# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Cole-Hamilton, David'
_publ_contact_author_email       djc@st-and.ac.uk

_publ_section_title              
;
Synthesis of Dendritic Molecules with Diazaphospholidine
Oxide Grafted at the surface of Octavinylsilsesquioxane (OVS)
;
loop_
_publ_author_name
G.Cheng
A.Slawin
N.Vautravers
P.Andre
R.Morris
;
D.Cole-Hamilton
;
I.Samuel

# Attachment 'ob-art-06-2010-000297-File004_v1_0.cif'

data_4
_database_code_depnum_ccdc_archive 'CCDC 782247'
#TrackingRef 'ob-art-06-2010-000297-File004_v1_0.cif'

# start Validation Reply Form

_vrf_PLAT113_4                   
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New Space-group. P21212
RESPONSE: Poor quality crystals - artificial high symmety alert.
;
_vrf_PLAT201_4                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 48
RESPONSE: Very poor quality crystals.
;
_vrf_PLAT213_4                   
;
PROBLEM: Atom Br16 has ADP max/min Ratio ..... 6.10 prola
RESPONSE:Unresolved disorder- very poor quality crystals.
;
_vrf_PLAT220_4                   
;
PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.11 Ratio
RESPONSE: Unresolved disorder- very poor quality crystals.
;
_vrf_PLAT412_4                   
;
PROBLEM: Short Intra XH3 .. XHn H3A .. H7C .. 1.63 Ang.
RESPONSE: Unresolved disorder- very poor quality crystals.
;
_vrf_PLAT035_4                   
;
PROBLEM: No _chemical_absolute_configuration info given . ?
RESPONSE: Unresolved disorder- very poor quality crystals.
;
_vrf_PLAT036_4                   
;
PROBLEM: No s.u. Given for Flack Parameter .............. ?
RESPONSE: Very poor quality crystals.

;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 Br2 N2 O3 P'
_chemical_formula_sum            'C19 H23 Br2 N2 O3 P'
_chemical_formula_weight         518.18

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.529(2)
_cell_length_b                   13.009(4)
_cell_length_c                   23.237(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.360(6)
_cell_angle_gamma                90.00
_cell_volume                     2275.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    176
_cell_measurement_theta_min      12
_cell_measurement_theta_max      34

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    3.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.493195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11712
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.56
_reflns_number_total             7887
_reflns_number_gt                7210
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1201P)^2^+98.3051P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         7887
_refine_ls_number_parameters     252
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.1516
_refine_ls_wR_factor_ref         0.3628
_refine_ls_wR_factor_gt          0.3528
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.018

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
P1 P 0.6970(7) 0.8353(4) 0.0522(2) 0.0197(11) Uani 1 1 d . . .
O1 O 0.8134(19) 0.7703(12) 0.0904(6) 0.026(3) Uiso 1 1 d . . .
C1 C 0.770(3) 0.9621(18) 0.0368(10) 0.032(5) Uiso 1 1 d . . .
C2 C 0.802(2) 1.0291(14) 0.0860(7) 0.014(3) Uiso 1 1 d . . .
C3 C 0.867(3) 1.1298(18) 0.0774(10) 0.032(5) Uiso 1 1 d . . .
H3A H 0.8872 1.1735 0.1096 0.039 Uiso 1 1 calc R . .
C4 C 0.902(3) 1.1647(16) 0.0232(8) 0.024(4) Uiso 1 1 d . . .
H4A H 0.9400 1.2338 0.0187 0.028 Uiso 1 1 calc R . .
C5 C 0.882(3) 1.0994(17) -0.0295(9) 0.027(4) Uiso 1 1 d . . .
H5A H 0.9107 1.1220 -0.0671 0.033 Uiso 1 1 calc R . .
C6 C 0.815(3) 0.9995(19) -0.0169(10) 0.033(5) Uiso 1 1 d . . .
H6A H 0.8006 0.9539 -0.0486 0.039 Uiso 1 1 calc R . .
O2 O 0.7595(18) 0.9912(13) 0.1392(6) 0.028(3) Uiso 1 1 d . . .
C7 C 0.772(4) 1.058(2) 0.1835(12) 0.048(7) Uiso 1 1 d . . .
H7A H 0.8459 1.0275 0.2140 0.072 Uiso 1 1 calc R . .
H7B H 0.6527 1.0714 0.1986 0.072 Uiso 1 1 calc R . .
H7C H 0.8251 1.1219 0.1703 0.072 Uiso 1 1 calc R . .
N1 N 0.494(2) 0.8377(14) 0.0758(8) 0.026(4) Uiso 1 1 d . . .
C8 C 0.356(3) 0.896(2) 0.0433(11) 0.037(5) Uiso 1 1 d . . .
H8A H 0.4084 0.9578 0.0250 0.044 Uiso 1 1 calc R . .
H8B H 0.3015 0.8526 0.0131 0.044 Uiso 1 1 calc R . .
C9 C 0.226(4) 0.925(2) 0.0864(11) 0.041(6) Uiso 1 1 d . . .
H9A H 0.1226 0.8785 0.0841 0.049 Uiso 1 1 calc R . .
H9B H 0.1848 0.9962 0.0792 0.049 Uiso 1 1 calc R . .
C10 C 0.316(3) 0.9176(19) 0.1489(10) 0.032(5) Uiso 1 1 d . . .
H10A H 0.3740 0.9830 0.1602 0.039 Uiso 1 1 calc R . .
H10B H 0.2295 0.8972 0.1786 0.039 Uiso 1 1 calc R . .
C11 C 0.449(3) 0.8350(17) 0.1378(10) 0.029(5) Uiso 1 1 d . . .
H11A H 0.5578 0.8474 0.1616 0.034 Uiso 1 1 calc R . .
C12 C 0.367(3) 0.7248(17) 0.1532(9) 0.029(4) Uiso 1 1 d . . .
H12A H 0.3365 0.7228 0.1946 0.035 Uiso 1 1 calc R . .
H12B H 0.2558 0.7143 0.1308 0.035 Uiso 1 1 calc R . .
N13 N 0.487(2) 0.6457(13) 0.1408(7) 0.025(4) Uiso 1 1 d . . .
H13A H 0.6041 0.6624 0.1255 0.030 Uiso 1 1 calc R . .
C13 C 0.439(3) 0.5412(17) 0.1502(9) 0.029(5) Uiso 1 1 d . . .
C14 C 0.548(3) 0.4636(15) 0.1370(9) 0.024(4) Uiso 1 1 d . . .
Br14 Br 0.7753(3) 0.48862(16) 0.10288(12) 0.0396(7) Uani 1 1 d . . .
C15 C 0.517(3) 0.3557(18) 0.1467(9) 0.025(4) Uiso 1 1 d . . .
H15A H 0.5998 0.3032 0.1374 0.030 Uiso 1 1 calc R . .
C16 C 0.342(3) 0.3361(18) 0.1727(10) 0.033(5) Uiso 1 1 d . . .
Br16 Br 0.2864(5) 0.19962(15) 0.18811(11) 0.0549(10) Uani 1 1 d . . .
C17 C 0.237(3) 0.4152(19) 0.1888(10) 0.031(5) Uiso 1 1 d . . .
H17A H 0.1293 0.3997 0.2082 0.037 Uiso 1 1 calc R . .
C18 C 0.278(2) 0.5198(15) 0.1786(7) 0.015(4) Uiso 1 1 d . . .
H18A H 0.2007 0.5734 0.1904 0.018 Uiso 1 1 calc R . .
O19 O 0.678(2) 0.7960(12) -0.0116(6) 0.029(3) Uiso 1 1 d . . .
C19 C 0.616(3) 0.6857(18) -0.0226(10) 0.032(5) Uiso 1 1 d . . .
H19A H 0.6724 0.6396 0.0055 0.049 Uiso 1 1 calc R . .
H19B H 0.6500 0.6649 -0.0616 0.049 Uiso 1 1 calc R . .
H19C H 0.4870 0.6820 -0.0188 0.049 Uiso 1 1 calc R . .
P21 P 0.7020(7) 0.3802(4) 0.4481(2) 0.0207(11) Uani 1 1 d . . .
O21 O 0.8181(18) 0.4453(11) 0.4119(6) 0.022(3) Uiso 1 1 d . . .
C21 C 0.785(2) 0.2505(12) 0.4605(7) 0.009(3) Uiso 1 1 d . . .
C22 C 0.818(3) 0.191(2) 0.4175(10) 0.033(5) Uiso 1 1 d . . .
C23 C 0.874(3) 0.0878(17) 0.4231(9) 0.029(5) Uiso 1 1 d . . .
H23A H 0.8924 0.0460 0.3902 0.035 Uiso 1 1 calc R . .
C24 C 0.901(3) 0.050(2) 0.4765(11) 0.038(5) Uiso 1 1 d . . .
H24A H 0.9371 -0.0189 0.4823 0.046 Uiso 1 1 calc R . .
C25 C 0.875(3) 0.1147(18) 0.5222(10) 0.032(5) Uiso 1 1 d . . .
H25A H 0.9013 0.0905 0.5599 0.038 Uiso 1 1 calc R . .
C26 C 0.810(3) 0.2140(17) 0.5158(9) 0.029(5) Uiso 1 1 d . . .
H26A H 0.7848 0.2555 0.5484 0.035 Uiso 1 1 calc R . .
O22 O 0.7715(18) 0.2298(12) 0.3638(6) 0.025(3) Uiso 1 1 d . . .
C27 C 0.795(4) 0.175(2) 0.3078(12) 0.049(7) Uiso 1 1 d . . .
H27A H 0.9215 0.1616 0.3016 0.073 Uiso 1 1 calc R . .
H27B H 0.7488 0.2180 0.2764 0.073 Uiso 1 1 calc R . .
H27C H 0.7301 0.1098 0.3086 0.073 Uiso 1 1 calc R . .
N21 N 0.507(2) 0.3798(14) 0.4219(7) 0.026(4) Uiso 1 1 d . . .
C28 C 0.363(3) 0.3167(19) 0.4487(10) 0.033(5) Uiso 1 1 d . . .
H28A H 0.4124 0.2515 0.4638 0.040 Uiso 1 1 calc R . .
H28B H 0.3088 0.3549 0.4810 0.040 Uiso 1 1 calc R . .
C29 C 0.229(4) 0.295(3) 0.4044(13) 0.055(7) Uiso 1 1 d . . .
H29A H 0.1330 0.3476 0.4049 0.066 Uiso 1 1 calc R . .
H29B H 0.1756 0.2264 0.4098 0.066 Uiso 1 1 calc R . .
C30 C 0.336(3) 0.3008(19) 0.3479(10) 0.034(5) Uiso 1 1 d . . .
H30A H 0.4037 0.2367 0.3411 0.041 Uiso 1 1 calc R . .
H30B H 0.2582 0.3148 0.3143 0.041 Uiso 1 1 calc R . .
C31 C 0.457(3) 0.3897(17) 0.3607(9) 0.027(4) Uiso 1 1 d . . .
H31A H 0.5669 0.3790 0.3377 0.033 Uiso 1 1 calc R . .
C32 C 0.384(3) 0.4931(18) 0.3443(9) 0.028(4) Uiso 1 1 d . . .
H32A H 0.3740 0.4969 0.3018 0.034 Uiso 1 1 calc R . .
H32B H 0.2626 0.5001 0.3602 0.034 Uiso 1 1 calc R . .
N33 N 0.491(2) 0.5778(14) 0.3645(8) 0.027(4) Uiso 1 1 d . . .
H33A H 0.5943 0.5638 0.3893 0.032 Uiso 1 1 calc R . .
C33 C 0.453(2) 0.6762(13) 0.3498(7) 0.013(3) Uiso 1 1 d . . .
C34 C 0.573(3) 0.7609(16) 0.3646(8) 0.023(4) Uiso 1 1 d . . .
Br34 Br 0.7802(4) 0.73014(16) 0.40404(11) 0.0396(7) Uani 1 1 d . . .
C35 C 0.517(3) 0.8621(18) 0.3531(9) 0.026(4) Uiso 1 1 d . . .
H35A H 0.5906 0.9184 0.3639 0.032 Uiso 1 1 calc R . .
C36 C 0.362(4) 0.879(2) 0.3271(12) 0.045(6) Uiso 1 1 d . . .
Br36 Br 0.3146(5) 1.02303(18) 0.30785(13) 0.0596(10) Uani 1 1 d . . .
C37 C 0.252(2) 0.8086(14) 0.3107(7) 0.014(3) Uiso 1 1 d . . .
H37A H 0.1455 0.8248 0.2907 0.017 Uiso 1 1 calc R . .
C38 C 0.301(3) 0.7007(18) 0.3246(9) 0.027(4) Uiso 1 1 d . . .
H38A H 0.2202 0.6474 0.3150 0.033 Uiso 1 1 calc R . .
O39 O 0.6859(17) 0.4219(10) 0.5122(5) 0.018(3) Uiso 1 1 d . . .
C39 C 0.620(3) 0.5304(15) 0.5244(8) 0.020(4) Uiso 1 1 d . . .
H39A H 0.7158 0.5797 0.5171 0.031 Uiso 1 1 calc R . .
H39B H 0.5835 0.5354 0.5647 0.031 Uiso 1 1 calc R . .
H39C H 0.5186 0.5460 0.4993 0.031 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.032(3) 0.009(2) 0.018(2) -0.0034(18) 0.002(2) -0.0014(19)
Br14 0.0338(11) 0.0171(10) 0.0678(16) -0.0068(11) -0.0138(10) 0.0036(10)
Br16 0.125(3) 0.0049(9) 0.0353(12) -0.0039(9) 0.0357(14) -0.0118(12)
P21 0.036(3) 0.013(2) 0.012(2) 0.0037(18) -0.004(2) -0.001(2)
Br34 0.0512(14) 0.0208(11) 0.0469(14) -0.0091(9) -0.0031(11) 0.0013(10)
Br36 0.116(3) 0.0122(11) 0.0502(16) 0.0031(10) -0.0172(16) 0.0085(13)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.504(15) . ?
P1 O19 1.574(15) . ?
P1 N1 1.624(19) . ?
P1 C1 1.78(2) . ?
C1 C6 1.39(3) . ?
C1 C2 1.46(3) . ?
C2 O2 1.37(2) . ?
C2 C3 1.41(3) . ?
C3 C4 1.37(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.50(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.42(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
O2 C7 1.35(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 C11 1.48(3) . ?
N1 C8 1.49(3) . ?
C8 C9 1.45(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.60(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.49(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.60(3) . ?
C11 H11A 1.0000 . ?
C12 N13 1.40(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N13 C13 1.42(3) . ?
N13 H13A 0.9800 . ?
C13 C14 1.34(3) . ?
C13 C18 1.41(3) . ?
C14 C15 1.44(3) . ?
C14 Br14 1.92(2) . ?
C15 C16 1.48(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.35(3) . ?
C16 Br16 1.86(2) . ?
C17 C18 1.42(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
O19 C19 1.53(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
P21 O21 1.482(15) . ?
P21 N21 1.584(18) . ?
P21 O39 1.590(13) . ?
P21 C21 1.822(17) . ?
C21 C22 1.29(3) . ?
C21 C26 1.38(3) . ?
C22 O22 1.39(3) . ?
C22 C23 1.41(3) . ?
C23 C24 1.35(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.37(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.39(3) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
O22 C27 1.49(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N21 C31 1.47(3) . ?
N21 C28 1.50(3) . ?
C28 C29 1.46(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.55(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.50(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.50(3) . ?
C31 H31A 1.0000 . ?
C32 N33 1.45(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
N33 C33 1.36(3) . ?
N33 H33A 0.9800 . ?
C33 C38 1.32(3) . ?
C33 C34 1.47(3) . ?
C34 C35 1.41(3) . ?
C34 Br34 1.845(19) . ?
C35 C36 1.33(4) . ?
C35 H35A 0.9500 . ?
C36 C37 1.29(3) . ?
C36 Br36 1.95(3) . ?
C37 C38 1.49(3) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?
O39 C39 1.52(2) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

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_3
_geom_angle_publ_flag
O1 P1 O19 115.0(8) . . ?
O1 P1 N1 110.8(9) . . ?
O19 P1 N1 104.2(9) . . ?
O1 P1 C1 117.5(10) . . ?
O19 P1 C1 97.9(10) . . ?
N1 P1 C1 109.9(10) . . ?
C6 C1 C2 117(2) . . ?
C6 C1 P1 125.9(19) . . ?
C2 C1 P1 116.6(16) . . ?
O2 C2 C1 117.0(17) . . ?
O2 C2 C3 122.9(17) . . ?
C1 C2 C3 120.1(18) . . ?
C4 C3 C2 120(2) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 123(2) . . ?
C3 C4 H4A 118.4 . . ?
C5 C4 H4A 118.4 . . ?
C6 C5 C4 112.6(19) . . ?
C6 C5 H5A 123.7 . . ?
C4 C5 H5A 123.7 . . ?
C1 C6 C5 126(2) . . ?
C1 C6 H6A 116.8 . . ?
C5 C6 H6A 116.8 . . ?
C7 O2 C2 116.4(19) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.4 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 N1 C8 109.8(17) . . ?
C11 N1 P1 123.5(14) . . ?
C8 N1 P1 119.5(15) . . ?
C9 C8 N1 105(2) . . ?
C9 C8 H8A 110.8 . . ?
N1 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
N1 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C8 C9 C10 109(2) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C11 C10 C9 99.6(19) . . ?
C11 C10 H10A 111.9 . . ?
C9 C10 H10A 111.9 . . ?
C11 C10 H10B 111.9 . . ?
C9 C10 H10B 111.8 . . ?
H10A C10 H10B 109.6 . . ?
N1 C11 C10 108.1(18) . . ?
N1 C11 C12 109.3(17) . . ?
C10 C11 C12 110.3(18) . . ?
N1 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N13 C12 C11 111.2(17) . . ?
N13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.4 . . ?
N13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 N13 C13 120.6(18) . . ?
C12 N13 H13A 119.7 . . ?
C13 N13 H13A 119.7 . . ?
C14 C13 N13 122(2) . . ?
C14 C13 C18 119(2) . . ?
N13 C13 C18 118.4(19) . . ?
C13 C14 C15 127(2) . . ?
C13 C14 Br14 121.1(16) . . ?
C15 C14 Br14 112.2(15) . . ?
C14 C15 C16 112.3(19) . . ?
C14 C15 H15A 123.9 . . ?
C16 C15 H15A 123.9 . . ?
C17 C16 C15 121(2) . . ?
C17 C16 Br16 122.7(19) . . ?
C15 C16 Br16 116.5(17) . . ?
C16 C17 C18 124(2) . . ?
C16 C17 H17A 118.1 . . ?
C18 C17 H17A 118.2 . . ?
C17 C18 C13 117.2(18) . . ?
C17 C18 H18A 121.4 . . ?
C13 C18 H18A 121.4 . . ?
C19 O19 P1 119.2(13) . . ?
O19 C19 H19A 109.5 . . ?
O19 C19 H19B 109.4 . . ?
H19A C19 H19B 109.5 . . ?
O19 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O21 P21 N21 109.3(9) . . ?
O21 P21 O39 112.6(8) . . ?
N21 P21 O39 106.6(9) . . ?
O21 P21 C21 114.6(8) . . ?
N21 P21 C21 111.9(9) . . ?
O39 P21 C21 101.4(7) . . ?
C22 C21 C26 119.1(19) . . ?
C22 C21 P21 120.2(15) . . ?
C26 C21 P21 120.7(14) . . ?
C21 C22 O22 115(2) . . ?
C21 C22 C23 124(2) . . ?
O22 C22 C23 120(2) . . ?
C24 C23 C22 118(2) . . ?
C24 C23 H23A 120.9 . . ?
C22 C23 H23A 120.9 . . ?
C23 C24 C25 118(2) . . ?
C23 C24 H24A 120.9 . . ?
C25 C24 H24A 120.9 . . ?
C24 C25 C26 123(2) . . ?
C24 C25 H25A 118.7 . . ?
C26 C25 H25A 118.7 . . ?
C21 C26 C25 118(2) . . ?
C21 C26 H26A 121.1 . . ?
C25 C26 H26A 121.1 . . ?
C22 O22 C27 125.2(18) . . ?
O22 C27 H27A 109.5 . . ?
O22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C31 N21 C28 105.3(16) . . ?
C31 N21 P21 127.2(15) . . ?
C28 N21 P21 120.8(14) . . ?
C29 C28 N21 108(2) . . ?
C29 C28 H28A 110.1 . . ?
N21 C28 H28A 110.1 . . ?
C29 C28 H28B 110.1 . . ?
N21 C28 H28B 110.1 . . ?
H28A C28 H28B 108.4 . . ?
C28 C29 C30 103(2) . . ?
C28 C29 H29A 111.1 . . ?
C30 C29 H29A 111.2 . . ?
C28 C29 H29B 111.2 . . ?
C30 C29 H29B 111.2 . . ?
H29A C29 H29B 109.1 . . ?
C31 C30 C29 101(2) . . ?
C31 C30 H30A 111.6 . . ?
C29 C30 H30A 111.6 . . ?
C31 C30 H30B 111.6 . . ?
C29 C30 H30B 111.7 . . ?
H30A C30 H30B 109.4 . . ?
N21 C31 C32 114.6(18) . . ?
N21 C31 C30 106.1(17) . . ?
C32 C31 C30 114.9(18) . . ?
N21 C31 H31A 106.9 . . ?
C32 C31 H31A 106.9 . . ?
C30 C31 H31A 107.0 . . ?
N33 C32 C31 113.4(17) . . ?
N33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
N33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C33 N33 C32 121.3(17) . . ?
C33 N33 H33A 119.3 . . ?
C32 N33 H33A 119.4 . . ?
C38 C33 N33 121.6(18) . . ?
C38 C33 C34 117.1(18) . . ?
N33 C33 C34 121.2(17) . . ?
C35 C34 C33 118.2(17) . . ?
C35 C34 Br34 123.3(15) . . ?
C33 C34 Br34 118.2(14) . . ?
C36 C35 C34 120(2) . . ?
C36 C35 H35A 119.8 . . ?
C34 C35 H35A 119.8 . . ?
C37 C36 C35 125(3) . . ?
C37 C36 Br36 120(2) . . ?
C35 C36 Br36 115(2) . . ?
C36 C37 C38 117(2) . . ?
C36 C37 H37A 121.6 . . ?
C38 C37 H37A 121.6 . . ?
C33 C38 C37 122.5(19) . . ?
C33 C38 H38A 118.7 . . ?
C37 C38 H38A 118.8 . . ?
C39 O39 P21 121.2(11) . . ?
O39 C39 H39A 109.5 . . ?
O39 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O39 C39 H39C 109.4 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 C6 116(2) . . . . ?
O19 P1 C1 C6 -8(2) . . . . ?
N1 P1 C1 C6 -116(2) . . . . ?
O1 P1 C1 C2 -57(2) . . . . ?
O19 P1 C1 C2 179.0(16) . . . . ?
N1 P1 C1 C2 70.7(19) . . . . ?
C6 C1 C2 O2 -178.9(18) . . . . ?
P1 C1 C2 O2 -5(2) . . . . ?
C6 C1 C2 C3 4(3) . . . . ?
P1 C1 C2 C3 177.3(16) . . . . ?
O2 C2 C3 C4 -177.8(18) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C2 C3 C4 C5 -3(3) . . . . ?
C3 C4 C5 C6 3(3) . . . . ?
C2 C1 C6 C5 -4(3) . . . . ?
P1 C1 C6 C5 -176.7(18) . . . . ?
C4 C5 C6 C1 1(3) . . . . ?
C1 C2 O2 C7 -173(2) . . . . ?
C3 C2 O2 C7 4(3) . . . . ?
O1 P1 N1 C11 34.1(19) . . . . ?
O19 P1 N1 C11 158.4(16) . . . . ?
C1 P1 N1 C11 -97.5(18) . . . . ?
O1 P1 N1 C8 -178.7(16) . . . . ?
O19 P1 N1 C8 -54.3(18) . . . . ?
C1 P1 N1 C8 50(2) . . . . ?
C11 N1 C8 C9 -2(3) . . . . ?
P1 N1 C8 C9 -153.0(17) . . . . ?
N1 C8 C9 C10 19(3) . . . . ?
C8 C9 C10 C11 -29(3) . . . . ?
C8 N1 C11 C10 -18(2) . . . . ?
P1 N1 C11 C10 132.1(17) . . . . ?
C8 N1 C11 C12 102(2) . . . . ?
P1 N1 C11 C12 -107.8(18) . . . . ?
C9 C10 C11 N1 27(2) . . . . ?
C9 C10 C11 C12 -92(2) . . . . ?
N1 C11 C12 N13 59(2) . . . . ?
C10 C11 C12 N13 177.5(18) . . . . ?
C11 C12 N13 C13 -178.8(17) . . . . ?
C12 N13 C13 C14 178(2) . . . . ?
C12 N13 C13 C18 -7(3) . . . . ?
N13 C13 C14 C15 177.4(19) . . . . ?
C18 C13 C14 C15 3(3) . . . . ?
N13 C13 C14 Br14 -1(3) . . . . ?
C18 C13 C14 Br14 -176.0(14) . . . . ?
C13 C14 C15 C16 2(3) . . . . ?
Br14 C14 C15 C16 -179.7(15) . . . . ?
C14 C15 C16 C17 -5(3) . . . . ?
C14 C15 C16 Br16 -179.3(15) . . . . ?
C15 C16 C17 C18 5(3) . . . . ?
Br16 C16 C17 C18 178.7(16) . . . . ?
C16 C17 C18 C13 0(3) . . . . ?
C14 C13 C18 C17 -3(3) . . . . ?
N13 C13 C18 C17 -178.3(18) . . . . ?
O1 P1 O19 C19 54.6(16) . . . . ?
N1 P1 O19 C19 -67.0(16) . . . . ?
C1 P1 O19 C19 180.0(15) . . . . ?
O21 P21 C21 C22 -57.6(18) . . . . ?
N21 P21 C21 C22 67.6(19) . . . . ?
O39 P21 C21 C22 -179.2(16) . . . . ?
O21 P21 C21 C26 123.6(15) . . . . ?
N21 P21 C21 C26 -111.3(16) . . . . ?
O39 P21 C21 C26 2.0(16) . . . . ?
C26 C21 C22 O22 173.7(17) . . . . ?
P21 C21 C22 O22 -5(3) . . . . ?
C26 C21 C22 C23 2(3) . . . . ?
P21 C21 C22 C23 -176.8(17) . . . . ?
C21 C22 C23 C24 -2(3) . . . . ?
O22 C22 C23 C24 -174(2) . . . . ?
C22 C23 C24 C25 -1(3) . . . . ?
C23 C24 C25 C26 4(4) . . . . ?
C22 C21 C26 C25 1(3) . . . . ?
P21 C21 C26 C25 -179.7(16) . . . . ?
C24 C25 C26 C21 -5(3) . . . . ?
C21 C22 O22 C27 -179(2) . . . . ?
C23 C22 O22 C27 -7(3) . . . . ?
O21 P21 N21 C31 31(2) . . . . ?
O39 P21 N21 C31 152.8(17) . . . . ?
C21 P21 N21 C31 -97.3(18) . . . . ?
O21 P21 N21 C28 177.8(16) . . . . ?
O39 P21 N21 C28 -60.2(18) . . . . ?
C21 P21 N21 C28 49.7(19) . . . . ?
C31 N21 C28 C29 -3(3) . . . . ?
P21 N21 C28 C29 -155.9(19) . . . . ?
N21 C28 C29 C30 26(3) . . . . ?
C28 C29 C30 C31 -39(3) . . . . ?
C28 N21 C31 C32 105(2) . . . . ?
P21 N21 C31 C32 -104(2) . . . . ?
C28 N21 C31 C30 -23(2) . . . . ?
P21 N21 C31 C30 127.8(18) . . . . ?
C29 C30 C31 N21 38(2) . . . . ?
C29 C30 C31 C32 -89(2) . . . . ?
N21 C31 C32 N33 48(3) . . . . ?
C30 C31 C32 N33 171.7(19) . . . . ?
C31 C32 N33 C33 174.9(18) . . . . ?
C32 N33 C33 C38 11(3) . . . . ?
C32 N33 C33 C34 -172.7(18) . . . . ?
C38 C33 C34 C35 2(3) . . . . ?
N33 C33 C34 C35 -174.0(18) . . . . ?
C38 C33 C34 Br34 176.2(15) . . . . ?
N33 C33 C34 Br34 0(2) . . . . ?
C33 C34 C35 C36 -3(3) . . . . ?
Br34 C34 C35 C36 -176.5(19) . . . . ?
C34 C35 C36 C37 0(4) . . . . ?
C34 C35 C36 Br36 -174.5(17) . . . . ?
C35 C36 C37 C38 3(4) . . . . ?
Br36 C36 C37 C38 177.4(16) . . . . ?
N33 C33 C38 C37 177.0(17) . . . . ?
C34 C33 C38 C37 1(3) . . . . ?
C36 C37 C38 C33 -3(3) . . . . ?
O21 P21 O39 C39 57.1(14) . . . . ?
N21 P21 O39 C39 -62.8(14) . . . . ?
C21 P21 O39 C39 180.0(12) . . . . ?

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
_geom_hbond_site_symmetry_A
N13 H13A O1 0.98 2.27 3.18(2) 154.2 .
N13 H13A Br14 0.98 2.66 3.115(18) 108.8 .
N33 H33A Br34 0.98 2.60 3.078(19) 110.3 .
N33 H33A O21 0.98 2.34 3.19(2) 145.0 .

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         3.255
_refine_diff_density_min         -2.539
_refine_diff_density_rms         0.353

# Attachment 'ob-art-06-2010-000297-File006_v1_0.cif'

data_11
_database_code_depnum_ccdc_archive 'CCDC 782248'
#TrackingRef 'ob-art-06-2010-000297-File006_v1_0.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 I N2 O3 P'
_chemical_formula_sum            'C25 H26 I N2 O3 P'
_chemical_formula_weight         560.35

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.786(3)
_cell_length_b                   9.781(2)
_cell_length_c                   16.323(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.211(4)
_cell_angle_gamma                90.00
_cell_volume                     2315.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    91
_cell_measurement_theta_min      12
_cell_measurement_theta_max      28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .12
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11581
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.42
_reflns_number_total             4199
_reflns_number_gt                2660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0277P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00019(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4199
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
P1 P 0.33801(7) 1.23977(11) 0.87405(6) 0.0156(3) Uani 1 1 d . . .
O1 O 0.34942(18) 1.0911(3) 0.88521(16) 0.0168(7) Uani 1 1 d . . .
N1 N 0.3895(2) 1.3135(3) 0.8039(2) 0.0179(9) Uani 1 1 d . . .
C1 C 0.3784(3) 1.3294(4) 0.9722(2) 0.0159(10) Uani 1 1 d . . .
C2 C 0.3277(3) 1.4157(4) 1.0142(3) 0.0161(10) Uani 1 1 d . . .
O2 O 0.2401(2) 1.4503(3) 0.97326(18) 0.0249(8) Uani 1 1 d . . .
C3 C 0.3646(3) 1.4703(4) 1.0917(3) 0.0204(11) Uani 1 1 d . . .
H3A H 0.3283 1.5266 1.1201 0.024 Uiso 1 1 calc R . .
C4 C 0.4549(3) 1.4417(4) 1.1270(3) 0.0201(11) Uani 1 1 d . . .
H4A H 0.4799 1.4770 1.1809 0.024 Uiso 1 1 calc R . .
C5 C 0.5098(3) 1.3635(4) 1.0867(3) 0.0193(10) Uani 1 1 d . . .
H5A H 0.5727 1.3478 1.1110 0.023 Uiso 1 1 calc R . .
C6 C 0.4714(3) 1.3082(4) 1.0098(3) 0.0179(10) Uani 1 1 d . . .
C7 C 0.1748(3) 1.4910(5) 1.0226(3) 0.0276(12) Uani 1 1 d . . .
H7A H 0.1760 1.4258 1.0683 0.041 Uiso 1 1 calc R . .
H7B H 0.1129 1.4929 0.9876 0.041 Uiso 1 1 calc R . .
H7C H 0.1906 1.5823 1.0456 0.041 Uiso 1 1 calc R . .
O6 O 0.51964(18) 1.2275(3) 0.96428(16) 0.0191(7) Uani 1 1 d . . .
C8 C 0.4544(3) 1.2370(5) 0.7635(2) 0.0231(11) Uani 1 1 d . . .
H8A H 0.4502 1.1377 0.7741 0.028 Uiso 1 1 calc R . .
H8B H 0.5185 1.2675 0.7848 0.028 Uiso 1 1 calc R . .
C9 C 0.4250(3) 1.2685(5) 0.6697(3) 0.0332(12) Uani 1 1 d . . .
H9A H 0.4630 1.3427 0.6528 0.040 Uiso 1 1 calc R . .
H9B H 0.4305 1.1863 0.6356 0.040 Uiso 1 1 calc R . .
C10 C 0.3248(3) 1.3125(5) 0.6603(3) 0.0288(12) Uani 1 1 d . . .
H10A H 0.3059 1.3712 0.6105 0.035 Uiso 1 1 calc R . .
H10B H 0.2833 1.2324 0.6560 0.035 Uiso 1 1 calc R . .
C11 C 0.3249(3) 1.3918(5) 0.7402(3) 0.0221(11) Uani 1 1 d . . .
H11A H 0.3498 1.4858 0.7351 0.027 Uiso 1 1 calc R . .
C12 C 0.2333(3) 1.4009(5) 0.7699(3) 0.0261(12) Uani 1 1 d . . .
H12A H 0.2283 1.4897 0.7977 0.031 Uiso 1 1 calc R . .
H12B H 0.1812 1.3927 0.7218 0.031 Uiso 1 1 calc R . .
N13 N 0.2313(2) 1.2884(4) 0.8287(2) 0.0196(8) Uani 1 1 d . . .
C13 C 0.1512(3) 1.2635(4) 0.8603(3) 0.0209(10) Uani 1 1 d . . .
C14 C 0.0683(3) 1.3338(5) 0.8293(3) 0.0301(12) Uani 1 1 d . . .
H14A H 0.0659 1.3974 0.7849 0.036 Uiso 1 1 calc R . .
C15 C -0.0090(3) 1.3110(5) 0.8625(3) 0.0370(14) Uani 1 1 d . . .
H15A H -0.0642 1.3593 0.8406 0.044 Uiso 1 1 calc R . .
C16 C -0.0081(3) 1.2208(5) 0.9261(3) 0.0345(12) Uani 1 1 d . . .
H16A H -0.0615 1.2072 0.9493 0.041 Uiso 1 1 calc R . .
C17 C 0.0721(3) 1.1492(5) 0.9564(3) 0.0360(13) Uani 1 1 d . . .
H17A H 0.0734 1.0859 1.0007 0.043 Uiso 1 1 calc R . .
C18 C 0.1502(3) 1.1681(4) 0.9233(3) 0.0237(11) Uani 1 1 d . . .
H18A H 0.2038 1.1154 0.9437 0.028 Uiso 1 1 calc R . .
C19 C 0.6122(3) 1.1938(4) 1.0011(3) 0.0200(11) Uani 1 1 d . . .
H19A H 0.6145 1.1501 1.0562 0.024 Uiso 1 1 calc R . .
H19B H 0.6505 1.2776 1.0094 0.024 Uiso 1 1 calc R . .
C20 C 0.6483(3) 1.0973(4) 0.9435(2) 0.0148(10) Uani 1 1 d . . .
C21 C 0.7375(3) 1.1104(4) 0.9299(2) 0.0174(10) Uani 1 1 d . . .
H21A H 0.7747 1.1842 0.9549 0.021 Uiso 1 1 calc R . .
C22 C 0.7735(3) 1.0178(5) 0.8805(3) 0.0229(11) Uani 1 1 d . . .
H22A H 0.8351 1.0275 0.8724 0.028 Uiso 1 1 calc R . .
C23 C 0.7204(3) 0.9134(4) 0.8438(3) 0.0183(10) Uani 1 1 d . . .
C24 C 0.6298(3) 0.8986(4) 0.8550(3) 0.0209(11) Uani 1 1 d . . .
H24A H 0.5928 0.8258 0.8284 0.025 Uiso 1 1 calc R . .
C25 C 0.5939(3) 0.9903(4) 0.9050(3) 0.0213(11) Uani 1 1 d . . .
H25A H 0.5323 0.9801 0.9130 0.026 Uiso 1 1 calc R . .
I23 I 0.77288(2) 0.77502(3) 0.76701(2) 0.03000(12) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0166(6) 0.0143(7) 0.0148(5) 0.0011(5) 0.0001(4) 0.0000(5)
O1 0.0192(17) 0.0101(17) 0.0187(17) 0.0007(13) -0.0018(13) 0.0020(12)
N1 0.019(2) 0.014(2) 0.019(2) -0.0002(15) -0.0009(16) 0.0011(16)
C1 0.022(3) 0.009(2) 0.016(2) 0.0007(19) 0.002(2) -0.0029(19)
C2 0.016(3) 0.012(2) 0.022(3) 0.007(2) 0.008(2) 0.0025(19)
O2 0.0198(19) 0.030(2) 0.0237(18) -0.0024(14) 0.0005(14) 0.0087(14)
C3 0.026(3) 0.016(3) 0.022(3) -0.005(2) 0.012(2) -0.001(2)
C4 0.021(3) 0.021(3) 0.016(3) -0.002(2) -0.001(2) -0.005(2)
C5 0.014(3) 0.022(3) 0.020(3) -0.002(2) -0.002(2) -0.004(2)
C6 0.019(3) 0.014(3) 0.021(2) 0.000(2) 0.006(2) -0.0026(19)
C7 0.019(3) 0.025(3) 0.039(3) -0.005(2) 0.005(2) 0.005(2)
O6 0.0140(15) 0.0228(17) 0.0180(15) -0.0037(14) -0.0030(12) 0.0048(14)
C8 0.022(2) 0.024(3) 0.023(2) 0.000(2) 0.0045(19) 0.002(2)
C9 0.036(3) 0.044(3) 0.022(3) 0.000(3) 0.009(2) -0.001(3)
C10 0.037(3) 0.033(3) 0.014(2) 0.005(2) -0.002(2) -0.005(2)
C11 0.027(3) 0.021(3) 0.016(3) 0.006(2) -0.002(2) -0.007(2)
C12 0.029(3) 0.031(3) 0.017(3) 0.010(2) 0.002(2) 0.007(2)
N13 0.022(2) 0.017(2) 0.0178(19) 0.0022(17) -0.0021(16) 0.0016(17)
C13 0.014(2) 0.022(3) 0.026(2) -0.001(2) 0.0021(19) -0.003(2)
C14 0.018(3) 0.035(3) 0.034(3) 0.005(2) -0.002(2) 0.001(2)
C15 0.014(3) 0.045(4) 0.050(3) -0.004(3) 0.001(2) 0.005(2)
C16 0.021(3) 0.040(3) 0.043(3) -0.006(3) 0.009(2) -0.005(3)
C17 0.026(3) 0.037(3) 0.044(3) 0.007(3) 0.006(3) -0.010(3)
C18 0.022(3) 0.020(3) 0.028(3) 0.002(2) 0.003(2) 0.001(2)
C19 0.017(2) 0.020(3) 0.022(2) 0.004(2) -0.002(2) -0.002(2)
C20 0.013(2) 0.020(3) 0.012(2) 0.001(2) 0.0017(19) 0.003(2)
C21 0.014(3) 0.019(3) 0.016(2) 0.0012(19) -0.0026(19) -0.006(2)
C22 0.015(3) 0.031(3) 0.024(3) 0.002(2) 0.005(2) -0.001(2)
C23 0.028(3) 0.013(3) 0.016(2) 0.0026(19) 0.009(2) 0.003(2)
C24 0.021(3) 0.017(3) 0.024(3) -0.002(2) 0.001(2) -0.008(2)
C25 0.017(3) 0.021(3) 0.026(3) 0.006(2) 0.006(2) 0.003(2)
I23 0.0343(2) 0.03033(19) 0.02909(18) -0.00117(18) 0.01525(13) 0.00589(18)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.471(3) . ?
P1 N1 1.658(3) . ?
P1 N13 1.676(3) . ?
P1 C1 1.822(4) . ?
N1 C8 1.470(5) . ?
N1 C11 1.482(5) . ?
C1 C2 1.395(6) . ?
C1 C6 1.408(6) . ?
C2 O2 1.380(5) . ?
C2 C3 1.384(6) . ?
O2 C7 1.429(5) . ?
C3 C4 1.375(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.373(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(6) . ?
C5 H5A 0.9500 . ?
C6 O6 1.374(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O6 C19 1.423(5) . ?
C8 C9 1.540(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.521(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.517(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.527(6) . ?
C11 H11A 1.0000 . ?
C12 N13 1.465(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N13 C13 1.402(5) . ?
C13 C18 1.391(6) . ?
C13 C14 1.411(6) . ?
C14 C15 1.376(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.361(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.383(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.379(6) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.502(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.386(6) . ?
C20 C25 1.394(6) . ?
C21 C22 1.385(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.356(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.393(6) . ?
C23 I23 2.094(4) . ?
C24 C25 1.386(6) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?

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_3
_geom_angle_publ_flag
O1 P1 N1 117.29(17) . . ?
O1 P1 N13 114.23(17) . . ?
N1 P1 N13 95.21(17) . . ?
O1 P1 C1 110.90(17) . . ?
N1 P1 C1 106.35(18) . . ?
N13 P1 C1 111.81(19) . . ?
C8 N1 C11 109.6(3) . . ?
C8 N1 P1 121.0(3) . . ?
C11 N1 P1 112.9(3) . . ?
C2 C1 C6 116.6(4) . . ?
C2 C1 P1 127.4(3) . . ?
C6 C1 P1 115.9(3) . . ?
O2 C2 C3 121.0(4) . . ?
O2 C2 C1 117.0(4) . . ?
C3 C2 C1 121.9(4) . . ?
C2 O2 C7 118.0(3) . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5A 120.8 . . ?
C6 C5 H5A 120.8 . . ?
O6 C6 C5 123.4(4) . . ?
O6 C6 C1 114.5(4) . . ?
C5 C6 C1 122.1(4) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 O6 C19 117.6(3) . . ?
N1 C8 C9 105.2(3) . . ?
N1 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
N1 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C10 C9 C8 103.7(3) . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C9 102.7(4) . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
N1 C11 C10 103.4(3) . . ?
N1 C11 C12 107.3(3) . . ?
C10 C11 C12 116.7(4) . . ?
N1 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N13 C12 C11 107.2(3) . . ?
N13 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
N13 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C13 N13 C12 119.9(3) . . ?
C13 N13 P1 125.3(3) . . ?
C12 N13 P1 111.4(3) . . ?
C18 C13 N13 121.3(4) . . ?
C18 C13 C14 117.3(4) . . ?
N13 C13 C14 121.3(4) . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C16 C15 C14 121.3(5) . . ?
C16 C15 H15A 119.3 . . ?
C14 C15 H15A 119.3 . . ?
C15 C16 C17 118.8(5) . . ?
C15 C16 H16A 120.6 . . ?
C17 C16 H16A 120.6 . . ?
C18 C17 C16 121.1(5) . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C17 C18 C13 120.6(4) . . ?
C17 C18 H18A 119.7 . . ?
C13 C18 H18A 119.7 . . ?
O6 C19 C20 108.1(3) . . ?
O6 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O6 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C21 C20 C25 118.7(4) . . ?
C21 C20 C19 120.5(4) . . ?
C25 C20 C19 120.7(4) . . ?
C20 C21 C22 121.2(4) . . ?
C20 C21 H21A 119.4 . . ?
C22 C21 H21A 119.4 . . ?
C23 C22 C21 119.6(4) . . ?
C23 C22 H22A 120.2 . . ?
C21 C22 H22A 120.2 . . ?
C22 C23 C24 120.6(4) . . ?
C22 C23 I23 120.1(3) . . ?
C24 C23 I23 119.3(3) . . ?
C25 C24 C23 119.9(4) . . ?
C25 C24 H24A 120.1 . . ?
C23 C24 H24A 120.1 . . ?
C24 C25 C20 119.9(4) . . ?
C24 C25 H25A 120.1 . . ?
C20 C25 H25A 120.1 . . ?

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
O1 P1 N1 C8 -8.5(4) . . . . ?
N13 P1 N1 C8 -129.2(3) . . . . ?
C1 P1 N1 C8 116.2(3) . . . . ?
O1 P1 N1 C11 124.4(3) . . . . ?
N13 P1 N1 C11 3.7(3) . . . . ?
C1 P1 N1 C11 -110.9(3) . . . . ?
O1 P1 C1 C2 -120.8(4) . . . . ?
N1 P1 C1 C2 110.6(4) . . . . ?
N13 P1 C1 C2 7.9(4) . . . . ?
O1 P1 C1 C6 58.8(4) . . . . ?
N1 P1 C1 C6 -69.8(3) . . . . ?
N13 P1 C1 C6 -172.4(3) . . . . ?
C6 C1 C2 O2 172.4(3) . . . . ?
P1 C1 C2 O2 -7.9(6) . . . . ?
C6 C1 C2 C3 -4.4(6) . . . . ?
P1 C1 C2 C3 175.2(3) . . . . ?
C3 C2 O2 C7 -27.0(6) . . . . ?
C1 C2 O2 C7 156.2(4) . . . . ?
O2 C2 C3 C4 -174.7(4) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C3 C4 C5 C6 -2.5(7) . . . . ?
C4 C5 C6 O6 -179.4(4) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C2 C1 C6 O6 -177.2(4) . . . . ?
P1 C1 C6 O6 3.1(5) . . . . ?
C2 C1 C6 C5 3.4(6) . . . . ?
P1 C1 C6 C5 -176.2(3) . . . . ?
C5 C6 O6 C19 3.7(6) . . . . ?
C1 C6 O6 C19 -175.7(3) . . . . ?
C11 N1 C8 C9 -1.6(5) . . . . ?
P1 N1 C8 C9 132.6(3) . . . . ?
N1 C8 C9 C10 -22.1(5) . . . . ?
C8 C9 C10 C11 36.8(5) . . . . ?
C8 N1 C11 C10 24.7(4) . . . . ?
P1 N1 C11 C10 -113.5(3) . . . . ?
C8 N1 C11 C12 148.7(4) . . . . ?
P1 N1 C11 C12 10.5(4) . . . . ?
C9 C10 C11 N1 -37.7(4) . . . . ?
C9 C10 C11 C12 -155.3(4) . . . . ?
N1 C11 C12 N13 -22.1(5) . . . . ?
C10 C11 C12 N13 93.3(4) . . . . ?
C11 C12 N13 C13 -174.1(4) . . . . ?
C11 C12 N13 P1 25.6(4) . . . . ?
O1 P1 N13 C13 60.2(4) . . . . ?
N1 P1 N13 C13 -176.7(4) . . . . ?
C1 P1 N13 C13 -66.8(4) . . . . ?
O1 P1 N13 C12 -140.8(3) . . . . ?
N1 P1 N13 C12 -17.7(3) . . . . ?
C1 P1 N13 C12 92.3(3) . . . . ?
C12 N13 C13 C18 -172.5(4) . . . . ?
P1 N13 C13 C18 -15.2(6) . . . . ?
C12 N13 C13 C14 7.8(6) . . . . ?
P1 N13 C13 C14 165.2(3) . . . . ?
C18 C13 C14 C15 2.1(7) . . . . ?
N13 C13 C14 C15 -178.2(4) . . . . ?
C13 C14 C15 C16 0.1(8) . . . . ?
C14 C15 C16 C17 -1.2(8) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C16 C17 C18 C13 2.2(7) . . . . ?
N13 C13 C18 C17 177.1(4) . . . . ?
C14 C13 C18 C17 -3.3(6) . . . . ?
C6 O6 C19 C20 175.8(3) . . . . ?
O6 C19 C20 C21 139.3(4) . . . . ?
O6 C19 C20 C25 -42.9(5) . . . . ?
C25 C20 C21 C22 -1.4(6) . . . . ?
C19 C20 C21 C22 176.4(4) . . . . ?
C20 C21 C22 C23 0.9(6) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C21 C22 C23 I23 178.7(3) . . . . ?
C22 C23 C24 C25 -0.8(6) . . . . ?
I23 C23 C24 C25 -179.3(3) . . . . ?
C23 C24 C25 C20 0.3(6) . . . . ?
C21 C20 C25 C24 0.7(6) . . . . ?
C19 C20 C25 C24 -177.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.102


# Attachment '81.cif'

data_8
_database_code_depnum_ccdc_archive 'CCDC 804012'
#TrackingRef '81.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 Br N2 O2 P'
_chemical_formula_sum            'C18 H20 Br N2 O2 P'
_chemical_formula_weight         407.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3517(18)
_cell_length_b                   16.960(3)
_cell_length_c                   11.251(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.824(3)
_cell_angle_gamma                90.00
_cell_volume                     1732.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    112
_cell_measurement_theta_min      12
_cell_measurement_theta_max      28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    2.478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.739257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10231
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3132
_reflns_number_gt                1833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1449P)^2^+8.3970P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3132
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0821
_refine_ls_wR_factor_ref         0.2893
_refine_ls_wR_factor_gt          0.2086
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
P1 P -0.3075(3) 0.40907(12) 0.65039(19) 0.0349(7) Uani 1 1 d . . .
O1 O -0.3280(6) 0.3975(3) 0.5175(5) 0.0372(14) Uani 1 1 d . . .
C1 C -0.1490(10) 0.3509(5) 0.7272(7) 0.037(2) Uani 1 1 d . . .
C2 C -0.0867(11) 0.3535(5) 0.8549(8) 0.042(2) Uani 1 1 d . . .
O2 O -0.1477(7) 0.4051(4) 0.9213(5) 0.0441(16) Uani 1 1 d . . .
C3 C 0.0262(11) 0.3022(6) 0.9061(8) 0.044(2) Uani 1 1 d . . .
H3A H 0.0658 0.3025 0.9921 0.052 Uiso 1 1 calc R . .
C4 C 0.0818(10) 0.2506(6) 0.8338(8) 0.048(2) Uani 1 1 d . . .
H4A H 0.1584 0.2152 0.8704 0.058 Uiso 1 1 calc R . .
C5 C 0.0271(10) 0.2501(5) 0.7091(9) 0.045(2) Uani 1 1 d . . .
Br5 Br 0.10152(12) 0.18004(5) 0.60702(10) 0.0546(6) Uani 1 1 d . . .
C6 C -0.0888(11) 0.3001(5) 0.6560(8) 0.041(2) Uani 1 1 d . . .
H6A H -0.1270 0.2992 0.5699 0.049 Uiso 1 1 calc R . .
C7 C -0.0798(13) 0.4158(7) 1.0466(8) 0.059(3) Uani 1 1 d . . .
H7A H -0.0850 0.3665 1.0909 0.088 Uiso 1 1 calc R . .
H7B H -0.1309 0.4576 1.0802 0.088 Uiso 1 1 calc R . .
H7C H 0.0235 0.4306 1.0557 0.088 Uiso 1 1 calc R . .
N1 N -0.4443(7) 0.3861(4) 0.7093(6) 0.0351(16) Uani 1 1 d . . .
C8 C -0.5873(10) 0.3530(5) 0.6324(8) 0.042(2) Uani 1 1 d . . .
H8A H -0.5814 0.3452 0.5465 0.050 Uiso 1 1 calc R . .
H8B H -0.6117 0.3020 0.6657 0.050 Uiso 1 1 calc R . .
C9 C -0.6996(10) 0.4153(5) 0.6412(9) 0.045(2) Uani 1 1 d . . .
H9A H -0.7995 0.3923 0.6275 0.054 Uiso 1 1 calc R . .
H9B H -0.7008 0.4579 0.5807 0.054 Uiso 1 1 calc R . .
C10 C -0.6467(10) 0.4463(5) 0.7725(8) 0.043(2) Uani 1 1 d . . .
H10A H -0.6851 0.5000 0.7803 0.052 Uiso 1 1 calc R . .
H10B H -0.6780 0.4110 0.8316 0.052 Uiso 1 1 calc R . .
C11 C -0.4796(9) 0.4470(5) 0.7929(8) 0.040(2) Uani 1 1 d . . .
H11A H -0.4320 0.4335 0.8798 0.048 Uiso 1 1 calc R . .
C12 C -0.4144(9) 0.5244(5) 0.7561(8) 0.0357(19) Uani 1 1 d . . .
H12A H -0.4896 0.5535 0.6950 0.043 Uiso 1 1 calc R . .
H12B H -0.3796 0.5585 0.8286 0.043 Uiso 1 1 calc R . .
C13 C -0.1910(9) 0.5581(5) 0.6826(7) 0.0341(19) Uani 1 1 d . . .
N13 N -0.2909(7) 0.5017(4) 0.7038(6) 0.0325(16) Uani 1 1 d . . .
C14 C -0.2163(10) 0.6386(5) 0.6947(7) 0.0354(19) Uani 1 1 d . . .
H14A H -0.3030 0.6553 0.7174 0.042 Uiso 1 1 calc R . .
C15 C -0.1166(10) 0.6943(5) 0.6740(8) 0.038(2) Uani 1 1 d . . .
H15A H -0.1363 0.7488 0.6813 0.045 Uiso 1 1 calc R . .
C16 C 0.0113(10) 0.6711(5) 0.6427(8) 0.040(2) Uani 1 1 d . . .
H16A H 0.0799 0.7097 0.6301 0.048 Uiso 1 1 calc R . .
C17 C 0.0397(9) 0.5920(5) 0.6295(7) 0.036(2) Uani 1 1 d . . .
H17A H 0.1277 0.5762 0.6081 0.044 Uiso 1 1 calc R . .
C18 C -0.0616(9) 0.5355(5) 0.6478(7) 0.037(2) Uani 1 1 d . . .
H18A H -0.0432 0.4813 0.6366 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0440(14) 0.0256(11) 0.0328(13) 0.0015(8) 0.0046(10) 0.0011(9)
O1 0.042(3) 0.030(3) 0.037(3) -0.004(2) 0.004(3) -0.001(3)
C1 0.039(5) 0.038(5) 0.026(4) 0.003(3) -0.004(4) -0.011(4)
C2 0.056(6) 0.029(4) 0.039(5) 0.009(4) 0.007(4) 0.001(4)
O2 0.048(4) 0.054(4) 0.026(3) -0.001(3) 0.000(3) 0.006(3)
C3 0.053(6) 0.048(5) 0.029(4) 0.010(4) 0.007(4) -0.006(5)
C4 0.041(5) 0.046(5) 0.047(5) 0.017(4) -0.010(4) 0.002(4)
C5 0.034(5) 0.033(4) 0.069(6) 0.010(4) 0.015(4) 0.004(4)
Br5 0.0592(9) 0.0367(8) 0.0702(9) 0.0071(4) 0.0199(6) 0.0101(4)
C6 0.057(6) 0.026(4) 0.037(5) 0.003(4) 0.008(4) -0.003(4)
C7 0.069(7) 0.072(7) 0.029(5) 0.001(5) 0.001(5) 0.001(6)
N1 0.033(4) 0.031(4) 0.040(4) 0.003(3) 0.007(3) 0.003(3)
C8 0.037(5) 0.039(5) 0.047(5) -0.002(4) 0.007(4) -0.001(4)
C9 0.040(5) 0.035(5) 0.055(6) 0.001(4) 0.002(4) 0.000(4)
C10 0.052(6) 0.036(5) 0.043(5) 0.003(4) 0.015(4) 0.004(4)
C11 0.036(5) 0.041(5) 0.045(5) 0.005(4) 0.012(4) -0.004(4)
C12 0.034(4) 0.040(5) 0.037(4) -0.005(4) 0.016(4) 0.003(4)
C13 0.040(5) 0.033(4) 0.025(4) 0.002(3) -0.001(3) -0.004(4)
N13 0.030(4) 0.027(3) 0.040(4) 0.001(3) 0.007(3) -0.004(3)
C14 0.040(5) 0.028(4) 0.035(4) -0.001(3) 0.001(4) 0.000(4)
C15 0.042(5) 0.030(4) 0.040(5) 0.004(4) 0.006(4) 0.001(4)
C16 0.032(5) 0.042(5) 0.046(5) 0.000(4) 0.011(4) -0.002(4)
C17 0.039(5) 0.033(4) 0.036(5) 0.000(4) 0.006(4) 0.000(4)
C18 0.038(5) 0.029(4) 0.040(5) -0.004(3) -0.001(4) 0.003(4)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.474(6) . ?
P1 N1 1.622(7) . ?
P1 N13 1.676(7) . ?
P1 C1 1.817(9) . ?
C1 C6 1.385(13) . ?
C1 C2 1.416(12) . ?
C2 O2 1.360(11) . ?
C2 C3 1.383(13) . ?
O2 C7 1.414(10) . ?
C3 C4 1.379(14) . ?
C3 H3A 0.9500 . ?
C4 C5 1.374(13) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(12) . ?
C5 Br5 1.897(9) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 C11 1.486(11) . ?
N1 C8 1.517(11) . ?
C8 C9 1.510(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.535(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.525(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.544(12) . ?
C11 H11A 1.0000 . ?
C12 N13 1.467(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N13 1.397(10) . ?
C13 C14 1.398(11) . ?
C13 C18 1.411(12) . ?
C14 C15 1.386(12) . ?
C14 H14A 0.9500 . ?
C15 C16 1.382(12) . ?
C15 H15A 0.9500 . ?
C16 C17 1.382(12) . ?
C16 H16A 0.9500 . ?
C17 C18 1.397(12) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?

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_3
_geom_angle_publ_flag
O1 P1 N1 117.3(4) . . ?
O1 P1 N13 117.8(3) . . ?
N1 P1 N13 95.3(3) . . ?
O1 P1 C1 107.7(4) . . ?
N1 P1 C1 108.0(4) . . ?
N13 P1 C1 110.1(4) . . ?
C6 C1 C2 118.7(8) . . ?
C6 C1 P1 117.5(6) . . ?
C2 C1 P1 123.8(7) . . ?
O2 C2 C3 123.6(8) . . ?
O2 C2 C1 116.9(8) . . ?
C3 C2 C1 119.4(9) . . ?
C2 O2 C7 118.9(7) . . ?
C4 C3 C2 120.8(8) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C5 C4 C3 120.3(8) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 119.8(9) . . ?
C4 C5 Br5 121.4(7) . . ?
C6 C5 Br5 118.8(7) . . ?
C1 C6 C5 120.9(8) . . ?
C1 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 N1 C8 108.6(6) . . ?
C11 N1 P1 114.1(5) . . ?
C8 N1 P1 122.0(6) . . ?
C9 C8 N1 103.6(7) . . ?
C9 C8 H8A 111.0 . . ?
N1 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
N1 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C8 C9 C10 103.5(7) . . ?
C8 C9 H9A 111.1 . . ?
C10 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C9 103.3(7) . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
N1 C11 C10 105.9(7) . . ?
N1 C11 C12 105.0(6) . . ?
C10 C11 C12 115.0(7) . . ?
N1 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
N13 C12 C11 106.5(6) . . ?
N13 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
N13 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
N13 C13 C14 121.1(8) . . ?
N13 C13 C18 121.0(7) . . ?
C14 C13 C18 117.9(8) . . ?
C13 N13 C12 120.8(7) . . ?
C13 N13 P1 126.1(6) . . ?
C12 N13 P1 112.1(5) . . ?
C15 C14 C13 120.9(9) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C14 120.5(8) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C17 C16 C15 120.2(8) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C18 119.7(8) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C17 C18 C13 120.8(8) . . ?
C17 C18 H18A 119.6 . . ?
C13 C18 H18A 119.6 . . ?

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
O1 P1 C1 C6 -8.2(8) . . . . ?
N1 P1 C1 C6 119.3(7) . . . . ?
N13 P1 C1 C6 -137.8(7) . . . . ?
O1 P1 C1 C2 173.3(7) . . . . ?
N1 P1 C1 C2 -59.2(8) . . . . ?
N13 P1 C1 C2 43.7(8) . . . . ?
C6 C1 C2 O2 179.1(8) . . . . ?
P1 C1 C2 O2 -2.4(12) . . . . ?
C6 C1 C2 C3 -3.9(13) . . . . ?
P1 C1 C2 C3 174.6(7) . . . . ?
C3 C2 O2 C7 9.7(14) . . . . ?
C1 C2 O2 C7 -173.4(8) . . . . ?
O2 C2 C3 C4 179.1(9) . . . . ?
C1 C2 C3 C4 2.2(14) . . . . ?
C2 C3 C4 C5 0.9(14) . . . . ?
C3 C4 C5 C6 -2.3(14) . . . . ?
C3 C4 C5 Br5 179.9(7) . . . . ?
C2 C1 C6 C5 2.5(13) . . . . ?
P1 C1 C6 C5 -176.1(7) . . . . ?
C4 C5 C6 C1 0.6(13) . . . . ?
Br5 C5 C6 C1 178.5(7) . . . . ?
O1 P1 N1 C11 -132.9(6) . . . . ?
N13 P1 N1 C11 -7.8(6) . . . . ?
C1 P1 N1 C11 105.3(6) . . . . ?
O1 P1 N1 C8 0.9(8) . . . . ?
N13 P1 N1 C8 126.0(6) . . . . ?
C1 P1 N1 C8 -120.9(6) . . . . ?
C11 N1 C8 C9 19.8(9) . . . . ?
P1 N1 C8 C9 -116.1(7) . . . . ?
N1 C8 C9 C10 -35.6(9) . . . . ?
C8 C9 C10 C11 38.3(9) . . . . ?
C8 N1 C11 C10 4.1(9) . . . . ?
P1 N1 C11 C10 143.8(6) . . . . ?
C8 N1 C11 C12 -118.0(7) . . . . ?
P1 N1 C11 C12 21.7(8) . . . . ?
C9 C10 C11 N1 -25.9(8) . . . . ?
C9 C10 C11 C12 89.6(9) . . . . ?
N1 C11 C12 N13 -27.1(8) . . . . ?
C10 C11 C12 N13 -143.1(7) . . . . ?
C14 C13 N13 C12 -8.8(11) . . . . ?
C18 C13 N13 C12 171.5(7) . . . . ?
C14 C13 N13 P1 158.3(6) . . . . ?
C18 C13 N13 P1 -21.4(11) . . . . ?
C11 C12 N13 C13 -167.8(7) . . . . ?
C11 C12 N13 P1 23.4(8) . . . . ?
O1 P1 N13 C13 -53.4(8) . . . . ?
N1 P1 N13 C13 -178.1(7) . . . . ?
C1 P1 N13 C13 70.6(7) . . . . ?
O1 P1 N13 C12 114.7(6) . . . . ?
N1 P1 N13 C12 -10.0(6) . . . . ?
C1 P1 N13 C12 -121.4(6) . . . . ?
N13 C13 C14 C15 179.8(7) . . . . ?
C18 C13 C14 C15 -0.5(12) . . . . ?
C13 C14 C15 C16 -1.0(13) . . . . ?
C14 C15 C16 C17 1.2(13) . . . . ?
C15 C16 C17 C18 0.1(13) . . . . ?
C16 C17 C18 C13 -1.6(12) . . . . ?
N13 C13 C18 C17 -178.5(7) . . . . ?
C14 C13 C18 C17 1.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.236
_refine_diff_density_min         -2.114
_refine_diff_density_rms         0.184