# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_121104d

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Br N0 O3 P'
_chemical_formula_weight         479.37
_chemical_absolute_configuration unk

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                   19.80(2)
_cell_length_b                   5.863(6)
_cell_length_c                   20.83(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.188(12)
_cell_angle_gamma                90.00
_cell_volume                     2372(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.433
_cell_measurement_theta_max      22.901

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4751
_exptl_absorpt_correction_T_max  0.6391
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            11609
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0966
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             7063
_reflns_number_gt                4897
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+53.2615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0089(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_number_reflns         7063
_refine_ls_number_parameters     558
_refine_ls_number_restraints     325
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.1350
_refine_ls_wR_factor_ref         0.3188
_refine_ls_wR_factor_gt          0.2983
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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 0.00233(19) 0.7849(6) 0.69807(15) 0.0234(8) Uani 1 1 d . . .
P2 P 0.5186(2) 0.2893(9) 0.8054(3) 0.0533(14) Uani 1 1 d . . .
O10 O -0.0700(6) 0.407(2) 0.6563(6) 0.044(3) Uani 1 1 d U . .
H10A H -0.1060 0.3563 0.6351 0.067 Uiso 1 1 calc R . .
O2 O -0.0053(5) 1.026(2) 0.7147(5) 0.038(3) Uani 1 1 d U . .
C52 C 0.0403(14) 1.077(5) 0.8852(14) 0.104(9) Uani 1 1 d U . .
H52A H 0.0696 1.1200 0.9257 0.157 Uiso 1 1 calc R . .
H52B H -0.0043 1.1450 0.8828 0.157 Uiso 1 1 calc R . .
H52C H 0.0599 1.1305 0.8493 0.157 Uiso 1 1 calc R . .
C50 C 0.4859(19) 0.616(8) 0.6218(18) 0.164(15) Uani 1 1 d U . .
H50A H 0.5272 0.6980 0.6397 0.246 Uiso 1 1 calc R . .
H50B H 0.4517 0.6450 0.6479 0.246 Uiso 1 1 calc R . .
H50C H 0.4689 0.6659 0.5778 0.246 Uiso 1 1 calc R . .
O6 O 0.5263(6) 0.530(2) 0.7919(6) 0.058(3) Uani 1 1 d U . .
O7 O 0.0442(4) 0.6297(17) 0.7554(4) 0.024(2) Uani 1 1 d U . .
O8 O 0.4802(6) 0.139(2) 0.7465(5) 0.050(3) Uani 1 1 d U . .
C1 C -0.1691(8) 0.653(3) 0.8526(7) 0.041(4) Uani 1 1 d U . .
C2 C -0.1344(9) 0.469(3) 0.8379(8) 0.045(4) Uani 1 1 d U . .
H2A H -0.1302 0.3441 0.8660 0.054 Uiso 1 1 calc R . .
C3 C -0.1053(8) 0.456(3) 0.7836(8) 0.040(4) Uani 1 1 d U . .
H3 H -0.0791 0.3290 0.7773 0.048 Uiso 1 1 calc R . .
C4 C -0.1145(7) 0.632(3) 0.7374(6) 0.027(3) Uani 1 1 d U . .
C5 C -0.1498(7) 0.833(3) 0.7526(7) 0.031(4) Uani 1 1 d U . .
H5 H -0.1548 0.9572 0.7242 0.037 Uiso 1 1 calc R . .
C6 C -0.1784(9) 0.843(3) 0.8133(8) 0.046(5) Uani 1 1 d U . .
H6A H -0.2014 0.9718 0.8242 0.056 Uiso 1 1 calc R . .
C7 C -0.0804(6) 0.632(3) 0.6751(6) 0.024(3) Uani 1 1 d U . .
C8 C -0.1278(8) 0.750(3) 0.6191(8) 0.046(4) Uani 1 1 d U . .
H8A H -0.1099 0.7326 0.5797 0.069 Uiso 1 1 calc R . .
H8B H -0.1306 0.9096 0.6289 0.069 Uiso 1 1 calc R . .
H8C H -0.1728 0.6835 0.6131 0.069 Uiso 1 1 calc R . .
C9 C 0.0447(6) 0.757(2) 0.6240(5) 0.016(3) Uani 1 1 d U . .
C10 C 0.0811(7) 0.553(3) 0.6161(7) 0.026(3) Uani 1 1 d U . .
H10 H 0.0847 0.4303 0.6449 0.031 Uiso 1 1 calc R . .
C11 C 0.1113(9) 0.555(3) 0.5597(8) 0.045(4) Uani 1 1 d U . .
H11 H 0.1384 0.4326 0.5520 0.053 Uiso 1 1 calc R . .
C12 C 0.1022(8) 0.730(3) 0.5170(8) 0.051(5) Uani 1 1 d U . .
H12 H 0.1207 0.7182 0.4794 0.061 Uiso 1 1 calc R . .
C13 C 0.0667(8) 0.925(3) 0.5266(8) 0.046(4) Uani 1 1 d U . .
H13 H 0.0630 1.0463 0.4974 0.055 Uiso 1 1 calc R . .
C14 C 0.0358(7) 0.935(3) 0.5826(7) 0.027(3) Uani 1 1 d U . .
H14 H 0.0102 1.0619 0.5904 0.033 Uiso 1 1 calc R . .
C15 C 0.0330(9) 0.811(3) 0.8817(9) 0.046(4) Uani 1 1 d U . .
H15 H -0.006(8) 0.77(3) 0.847(8) 0.055 Uiso 1 1 calc . . .
C16 C 0.0183(12) 0.736(5) 0.9484(10) 0.085(7) Uani 1 1 d U . .
H16A H -0.0026 0.5876 0.9443 0.128 Uiso 1 1 calc R . .
H16B H -0.0124 0.8432 0.9626 0.128 Uiso 1 1 calc R . .
H16C H 0.0607 0.7300 0.9799 0.128 Uiso 1 1 calc R . .
C17 C 0.0954(8) 0.688(4) 0.8691(7) 0.039(4) Uani 1 1 d U . .
H17 H 0.086(8) 0.53(3) 0.875(8) 0.047 Uiso 1 1 calc . . .
C18 C 0.1638(8) 0.740(3) 0.9155(8) 0.051(5) Uani 1 1 d U . .
H18A H 0.1747 0.8997 0.9117 0.062 Uiso 1 1 calc R . .
H18B H 0.1582 0.7126 0.9601 0.062 Uiso 1 1 calc R . .
C19 C 0.2237(10) 0.597(4) 0.9021(9) 0.060(5) Uani 1 1 d U . .
H19A H 0.2141 0.4359 0.9066 0.072 Uiso 1 1 calc R . .
H19B H 0.2653 0.6346 0.9333 0.072 Uiso 1 1 calc R . .
C20 C 0.2337(10) 0.648(4) 0.8309(9) 0.056(5) Uani 1 1 d U . .
H20 H 0.243(10) 0.81(4) 0.827(9) 0.067 Uiso 1 1 calc . . .
C21 C 0.1655(7) 0.586(3) 0.7811(7) 0.033(4) Uani 1 1 d U . .
H21A H 0.1703 0.6250 0.7370 0.040 Uiso 1 1 calc R . .
H21B H 0.1571 0.4228 0.7826 0.040 Uiso 1 1 calc R . .
C22 C 0.1066(7) 0.713(3) 0.7986(6) 0.028(3) Uani 1 1 d U . .
H22 H 0.112(7) 0.87(3) 0.790(7) 0.034 Uiso 1 1 calc . . .
C23 C 0.2941(11) 0.506(4) 0.8130(11) 0.072(6) Uani 1 1 d U . .
H23A H 0.2846 0.3467 0.8164 0.108 Uiso 1 1 calc R . .
H23B H 0.3361 0.5436 0.8426 0.108 Uiso 1 1 calc R . .
H23C H 0.2987 0.5413 0.7691 0.108 Uiso 1 1 calc R . .
C24 C 0.2318(12) -0.009(5) 0.6631(12) 0.086(7) Uani 1 1 d U . .
H24A H 0.2462 -0.1653 0.6673 0.129 Uiso 1 1 calc R . .
H24B H 0.1962 0.0083 0.6249 0.129 Uiso 1 1 calc R . .
H24C H 0.2144 0.0360 0.7011 0.129 Uiso 1 1 calc R . .
C25 C 0.2909(12) 0.136(5) 0.6568(11) 0.071(6) Uani 1 1 d U . .
H25 H 0.279(11) 0.29(4) 0.666(11) 0.085 Uiso 1 1 calc . . .
C26 C 0.3081(13) 0.127(5) 0.5868(12) 0.092(8) Uani 1 1 d U . .
H26A H 0.3178 -0.0298 0.5766 0.111 Uiso 1 1 calc R . .
H26B H 0.2682 0.1765 0.5552 0.111 Uiso 1 1 calc R . .
C27 C 0.3690(11) 0.274(4) 0.5804(11) 0.075(6) Uani 1 1 d U . .
H27A H 0.3581 0.4326 0.5873 0.090 Uiso 1 1 calc R . .
H27B H 0.3780 0.2603 0.5364 0.090 Uiso 1 1 calc R . .
C28 C 0.4336(11) 0.206(5) 0.6299(10) 0.066(6) Uani 1 1 d U . .
H28 H 0.443(10) 0.05(4) 0.622(10) 0.079 Uiso 1 1 calc . . .
C29 C 0.4199(9) 0.224(4) 0.6971(8) 0.052(5) Uani 1 1 d U . .
H29 H 0.411(9) 0.38(4) 0.707(9) 0.063 Uiso 1 1 calc . . .
C30 C 0.3547(8) 0.074(3) 0.7020(8) 0.044(4) Uani 1 1 d U . .
H30A H 0.3652 -0.0837 0.6943 0.053 Uiso 1 1 calc R . .
H30B H 0.3465 0.0846 0.7464 0.053 Uiso 1 1 calc R . .
C31 C 0.5274(12) 0.274(5) 0.5613(11) 0.086(7) Uani 1 1 d U . .
H31A H 0.4906 0.2846 0.5238 0.129 Uiso 1 1 calc R . .
H31B H 0.5426 0.1184 0.5670 0.129 Uiso 1 1 calc R . .
H31C H 0.5650 0.3685 0.5547 0.129 Uiso 1 1 calc R . .
C32 C 0.5018(10) 0.353(3) 0.6221(10) 0.050(5) Uani 1 1 d U . .
H32 H 0.538(9) 0.32(3) 0.660(9) 0.060 Uiso 1 1 calc . . .
C33 C 0.4740(11) 0.436(4) 0.9126(10) 0.066(6) Uani 1 1 d U . .
H33 H 0.4987 0.5691 0.9093 0.079 Uiso 1 1 calc R . .
C34 C 0.4727(7) 0.260(2) 0.8647(6) 0.024(3) Uani 1 1 d U . .
C35 C 0.4346(9) 0.068(3) 0.8734(8) 0.046(4) Uani 1 1 d U . .
H35 H 0.4332 -0.0522 0.8439 0.055 Uiso 1 1 calc R . .
C36 C 0.3982(10) 0.046(4) 0.9242(9) 0.054(5) Uani 1 1 d U . .
H36 H 0.3737 -0.0871 0.9285 0.064 Uiso 1 1 calc R . .
C37 C 0.3988(9) 0.236(4) 0.9712(9) 0.059(5) Uani 1 1 d U . .
H37 H 0.3728 0.2337 1.0039 0.071 Uiso 1 1 calc R . .
C38 C 0.4393(10) 0.411(4) 0.9633(10) 0.058(5) Uani 1 1 d U . .
H38 H 0.4446 0.5253 0.9948 0.069 Uiso 1 1 calc R . .
C39 C 0.6410(10) 0.257(4) 0.8937(9) 0.063(5) Uani 1 1 d U . .
H39A H 0.6824 0.1744 0.9110 0.094 Uiso 1 1 calc R . .
H39B H 0.6108 0.2533 0.9246 0.094 Uiso 1 1 calc R . .
H39C H 0.6523 0.4127 0.8858 0.094 Uiso 1 1 calc R . .
C40 C 0.6025(11) 0.140(5) 0.8247(10) 0.076(6) Uani 1 1 d U . .
C41 C 0.6754(12) 0.322(5) 0.7639(12) 0.080(7) Uani 1 1 d U . .
H41 H 0.6827 0.4363 0.7954 0.096 Uiso 1 1 calc R . .
C42 C 0.6384(10) 0.137(4) 0.7718(9) 0.064(5) Uani 1 1 d U . .
C43 C 0.6343(10) -0.042(4) 0.7278(10) 0.065(6) Uani 1 1 d U . .
H43 H 0.6120 -0.1747 0.7366 0.077 Uiso 1 1 calc R . .
C44 C 0.6619(11) -0.034(4) 0.6707(11) 0.071(6) Uani 1 1 d U . .
H44 H 0.6597 -0.1569 0.6421 0.085 Uiso 1 1 calc R . .
C45 C 0.6921(12) 0.167(6) 0.6605(11) 0.085(7) Uani 1 1 d U . .
C46 C 0.7019(11) 0.339(4) 0.7087(10) 0.062(6) Uani 1 1 d U . .
H46 H 0.7272 0.4680 0.7025 0.074 Uiso 1 1 calc R . .
Br1 Br -0.20366(11) 0.6827(5) 0.93076(9) 0.0749(8) Uani 1 1 d . . .
Br3 Br 0.72982(13) 0.1872(7) 0.58178(18) 0.1189(13) Uani 1 1 d . . .
O11 O 0.5877(6) -0.091(2) 0.8536(6) 0.050(3) Uani 1 1 d U . .
H11A H 0.5593 -0.0740 0.8771 0.075 Uiso 1 1 calc R . .


_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 O2 1.468(12) . ?
P1 O7 1.599(9) . ?
P1 C7 1.846(14) . ?
P1 C9 1.900(12) . ?
P2 O6 1.455(15) . ?
P2 O8 1.582(13) . ?
P2 C34 1.679(14) . ?
P2 C40 1.85(2) . ?
O10 C7 1.403(18) . ?
C52 C15 1.57(3) . ?
C50 C32 1.57(5) . ?
O7 C22 1.463(16) . ?
O8 C29 1.50(2) . ?
C1 C2 1.35(3) . ?
C1 C6 1.37(3) . ?
C1 Br1 1.893(15) . ?
C2 C3 1.37(2) . ?
C3 C4 1.40(2) . ?
C4 C5 1.44(2) . ?
C4 C7 1.575(17) . ?
C5 C6 1.48(2) . ?
C7 C8 1.52(2) . ?
C9 C14 1.347(19) . ?
C9 C10 1.423(19) . ?
C10 C11 1.42(2) . ?
C11 C12 1.34(2) . ?
C12 C13 1.38(3) . ?
C13 C14 1.42(2) . ?
C15 C17 1.50(2) . ?
C15 C16 1.54(3) . ?
C17 C18 1.53(2) . ?
C17 C22 1.534(19) . ?
C18 C19 1.52(2) . ?
C19 C20 1.56(3) . ?
C20 C23 1.56(3) . ?
C20 C21 1.58(2) . ?
C21 C22 1.49(2) . ?
C24 C25 1.47(3) . ?
C25 C30 1.47(3) . ?
C25 C26 1.56(3) . ?
C26 C27 1.51(3) . ?
C27 C28 1.53(3) . ?
C28 C29 1.48(3) . ?
C28 C32 1.64(3) . ?
C29 C30 1.58(2) . ?
C31 C32 1.53(3) . ?
C33 C38 1.38(3) . ?
C33 C34 1.43(3) . ?
C34 C35 1.39(2) . ?
C35 C36 1.40(2) . ?
C36 C37 1.48(3) . ?
C37 C38 1.33(3) . ?
C39 C40 1.64(3) . ?
C40 C42 1.42(3) . ?
C40 O11 1.53(3) . ?
C41 C42 1.34(3) . ?
C41 C46 1.36(3) . ?
C42 C43 1.38(3) . ?
C43 C44 1.40(3) . ?
C44 C45 1.36(4) . ?
C45 C46 1.41(3) . ?
C45 Br3 1.93(2) . ?

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
O2 P1 O7 115.7(6) . . ?
O2 P1 C7 113.6(7) . . ?
O7 P1 C7 102.9(6) . . ?
O2 P1 C9 110.9(6) . . ?
O7 P1 C9 108.1(5) . . ?
C7 P1 C9 104.9(5) . . ?
O6 P2 O8 116.3(8) . . ?
O6 P2 C34 109.6(8) . . ?
O8 P2 C34 105.5(7) . . ?
O6 P2 C40 112.2(10) . . ?
O8 P2 C40 100.4(9) . . ?
C34 P2 C40 112.5(9) . . ?
C22 O7 P1 121.6(10) . . ?
C29 O8 P2 123.0(12) . . ?
C2 C1 C6 122.1(15) . . ?
C2 C1 Br1 123.6(14) . . ?
C6 C1 Br1 114.2(14) . . ?
C1 C2 C3 123.2(18) . . ?
C2 C3 C4 120.5(17) . . ?
C3 C4 C5 117.3(13) . . ?
C3 C4 C7 123.2(13) . . ?
C5 C4 C7 119.0(13) . . ?
C4 C5 C6 120.2(14) . . ?
C1 C6 C5 116.5(16) . . ?
O10 C7 C8 108.5(12) . . ?
O10 C7 C4 109.8(12) . . ?
C8 C7 C4 109.6(11) . . ?
O10 C7 P1 110.9(9) . . ?
C8 C7 P1 111.3(11) . . ?
C4 C7 P1 106.7(9) . . ?
C14 C9 C10 125.8(12) . . ?
C14 C9 P1 115.5(10) . . ?
C10 C9 P1 118.7(9) . . ?
C11 C10 C9 113.1(14) . . ?
C12 C11 C10 122.1(17) . . ?
C11 C12 C13 122.9(17) . . ?
C12 C13 C14 117.9(17) . . ?
C9 C14 C13 118.0(15) . . ?
C17 C15 C16 109.2(16) . . ?
C17 C15 C52 114.6(18) . . ?
C16 C15 C52 105.9(19) . . ?
C15 C17 C18 116.8(15) . . ?
C15 C17 C22 113.7(14) . . ?
C18 C17 C22 108.2(12) . . ?
C19 C18 C17 113.6(15) . . ?
C18 C19 C20 108.3(16) . . ?
C23 C20 C19 111.6(17) . . ?
C23 C20 C21 108.4(16) . . ?
C19 C20 C21 109.2(15) . . ?
C22 C21 C20 109.5(13) . . ?
O7 C22 C21 107.0(12) . . ?
O7 C22 C17 107.2(11) . . ?
C21 C22 C17 117.0(13) . . ?
C30 C25 C24 113(2) . . ?
C30 C25 C26 105.9(18) . . ?
C24 C25 C26 113(2) . . ?
C27 C26 C25 113(2) . . ?
C26 C27 C28 112(2) . . ?
C29 C28 C27 109.6(18) . . ?
C29 C28 C32 111.1(17) . . ?
C27 C28 C32 113.1(19) . . ?
C28 C29 O8 110.8(15) . . ?
C28 C29 C30 108.8(16) . . ?
O8 C29 C30 108.7(15) . . ?
C25 C30 C29 115.5(16) . . ?
C31 C32 C50 113(2) . . ?
C31 C32 C28 109.5(18) . . ?
C50 C32 C28 110(2) . . ?
C38 C33 C34 121(2) . . ?
C35 C34 C33 115.6(15) . . ?
C35 C34 P2 124.4(12) . . ?
C33 C34 P2 119.9(13) . . ?
C34 C35 C36 123.1(17) . . ?
C35 C36 C37 119.4(19) . . ?
C38 C37 C36 115.2(18) . . ?
C37 C38 C33 126(2) . . ?
C42 C40 O11 117(2) . . ?
C42 C40 C39 117.8(18) . . ?
O11 C40 C39 96.8(15) . . ?
C42 C40 P2 113.6(16) . . ?
O11 C40 P2 105.7(13) . . ?
C39 C40 P2 103.6(15) . . ?
C42 C41 C46 118(2) . . ?
C41 C42 C43 120(2) . . ?
C41 C42 C40 117(2) . . ?
C43 C42 C40 123(2) . . ?
C42 C43 C44 124(2) . . ?
C45 C44 C43 115(2) . . ?
C44 C45 C46 121(2) . . ?
C44 C45 Br3 116(2) . . ?
C46 C45 Br3 123(2) . . ?
C41 C46 C45 122(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.442
_refine_diff_density_min         -1.809
_refine_diff_density_rms         0.151
_database_code_depnum_ccdc_archive 'CCDC 950075'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_121201b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H30 N0 O4 P'
_chemical_formula_weight         425.46

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   12.436(13)
_cell_length_b                   5.7781(7)
_cell_length_c                   15.9687(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5340(10)
_cell_angle_gamma                90.00
_cell_volume                     1146.3(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9392
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5868
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_av_sigmaI/netI    0.1382
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3683
_reflns_number_gt                2107
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_number_reflns         3683
_refine_ls_number_parameters     288
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1811
_refine_ls_R_factor_gt           0.1367
_refine_ls_wR_factor_ref         0.3557
_refine_ls_wR_factor_gt          0.3229
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.007

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 0.18598(18) 0.1980(4) 0.79796(15) 0.0442(7) Uani 1 1 d . . .
O3 O 0.0644(5) 0.5741(12) 0.7778(4) 0.0499(17) Uani 1 1 d U . .
H3 H 0.0016 0.6157 0.7710 0.075 Uiso 1 1 calc R . .
O2 O 0.1944(6) -0.0499(11) 0.7747(4) 0.0565(18) Uani 1 1 d U . .
O4 O 0.2866(5) 0.3465(12) 0.7806(4) 0.0479(17) Uani 1 1 d U . .
C11 C 0.1653(6) 0.2246(17) 0.9068(5) 0.040(2) Uani 1 1 d . . .
C12 C 0.1142(7) 0.0493(19) 0.9482(6) 0.047(2) Uani 1 1 d . . .
H12 H 0.0926 -0.0822 0.9183 0.057 Uiso 1 1 calc R . .
C19 C 0.1006(9) 0.3678(17) 0.6487(6) 0.053(3) Uani 1 1 d . . .
C17 C 0.0777(7) 0.3494(17) 0.7398(5) 0.043(2) Uani 1 1 d . . .
C5 C 0.3953(8) 0.2642(19) 0.7948(7) 0.051(3) Uani 1 1 d . . .
H5 H 0.393(7) 0.10(2) 0.809(6) 0.061 Uiso 1 1 calc . . .
C15 C 0.1763(7) 0.437(2) 1.0365(6) 0.052(3) Uani 1 1 d . . .
H15 H 0.2001 0.5647 1.0676 0.062 Uiso 1 1 calc R . .
C3 C 0.4034(12) 0.165(2) 0.6397(8) 0.079(4) Uani 1 1 d . . .
H3A H 0.326(9) 0.20(3) 0.636(7) 0.094 Uiso 1 1 calc . . .
C16 C 0.1918(7) 0.4273(18) 0.9524(6) 0.044(2) Uani 1 1 d . . .
H16 H 0.2198 0.5545 0.9251 0.052 Uiso 1 1 calc R . .
C18 C -0.0268(9) 0.223(2) 0.7536(6) 0.061(3) Uani 1 1 d . . .
H18A H -0.0844 0.2963 0.7215 0.092 Uiso 1 1 calc R . .
H18B H -0.0419 0.2276 0.8120 0.092 Uiso 1 1 calc R . .
H18C H -0.0204 0.0648 0.7360 0.092 Uiso 1 1 calc R . .
C13 C 0.0943(7) 0.062(2) 1.0304(6) 0.053(3) Uani 1 1 d . . .
H13 H 0.0601 -0.0600 1.0563 0.063 Uiso 1 1 calc R . .
C4 C 0.4561(11) 0.2890(19) 0.7167(8) 0.073(4) Uani 1 1 d . . .
H4 H 0.454(9) 0.45(3) 0.703(7) 0.088 Uiso 1 1 calc . . .
C20 C 0.1578(10) 0.560(2) 0.6178(6) 0.063(3) Uani 1 1 d . . .
H20 H 0.1762 0.6813 0.6538 0.076 Uiso 1 1 calc R . .
C21 C 0.1861(10) 0.569(2) 0.5375(7) 0.068(3) Uani 1 1 d . . .
H21 H 0.2195 0.7022 0.5185 0.082 Uiso 1 1 calc R . .
C6 C 0.4477(7) 0.395(2) 0.8689(7) 0.063(3) Uani 1 1 d . . .
H6A H 0.4405 0.5596 0.8585 0.076 Uiso 1 1 calc R . .
H6B H 0.4090 0.3592 0.9187 0.076 Uiso 1 1 calc R . .
O1 O 0.1990(7) 0.4201(16) 0.4038(5) 0.083(2) Uani 1 1 d U . .
C9 C 0.5762(10) 0.230(3) 0.7367(9) 0.094(5) Uani 1 1 d . . .
H9A H 0.5825 0.0677 0.7510 0.113 Uiso 1 1 calc R . .
H9B H 0.6167 0.2570 0.6870 0.113 Uiso 1 1 calc R . .
C23 C 0.1104(9) 0.201(2) 0.5126(6) 0.068(3) Uani 1 1 d . . .
H23 H 0.0913 0.0804 0.4763 0.081 Uiso 1 1 calc R . .
C24 C 0.0832(9) 0.192(2) 0.5932(6) 0.065(3) Uani 1 1 d . . .
H24 H 0.0507 0.0578 0.6119 0.078 Uiso 1 1 calc R . .
C8 C 0.6243(9) 0.373(3) 0.8078(11) 0.097(5) Uani 1 1 d . . .
C22 C 0.1675(11) 0.392(2) 0.4836(6) 0.070(3) Uani 1 1 d . . .
C7 C 0.5597(10) 0.342(3) 0.8849(10) 0.084(4) Uani 1 1 d . . .
H7 H 0.564(10) 0.18(3) 0.900(8) 0.101 Uiso 1 1 calc . . .
C25 C 0.1861(15) 0.227(4) 0.3495(7) 0.120(6) Uani 1 1 d . . .
H25A H 0.1112 0.1877 0.3431 0.180 Uiso 1 1 calc R . .
H25B H 0.2255 0.0975 0.3729 0.180 Uiso 1 1 calc R . .
H25C H 0.2130 0.2647 0.2958 0.180 Uiso 1 1 calc R . .
C14 C 0.1241(8) 0.253(2) 1.0758(6) 0.059(3) Uani 1 1 d . . .
H14 H 0.1100 0.2624 1.1325 0.071 Uiso 1 1 calc R . .
C1 C 0.4520(16) 0.242(3) 0.5624(9) 0.152(9) Uani 1 1 d . . .
H1A H 0.4041 0.2078 0.5152 0.228 Uiso 1 1 calc R . .
H1B H 0.5191 0.1629 0.5562 0.228 Uiso 1 1 calc R . .
H1C H 0.4646 0.4059 0.5650 0.228 Uiso 1 1 calc R . .
C10 C 0.6086(11) 0.482(3) 0.9608(10) 0.111(6) Uani 1 1 d . . .
C2 C 0.4167(13) -0.098(2) 0.6482(9) 0.093(4) Uani 1 1 d . . .
H2A H 0.4918 -0.1349 0.6552 0.140 Uiso 1 1 calc R . .
H2B H 0.3870 -0.1717 0.5986 0.140 Uiso 1 1 calc R . .
H2C H 0.3796 -0.1507 0.6960 0.140 Uiso 1 1 calc R . .


_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 O2 1.485(7) . ?
P1 O4 1.552(7) . ?
P1 C11 1.774(8) . ?
P1 C17 1.825(10) . ?
O3 C17 1.446(11) . ?
O4 C5 1.441(13) . ?
C11 C12 1.380(13) . ?
C11 C16 1.410(13) . ?
C12 C13 1.349(12) . ?
C19 C24 1.360(14) . ?
C19 C20 1.417(15) . ?
C19 C17 1.498(13) . ?
C17 C18 1.516(13) . ?
C5 C4 1.494(14) . ?
C5 C6 1.525(15) . ?
C15 C16 1.367(12) . ?
C15 C14 1.406(15) . ?
C3 C1 1.468(16) . ?
C3 C2 1.533(17) . ?
C3 C4 1.54(2) . ?
C13 C14 1.365(15) . ?
C4 C9 1.551(19) . ?
C20 C21 1.346(14) . ?
C21 C22 1.351(16) . ?
C6 C7 1.438(17) . ?
O1 C22 1.359(11) . ?
O1 C25 1.418(18) . ?
C9 C8 1.51(2) . ?
C23 C24 1.345(13) . ?
C23 C22 1.403(17) . ?
C8 C7 1.510(19) . ?
C7 C10 1.56(2) . ?

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
O2 P1 O4 115.0(4) . . ?
O2 P1 C11 110.1(4) . . ?
O4 P1 C11 106.2(4) . . ?
O2 P1 C17 113.2(4) . . ?
O4 P1 C17 103.1(4) . . ?
C11 P1 C17 108.8(4) . . ?
C5 O4 P1 123.2(7) . . ?
C12 C11 C16 117.6(8) . . ?
C12 C11 P1 119.7(7) . . ?
C16 C11 P1 122.5(7) . . ?
C13 C12 C11 122.3(10) . . ?
C24 C19 C20 115.2(9) . . ?
C24 C19 C17 123.3(9) . . ?
C20 C19 C17 120.8(8) . . ?
O3 C17 C19 112.0(8) . . ?
O3 C17 C18 104.9(7) . . ?
C19 C17 C18 112.1(7) . . ?
O3 C17 P1 108.2(6) . . ?
C19 C17 P1 111.1(7) . . ?
C18 C17 P1 108.2(7) . . ?
O4 C5 C4 110.0(10) . . ?
O4 C5 C6 108.9(8) . . ?
C4 C5 C6 112.7(9) . . ?
C16 C15 C14 119.7(10) . . ?
C1 C3 C2 109.1(12) . . ?
C1 C3 C4 110.8(13) . . ?
C2 C3 C4 110.4(12) . . ?
C15 C16 C11 120.2(9) . . ?
C12 C13 C14 120.3(10) . . ?
C5 C4 C3 114.1(10) . . ?
C5 C4 C9 109.0(11) . . ?
C3 C4 C9 115.7(10) . . ?
C21 C20 C19 121.4(10) . . ?
C20 C21 C22 122.0(11) . . ?
C7 C6 C5 114.2(10) . . ?
C22 O1 C25 116.7(10) . . ?
C8 C9 C4 112.5(11) . . ?
C24 C23 C22 119.9(10) . . ?
C23 C24 C19 123.8(11) . . ?
C9 C8 C7 110.0(11) . . ?
C21 C22 O1 117.2(11) . . ?
C21 C22 C23 117.5(9) . . ?
O1 C22 C23 125.1(10) . . ?
C6 C7 C8 112.0(13) . . ?
C6 C7 C10 111.6(11) . . ?
C8 C7 C10 111.6(12) . . ?
C13 C14 C15 119.6(9) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.187
_database_code_depnum_ccdc_archive 'CCDC 950076'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_121229d

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H37 N0 O3 P'
_chemical_formula_weight         380.49
_chemical_absolute_configuration R

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.7766(4)
_cell_length_b                   12.2080(12)
_cell_length_c                   16.2225(15)
_cell_angle_alpha                83.552(2)
_cell_angle_beta                 82.7850(10)
_cell_angle_gamma                78.7770(10)
_cell_volume                     1108.71(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1829
_cell_measurement_theta_min      2.5363
_cell_measurement_theta_max      28.3000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'multiwire proportional'
_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            6610
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5141
_reflns_number_gt                4536
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_number_reflns         5141
_refine_ls_number_parameters     483
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_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 0.92067(14) 0.82379(7) 0.46314(6) 0.0146(2) Uani 1 1 d . . .
O4 O 0.7962(4) 0.72978(18) 0.51588(14) 0.0161(5) Uani 1 1 d . . .
O3 O 1.1492(4) 0.83488(19) 0.49189(15) 0.0192(6) Uani 1 1 d . . .
C15 C 0.8681(7) 0.5322(3) 0.5029(2) 0.0190(8) Uani 1 1 d . . .
H15A H 0.9223 0.5437 0.4440 0.023 Uiso 1 1 calc R . .
H15B H 0.6968 0.5393 0.5082 0.023 Uiso 1 1 calc R . .
C17 C 0.8645(6) 0.6059(3) 0.6427(2) 0.0153(8) Uani 1 1 d . . .
H17 H 0.6928 0.6081 0.6513 0.018 Uiso 1 1 calc R . .
C16 C 0.9312(6) 0.6221(3) 0.5481(2) 0.0163(8) Uani 1 1 d . . .
H16 H 1.1016 0.6227 0.5365 0.020 Uiso 1 1 calc R . .
C1 C 0.8056(6) 0.7350(3) 0.3250(2) 0.0182(8) Uani 1 1 d . . .
H1 H 0.6761 0.7154 0.3595 0.022 Uiso 1 1 calc R . .
C6 C 0.9591(6) 0.7915(3) 0.3562(2) 0.0164(8) Uani 1 1 d . . .
C20 C 0.9141(6) 0.6996(3) 0.6912(2) 0.0200(8) Uani 1 1 d . . .
H20 H 0.8502 0.7713 0.6614 0.024 Uiso 1 1 calc R . .
C18 C 0.9823(7) 0.4877(3) 0.6744(2) 0.0208(8) Uani 1 1 d . . .
H18A H 1.1534 0.4813 0.6654 0.025 Uiso 1 1 calc R . .
H18B H 0.9379 0.4754 0.7339 0.025 Uiso 1 1 calc R . .
C2 C 0.8440(7) 0.7076(3) 0.2431(2) 0.0234(9) Uani 1 1 d . . .
H2 H 0.7428 0.6685 0.2232 0.028 Uiso 1 1 calc R . .
C4 C 1.1834(7) 0.7975(3) 0.2202(2) 0.0239(9) Uani 1 1 d . . .
H4 H 1.3080 0.8199 0.1845 0.029 Uiso 1 1 calc R . .
C9 C 0.5885(6) 0.9564(3) 0.5647(2) 0.0203(8) Uani 1 1 d . . .
H9A H 0.7196 0.9554 0.5968 0.024 Uiso 1 1 calc R . .
H9B H 0.5220 0.8898 0.5837 0.024 Uiso 1 1 calc R . .
C5 C 1.1499(6) 0.8234(3) 0.3025(2) 0.0191(8) Uani 1 1 d . . .
H5 H 1.2534 0.8616 0.3220 0.023 Uiso 1 1 calc R . .
C22 C 0.7826(7) 0.6974(4) 0.7783(2) 0.0329(10) Uani 1 1 d . . .
H22A H 0.8430 0.6288 0.8100 0.049 Uiso 1 1 calc R . .
H22B H 0.6164 0.7018 0.7746 0.049 Uiso 1 1 calc R . .
H22C H 0.8053 0.7600 0.8053 0.049 Uiso 1 1 calc R . .
C19 C 0.9093(7) 0.3983(3) 0.6302(2) 0.0216(9) Uani 1 1 d . . .
H19A H 0.7390 0.4024 0.6412 0.026 Uiso 1 1 calc R . .
H19B H 0.9858 0.3247 0.6522 0.026 Uiso 1 1 calc R . .
C21 C 1.1787(7) 0.6974(3) 0.6940(3) 0.0280(9) Uani 1 1 d . . .
H21A H 1.1984 0.7599 0.7217 0.042 Uiso 1 1 calc R . .
H21B H 1.2562 0.7021 0.6381 0.042 Uiso 1 1 calc R . .
H21C H 1.2474 0.6288 0.7238 0.042 Uiso 1 1 calc R . .
C14 C 0.9778(7) 0.4133(3) 0.5363(2) 0.0214(8) Uani 1 1 d . . .
H14 H 1.1509 0.4051 0.5262 0.026 Uiso 1 1 calc R . .
C10 C 0.3969(6) 1.0603(3) 0.5836(2) 0.0229(9) Uani 1 1 d . . .
H10 H 0.3391 1.0956 0.5309 0.028 Uiso 1 1 calc R . .
C13 C 0.9015(7) 0.3263(3) 0.4903(2) 0.0260(9) Uani 1 1 d . . .
H13A H 0.9793 0.2526 0.5095 0.039 Uiso 1 1 calc R . .
H13B H 0.9445 0.3400 0.4315 0.039 Uiso 1 1 calc R . .
H13C H 0.7327 0.3313 0.5010 0.039 Uiso 1 1 calc R . .
C12 C 0.1888(7) 1.0252(3) 0.6406(3) 0.0316(10) Uani 1 1 d . . .
H12A H 0.2429 0.9895 0.6923 0.047 Uiso 1 1 calc R . .
H12B H 0.1223 0.9738 0.6141 0.047 Uiso 1 1 calc R . .
H12C H 0.0699 1.0903 0.6514 0.047 Uiso 1 1 calc R . .
C3 C 1.0349(7) 0.7391(3) 0.1906(2) 0.0233(9) Uani 1 1 d . . .
H3 H 1.0619 0.7205 0.1357 0.028 Uiso 1 1 calc R . .
C11 C 0.4986(7) 1.1461(3) 0.6233(3) 0.0347(11) Uani 1 1 d . . .
H11A H 0.3770 1.2105 0.6330 0.052 Uiso 1 1 calc R . .
H11B H 0.6280 1.1685 0.5865 0.052 Uiso 1 1 calc R . .
H11C H 0.5545 1.1131 0.6754 0.052 Uiso 1 1 calc R . .
P2 P 0.39664(15) 0.41429(8) 0.00013(6) 0.0186(2) Uani 1 1 d . . .
O5 O 0.5362(4) 0.3608(2) 0.07753(15) 0.0194(6) Uani 1 1 d . . .
O6 O 0.1571(4) 0.3861(2) 0.00315(16) 0.0254(7) Uani 1 1 d . . .
O1 O 0.8095(4) 0.4137(2) -0.09789(16) 0.0234(6) Uani 1 1 d . . .
H1A H 0.8852 0.3920 -0.0578 0.035 Uiso 1 1 calc R . .
C39 C 0.4895(6) 0.2293(3) 0.2011(2) 0.0177(8) Uani 1 1 d . . .
H39 H 0.6609 0.2197 0.2037 0.021 Uiso 1 1 calc R . .
C42 C 0.4512(7) 0.1370(3) 0.1492(2) 0.0227(9) Uani 1 1 d . . .
H42 H 0.5183 0.1545 0.0917 0.027 Uiso 1 1 calc R . .
C23 C 0.1993(7) 0.6346(3) -0.0424(2) 0.0256(9) Uani 1 1 d . . .
H23 H 0.0811 0.6050 -0.0613 0.031 Uiso 1 1 calc R . .
C36 C 0.3618(7) 0.4262(3) 0.3031(2) 0.0203(8) Uani 1 1 d . . .
H36 H 0.1884 0.4408 0.3051 0.024 Uiso 1 1 calc R . .
C27 C 0.5630(7) 0.6093(3) 0.0217(2) 0.0246(9) Uani 1 1 d . . .
H27 H 0.6895 0.5625 0.0453 0.030 Uiso 1 1 calc R . .
C28 C 0.3861(6) 0.5634(3) -0.0056(2) 0.0199(8) Uani 1 1 d . . .
C37 C 0.4412(7) 0.3071(3) 0.3412(2) 0.0219(8) Uani 1 1 d . . .
H37A H 0.6118 0.2926 0.3427 0.026 Uiso 1 1 calc R . .
H37B H 0.3672 0.2991 0.3981 0.026 Uiso 1 1 calc R . .
C40 C 0.4094(6) 0.3485(3) 0.1620(2) 0.0179(8) Uani 1 1 d . . .
H40 H 0.2381 0.3616 0.1580 0.021 Uiso 1 1 calc R . .
C43 C 0.5860(7) 0.0223(3) 0.1799(3) 0.0334(10) Uani 1 1 d . . .
H43A H 0.5223 0.0017 0.2357 0.050 Uiso 1 1 calc R . .
H43B H 0.7509 0.0257 0.1792 0.050 Uiso 1 1 calc R . .
H43C H 0.5696 -0.0325 0.1440 0.050 Uiso 1 1 calc R . .
C31 C 0.6638(7) 0.2338(3) -0.0743(2) 0.0245(9) Uani 1 1 d . . .
H31A H 0.5150 0.2070 -0.0600 0.029 Uiso 1 1 calc R . .
H31B H 0.7508 0.2155 -0.0257 0.029 Uiso 1 1 calc R . .
C41 C 0.4658(7) 0.4370(3) 0.2113(2) 0.0214(8) Uani 1 1 d . . .
H41A H 0.4024 0.5108 0.1859 0.026 Uiso 1 1 calc R . .
H41B H 0.6366 0.4302 0.2086 0.026 Uiso 1 1 calc R . .
C38 C 0.3747(7) 0.2218(3) 0.2912(2) 0.0220(8) Uani 1 1 d . . .
H38A H 0.2035 0.2347 0.2914 0.026 Uiso 1 1 calc R . .
H38B H 0.4250 0.1470 0.3174 0.026 Uiso 1 1 calc R . .
C25 C 0.3655(8) 0.7942(3) -0.0228(3) 0.0339(10) Uani 1 1 d . . .
H25 H 0.3587 0.8714 -0.0288 0.041 Uiso 1 1 calc R . .
C44 C 0.1882(7) 0.1325(3) 0.1463(3) 0.0340(10) Uani 1 1 d . . .
H44A H 0.1760 0.0756 0.1116 0.051 Uiso 1 1 calc R . .
H44B H 0.1077 0.2039 0.1239 0.051 Uiso 1 1 calc R . .
H44C H 0.1166 0.1151 0.2017 0.051 Uiso 1 1 calc R . .
C35 C 0.4329(7) 0.5132(3) 0.3504(2) 0.0260(9) Uani 1 1 d . . .
H35A H 0.3716 0.5039 0.4081 0.039 Uiso 1 1 calc R . .
H35B H 0.3690 0.5870 0.3270 0.039 Uiso 1 1 calc R . .
H35C H 0.6028 0.5034 0.3460 0.039 Uiso 1 1 calc R . .
C29 C 0.6048(6) 0.3619(3) -0.0893(2) 0.0201(8) Uani 1 1 d . . .
C32 C 0.8060(7) 0.1663(3) -0.1442(2) 0.0273(9) Uani 1 1 d . . .
H32 H 0.7319 0.1925 -0.1957 0.033 Uiso 1 1 calc R . .
C26 C 0.5508(7) 0.7253(3) 0.0138(2) 0.0299(10) Uani 1 1 d . . .
H26 H 0.6669 0.7559 0.0331 0.036 Uiso 1 1 calc R . .
C24 C 0.1910(8) 0.7502(3) -0.0506(2) 0.0322(10) Uani 1 1 d . . .
H24 H 0.0668 0.7977 -0.0749 0.039 Uiso 1 1 calc R . .
C33 C 1.0599(8) 0.1839(4) -0.1589(3) 0.0555(15) Uani 1 1 d . . .
H33A H 1.1332 0.1634 -0.1081 0.083 Uiso 1 1 calc R . .
H33B H 1.0630 0.2614 -0.1766 0.083 Uiso 1 1 calc R . .
H33C H 1.1450 0.1381 -0.2013 0.083 Uiso 1 1 calc R . .
C34 C 0.7936(9) 0.0438(4) -0.1243(3) 0.0506(14) Uani 1 1 d . . .
H34A H 0.8797 0.0022 -0.1688 0.076 Uiso 1 1 calc R . .
H34B H 0.6308 0.0347 -0.1180 0.076 Uiso 1 1 calc R . .
H34C H 0.8625 0.0166 -0.0733 0.076 Uiso 1 1 calc R . .
O2 O 0.5030(4) 0.9438(2) 0.42230(15) 0.0194(6) Uani 1 1 d . . .
H2A H 0.4108 0.9060 0.4486 0.029 Uiso 1 1 calc R . .
C30 C 0.4810(7) 0.4029(3) -0.1672(2) 0.0250(9) Uani 1 1 d . . .
H30A H 0.4495 0.4834 -0.1733 0.037 Uiso 1 1 calc R . .
H30B H 0.3341 0.3759 -0.1625 0.037 Uiso 1 1 calc R . .
H30C H 0.5811 0.3754 -0.2152 0.037 Uiso 1 1 calc R . .
C7 C 0.6866(6) 0.9499(3) 0.4725(2) 0.0179(8) Uani 1 1 d . . .
C8 C 0.7988(6) 1.0496(3) 0.4343(2) 0.0211(8) Uani 1 1 d . . .
H8A H 0.8464 1.0423 0.3760 0.032 Uiso 1 1 calc R . .
H8B H 0.9351 1.0517 0.4619 0.032 Uiso 1 1 calc R . .
H8C H 0.6854 1.1177 0.4408 0.032 Uiso 1 1 calc R . .


_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 O3 1.489(2) . ?
P1 O4 1.585(2) . ?
P1 C6 1.799(3) . ?
P1 C7 1.847(4) . ?
O4 C16 1.469(4) . ?
C15 C16 1.511(4) . ?
C15 C14 1.535(5) . ?
C17 C18 1.533(5) . ?
C17 C16 1.534(5) . ?
C17 C20 1.548(5) . ?
C1 C2 1.386(5) . ?
C1 C6 1.396(4) . ?
C6 C5 1.406(4) . ?
C20 C22 1.517(5) . ?
C20 C21 1.529(5) . ?
C18 C19 1.521(5) . ?
C2 C3 1.394(5) . ?
C4 C3 1.375(5) . ?
C4 C5 1.388(5) . ?
C9 C7 1.536(5) . ?
C9 C10 1.544(5) . ?
C19 C14 1.525(5) . ?
C14 C13 1.523(5) . ?
C10 C12 1.522(5) . ?
C10 C11 1.531(5) . ?
P2 O6 1.483(2) . ?
P2 O5 1.587(3) . ?
P2 C28 1.802(4) . ?
P2 C29 1.852(4) . ?
O5 C40 1.477(4) . ?
O1 C29 1.431(4) . ?
C39 C38 1.527(5) . ?
C39 C40 1.529(5) . ?
C39 C42 1.544(5) . ?
C42 C43 1.527(5) . ?
C42 C44 1.538(5) . ?
C23 C24 1.394(5) . ?
C23 C28 1.399(5) . ?
C36 C35 1.521(5) . ?
C36 C37 1.523(5) . ?
C36 C41 1.536(5) . ?
C27 C26 1.396(5) . ?
C27 C28 1.396(5) . ?
C37 C38 1.521(5) . ?
C40 C41 1.520(5) . ?
C31 C29 1.533(5) . ?
C31 C32 1.533(5) . ?
C25 C24 1.373(6) . ?
C25 C26 1.380(6) . ?
C29 C30 1.519(5) . ?
C32 C34 1.507(5) . ?
C32 C33 1.509(5) . ?
O2 C7 1.434(4) . ?
C7 C8 1.524(4) . ?

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
O3 P1 O4 114.18(14) . . ?
O3 P1 C6 111.61(15) . . ?
O4 P1 C6 106.69(14) . . ?
O3 P1 C7 113.96(14) . . ?
O4 P1 C7 102.00(14) . . ?
C6 P1 C7 107.66(16) . . ?
C16 O4 P1 122.4(2) . . ?
C16 C15 C14 112.9(3) . . ?
C18 C17 C16 108.4(3) . . ?
C18 C17 C20 113.8(3) . . ?
C16 C17 C20 114.1(3) . . ?
O4 C16 C15 107.0(3) . . ?
O4 C16 C17 108.6(3) . . ?
C15 C16 C17 112.3(3) . . ?
C2 C1 C6 120.8(3) . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 P1 121.9(2) . . ?
C5 C6 P1 119.2(3) . . ?
C22 C20 C21 111.2(3) . . ?
C22 C20 C17 111.1(3) . . ?
C21 C20 C17 113.3(3) . . ?
C19 C18 C17 111.6(3) . . ?
C1 C2 C3 119.8(3) . . ?
C3 C4 C5 121.0(3) . . ?
C7 C9 C10 115.4(3) . . ?
C4 C5 C6 119.7(3) . . ?
C18 C19 C14 111.3(3) . . ?
C13 C14 C19 112.4(3) . . ?
C13 C14 C15 110.5(3) . . ?
C19 C14 C15 109.1(3) . . ?
C12 C10 C11 110.2(3) . . ?
C12 C10 C9 110.2(3) . . ?
C11 C10 C9 111.2(3) . . ?
C4 C3 C2 119.9(3) . . ?
O6 P2 O5 114.42(14) . . ?
O6 P2 C28 112.05(17) . . ?
O5 P2 C28 106.59(15) . . ?
O6 P2 C29 113.86(16) . . ?
O5 P2 C29 102.35(15) . . ?
C28 P2 C29 106.76(15) . . ?
C40 O5 P2 120.8(2) . . ?
C38 C39 C40 107.9(3) . . ?
C38 C39 C42 114.5(3) . . ?
C40 C39 C42 113.9(3) . . ?
C43 C42 C44 110.4(3) . . ?
C43 C42 C39 111.1(3) . . ?
C44 C42 C39 113.5(3) . . ?
C24 C23 C28 119.7(4) . . ?
C35 C36 C37 112.3(3) . . ?
C35 C36 C41 110.2(3) . . ?
C37 C36 C41 109.5(3) . . ?
C26 C27 C28 120.2(4) . . ?
C27 C28 C23 119.3(3) . . ?
C27 C28 P2 122.2(3) . . ?
C23 C28 P2 118.4(3) . . ?
C38 C37 C36 111.2(3) . . ?
O5 C40 C41 107.3(3) . . ?
O5 C40 C39 108.8(3) . . ?
C41 C40 C39 112.6(3) . . ?
C29 C31 C32 119.0(3) . . ?
C40 C41 C36 112.4(3) . . ?
C37 C38 C39 111.7(3) . . ?
C24 C25 C26 120.8(4) . . ?
O1 C29 C30 106.0(3) . . ?
O1 C29 C31 113.3(3) . . ?
C30 C29 C31 113.4(3) . . ?
O1 C29 P2 109.6(2) . . ?
C30 C29 P2 106.7(3) . . ?
C31 C29 P2 107.6(2) . . ?
C34 C32 C33 111.2(4) . . ?
C34 C32 C31 109.8(3) . . ?
C33 C32 C31 111.8(3) . . ?
C25 C26 C27 119.7(4) . . ?
C25 C24 C23 120.3(4) . . ?
O2 C7 C8 106.6(3) . . ?
O2 C7 C9 111.1(3) . . ?
C8 C7 C9 114.1(3) . . ?
O2 C7 P1 109.3(2) . . ?
C8 C7 P1 106.7(2) . . ?
C9 C7 P1 109.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 950077'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130123e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H33 N O5 P'
_chemical_formula_weight         446.48
_chemical_absolute_configuration ' unk '

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   5.8926(18)
_cell_length_b                   18.289(2)
_cell_length_c                   22.043
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2375.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9357
_exptl_absorpt_correction_T_max  0.9551
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17624
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0942
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         28.46
_reflns_number_total             5517
_reflns_number_gt                3477
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_number_reflns         5517
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_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 0.69080(15) 0.63878(4) 0.78982(4) 0.03028(19) Uani 1 1 d . . .
O2 O 0.4642(3) 0.60519(11) 0.78463(9) 0.0389(5) Uani 1 1 d . . .
O3 O 0.8384(4) 0.60935(11) 0.84404(8) 0.0339(5) Uani 1 1 d . . .
C10 C 0.6786(6) 0.73685(16) 0.79553(12) 0.0334(7) Uani 1 1 d . . .
O1 O 1.0851(4) 0.65688(12) 0.73273(10) 0.0443(6) Uani 1 1 d . . .
H1A H 1.1676 0.6335 0.7556 0.066 Uiso 1 1 calc R . .
C8 C 0.8805(5) 0.61832(17) 0.72360(14) 0.0332(8) Uani 1 1 d . . .
H8 H 0.783(6) 0.6281(17) 0.7586(15) 0.040 Uiso 1 1 calc . . .
O5 O 0.1766(5) 0.64052(18) 0.52524(12) 0.0885(10) Uani 1 1 d . . .
C2 C 0.4739(6) 0.64725(19) 0.59315(13) 0.0378(8) Uani 1 1 d . . .
C15 C 0.7405(6) 0.59771(19) 0.90518(14) 0.0373(8) Uani 1 1 d . . .
H15 H 0.577(6) 0.6075(16) 0.9040(13) 0.045 Uiso 1 1 calc . . .
C3 C 0.5769(6) 0.61589(17) 0.64265(13) 0.0361(8) Uani 1 1 d . . .
H3 H 0.5214 0.5724 0.6587 0.043 Uiso 1 1 calc R . .
C4 C 0.7649(5) 0.64974(17) 0.66848(12) 0.0315(7) Uani 1 1 d . . .
C9 C 0.4911(6) 0.77370(17) 0.77233(14) 0.0421(8) Uani 1 1 d . . .
H9 H 0.3713 0.7474 0.7556 0.050 Uiso 1 1 calc R . .
C11 C 0.8561(6) 0.77736(19) 0.81994(14) 0.0441(9) Uani 1 1 d . . .
H11 H 0.9840 0.7537 0.8350 0.053 Uiso 1 1 calc R . .
C5 C 0.8387(6) 0.71505(18) 0.64319(13) 0.0424(8) Uani 1 1 d . . .
H5 H 0.9625 0.7390 0.6603 0.051 Uiso 1 1 calc R . .
N1 N 0.2773(6) 0.60961(19) 0.56656(13) 0.0556(9) Uani 1 1 d . . .
O4 O 0.2195(5) 0.55079(17) 0.58730(11) 0.0705(8) Uani 1 1 d . . .
C20 C 0.7801(7) 0.51886(19) 0.92402(15) 0.0439(9) Uani 1 1 d . . .
H20 H 0.945(6) 0.5112(17) 0.9235(14) 0.053 Uiso 1 1 calc . . .
C12 C 0.8429(7) 0.8532(2) 0.82195(17) 0.0594(10) Uani 1 1 d . . .
H12 H 0.9606 0.8802 0.8390 0.071 Uiso 1 1 calc R . .
C17 C 0.7756(8) 0.6414(3) 1.01335(15) 0.0593(11) Uani 1 1 d . . .
H17 H 0.612(7) 0.650(2) 1.0148(15) 0.071 Uiso 1 1 calc . . .
C14 C 0.4822(6) 0.84931(19) 0.77400(16) 0.0544(10) Uani 1 1 d . . .
H14 H 0.3570 0.8737 0.7582 0.065 Uiso 1 1 calc R . .
C6 C 0.7326(6) 0.74551(18) 0.59314(14) 0.0519(10) Uani 1 1 d . . .
H6 H 0.7857 0.7891 0.5768 0.062 Uiso 1 1 calc R . .
C22 C 0.6776(7) 0.4621(2) 0.88052(17) 0.0505(9) Uani 1 1 d . . .
H22 H 0.724(6) 0.4759(18) 0.8394(14) 0.061 Uiso 1 1 calc . . .
C13 C 0.6568(7) 0.88822(19) 0.79886(18) 0.0638(11) Uani 1 1 d . . .
H13 H 0.6491 0.9390 0.8001 0.077 Uiso 1 1 calc R . .
C7 C 0.9170(6) 0.53592(17) 0.72058(15) 0.0454(9) Uani 1 1 d . . .
H7A H 1.0026 0.5241 0.6848 0.068 Uiso 1 1 calc R . .
H7B H 0.7726 0.5117 0.7191 0.068 Uiso 1 1 calc R . .
H7C H 0.9988 0.5201 0.7559 0.068 Uiso 1 1 calc R . .
C16 C 0.8536(7) 0.6515(2) 0.94765(13) 0.0493(10) Uani 1 1 d . . .
H16A H 0.8187 0.7009 0.9346 0.059 Uiso 1 1 calc R . .
H16B H 1.0168 0.6452 0.9455 0.059 Uiso 1 1 calc R . .
C1 C 0.5478(6) 0.71080(19) 0.56770(14) 0.0469(9) Uani 1 1 d . . .
H1 H 0.4753 0.7304 0.5339 0.056 Uiso 1 1 calc R . .
C18 C 0.8165(9) 0.5631(2) 1.03226(15) 0.0720(13) Uani 1 1 d . . .
H18A H 0.9785 0.5538 1.0330 0.086 Uiso 1 1 calc R . .
H18B H 0.7583 0.5558 1.0730 0.086 Uiso 1 1 calc R . .
C19 C 0.7042(8) 0.5097(2) 0.98992(15) 0.0632(12) Uani 1 1 d . . .
H19A H 0.5410 0.5161 0.9922 0.076 Uiso 1 1 calc R . .
H19B H 0.7388 0.4603 1.0031 0.076 Uiso 1 1 calc R . .
C23 C 0.7749(8) 0.3854(2) 0.8928(2) 0.0811(14) Uani 1 1 d . . .
H23A H 0.9375 0.3871 0.8907 0.122 Uiso 1 1 calc R . .
H23B H 0.7184 0.3518 0.8630 0.122 Uiso 1 1 calc R . .
H23C H 0.7294 0.3695 0.9325 0.122 Uiso 1 1 calc R . .
C21 C 0.8904(9) 0.6974(3) 1.05468(17) 0.0901(17) Uani 1 1 d . . .
H21A H 0.8393 0.6904 1.0956 0.135 Uiso 1 1 calc R . .
H21B H 0.8521 0.7458 1.0415 0.135 Uiso 1 1 calc R . .
H21C H 1.0520 0.6910 1.0529 0.135 Uiso 1 1 calc R . .
C24 C 0.4186(7) 0.4598(2) 0.88105(17) 0.0652(12) Uani 1 1 d . . .
H24A H 0.3667 0.4445 0.9203 0.098 Uiso 1 1 calc R . .
H24B H 0.3662 0.4260 0.8509 0.098 Uiso 1 1 calc R . .
H24C H 0.3600 0.5077 0.8723 0.098 Uiso 1 1 calc R . .


_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 O2 1.474(2) . ?
P1 O3 1.573(2) . ?
P1 C10 1.800(3) . ?
P1 C8 1.876(3) . ?
O3 C15 1.481(4) . ?
C10 C11 1.390(4) . ?
C10 C9 1.391(4) . ?
O1 C8 1.411(4) . ?
C8 C4 1.507(4) . ?
C8 C7 1.524(4) . ?
O5 N1 1.225(4) . ?
C2 C1 1.362(5) . ?
C2 C3 1.374(4) . ?
C2 N1 1.469(4) . ?
C15 C16 1.513(4) . ?
C15 C20 1.519(5) . ?
C3 C4 1.391(4) . ?
C4 C5 1.388(4) . ?
C9 C14 1.384(4) . ?
C11 C12 1.390(5) . ?
C5 C6 1.385(4) . ?
N1 O4 1.218(4) . ?
C20 C19 1.529(5) . ?
C20 C22 1.537(5) . ?
C12 C13 1.368(5) . ?
C17 C18 1.511(6) . ?
C17 C21 1.528(6) . ?
C17 C16 1.531(5) . ?
C14 C13 1.366(5) . ?
C6 C1 1.380(5) . ?
C22 C24 1.527(5) . ?
C22 C23 1.539(5) . ?
C18 C19 1.505(5) . ?

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
O2 P1 O3 114.65(12) . . ?
O2 P1 C10 112.62(15) . . ?
O3 P1 C10 108.06(13) . . ?
O2 P1 C8 113.33(13) . . ?
O3 P1 C8 101.16(12) . . ?
C10 P1 C8 106.08(14) . . ?
C15 O3 P1 121.68(19) . . ?
C11 C10 C9 118.8(3) . . ?
C11 C10 P1 121.9(3) . . ?
C9 C10 P1 119.3(2) . . ?
O1 C8 C4 108.1(2) . . ?
O1 C8 C7 112.3(3) . . ?
C4 C8 C7 113.9(3) . . ?
O1 C8 P1 107.4(2) . . ?
C4 C8 P1 106.4(2) . . ?
C7 C8 P1 108.4(2) . . ?
C1 C2 C3 122.8(3) . . ?
C1 C2 N1 119.2(3) . . ?
C3 C2 N1 118.0(3) . . ?
O3 C15 C16 107.3(3) . . ?
O3 C15 C20 109.0(3) . . ?
C16 C15 C20 112.4(3) . . ?
C2 C3 C4 119.4(3) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C8 120.7(3) . . ?
C3 C4 C8 121.4(3) . . ?
C14 C9 C10 120.3(3) . . ?
C12 C11 C10 120.1(3) . . ?
C6 C5 C4 121.6(3) . . ?
O4 N1 O5 123.4(3) . . ?
O4 N1 C2 119.0(3) . . ?
O5 N1 C2 117.5(3) . . ?
C15 C20 C19 108.6(3) . . ?
C15 C20 C22 114.2(3) . . ?
C19 C20 C22 113.8(3) . . ?
C13 C12 C11 120.0(4) . . ?
C18 C17 C21 113.5(4) . . ?
C18 C17 C16 109.1(3) . . ?
C21 C17 C16 110.5(4) . . ?
C13 C14 C9 120.2(4) . . ?
C1 C6 C5 119.7(3) . . ?
C24 C22 C20 114.0(3) . . ?
C24 C22 C23 110.3(3) . . ?
C20 C22 C23 111.1(3) . . ?
C14 C13 C12 120.6(4) . . ?
C15 C16 C17 112.0(3) . . ?
C2 C1 C6 118.5(3) . . ?
C19 C18 C17 112.0(3) . . ?
C18 C19 C20 112.9(3) . . ?

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
O2 P1 O3 C15 -43.5(3) . . . . ?
C10 P1 O3 C15 83.0(2) . . . . ?
C8 P1 O3 C15 -165.8(2) . . . . ?
O2 P1 C10 C11 158.7(2) . . . . ?
O3 P1 C10 C11 31.1(3) . . . . ?
C8 P1 C10 C11 -76.7(3) . . . . ?
O2 P1 C10 C9 -24.3(3) . . . . ?
O3 P1 C10 C9 -152.0(2) . . . . ?
C8 P1 C10 C9 100.2(3) . . . . ?
O2 P1 C8 O1 176.71(18) . . . . ?
O3 P1 C8 O1 -60.0(2) . . . . ?
C10 P1 C8 O1 52.6(2) . . . . ?
O2 P1 C8 C4 61.2(2) . . . . ?
O3 P1 C8 C4 -175.6(2) . . . . ?
C10 P1 C8 C4 -62.9(2) . . . . ?
O2 P1 C8 C7 -61.7(2) . . . . ?
O3 P1 C8 C7 61.5(2) . . . . ?
C10 P1 C8 C7 174.2(2) . . . . ?
P1 O3 C15 C16 -114.3(3) . . . . ?
P1 O3 C15 C20 123.7(2) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
N1 C2 C3 C4 179.3(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 C8 178.7(3) . . . . ?
O1 C8 C4 C5 -12.2(4) . . . . ?
C7 C8 C4 C5 -137.8(3) . . . . ?
P1 C8 C4 C5 102.9(3) . . . . ?
O1 C8 C4 C3 170.1(3) . . . . ?
C7 C8 C4 C3 44.5(4) . . . . ?
P1 C8 C4 C3 -74.9(3) . . . . ?
C11 C10 C9 C14 -0.4(5) . . . . ?
P1 C10 C9 C14 -177.4(3) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
P1 C10 C11 C12 178.1(3) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C8 C4 C5 C6 -178.9(3) . . . . ?
C1 C2 N1 O4 176.0(3) . . . . ?
C3 C2 N1 O4 -3.4(5) . . . . ?
C1 C2 N1 O5 -5.8(5) . . . . ?
C3 C2 N1 O5 174.9(3) . . . . ?
O3 C15 C20 C19 173.3(3) . . . . ?
C16 C15 C20 C19 54.5(4) . . . . ?
O3 C15 C20 C22 -58.5(4) . . . . ?
C16 C15 C20 C22 -177.3(3) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
C10 C9 C14 C13 -0.5(5) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C15 C20 C22 C24 -69.4(4) . . . . ?
C19 C20 C22 C24 56.1(4) . . . . ?
C15 C20 C22 C23 165.3(3) . . . . ?
C19 C20 C22 C23 -69.2(4) . . . . ?
C9 C14 C13 C12 0.5(6) . . . . ?
C11 C12 C13 C14 0.4(6) . . . . ?
O3 C15 C16 C17 -176.6(3) . . . . ?
C20 C15 C16 C17 -56.8(4) . . . . ?
C18 C17 C16 C15 55.3(5) . . . . ?
C21 C17 C16 C15 -179.1(4) . . . . ?
C3 C2 C1 C6 -0.7(5) . . . . ?
N1 C2 C1 C6 -180.0(3) . . . . ?
C5 C6 C1 C2 0.4(5) . . . . ?
C21 C17 C18 C19 -179.0(4) . . . . ?
C16 C17 C18 C19 -55.3(5) . . . . ?
C17 C18 C19 C20 57.0(5) . . . . ?
C15 C20 C19 C18 -54.8(5) . . . . ?
C22 C20 C19 C18 176.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 950078'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130319g

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Br O3 P'
_chemical_formula_weight         423.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   10.4511(12)
_cell_length_b                   19.5742(6)
_cell_length_c                   11.0005(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.362(2)
_cell_angle_gamma                90.00
_cell_volume                     1998.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    2.152
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.4126
_exptl_absorpt_correction_T_max  0.6728
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7242
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_sigmaI/netI    0.0983
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3373
_reflns_number_gt                1757
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1051P)²+5.1791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3373
_refine_ls_number_parameters     228
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2117
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.003

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
Br1 Br 0.10301(18) 1.13010(6) 0.32801(14) 0.1022(7) Uani 1 1 d . . .
P1 P 0.0192(3) 0.77182(10) 0.2492(2) 0.0414(6) Uani 1 1 d U . .
O1 O 0.0876(7) 0.7664(3) 0.3992(5) 0.0504(15) Uani 1 1 d . . .
O2 O -0.0634(7) 0.7056(3) 0.1700(5) 0.0491(14) Uani 1 1 d U . .
O3 O -0.1973(7) 0.8284(3) 0.0319(5) 0.0516(16) Uani 1 1 d . . .
H3 H -0.2579 0.7980 0.0087 0.077 Uiso 1 1 calc R . .
C3 C -0.0661(10) 0.9072(4) 0.2141(8) 0.0426(16) Uani 1 1 d U . .
C2 C -0.1279(9) 0.8346(4) 0.1772(8) 0.0419(18) Uani 1 1 d U . .
C9 C 0.1474(10) 0.7900(4) 0.1895(9) 0.0493(18) Uani 1 1 d U . .
C15 C -0.0218(14) 0.6383(5) 0.2297(12) 0.076(2) Uani 1 1 d U . .
H15 H 0.0678 0.6419 0.3156 0.091 Uiso 1 1 calc R . .
C14 C 0.2865(10) 0.8069(5) 0.2815(10) 0.0590(19) Uani 1 1 d U . .
H14 H 0.3109 0.8105 0.3739 0.071 Uiso 1 1 calc R . .
C8 C 0.0123(11) 0.9264(4) 0.3487(9) 0.0567(19) Uani 1 1 d U . .
H8 H 0.0310 0.8950 0.4183 0.068 Uiso 1 1 calc R . .
C18 C -0.0605(18) 0.4937(7) 0.2353(17) 0.122(3) Uani 1 1 d U . .
H18A H -0.0249 0.4509 0.2835 0.146 Uiso 1 1 calc R . .
H18B H -0.1475 0.4839 0.1516 0.146 Uiso 1 1 calc R . .
C1 C -0.2359(10) 0.8206(5) 0.2335(10) 0.056(2) Uani 1 1 d U . .
H1A H -0.3133 0.8530 0.1954 0.085 Uiso 1 1 calc R . .
H1B H -0.1878 0.8249 0.3314 0.085 Uiso 1 1 calc R . .
H1C H -0.2737 0.7752 0.2088 0.085 Uiso 1 1 calc R . .
C6 C 0.0371(12) 1.0388(4) 0.2803(10) 0.060(2) Uani 1 1 d U . .
C13 C 0.3913(12) 0.8188(5) 0.2397(11) 0.070(2) Uani 1 1 d U . .
H13 H 0.4852 0.8295 0.3033 0.084 Uiso 1 1 calc R . .
C4 C -0.0897(11) 0.9542(4) 0.1146(9) 0.0547(19) Uani 1 1 d U . .
H4 H -0.1405 0.9412 0.0233 0.066 Uiso 1 1 calc R . .
C10 C 0.1111(11) 0.7872(5) 0.0499(10) 0.0591(19) Uani 1 1 d U . .
H10 H 0.0174 0.7772 -0.0152 0.071 Uiso 1 1 calc R . .
C7 C 0.0631(12) 0.9924(5) 0.3802(10) 0.064(2) Uani 1 1 d U . .
H7 H 0.1160 1.0052 0.4714 0.077 Uiso 1 1 calc R . .
C5 C -0.0408(11) 1.0199(4) 0.1451(10) 0.063(2) Uani 1 1 d U . .
H5 H -0.0598 1.0514 0.0755 0.075 Uiso 1 1 calc R . .
C11 C 0.2184(12) 0.7997(5) 0.0111(11) 0.067(2) Uani 1 1 d U . .
H11 H 0.1952 0.7977 -0.0812 0.081 Uiso 1 1 calc R . .
C12 C 0.3541(12) 0.8146(5) 0.1028(11) 0.069(2) Uani 1 1 d U . .
H12 H 0.4235 0.8220 0.0735 0.083 Uiso 1 1 calc R . .
C16 C -0.1338(17) 0.6121(6) 0.2585(15) 0.103(3) Uani 1 1 d U . .
H16A H -0.2245 0.6114 0.1751 0.124 Uiso 1 1 calc R . .
H16B H -0.1448 0.6415 0.3240 0.124 Uiso 1 1 calc R . .
C20 C 0.0011(16) 0.5933(6) 0.1380(14) 0.099(3) Uani 1 1 d U . .
H20A H 0.0781 0.6110 0.1210 0.119 Uiso 1 1 calc R . .
H20B H -0.0857 0.5909 0.0513 0.119 Uiso 1 1 calc R . .
C19 C 0.0415(18) 0.5206(6) 0.2020(16) 0.114(3) Uani 1 1 d U . .
H19A H 0.0526 0.4903 0.1376 0.137 Uiso 1 1 calc R . .
H19B H 0.1334 0.5228 0.2839 0.137 Uiso 1 1 calc R . .
C17 C -0.0950(18) 0.5381(7) 0.3180(16) 0.119(3) Uani 1 1 d U . .
H17A H -0.0135 0.5403 0.4086 0.143 Uiso 1 1 calc R . .
H17B H -0.1759 0.5193 0.3272 0.143 Uiso 1 1 calc R . .


_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
Br1 C6 1.900(9) . ?
P1 O1 1.470(6) . ?
P1 O2 1.579(6) . ?
P1 C9 1.778(9) . ?
P1 C2 1.838(8) . ?
O2 C15 1.447(11) . ?
O3 C2 1.424(9) . ?
O3 H3 0.8200 . ?
C3 C4 1.363(11) . ?
C3 C8 1.374(12) . ?
C3 C2 1.538(11) . ?
C2 C1 1.541(11) . ?
C9 C14 1.377(13) . ?
C9 C10 1.404(12) . ?
C15 C20 1.439(14) . ?
C15 C16 1.441(17) . ?
C15 H15 0.9800 . ?
C14 C13 1.389(13) . ?
C14 H14 0.9300 . ?
C8 C7 1.378(12) . ?
C8 H8 0.9300 . ?
C18 C19 1.381(18) . ?
C18 C17 1.420(17) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 C7 1.353(12) . ?
C6 C5 1.379(13) . ?
C13 C12 1.374(14) . ?
C13 H13 0.9300 . ?
C4 C5 1.368(11) . ?
C4 H4 0.9300 . ?
C10 C11 1.393(13) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C11 C12 1.341(14) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C16 C17 1.563(16) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C20 C19 1.558(16) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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 O2 114.8(3) . . ?
O1 P1 C9 111.7(4) . . ?
O2 P1 C9 105.9(4) . . ?
O1 P1 C2 114.3(3) . . ?
O2 P1 C2 100.0(4) . . ?
C9 P1 C2 109.3(4) . . ?
C15 O2 P1 121.5(7) . . ?
C2 O3 H3 109.5 . . ?
C4 C3 C8 118.6(8) . . ?
C4 C3 C2 120.8(7) . . ?
C8 C3 C2 120.5(7) . . ?
O3 C2 C3 108.1(6) . . ?
O3 C2 C1 110.3(8) . . ?
C3 C2 C1 110.7(6) . . ?
O3 C2 P1 108.7(5) . . ?
C3 C2 P1 109.7(6) . . ?
C1 C2 P1 109.3(6) . . ?
C14 C9 C10 118.5(9) . . ?
C14 C9 P1 119.8(7) . . ?
C10 C9 P1 121.7(8) . . ?
C20 C15 C16 110.5(11) . . ?
C20 C15 O2 110.5(8) . . ?
C16 C15 O2 108.6(10) . . ?
C20 C15 H15 109.1 . . ?
C16 C15 H15 109.1 . . ?
O2 C15 H15 109.1 . . ?
C9 C14 C13 121.6(9) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C3 C8 C7 119.8(8) . . ?
C3 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C19 C18 C17 113.0(14) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C6 C5 119.7(8) . . ?
C7 C6 Br1 119.7(7) . . ?
C5 C6 Br1 120.6(7) . . ?
C12 C13 C14 119.0(11) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C3 C4 C5 121.9(9) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C11 C10 C9 118.5(10) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C6 C7 C8 121.0(9) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C4 C5 C6 119.0(9) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C12 C11 C10 122.0(10) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.4(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C15 C16 C17 110.0(12) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C15 C20 C19 109.9(10) . . ?
C15 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
C15 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C18 C19 C20 112.7(13) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C18 C17 C16 113.1(12) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 950079'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130404h

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 O3 P'
_chemical_formula_weight         475.56
_chemical_absolute_configuration ' unk '

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2   '

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

_cell_length_a                   24.450(4)
_cell_length_b                   5.8577(7)
_cell_length_c                   20.328(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.063(17)
_cell_angle_gamma                90.00
_cell_volume                     2658.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1020
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8280
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.1546
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4237
_reflns_number_gt                2403
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0230P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_number_reflns         4237
_refine_ls_number_parameters     312
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_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 0.61315(7) 0.2107(3) 0.73801(8) 0.0341(4) Uani 1 1 d . . .
O3 O 0.59543(19) -0.1678(7) 0.6562(2) 0.0425(11) Uani 1 1 d . . .
H3 H 0.5897 -0.2396 0.6874 0.064 Uiso 1 1 calc R . .
O1 O 0.59650(17) 0.4548(7) 0.7370(2) 0.0449(11) Uani 1 1 d . . .
O2 O 0.59782(15) 0.0578(6) 0.79243(19) 0.0338(10) Uani 1 1 d . . .
C1 C 0.6916(2) 0.1785(11) 0.7604(3) 0.0342(15) Uani 1 1 d . . .
C7 C 0.5724(2) 0.0593(10) 0.6521(3) 0.0339(15) Uani 1 1 d . . .
C15 C 0.3205(2) 0.1113(10) 0.6036(3) 0.0365(16) Uani 1 1 d . . .
C12 C 0.3839(2) 0.0959(11) 0.6146(3) 0.0367(16) Uani 1 1 d . . .
C9 C 0.5058(2) 0.0654(10) 0.6358(3) 0.0307(14) Uani 1 1 d . . .
C17 C 0.2208(3) -0.0474(11) 0.5629(3) 0.0461(18) Uani 1 1 d . . .
H17 H 0.1945 -0.1668 0.5413 0.055 Uiso 1 1 calc R . .
C2 C 0.7230(2) -0.0195(10) 0.7923(3) 0.0387(16) Uani 1 1 d . . .
H2 H 0.7030 -0.1394 0.8029 0.046 Uiso 1 1 calc R . .
C14 C 0.4763(3) -0.1167(10) 0.6507(3) 0.0415(17) Uani 1 1 d . . .
H14 H 0.4972 -0.2513 0.6689 0.050 Uiso 1 1 calc R . .
C5 C 0.7821(3) 0.3336(13) 0.7593(3) 0.0540(19) Uani 1 1 d . . .
H5 H 0.8018 0.4524 0.7475 0.065 Uiso 1 1 calc R . .
C6 C 0.7217(2) 0.3538(11) 0.7442(3) 0.0405(16) Uani 1 1 d . . .
H6 H 0.7013 0.4867 0.7231 0.049 Uiso 1 1 calc R . .
C11 C 0.4128(2) 0.2779(9) 0.5991(3) 0.0413(17) Uani 1 1 d . . .
H11 H 0.3917 0.4121 0.5809 0.050 Uiso 1 1 calc R . .
C10 C 0.4728(2) 0.2646(9) 0.6101(3) 0.0383(17) Uani 1 1 d . . .
H10 H 0.4911 0.3909 0.6000 0.046 Uiso 1 1 calc R . .
C8 C 0.5863(2) 0.1744(11) 0.5929(3) 0.0465(17) Uani 1 1 d . . .
H8A H 0.5623 0.1063 0.5472 0.070 Uiso 1 1 calc R . .
H8B H 0.6280 0.1544 0.6030 0.070 Uiso 1 1 calc R . .
H8C H 0.5774 0.3344 0.5914 0.070 Uiso 1 1 calc R . .
C13 C 0.4168(3) -0.1025(10) 0.6392(3) 0.0416(17) Uani 1 1 d . . .
H13 H 0.3982 -0.2298 0.6482 0.050 Uiso 1 1 calc R . .
C22 C 0.4932(2) 0.2293(11) 0.8151(3) 0.0457(17) Uani 1 1 d . . .
H22 H 0.4926 0.1874 0.7682 0.055 Uiso 1 1 calc R . .
C18 C 0.2004(3) 0.1454(12) 0.5848(3) 0.051(2) Uani 1 1 d . . .
H18 H 0.1604 0.1571 0.5778 0.061 Uiso 1 1 calc R . .
C24 C 0.5467(2) 0.1107(10) 0.8713(3) 0.0376(16) Uani 1 1 d . . .
H24 H 0.5372 -0.0526 0.8659 0.045 Uiso 1 1 calc R . .
C16 C 0.2799(2) -0.0643(10) 0.5728(3) 0.0399(16) Uani 1 1 d . . .
H16 H 0.2930 -0.1968 0.5585 0.048 Uiso 1 1 calc R . .
C3 C 0.7841(3) -0.0396(12) 0.8087(3) 0.0535(19) Uani 1 1 d . . .
H3A H 0.8051 -0.1705 0.8308 0.064 Uiso 1 1 calc R . .
C19 C 0.2400(3) 0.3206(12) 0.6173(3) 0.0511(18) Uani 1 1 d . . .
H19 H 0.2270 0.4495 0.6334 0.061 Uiso 1 1 calc R . .
C20 C 0.2993(3) 0.3057(11) 0.6260(3) 0.0464(18) Uani 1 1 d . . .
H20 H 0.3254 0.4263 0.6471 0.056 Uiso 1 1 calc R . .
C25 C 0.6056(2) 0.1356(10) 0.8634(3) 0.0394(16) Uani 1 1 d . . .
H25 H 0.6166 0.2976 0.8680 0.047 Uiso 1 1 calc R . .
C4 C 0.8131(3) 0.1420(13) 0.7911(4) 0.058(2) Uani 1 1 d . . .
H4 H 0.8537 0.1313 0.8012 0.070 Uiso 1 1 calc R . .
C26 C 0.6559(3) 0.0040(11) 0.9188(3) 0.0450(17) Uani 1 1 d . . .
H26A H 0.6925 0.0333 0.9123 0.054 Uiso 1 1 calc R . .
H26B H 0.6473 -0.1579 0.9113 0.054 Uiso 1 1 calc R . .
C28 C 0.6086(3) 0.0359(14) 1.0047(3) 0.068(2) Uani 1 1 d . . .
H28A H 0.6143 0.0848 1.0527 0.082 Uiso 1 1 calc R . .
H28B H 0.5981 -0.1248 1.0001 0.082 Uiso 1 1 calc R . .
C29 C 0.5573(3) 0.1710(14) 0.9493(3) 0.069(2) Uani 1 1 d . . .
H29A H 0.5660 0.3328 0.9571 0.083 Uiso 1 1 calc R . .
H29B H 0.5209 0.1410 0.9561 0.083 Uiso 1 1 calc R . .
C27 C 0.6659(3) 0.0662(14) 0.9959(3) 0.061(2) Uani 1 1 d . . .
H27 H 0.6772 0.2276 1.0037 0.073 Uiso 1 1 calc R . .
C23 C 0.4337(3) 0.1485(12) 0.8152(4) 0.072(2) Uani 1 1 d . . .
H23A H 0.4306 0.2002 0.8584 0.107 Uiso 1 1 calc R . .
H23B H 0.4321 -0.0152 0.8134 0.107 Uiso 1 1 calc R . .
H23C H 0.4012 0.2099 0.7740 0.107 Uiso 1 1 calc R . .
C21 C 0.4964(3) 0.4911(11) 0.8195(4) 0.071(2) Uani 1 1 d . . .
H21A H 0.5343 0.5414 0.8210 0.106 Uiso 1 1 calc R . .
H21B H 0.4922 0.5408 0.8622 0.106 Uiso 1 1 calc R . .
H21C H 0.4646 0.5547 0.7779 0.106 Uiso 1 1 calc R . .
C30 C 0.7177(3) -0.0768(15) 1.0505(3) 0.097(3) Uani 1 1 d . . .
H30A H 0.7083 -0.2362 1.0422 0.146 Uiso 1 1 calc R . .
H30B H 0.7229 -0.0379 1.0986 0.146 Uiso 1 1 calc R . .
H30C H 0.7539 -0.0450 1.0446 0.146 Uiso 1 1 calc R . .


_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 1.484(4) . ?
P1 O2 1.583(4) . ?
P1 C1 1.791(5) . ?
P1 C7 1.846(6) . ?
O3 C7 1.434(6) . ?
O2 C25 1.450(6) . ?
C1 C6 1.379(7) . ?
C1 C2 1.396(7) . ?
C7 C9 1.524(7) . ?
C7 C8 1.535(7) . ?
C15 C16 1.387(7) . ?
C15 C20 1.402(8) . ?
C15 C12 1.476(7) . ?
C12 C13 1.385(7) . ?
C12 C11 1.386(7) . ?
C9 C14 1.388(7) . ?
C9 C10 1.394(7) . ?
C17 C16 1.379(7) . ?
C17 C18 1.381(8) . ?
C2 C3 1.398(7) . ?
C14 C13 1.379(7) . ?
C5 C4 1.361(9) . ?
C5 C6 1.386(7) . ?
C11 C10 1.392(7) . ?
C22 C24 1.509(7) . ?
C22 C23 1.530(7) . ?
C22 C21 1.536(8) . ?
C18 C19 1.382(8) . ?
C24 C25 1.520(7) . ?
C24 C29 1.540(7) . ?
C3 C4 1.404(9) . ?
C19 C20 1.390(7) . ?
C25 C26 1.498(7) . ?
C26 C27 1.529(7) . ?
C28 C27 1.494(7) . ?
C28 C29 1.522(8) . ?
C27 C30 1.546(8) . ?

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 O2 114.4(2) . . ?
O1 P1 C1 111.4(3) . . ?
O2 P1 C1 107.3(2) . . ?
O1 P1 C7 114.2(3) . . ?
O2 P1 C7 101.5(2) . . ?
C1 P1 C7 107.4(2) . . ?
C25 O2 P1 123.0(3) . . ?
C6 C1 C2 118.9(5) . . ?
C6 C1 P1 118.8(5) . . ?
C2 C1 P1 122.3(4) . . ?
O3 C7 C9 113.2(5) . . ?
O3 C7 C8 104.1(4) . . ?
C9 C7 C8 112.2(5) . . ?
O3 C7 P1 110.1(4) . . ?
C9 C7 P1 108.2(4) . . ?
C8 C7 P1 108.9(4) . . ?
C16 C15 C20 117.3(5) . . ?
C16 C15 C12 122.4(5) . . ?
C20 C15 C12 120.2(5) . . ?
C13 C12 C11 116.9(5) . . ?
C13 C12 C15 121.7(5) . . ?
C11 C12 C15 121.4(5) . . ?
C14 C9 C10 116.9(5) . . ?
C14 C9 C7 122.5(5) . . ?
C10 C9 C7 120.3(5) . . ?
C16 C17 C18 120.5(6) . . ?
C1 C2 C3 120.8(6) . . ?
C13 C14 C9 121.5(5) . . ?
C4 C5 C6 120.8(7) . . ?
C1 C6 C5 120.6(6) . . ?
C12 C11 C10 121.5(5) . . ?
C11 C10 C9 121.2(5) . . ?
C14 C13 C12 122.0(5) . . ?
C24 C22 C23 112.8(5) . . ?
C24 C22 C21 114.1(6) . . ?
C23 C22 C21 109.5(6) . . ?
C17 C18 C19 119.1(6) . . ?
C22 C24 C25 116.2(5) . . ?
C22 C24 C29 113.8(5) . . ?
C25 C24 C29 108.6(4) . . ?
C17 C16 C15 121.7(6) . . ?
C2 C3 C4 118.5(6) . . ?
C18 C19 C20 120.5(6) . . ?
C19 C20 C15 120.9(6) . . ?
O2 C25 C26 108.7(4) . . ?
O2 C25 C24 109.2(4) . . ?
C26 C25 C24 113.2(5) . . ?
C5 C4 C3 120.3(6) . . ?
C25 C26 C27 112.7(5) . . ?
C27 C28 C29 112.3(6) . . ?
C28 C29 C24 112.6(5) . . ?
C28 C27 C26 109.3(5) . . ?
C28 C27 C30 112.5(6) . . ?
C26 C27 C30 110.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 950080'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130501f

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Br O3 P'
_chemical_formula_weight         397.24

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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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)/c

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

_cell_length_a                   15.6312(13)
_cell_length_b                   5.9562(4)
_cell_length_c                   19.6323(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.0060(10)
_cell_angle_gamma                90.00
_cell_volume                     1826.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.349
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.3863
_exptl_absorpt_correction_T_max  0.6909
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            8535
_diffrn_reflns_av_R_equivalents  0.1362
_diffrn_reflns_av_sigmaI/netI    0.2253
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3197
_reflns_number_gt                1554
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1008P)²+100.1347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3197
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2615
_refine_ls_R_factor_gt           0.1842
_refine_ls_wR_factor_ref         0.4999
_refine_ls_wR_factor_gt          0.4463
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.88659(19) 0.2379(5) 0.51219(14) 0.0655(11) Uani 1 1 d . . .
P1 P 0.7049(3) 0.6038(10) 0.2006(3) 0.0351(14) Uani 1 1 d . . .
O1 O 0.6662(10) 0.372(3) 0.2017(7) 0.045(4) Uani 1 1 d . . .
O2 O 0.6623(9) 0.789(2) 0.1522(8) 0.043(4) Uani 1 1 d . . .
O3 O 0.7314(11) 0.976(3) 0.2730(9) 0.053(4) Uani 1 1 d . . .
H3 H 0.7824 0.9693 0.2841 0.080 Uiso 1 1 calc R . .
C10 C 0.6208(14) 0.756(4) 0.0839(10) 0.041(5) Uani 1 1 d . . .
C16 C 0.8272(15) 0.403(4) 0.4407(11) 0.042(5) Uani 1 1 d . . .
C13 C 0.7410(14) 0.639(4) 0.3364(10) 0.037(5) Uani 1 1 d . . .
C14 C 0.8147(16) 0.721(4) 0.3666(16) 0.062(7) Uani 1 1 d . . .
H14 H 0.8377 0.8546 0.3507 0.074 Uiso 1 1 calc R . .
C11 C 0.5990(15) 0.784(5) 0.2956(16) 0.070(8) Uani 1 1 d . . .
H11A H 0.5925 0.8689 0.3366 0.105 Uiso 1 1 calc R . .
H11B H 0.5738 0.6382 0.3007 0.105 Uiso 1 1 calc R . .
H11C H 0.5710 0.8608 0.2581 0.105 Uiso 1 1 calc R . .
C1 C 0.8118(14) 0.600(3) 0.1842(11) 0.039(5) Uani 1 1 d . . .
C6 C 0.8528(14) 0.782(4) 0.1503(11) 0.041(5) Uani 1 1 d . . .
H6 H 0.8204 0.9039 0.1352 0.049 Uiso 1 1 calc R . .
C3 C 0.9557(18) 0.418(5) 0.1944(16) 0.071(9) Uani 1 1 d . . .
H3A H 0.9907 0.3030 0.2115 0.085 Uiso 1 1 calc R . .
C18 C 0.7133(14) 0.430(4) 0.3604(11) 0.041(5) Uani 1 1 d . . .
H18 H 0.6641 0.3669 0.3406 0.050 Uiso 1 1 calc R . .
C5 C 0.9382(15) 0.778(4) 0.1398(13) 0.055(6) Uani 1 1 d . . .
H5 H 0.9632 0.9025 0.1199 0.066 Uiso 1 1 calc R . .
C2 C 0.8685(15) 0.418(4) 0.2042(10) 0.045(6) Uani 1 1 d . . .
H2 H 0.8448 0.2926 0.2248 0.054 Uiso 1 1 calc R . .
C12 C 0.6929(14) 0.759(4) 0.2820(13) 0.049(6) Uani 1 1 d . . .
C15 C 0.8570(14) 0.607(5) 0.4224(12) 0.050(6) Uani 1 1 d . . .
H15 H 0.9039 0.6710 0.4455 0.059 Uiso 1 1 calc R . .
C17 C 0.7550(15) 0.317(4) 0.4112(11) 0.044(6) Uani 1 1 d . . .
H17 H 0.7340 0.1800 0.4259 0.052 Uiso 1 1 calc R . .
C9 C 0.5358(14) 0.659(5) 0.0910(13) 0.055(7) Uani 1 1 d . . .
H9A H 0.5014 0.7591 0.1170 0.082 Uiso 1 1 calc R . .
H9B H 0.5408 0.5173 0.1140 0.082 Uiso 1 1 calc R . .
H9C H 0.5092 0.6376 0.0467 0.082 Uiso 1 1 calc R . .
C7 C 0.6750(19) 0.614(5) 0.0393(17) 0.077(9) Uani 1 1 d . . .
H7A H 0.6629 0.4583 0.0471 0.116 Uiso 1 1 calc R . .
H7B H 0.7344 0.6429 0.0499 0.116 Uiso 1 1 calc R . .
H7C H 0.6624 0.6499 -0.0077 0.116 Uiso 1 1 calc R . .
C4 C 0.9893(16) 0.596(5) 0.1577(14) 0.060(7) Uani 1 1 d . . .
H4 H 1.0462 0.5933 0.1453 0.072 Uiso 1 1 calc R . .
C8 C 0.6166(18) 1.000(5) 0.0572(15) 0.065(7) Uani 1 1 d . . .
H8A H 0.6736 1.0545 0.0512 0.097 Uiso 1 1 calc R . .
H8B H 0.5885 1.0927 0.0895 0.097 Uiso 1 1 calc R . .
H8C H 0.5851 1.0033 0.0144 0.097 Uiso 1 1 calc R . .


_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
Br1 C16 1.93(2) . ?
P1 O1 1.509(16) . ?
P1 O2 1.586(15) . ?
P1 C1 1.71(2) . ?
P1 C12 1.86(2) . ?
O2 C10 1.48(2) . ?
O3 C12 1.44(3) . ?
C10 C9 1.46(3) . ?
C10 C7 1.50(3) . ?
C10 C8 1.54(3) . ?
C16 C17 1.35(3) . ?
C16 C15 1.35(3) . ?
C13 C14 1.37(3) . ?
C13 C18 1.40(3) . ?
C13 C12 1.47(3) . ?
C14 C15 1.43(4) . ?
C11 C12 1.51(3) . ?
C1 C6 1.43(3) . ?
C1 C2 1.45(3) . ?
C6 C5 1.36(3) . ?
C3 C2 1.38(3) . ?
C3 C4 1.40(4) . ?
C18 C17 1.35(3) . ?
C5 C4 1.38(3) . ?

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 O2 119.0(8) . . ?
O1 P1 C1 112.6(10) . . ?
O2 P1 C1 106.8(10) . . ?
O1 P1 C12 112.9(11) . . ?
O2 P1 C12 96.7(10) . . ?
C1 P1 C12 107.2(10) . . ?
C10 O2 P1 127.7(13) . . ?
C9 C10 O2 109.7(17) . . ?
C9 C10 C7 112(2) . . ?
O2 C10 C7 111(2) . . ?
C9 C10 C8 112(2) . . ?
O2 C10 C8 101.3(18) . . ?
C7 C10 C8 110(2) . . ?
C17 C16 C15 121(2) . . ?
C17 C16 Br1 119.6(17) . . ?
C15 C16 Br1 119.3(17) . . ?
C14 C13 C18 116(2) . . ?
C14 C13 C12 123(2) . . ?
C18 C13 C12 121(2) . . ?
C13 C14 C15 121(2) . . ?
C6 C1 C2 114(2) . . ?
C6 C1 P1 122.1(15) . . ?
C2 C1 P1 123.5(18) . . ?
C5 C6 C1 121(2) . . ?
C2 C3 C4 117(2) . . ?
C17 C18 C13 123(2) . . ?
C6 C5 C4 122(2) . . ?
C3 C2 C1 124(2) . . ?
O3 C12 C13 108.6(18) . . ?
O3 C12 C11 110.2(19) . . ?
C13 C12 C11 113(2) . . ?
O3 C12 P1 106.4(16) . . ?
C13 C12 P1 108.7(14) . . ?
C11 C12 P1 109.2(17) . . ?
C16 C15 C14 118(2) . . ?
C16 C17 C18 120(2) . . ?
C5 C4 C3 120(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.778
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.200
_database_code_depnum_ccdc_archive 'CCDC 950081'
