)      C(18)     3.3878      ?     . 66503
H(7)      C(19)     3.1244      ?     . 66503
H(10)     C(17)     3.0018      ?     . 65502
H(10)     C(18)     3.0096      ?     . 65502
H(10)     C(19)     3.1120      ?     . 65502
H(10)     C(20)     3.2178      ?     . 65502
H(10)     C(21)     3.2081      ?     . 65502
H(10)     C(22)     3.0855      ?     . 65502
H(11)     C(6)      3.1641      ?     . 56504
H(11)     C(7)      3.3677      ?     . 56504
H(11)     C(19)     3.4498      ?     . 65502
H(12)     Br(1)     3.2697      ?     . 54502
H(12)     O(1)      2.8357      ?     . 54502
H(12)     C(6)      3.1630      ?     . 56503
H(13)     Br(1)     3.3843      ?     . 54501
H(13)     O(1)      2.4877      ?     . 54502
H(13)     C(5)      3.2803      ?     . 55504
H(13)     C(6)      3.5100      ?     . 55504
H(14)     C(11)     3.1930      ?     . 54501
H(14)     C(12)     3.1087      ?     . 54501
H(14)     C(13)     2.9832      ?     . 54501
H(14)     C(14)     2.9290      ?     . 54501
H(14)     C(15)     3.0222      ?     . 54501
H(14)     C(16)     3.1448      ?     . 54501
H(15)     C(1)      3.4252      ?     . 66503
H(15)     C(7)      3.5630      ?     . 66503
H(15)     C(8)      3.1524      ?     . 66503
H(15)     C(9)      2.9920      ?     . 66503
H(15)     C(10)     3.3350      ?     . 66503
H(15)     C(13)     3.4113      ?     . 54501
H(15)     C(14)     3.2391      ?     . 54501
H(16)     C(3)      3.0566      ?     . 66503
H(16)     C(4)      2.8481      ?     . 66503
H(16)     C(5)      3.4984      ?     . 66503
H(16)     C(9)      3.5412      ?     . 66503
H(16)     C(10)     2.8183      ?     . 66503

#==============================================================================

# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one
# structure analysis in the CIF.

#==============================================================================

#     End of CIF

#==============================================================================






