# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

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#                                CCDC 
# 
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# 
#  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.
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#  fide research purposes only. It may contain copyright material
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data_cd21370

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 B Br O P'
_chemical_formula_weight         363.03

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'
B B 0.0013 0.0007 '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           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.4951(15)
_cell_length_b                   9.549(2)
_cell_length_c                   15.501(4)
_cell_angle_alpha                81.333(5)
_cell_angle_beta                 86.707(5)
_cell_angle_gamma                74.351(5)
_cell_volume                     915.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1711
_cell_measurement_theta_min      4.474
_cell_measurement_theta_max      45.634

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.045
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    2.329
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.35197
_exptl_absorpt_correction_T_max  1.00000
_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  '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            5255
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4178
_reflns_number_gt                2829
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of 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)+(0.0836P)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   -0.016(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4178
_refine_ls_number_parameters     407
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12837(19) 1.01039(10) 0.37410(9) 0.1288(6) Uani 1 1 d . . .
Br1' Br 1.27320(18) -0.16386(9) 1.09411(9) 0.1258(5) Uani 1 1 d . . .
P1 P 0.4301(3) 0.28292(19) 0.58130(14) 0.0559(5) Uani 1 1 d . . .
P1' P 0.9132(2) 0.57055(18) 0.89192(13) 0.0514(5) Uani 1 1 d . . .
O1 O 0.756(2) 0.3262(12) 0.3147(7) 0.163(4) Uani 1 1 d . . .
O1' O 1.1561(19) 0.5181(9) 1.1696(7) 0.147(4) Uani 1 1 d . . .
B1 B 0.1217(12) 0.3292(10) 0.5952(7) 0.067(2) Uani 1 1 d . . .
B1' B 0.6467(14) 0.5260(10) 0.8809(7) 0.067(2) Uani 1 1 d . . .
C1 C 0.5327(12) 0.3437(7) 0.4732(5) 0.0652(19) Uani 1 1 d . . .
H1 H 0.6877 0.3268 0.4772 0.078 Uiso 1 1 calc R . .
C2 C 0.4916(16) 0.2546(10) 0.4044(6) 0.079(2) Uani 1 1 d . . .
H2A H 0.5313 0.1513 0.4285 0.094 Uiso 1 1 calc R . .
H2B H 0.3395 0.2823 0.3933 0.094 Uiso 1 1 calc R . .
C3 C 0.608(3) 0.2731(11) 0.3200(8) 0.118(4) Uani 1 1 d . . .
C4 C 0.540(4) 0.2103(16) 0.2454(9) 0.182(8) Uani 1 1 d . . .
H4A H 0.5162 0.1161 0.2667 0.273 Uiso 1 1 calc R . .
H4B H 0.6504 0.1994 0.2011 0.273 Uiso 1 1 calc R . .
H4C H 0.4103 0.2756 0.2211 0.273 Uiso 1 1 calc R . .
C5 C 0.5474(11) 0.3654(8) 0.6571(6) 0.069(2) Uani 1 1 d . . .
H5A H 0.7004 0.3338 0.6522 0.104 Uiso 1 1 calc R . .
H5B H 0.5030 0.3357 0.7156 0.104 Uiso 1 1 calc R . .
H5C H 0.5007 0.4705 0.6437 0.104 Uiso 1 1 calc R . .
C6 C 0.5569(12) 0.0893(8) 0.6010(5) 0.0599(19) Uani 1 1 d . . .
C7 C 0.4335(14) -0.0088(9) 0.6252(6) 0.072(2) Uani 1 1 d . . .
H7 H 0.2860 0.0271 0.6308 0.087 Uiso 1 1 calc R . .
C8 C 0.5242(18) -0.1582(9) 0.6411(7) 0.092(3) Uani 1 1 d . . .
H8 H 0.4381 -0.2215 0.6581 0.111 Uiso 1 1 calc R . .
C9 C 0.7396(18) -0.2135(10) 0.6320(7) 0.086(3) Uani 1 1 d . . .
H9 H 0.8011 -0.3143 0.6421 0.103 Uiso 1 1 calc R . .
C10 C 0.8642(16) -0.1189(11) 0.6080(8) 0.099(3) Uani 1 1 d . . .
H10 H 1.0111 -0.1559 0.6011 0.119 Uiso 1 1 calc R . .
C11 C 0.7754(13) 0.0297(9) 0.5939(6) 0.078(2) Uani 1 1 d . . .
H11 H 0.8639 0.0920 0.5793 0.094 Uiso 1 1 calc R . .
C12 C 0.4352(13) 0.5089(9) 0.4477(6) 0.067(2) Uani 1 1 d . . .
C13 C 0.5489(13) 0.6072(8) 0.4553(6) 0.074(2) Uani 1 1 d . . .
H13 H 0.6872 0.5732 0.4765 0.089 Uiso 1 1 calc R . .
C14 C 0.4624(16) 0.7570(11) 0.4320(7) 0.088(3) Uani 1 1 d . . .
H14 H 0.5451 0.8220 0.4345 0.106 Uiso 1 1 calc R . .
C15 C 0.254(2) 0.8088(10) 0.4054(7) 0.091(3) Uani 1 1 d . . .
C16 C 0.1357(17) 0.7110(11) 0.4005(8) 0.102(3) Uani 1 1 d . . .
H16 H -0.0053 0.7447 0.3823 0.122 Uiso 1 1 calc R . .
C17 C 0.2267(17) 0.5632(10) 0.4227(7) 0.094(3) Uani 1 1 d . . .
H17 H 0.1441 0.4979 0.4207 0.112 Uiso 1 1 calc R . .
C1' C 1.0270(12) 0.5124(7) 1.0016(5) 0.0616(18) Uani 1 1 d . . .
H1' H 1.1594 0.5434 1.0001 0.074 Uiso 1 1 calc R . .
C2' C 0.8789(15) 0.5925(9) 1.0676(6) 0.073(2) Uani 1 1 d . . .
H2'1 H 0.7523 0.5562 1.0749 0.088 Uiso 1 1 calc R . .
H2'2 H 0.8339 0.6961 1.0445 0.088 Uiso 1 1 calc R . .
C3' C 0.976(3) 0.5765(11) 1.1568(7) 0.111(4) Uani 1 1 d . . .
C4' C 0.822(3) 0.639(2) 1.2233(10) 0.161(7) Uani 1 1 d . . .
H4'1 H 0.8836 0.6073 1.2800 0.242 Uiso 1 1 calc R . .
H4'2 H 0.6945 0.6068 1.2217 0.242 Uiso 1 1 calc R . .
H4'3 H 0.7862 0.7446 1.2114 0.242 Uiso 1 1 calc R . .
C5' C 1.1148(12) 0.4785(8) 0.8214(5) 0.0661(18) Uani 1 1 d . . .
H5'1 H 1.2503 0.4924 0.8341 0.099 Uiso 1 1 calc R . .
H5'2 H 1.0796 0.5181 0.7618 0.099 Uiso 1 1 calc R . .
H5'3 H 1.1229 0.3755 0.8304 0.099 Uiso 1 1 calc R . .
C6' C 0.8973(11) 0.7652(8) 0.8688(5) 0.0551(17) Uani 1 1 d . . .
C7' C 1.0793(12) 0.8157(9) 0.8538(6) 0.076(2) Uani 1 1 d . . .
H7' H 1.2131 0.7487 0.8538 0.091 Uiso 1 1 calc R . .
C8' C 1.0638(15) 0.9624(10) 0.8392(8) 0.097(3) Uani 1 1 d . . .
H8' H 1.1877 0.9944 0.8328 0.117 Uiso 1 1 calc R . .
C9' C 0.8718(16) 1.0619(9) 0.8339(6) 0.082(3) Uani 1 1 d . . .
H9' H 0.8626 1.1618 0.8226 0.098 Uiso 1 1 calc R . .
C10' C 0.6879(18) 1.0131(10) 0.8456(7) 0.088(3) Uani 1 1 d . . .
H10' H 0.5544 1.0806 0.8401 0.106 Uiso 1 1 calc R . .
C11' C 0.7020(13) 0.8660(8) 0.8651(6) 0.070(2) Uani 1 1 d . . .
H11' H 0.5782 0.8345 0.8759 0.085 Uiso 1 1 calc R . .
C12' C 1.0888(11) 0.3449(8) 1.0256(5) 0.0572(18) Uani 1 1 d . . .
C13' C 0.9372(14) 0.2727(11) 1.0482(7) 0.090(3) Uani 1 1 d . . .
H13' H 0.7940 0.3252 1.0492 0.108 Uiso 1 1 calc R . .
C14' C 0.9936(16) 0.1179(10) 1.0704(7) 0.088(3) Uani 1 1 d . . .
H14' H 0.8911 0.0672 1.0877 0.105 Uiso 1 1 calc R . .
C15' C 1.2019(15) 0.0480(9) 1.0654(7) 0.076(2) Uani 1 1 d . . .
C16' C 1.3555(15) 0.1140(10) 1.0377(7) 0.084(3) Uani 1 1 d . . .
H16' H 1.4963 0.0596 1.0315 0.101 Uiso 1 1 calc R . .
C17' C 1.2996(12) 0.2643(9) 1.0188(6) 0.076(2) Uani 1 1 d . . .
H17' H 1.4047 0.3128 1.0011 0.092 Uiso 1 1 calc R . .
H1E H 0.687(8) 0.405(6) 0.883(3) 0.033(13) Uiso 1 1 d . . .
H1F H 0.523(11) 0.572(7) 0.939(4) 0.061(18) Uiso 1 1 d . . .
H1D H 0.591(14) 0.576(9) 0.809(6) 0.09(2) Uiso 1 1 d . . .
H1B H 0.082(11) 0.280(7) 0.538(4) 0.062(18) Uiso 1 1 d . . .
H1A H 0.079(9) 0.445(7) 0.576(4) 0.045(15) Uiso 1 1 d . . .
H1C H 0.090(10) 0.265(7) 0.664(5) 0.056(17) Uiso 1 1 d . . .


_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 C15 1.878(10) . ?
Br1' C15' 1.937(9) . ?
P1 C6 1.797(8) . ?
P1 C5 1.813(6) . ?
P1 C1 1.837(9) . ?
P1 B1 1.938(8) . ?
P1' C5' 1.785(7) . ?
P1' C6' 1.815(7) . ?
P1' C1' 1.839(7) . ?
P1' B1' 1.912(8) . ?
O1 C3 1.195(17) . ?
O1' C3' 1.165(16) . ?
B1 H1B 1.13(7) . ?
B1 H1A 1.06(6) . ?
B1 H1C 1.18(7) . ?
B1' H1E 1.11(5) . ?
B1' H1F 1.22(7) . ?
B1' H1D 1.18(9) . ?
C1 C12 1.532(11) . ?
C1 C2 1.537(11) . ?
C1 H1 0.9800 . ?
C2 C3 1.484(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.52(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.384(11) . ?
C6 C7 1.387(12) . ?
C7 C8 1.379(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(12) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.363(10) . ?
C12 C17 1.369(12) . ?
C13 C14 1.388(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(14) . ?
C16 C17 1.374(13) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C1' C2' 1.511(11) . ?
C1' C12' 1.533(9) . ?
C1' H1' 0.9800 . ?
C2' C3' 1.523(15) . ?
C2' H2'1 0.9700 . ?
C2' H2'2 0.9700 . ?
C3' C4' 1.47(2) . ?
C4' H4'1 0.9600 . ?
C4' H4'2 0.9600 . ?
C4' H4'3 0.9600 . ?
C5' H5'1 0.9600 . ?
C5' H5'2 0.9600 . ?
C5' H5'3 0.9600 . ?
C6' C11' 1.368(11) . ?
C6' C7' 1.387(11) . ?
C7' C8' 1.362(12) . ?
C7' H7' 0.9300 . ?
C8' C9' 1.347(13) . ?
C8' H8' 0.9300 . ?
C9' C10' 1.388(14) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.371(12) . ?
C10' H10' 0.9300 . ?
C11' H11' 0.9300 . ?
C12' C13' 1.350(12) . ?
C12' C17' 1.385(11) . ?
C13' C14' 1.416(13) . ?
C13' H13' 0.9300 . ?
C14' C15' 1.341(13) . ?
C14' H14' 0.9300 . ?
C15' C16' 1.337(15) . ?
C16' C17' 1.372(12) . ?
C16' H16' 0.9300 . ?
C17' H17' 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 P1 C5 106.0(3) . . ?
C6 P1 C1 104.3(3) . . ?
C5 P1 C1 105.1(4) . . ?
C6 P1 B1 113.1(4) . . ?
C5 P1 B1 111.4(4) . . ?
C1 P1 B1 116.1(4) . . ?
C5' P1' C6' 107.5(4) . . ?
C5' P1' C1' 104.6(4) . . ?
C6' P1' C1' 104.8(3) . . ?
C5' P1' B1' 111.6(4) . . ?
C6' P1' B1' 113.7(4) . . ?
C1' P1' B1' 114.0(4) . . ?
P1 B1 H1B 100(3) . . ?
P1 B1 H1A 101(3) . . ?
H1B B1 H1A 106(5) . . ?
P1 B1 H1C 105(3) . . ?
H1B B1 H1C 113(5) . . ?
H1A B1 H1C 127(5) . . ?
P1' B1' H1E 106(3) . . ?
P1' B1' H1F 109(3) . . ?
H1E B1' H1F 114(4) . . ?
P1' B1' H1D 106(4) . . ?
H1E B1' H1D 106(5) . . ?
H1F B1' H1D 116(6) . . ?
C12 C1 C2 111.9(6) . . ?
C12 C1 P1 109.8(5) . . ?
C2 C1 P1 111.3(6) . . ?
C12 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
P1 C1 H1 107.9 . . ?
C3 C2 C1 115.2(9) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O1 C3 C2 120.3(13) . . ?
O1 C3 C4 123.1(14) . . ?
C2 C3 C4 116.4(14) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
P1 C5 H5A 109.5 . . ?
P1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
P1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 116.7(7) . . ?
C11 C6 P1 123.7(6) . . ?
C7 C6 P1 119.7(6) . . ?
C8 C7 C6 121.6(9) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C7 120.3(9) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.1(8) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.8(9) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 121.5(8) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
C13 C12 C17 117.8(8) . . ?
C13 C12 C1 120.9(7) . . ?
C17 C12 C1 121.1(7) . . ?
C12 C13 C14 121.3(8) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 119.7(8) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.4(9) . . ?
C14 C15 Br1 121.6(7) . . ?
C16 C15 Br1 119.0(8) . . ?
C17 C16 C15 119.6(9) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C12 C17 C16 122.0(8) . . ?
C12 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C2' C1' C12' 113.7(7) . . ?
C2' C1' P1' 110.2(5) . . ?
C12' C1' P1' 111.9(4) . . ?
C2' C1' H1' 106.9 . . ?
C12' C1' H1' 106.9 . . ?
P1' C1' H1' 106.9 . . ?
C1' C2' C3' 114.6(9) . . ?
C1' C2' H2'1 108.6 . . ?
C3' C2' H2'1 108.6 . . ?
C1' C2' H2'2 108.6 . . ?
C3' C2' H2'2 108.6 . . ?
H2'1 C2' H2'2 107.6 . . ?
O1' C3' C4' 124.6(12) . . ?
O1' C3' C2' 121.8(13) . . ?
C4' C3' C2' 113.7(14) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
P1' C5' H5'1 109.5 . . ?
P1' C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
P1' C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C11' C6' C7' 118.5(7) . . ?
C11' C6' P1' 119.8(6) . . ?
C7' C6' P1' 121.7(6) . . ?
C8' C7' C6' 120.6(8) . . ?
C8' C7' H7' 119.7 . . ?
C6' C7' H7' 119.7 . . ?
C9' C8' C7' 121.0(8) . . ?
C9' C8' H8' 119.5 . . ?
C7' C8' H8' 119.5 . . ?
C8' C9' C10' 119.1(8) . . ?
C8' C9' H9' 120.5 . . ?
C10' C9' H9' 120.5 . . ?
C11' C10' C9' 120.3(9) . . ?
C11' C10' H10' 119.8 . . ?
C9' C10' H10' 119.8 . . ?
C6' C11' C10' 120.3(8) . . ?
C6' C11' H11' 119.8 . . ?
C10' C11' H11' 119.8 . . ?
C13' C12' C17' 118.9(7) . . ?
C13' C12' C1' 120.6(7) . . ?
C17' C12' C1' 120.4(7) . . ?
C12' C13' C14' 120.7(8) . . ?
C12' C13' H13' 119.6 . . ?
C14' C13' H13' 119.6 . . ?
C15' C14' C13' 116.9(8) . . ?
C15' C14' H14' 121.6 . . ?
C13' C14' H14' 121.6 . . ?
C16' C15' C14' 124.3(9) . . ?
C16' C15' Br1' 119.7(7) . . ?
C14' C15' Br1' 115.9(7) . . ?
C15' C16' C17' 118.2(8) . . ?
C15' C16' H16' 120.9 . . ?
C17' C16' H16' 120.9 . . ?
C16' C17' C12' 120.8(8) . . ?
C16' C17' H17' 119.6 . . ?
C12' C17' H17' 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 P1 C1 C12 179.7(5) . . . . ?
C5 P1 C1 C12 -69.0(6) . . . . ?
B1 P1 C1 C12 54.5(6) . . . . ?
C6 P1 C1 C2 55.2(6) . . . . ?
C5 P1 C1 C2 166.5(6) . . . . ?
B1 P1 C1 C2 -70.0(7) . . . . ?
C12 C1 C2 C3 69.1(10) . . . . ?
P1 C1 C2 C3 -167.5(7) . . . . ?
C1 C2 C3 O1 16.0(15) . . . . ?
C1 C2 C3 C4 -168.8(9) . . . . ?
C5 P1 C6 C11 -58.5(8) . . . . ?
C1 P1 C6 C11 52.1(7) . . . . ?
B1 P1 C6 C11 179.2(7) . . . . ?
C5 P1 C6 C7 121.1(7) . . . . ?
C1 P1 C6 C7 -128.2(7) . . . . ?
B1 P1 C6 C7 -1.2(8) . . . . ?
C11 C6 C7 C8 -0.2(12) . . . . ?
P1 C6 C7 C8 -179.9(7) . . . . ?
C6 C7 C8 C9 -1.0(15) . . . . ?
C7 C8 C9 C10 0.7(15) . . . . ?
C8 C9 C10 C11 0.6(16) . . . . ?
C9 C10 C11 C6 -1.9(15) . . . . ?
C7 C6 C11 C10 1.6(12) . . . . ?
P1 C6 C11 C10 -178.8(7) . . . . ?
C2 C1 C12 C13 -134.6(8) . . . . ?
P1 C1 C12 C13 101.2(8) . . . . ?
C2 C1 C12 C17 50.3(11) . . . . ?
P1 C1 C12 C17 -73.9(9) . . . . ?
C17 C12 C13 C14 -5.0(13) . . . . ?
C1 C12 C13 C14 179.8(8) . . . . ?
C12 C13 C14 C15 3.7(14) . . . . ?
C13 C14 C15 C16 -1.2(16) . . . . ?
C13 C14 C15 Br1 179.5(8) . . . . ?
C14 C15 C16 C17 0.2(17) . . . . ?
Br1 C15 C16 C17 179.6(9) . . . . ?
C13 C12 C17 C16 4.0(15) . . . . ?
C1 C12 C17 C16 179.2(10) . . . . ?
C15 C16 C17 C12 -1.7(17) . . . . ?
C5' P1' C1' C2' 175.4(5) . . . . ?
C6' P1' C1' C2' 62.5(6) . . . . ?
B1' P1' C1' C2' -62.4(6) . . . . ?
C5' P1' C1' C12' -57.0(6) . . . . ?
C6' P1' C1' C12' -169.9(5) . . . . ?
B1' P1' C1' C12' 65.1(6) . . . . ?
C12' C1' C2' C3' 65.2(9) . . . . ?
P1' C1' C2' C3' -168.3(7) . . . . ?
C1' C2' C3' O1' 6.5(14) . . . . ?
C1' C2' C3' C4' -172.6(10) . . . . ?
C5' P1' C6' C11' 138.6(6) . . . . ?
C1' P1' C6' C11' -110.6(6) . . . . ?
B1' P1' C6' C11' 14.5(8) . . . . ?
C5' P1' C6' C7' -41.0(7) . . . . ?
C1' P1' C6' C7' 69.9(7) . . . . ?
B1' P1' C6' C7' -165.0(7) . . . . ?
C11' C6' C7' C8' 2.5(13) . . . . ?
P1' C6' C7' C8' -178.0(7) . . . . ?
C6' C7' C8' C9' -3.8(16) . . . . ?
C7' C8' C9' C10' 1.5(16) . . . . ?
C8' C9' C10' C11' 2.1(15) . . . . ?
C7' C6' C11' C10' 1.1(12) . . . . ?
P1' C6' C11' C10' -178.4(7) . . . . ?
C9' C10' C11' C6' -3.4(14) . . . . ?
C2' C1' C12' C13' 50.2(10) . . . . ?
P1' C1' C12' C13' -75.5(9) . . . . ?
C2' C1' C12' C17' -134.1(8) . . . . ?
P1' C1' C12' C17' 100.2(7) . . . . ?
C17' C12' C13' C14' 4.2(14) . . . . ?
C1' C12' C13' C14' -180.0(8) . . . . ?
C12' C13' C14' C15' -1.8(15) . . . . ?
C13' C14' C15' C16' -2.8(16) . . . . ?
C13' C14' C15' Br1' -178.9(7) . . . . ?
C14' C15' C16' C17' 4.7(16) . . . . ?
Br1' C15' C16' C17' -179.4(7) . . . . ?
C15' C16' C17' C12' -2.0(14) . . . . ?
C13' C12' C17' C16' -2.3(13) . . . . ?
C1' C12' C17' C16' -178.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 981792'
#######################################################################
#
#                 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_cd212400

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 B Br N O P'
_chemical_formula_weight         414.08

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'
B B 0.0013 0.0007 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   6.2364(5)
_cell_length_b                   17.7803(18)
_cell_length_c                   18.9588(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2102.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1397
_cell_measurement_theta_min      4.582
_cell_measurement_theta_max      36.790

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.056
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.038
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.08870
_exptl_absorpt_correction_T_max  1.00000
_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  '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            11836
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4132
_reflns_number_gt                2469
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of 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)+(0.0451P)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   0.001(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4132
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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
Br1 Br 1.04571(12) 0.55989(4) 0.06171(3) 0.0944(3) Uani 1 1 d . . .
P1 P 0.96774(19) 0.31975(7) 0.36295(5) 0.0438(3) Uani 1 1 d . . .
N1 N 0.8198(9) 0.5841(2) 0.4678(2) 0.0721(14) Uani 1 1 d . . .
O1 O 0.5854(7) 0.5368(2) 0.3885(2) 0.0876(13) Uani 1 1 d . . .
B1 B 1.2662(10) 0.3235(4) 0.3821(4) 0.0628(17) Uani 1 1 d . . .
C1 C 0.8411(7) 0.4124(2) 0.3499(2) 0.0450(11) Uani 1 1 d . . .
H1 H 0.6855 0.4048 0.3510 0.054 Uiso 1 1 calc R . .
C2 C 0.8989(9) 0.4634(3) 0.4119(2) 0.0596(14) Uani 1 1 d . . .
H2A H 0.8938 0.4342 0.4551 0.072 Uiso 1 1 calc R . .
H2B H 1.0448 0.4812 0.4059 0.072 Uiso 1 1 calc R . .
C3 C 0.7530(11) 0.5300(3) 0.4194(3) 0.0626(15) Uani 1 1 d . . .
C4 C 1.0079(13) 0.5875(3) 0.5043(3) 0.0848(18) Uani 1 1 d . . .
H4 H 1.1183 0.5525 0.5011 0.102 Uiso 1 1 calc R . .
C5 C 1.0100(18) 0.6493(4) 0.5456(4) 0.117(3) Uani 1 1 d . . .
H5 H 1.1199 0.6655 0.5751 0.140 Uiso 1 1 calc R . .
C6 C 0.8114(19) 0.6837(4) 0.5346(5) 0.131(3) Uani 1 1 d . . .
H6 H 0.7661 0.7277 0.5565 0.157 Uiso 1 1 calc R . .
C7 C 0.6946(14) 0.6441(4) 0.4875(4) 0.105(2) Uani 1 1 d . . .
H7 H 0.5571 0.6552 0.4716 0.126 Uiso 1 1 calc R . .
C8 C 0.8958(7) 0.4468(3) 0.2789(2) 0.0460(11) Uani 1 1 d . . .
C9 C 1.0947(8) 0.4772(3) 0.2653(3) 0.0632(14) Uani 1 1 d . . .
H9 H 1.2014 0.4755 0.2995 0.076 Uiso 1 1 calc R . .
C10 C 1.1357(9) 0.5108(3) 0.2000(3) 0.0693(15) Uani 1 1 d . . .
H10 H 1.2693 0.5321 0.1912 0.083 Uiso 1 1 calc R . .
C11 C 0.9830(10) 0.5126(3) 0.1497(2) 0.0621(13) Uani 1 1 d . . .
C12 C 0.7894(10) 0.4813(3) 0.1617(3) 0.0779(18) Uani 1 1 d . . .
H12 H 0.6855 0.4820 0.1265 0.093 Uiso 1 1 calc R . .
C13 C 0.7447(9) 0.4483(3) 0.2257(2) 0.0692(15) Uani 1 1 d . . .
H13 H 0.6108 0.4268 0.2332 0.083 Uiso 1 1 calc R . .
C14 C 0.9015(8) 0.2621(3) 0.2869(2) 0.0487(12) Uani 1 1 d . . .
C15 C 1.0525(10) 0.2516(3) 0.2355(3) 0.0741(16) Uani 1 1 d . . .
H15 H 1.1842 0.2759 0.2391 0.089 Uiso 1 1 calc R . .
C16 C 1.0121(12) 0.2055(4) 0.1782(3) 0.0891(19) Uani 1 1 d . . .
H16 H 1.1176 0.1981 0.1442 0.107 Uiso 1 1 calc R . .
C17 C 0.8168(13) 0.1709(3) 0.1714(3) 0.0826(19) Uani 1 1 d . . .
H17 H 0.7893 0.1399 0.1329 0.099 Uiso 1 1 calc R . .
C18 C 0.6642(11) 0.1821(4) 0.2212(4) 0.090(2) Uani 1 1 d . . .
H18 H 0.5311 0.1590 0.2168 0.108 Uiso 1 1 calc R . .
C19 C 0.7058(9) 0.2279(3) 0.2788(3) 0.0735(17) Uani 1 1 d . . .
H19 H 0.5995 0.2356 0.3124 0.088 Uiso 1 1 calc R . .
C20 C 0.8243(8) 0.2790(3) 0.4366(2) 0.0585(13) Uani 1 1 d . . .
H20A H 0.6728 0.2841 0.4290 0.088 Uiso 1 1 calc R . .
H20B H 0.8638 0.3045 0.4792 0.088 Uiso 1 1 calc R . .
H20C H 0.8601 0.2266 0.4405 0.088 Uiso 1 1 calc R . .
H1B H 1.274(7) 0.359(3) 0.429(3) 0.070(14) Uiso 1 1 d . . .
H1A H 1.311(8) 0.258(3) 0.397(3) 0.088(17) Uiso 1 1 d . . .
H1C H 1.340(7) 0.347(2) 0.335(2) 0.052(12) Uiso 1 1 d . . .


_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 C11 1.908(4) . ?
P1 C20 1.809(4) . ?
P1 C14 1.817(5) . ?
P1 C1 1.843(4) . ?
P1 B1 1.897(6) . ?
N1 C4 1.363(8) . ?
N1 C7 1.373(7) . ?
N1 C3 1.395(7) . ?
O1 C3 1.204(6) . ?
B1 H1B 1.09(5) . ?
B1 H1A 1.24(5) . ?
B1 H1C 1.09(4) . ?
C1 C8 1.516(6) . ?
C1 C2 1.529(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.499(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.349(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.350(11) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.378(6) . ?
C8 C13 1.381(6) . ?
C9 C10 1.398(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.349(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.349(7) . ?
C12 C13 1.377(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.368(6) . ?
C14 C19 1.372(7) . ?
C15 C16 1.385(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.356(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(7) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C20 P1 C14 105.9(2) . . ?
C20 P1 C1 104.5(2) . . ?
C14 P1 C1 107.5(2) . . ?
C20 P1 B1 110.6(3) . . ?
C14 P1 B1 113.2(3) . . ?
C1 P1 B1 114.5(3) . . ?
C4 N1 C7 108.5(6) . . ?
C4 N1 C3 128.4(5) . . ?
C7 N1 C3 123.1(6) . . ?
P1 B1 H1B 103(2) . . ?
P1 B1 H1A 103(2) . . ?
H1B B1 H1A 111(3) . . ?
P1 B1 H1C 106(2) . . ?
H1B B1 H1C 115(3) . . ?
H1A B1 H1C 117(3) . . ?
C8 C1 C2 113.0(4) . . ?
C8 C1 P1 112.5(3) . . ?
C2 C1 P1 109.0(3) . . ?
C8 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
P1 C1 H1 107.3 . . ?
C3 C2 C1 113.5(4) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 N1 120.6(5) . . ?
O1 C3 C2 124.1(5) . . ?
N1 C3 C2 115.2(5) . . ?
C5 C4 N1 109.8(7) . . ?
C5 C4 H4 125.1 . . ?
N1 C4 H4 125.1 . . ?
C4 C5 C6 105.1(8) . . ?
C4 C5 H5 127.4 . . ?
C6 C5 H5 127.4 . . ?
C7 C6 C5 110.4(7) . . ?
C7 C6 H6 124.8 . . ?
C5 C6 H6 124.8 . . ?
C6 C7 N1 106.1(8) . . ?
C6 C7 H7 126.9 . . ?
N1 C7 H7 126.9 . . ?
C9 C8 C13 118.0(4) . . ?
C9 C8 C1 121.8(4) . . ?
C13 C8 C1 120.2(4) . . ?
C8 C9 C10 119.9(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 Br1 119.0(4) . . ?
C12 C11 Br1 120.9(4) . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.9(5) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C15 C14 C19 118.2(5) . . ?
C15 C14 P1 119.0(4) . . ?
C19 C14 P1 122.8(4) . . ?
C14 C15 C16 121.0(6) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.1(6) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.5(6) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.2(6) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 121.0(6) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
P1 C20 H20A 109.5 . . ?
P1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
P1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 P1 C1 C8 -164.3(3) . . . . ?
C14 P1 C1 C8 -52.2(4) . . . . ?
B1 P1 C1 C8 74.5(4) . . . . ?
C20 P1 C1 C2 69.5(4) . . . . ?
C14 P1 C1 C2 -178.3(3) . . . . ?
B1 P1 C1 C2 -51.6(4) . . . . ?
C8 C1 C2 C3 72.5(5) . . . . ?
P1 C1 C2 C3 -161.6(3) . . . . ?
C4 N1 C3 O1 -176.1(5) . . . . ?
C7 N1 C3 O1 5.4(8) . . . . ?
C4 N1 C3 C2 6.4(7) . . . . ?
C7 N1 C3 C2 -172.1(5) . . . . ?
C1 C2 C3 O1 12.5(7) . . . . ?
C1 C2 C3 N1 -170.1(4) . . . . ?
C7 N1 C4 C5 -1.7(7) . . . . ?
C3 N1 C4 C5 179.7(5) . . . . ?
N1 C4 C5 C6 1.3(8) . . . . ?
C4 C5 C6 C7 -0.5(9) . . . . ?
C5 C6 C7 N1 -0.4(9) . . . . ?
C4 N1 C7 C6 1.3(7) . . . . ?
C3 N1 C7 C6 -180.0(5) . . . . ?
C2 C1 C8 C9 49.6(6) . . . . ?
P1 C1 C8 C9 -74.4(5) . . . . ?
C2 C1 C8 C13 -130.3(5) . . . . ?
P1 C1 C8 C13 105.7(5) . . . . ?
C13 C8 C9 C10 2.2(8) . . . . ?
C1 C8 C9 C10 -177.7(5) . . . . ?
C8 C9 C10 C11 -1.1(8) . . . . ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C9 C10 C11 Br1 179.4(4) . . . . ?
C10 C11 C12 C13 1.0(9) . . . . ?
Br1 C11 C12 C13 -179.0(5) . . . . ?
C11 C12 C13 C8 0.3(10) . . . . ?
C9 C8 C13 C12 -1.9(8) . . . . ?
C1 C8 C13 C12 178.0(5) . . . . ?
C20 P1 C14 C15 -146.7(4) . . . . ?
C1 P1 C14 C15 102.1(4) . . . . ?
B1 P1 C14 C15 -25.3(5) . . . . ?
C20 P1 C14 C19 32.9(5) . . . . ?
C1 P1 C14 C19 -78.3(5) . . . . ?
B1 P1 C14 C19 154.3(5) . . . . ?
C19 C14 C15 C16 -2.5(8) . . . . ?
P1 C14 C15 C16 177.2(5) . . . . ?
C14 C15 C16 C17 1.5(9) . . . . ?
C15 C16 C17 C18 0.0(10) . . . . ?
C16 C17 C18 C19 -0.4(10) . . . . ?
C15 C14 C19 C18 2.0(9) . . . . ?
P1 C14 C19 C18 -177.6(4) . . . . ?
C17 C18 C19 C14 -0.6(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 981793'
#######################################################################
#
#                 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_cd21374

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 B O P'
_chemical_formula_weight         374.24

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'
B B 0.0013 0.0007 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   10.135(7)
_cell_length_b                   13.483(9)
_cell_length_c                   15.598(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2132(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5539
_cell_measurement_theta_min      4.793
_cell_measurement_theta_max      55.008

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.66750
_exptl_absorpt_correction_T_max  1.00000
_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  '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            13040
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4197
_reflns_number_gt                3928
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of 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)+(0.0540P)²+0.1750P] 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       0.0147(19)
_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   -0.01(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4197
_refine_ls_number_parameters     259
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.124
_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 0.42755(4) 0.43709(3) 0.82765(3) 0.03396(13) Uani 1 1 d . . .
O1 O 0.37767(15) 0.45288(10) 0.54678(9) 0.0545(4) Uani 1 1 d . . .
B1 B 0.6115(2) 0.4218(2) 0.80339(16) 0.0514(6) Uani 1 1 d . . .
C1 C 0.34018(19) 0.45725(13) 0.72526(10) 0.0390(4) Uani 1 1 d . . .
H1 H 0.3946 0.5042 0.6929 0.047 Uiso 1 1 calc R . .
C2 C 0.3433(2) 0.36028(14) 0.67388(12) 0.0505(5) Uani 1 1 d . . .
H2A H 0.4216 0.3232 0.6898 0.061 Uiso 1 1 calc R . .
H2B H 0.2671 0.3207 0.6895 0.061 Uiso 1 1 calc R . .
C3 C 0.34339(18) 0.37508(14) 0.57814(11) 0.0396(4) Uani 1 1 d . . .
C4 C 0.31000(18) 0.28804(13) 0.52325(11) 0.0396(4) Uani 1 1 d . . .
C5 C 0.2304(2) 0.21101(15) 0.55118(13) 0.0493(5) Uani 1 1 d . . .
H5 H 0.1964 0.2120 0.6065 0.059 Uiso 1 1 calc R . .
C6 C 0.2015(2) 0.13282(16) 0.49722(16) 0.0599(6) Uani 1 1 d . . .
H6 H 0.1464 0.0821 0.5160 0.072 Uiso 1 1 calc R . .
C7 C 0.2530(3) 0.12958(18) 0.41677(15) 0.0644(7) Uani 1 1 d . . .
H7 H 0.2341 0.0762 0.3811 0.077 Uiso 1 1 calc R . .
C8 C 0.3321(3) 0.20410(18) 0.38840(14) 0.0639(6) Uani 1 1 d . . .
H8 H 0.3674 0.2012 0.3334 0.077 Uiso 1 1 calc R . .
C9 C 0.3605(2) 0.28447(16) 0.44068(12) 0.0492(5) Uani 1 1 d . . .
H9 H 0.4133 0.3358 0.4204 0.059 Uiso 1 1 calc R . .
C10 C 0.39232(17) 0.54294(12) 0.89643(11) 0.0372(4) Uani 1 1 d . . .
H10 H 0.2964 0.5487 0.9029 0.045 Uiso 1 1 calc R . .
C11 C 0.4526(2) 0.52797(16) 0.98437(13) 0.0518(5) Uani 1 1 d . . .
H11A H 0.5466 0.5221 0.9791 0.078 Uiso 1 1 calc R . .
H11B H 0.4176 0.4686 1.0096 0.078 Uiso 1 1 calc R . .
H11C H 0.4317 0.5837 1.0202 0.078 Uiso 1 1 calc R . .
C12 C 0.4438(2) 0.63769(14) 0.85497(14) 0.0514(5) Uani 1 1 d . . .
H12A H 0.4295 0.6927 0.8930 0.077 Uiso 1 1 calc R . .
H12B H 0.3979 0.6491 0.8021 0.077 Uiso 1 1 calc R . .
H12C H 0.5365 0.6310 0.8438 0.077 Uiso 1 1 calc R . .
C13 C 0.35745(19) 0.32920(13) 0.87996(11) 0.0391(4) Uani 1 1 d . . .
C14 C 0.2489(2) 0.33468(16) 0.93344(15) 0.0580(6) Uani 1 1 d . . .
H14 H 0.2070 0.3951 0.9428 0.070 Uiso 1 1 calc R . .
C15 C 0.2034(3) 0.2497(2) 0.97278(18) 0.0796(8) Uani 1 1 d . . .
H15 H 0.1309 0.2534 1.0091 0.096 Uiso 1 1 calc R . .
C16 C 0.2631(3) 0.16009(19) 0.95930(19) 0.0794(8) Uani 1 1 d . . .
H16 H 0.2309 0.1034 0.9860 0.095 Uiso 1 1 calc R . .
C17 C 0.3696(3) 0.15426(17) 0.90671(17) 0.0701(7) Uani 1 1 d . . .
H17 H 0.4102 0.0934 0.8973 0.084 Uiso 1 1 calc R . .
C18 C 0.4176(2) 0.23820(14) 0.86727(13) 0.0497(5) Uani 1 1 d . . .
H18 H 0.4912 0.2337 0.8318 0.060 Uiso 1 1 calc R . .
C19 C 0.2054(2) 0.50281(17) 0.72948(13) 0.0514(5) Uani 1 1 d . . .
C20 C 0.1842(3) 0.5962(2) 0.69533(17) 0.0745(7) Uani 1 1 d U . .
H20 H 0.2541 0.6312 0.6714 0.089 Uiso 1 1 calc R . .
C21 C 0.0582(4) 0.6380(3) 0.6966(2) 0.1044(10) Uani 1 1 d U . .
H21 H 0.0439 0.7007 0.6736 0.125 Uiso 1 1 calc R . .
C22 C -0.0419(4) 0.5869(4) 0.7313(3) 0.1140(12) Uani 1 1 d U . .
H22 H -0.1258 0.6148 0.7315 0.137 Uiso 1 1 calc R . .
C23 C -0.0242(3) 0.4965(4) 0.7658(2) 0.1064(11) Uani 1 1 d U . .
H23 H -0.0953 0.4635 0.7904 0.128 Uiso 1 1 calc R . .
C24 C 0.0996(2) 0.4518(3) 0.76501(19) 0.0815(8) Uani 1 1 d U . .
H24 H 0.1114 0.3887 0.7879 0.098 Uiso 1 1 calc R . .
H1A H 0.635(3) 0.4840(19) 0.7613(18) 0.073(7) Uiso 1 1 d . . .
H1C H 0.622(3) 0.354(2) 0.764(2) 0.089(9) Uiso 1 1 d . . .
H1B H 0.660(3) 0.412(2) 0.8634(19) 0.097(9) Uiso 1 1 d . . .


_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 C13 1.813(2) . ?
P1 C10 1.8208(19) . ?
P1 C1 1.846(2) . ?
P1 B1 1.913(3) . ?
O1 C3 1.208(2) . ?
B1 H1A 1.09(3) . ?
B1 H1C 1.10(3) . ?
B1 H1B 1.07(3) . ?
C1 C19 1.499(3) . ?
C1 C2 1.534(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.507(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.492(3) . ?
C4 C5 1.385(3) . ?
C4 C9 1.387(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.360(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.515(3) . ?
C10 C12 1.524(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.382(3) . ?
C13 C18 1.384(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.384(4) . ?
C19 C24 1.389(4) . ?
C20 C21 1.396(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.340(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.345(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 P1 C10 106.67(9) . . ?
C13 P1 C1 108.64(9) . . ?
C10 P1 C1 107.48(9) . . ?
C13 P1 B1 112.60(11) . . ?
C10 P1 B1 113.08(10) . . ?
C1 P1 B1 108.19(10) . . ?
P1 B1 H1A 104.5(14) . . ?
P1 B1 H1C 107.0(16) . . ?
H1A B1 H1C 106.3(19) . . ?
P1 B1 H1B 107.0(16) . . ?
H1A B1 H1B 122(2) . . ?
H1C B1 H1B 110(2) . . ?
C19 C1 C2 113.01(16) . . ?
C19 C1 P1 117.35(13) . . ?
C2 C1 P1 108.46(13) . . ?
C19 C1 H1 105.7 . . ?
C2 C1 H1 105.7 . . ?
P1 C1 H1 105.7 . . ?
C3 C2 C1 113.90(15) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 C4 121.06(16) . . ?
O1 C3 C2 121.09(17) . . ?
C4 C3 C2 117.68(16) . . ?
C5 C4 C9 118.75(18) . . ?
C5 C4 C3 122.79(17) . . ?
C9 C4 C3 118.46(18) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C11 C10 C12 110.97(16) . . ?
C11 C10 P1 110.49(13) . . ?
C12 C10 P1 109.86(13) . . ?
C11 C10 H10 108.5 . . ?
C12 C10 H10 108.5 . . ?
P1 C10 H10 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.96(18) . . ?
C14 C13 P1 122.72(15) . . ?
C18 C13 P1 118.30(15) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 C24 118.9(2) . . ?
C20 C19 C1 119.9(2) . . ?
C24 C19 C1 121.2(2) . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 121.8(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C24 120.6(4) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 119.0(3) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 P1 C1 C19 76.62(17) . . . . ?
C10 P1 C1 C19 -38.44(17) . . . . ?
B1 P1 C1 C19 -160.85(16) . . . . ?
C13 P1 C1 C2 -52.92(16) . . . . ?
C10 P1 C1 C2 -167.98(13) . . . . ?
B1 P1 C1 C2 69.61(16) . . . . ?
C19 C1 C2 C3 78.5(2) . . . . ?
P1 C1 C2 C3 -149.64(16) . . . . ?
C1 C2 C3 O1 20.9(3) . . . . ?
C1 C2 C3 C4 -163.86(16) . . . . ?
O1 C3 C4 C5 -157.67(19) . . . . ?
C2 C3 C4 C5 27.0(3) . . . . ?
O1 C3 C4 C9 22.1(3) . . . . ?
C2 C3 C4 C9 -153.19(19) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 179.21(18) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C4 1.2(3) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C3 C4 C9 C8 179.47(17) . . . . ?
C13 P1 C10 C11 59.40(16) . . . . ?
C1 P1 C10 C11 175.75(13) . . . . ?
B1 P1 C10 C11 -64.91(16) . . . . ?
C13 P1 C10 C12 -177.84(14) . . . . ?
C1 P1 C10 C12 -61.48(16) . . . . ?
B1 P1 C10 C12 57.85(17) . . . . ?
C10 P1 C13 C14 28.5(2) . . . . ?
C1 P1 C13 C14 -87.11(19) . . . . ?
B1 P1 C13 C14 153.08(18) . . . . ?
C10 P1 C13 C18 -149.84(16) . . . . ?
C1 P1 C13 C18 94.58(18) . . . . ?
B1 P1 C13 C18 -25.2(2) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
P1 C13 C14 C15 -178.3(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C14 C13 C18 C17 0.5(3) . . . . ?
P1 C13 C18 C17 178.91(19) . . . . ?
C2 C1 C19 C20 -118.7(2) . . . . ?
P1 C1 C19 C20 113.97(19) . . . . ?
C2 C1 C19 C24 59.4(3) . . . . ?
P1 C1 C19 C24 -67.9(2) . . . . ?
C24 C19 C20 C21 -0.1(3) . . . . ?
C1 C19 C20 C21 178.1(2) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 0.7(5) . . . . ?
C21 C22 C23 C24 -1.3(5) . . . . ?
C20 C19 C24 C23 -0.5(4) . . . . ?
C1 C19 C24 C23 -178.7(2) . . . . ?
C22 C23 C24 C19 1.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 981794'
