# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
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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_cd214116

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H30 Br Cl2 P'
_chemical_formula_weight         560.31

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.9037(7)
_cell_length_b                   21.1560(15)
_cell_length_c                   12.9480(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.929(2)
_cell_angle_gamma                90
_cell_volume                     2702.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2993
_cell_measurement_theta_min      4.555
_cell_measurement_theta_max      44.316

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    1.793
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6693
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16265
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5306
_reflns_number_gt                3734
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+0.9235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5306
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.78878(4) 0.09896(2) 0.86783(3) 0.05995(17) Uani 1 1 d . . . . .
Cl1 Cl 0.43689(19) 0.19310(9) 0.32289(16) 0.1204(6) Uani 1 1 d . . . . .
Cl2 Cl 0.58974(18) 0.27458(10) 0.20041(16) 0.1303(7) Uani 1 1 d . . . . .
P1 P 0.51645(8) 0.40553(4) 0.69827(7) 0.0365(2) Uani 1 1 d . . . . .
C1 C 0.6278(3) 0.42014(16) 0.8143(3) 0.0406(8) Uani 1 1 d . . . . .
C2 C 0.7436(4) 0.45472(18) 0.8030(3) 0.0503(9) Uani 1 1 d . . . . .
H2 H 0.7615 0.4691 0.7377 0.060 Uiso 1 1 calc R U . . .
C3 C 0.8342(4) 0.4683(2) 0.8887(3) 0.0597(11) Uani 1 1 d . . . . .
H3 H 0.9121 0.4918 0.8808 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8073(4) 0.4467(2) 0.9841(3) 0.0614(11) Uani 1 1 d . . . . .
H4 H 0.8684 0.4545 1.0414 0.074 Uiso 1 1 calc R U . . .
C5 C 0.6903(4) 0.41359(19) 0.9960(3) 0.0572(10) Uani 1 1 d . . . . .
H5 H 0.6734 0.3997 1.0619 0.069 Uiso 1 1 calc R U . . .
C6 C 0.5964(4) 0.40016(16) 0.9129(3) 0.0465(8) Uani 1 1 d . . . . .
C7 C 0.4666(4) 0.36703(19) 0.9360(3) 0.0549(10) Uani 1 1 d . . . . .
H7A H 0.4155 0.3565 0.8710 0.066 Uiso 1 1 calc R U . . .
H7B H 0.4895 0.3278 0.9721 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3781(6) 0.4063(2) 1.0009(5) 0.0944(19) Uani 1 1 d . . . . .
H8A H 0.3589 0.4464 0.9666 0.113 Uiso 1 1 calc R U . . .
H8B H 0.4272 0.4149 1.0675 0.113 Uiso 1 1 calc R U . . .
C9 C 0.2442(6) 0.3735(2) 1.0185(5) 0.0968(19) Uani 1 1 d . . . . .
H9A H 0.1938 0.3661 0.9529 0.145 Uiso 1 1 calc R U . . .
H9B H 0.1923 0.3999 1.0606 0.145 Uiso 1 1 calc R U . . .
H9C H 0.2626 0.3338 1.0530 0.145 Uiso 1 1 calc R U . . .
C10 C 0.5855(3) 0.43267(16) 0.5805(3) 0.0405(8) Uani 1 1 d . . . . .
H10A H 0.5140 0.4304 0.5245 0.049 Uiso 1 1 calc R U . . .
H10B H 0.6096 0.4769 0.5897 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7078(4) 0.39809(16) 0.5460(3) 0.0432(8) Uani 1 1 d . . . . .
C12 C 0.6963(5) 0.33845(19) 0.5026(3) 0.0617(11) Uani 1 1 d . . . . .
H12 H 0.6128 0.3181 0.4973 0.074 Uiso 1 1 calc R U . . .
C13 C 0.8076(6) 0.3089(2) 0.4671(4) 0.0810(15) Uani 1 1 d . . . . .
H13 H 0.7988 0.2686 0.4384 0.097 Uiso 1 1 calc R U . . .
C14 C 0.9322(6) 0.3388(3) 0.4740(4) 0.0823(16) Uani 1 1 d . . . . .
H14 H 1.0075 0.3184 0.4515 0.099 Uiso 1 1 calc R U . . .
C15 C 0.9443(4) 0.3989(3) 0.5142(3) 0.0703(13) Uani 1 1 d . . . . .
H15 H 1.0274 0.4196 0.5174 0.084 Uiso 1 1 calc R U . . .
C16 C 0.8325(4) 0.4287(2) 0.5500(3) 0.0543(10) Uani 1 1 d . . . . .
H16 H 0.8410 0.4694 0.5769 0.065 Uiso 1 1 calc R U . . .
C17 C 0.4822(3) 0.32253(15) 0.6822(3) 0.0385(7) Uani 1 1 d . . . . .
C18 C 0.3866(4) 0.30310(17) 0.6042(3) 0.0473(8) Uani 1 1 d . . . . .
H18 H 0.3342 0.3327 0.5657 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3698(4) 0.2395(2) 0.5843(3) 0.0599(11) Uani 1 1 d . . . . .
H19 H 0.3055 0.2261 0.5324 0.072 Uiso 1 1 calc R U . . .
C20 C 0.4476(5) 0.19567(19) 0.6407(4) 0.0647(12) Uani 1 1 d . . . . .
H20 H 0.4356 0.1528 0.6266 0.078 Uiso 1 1 calc R U . . .
C21 C 0.5424(4) 0.21470(18) 0.7174(3) 0.0604(11) Uani 1 1 d . . . . .
H21 H 0.5944 0.1847 0.7554 0.073 Uiso 1 1 calc R U . . .
C22 C 0.5613(4) 0.27810(16) 0.7386(3) 0.0465(8) Uani 1 1 d . . . . .
H22 H 0.6265 0.2910 0.7903 0.056 Uiso 1 1 calc R U . . .
C23 C 0.3634(3) 0.45001(16) 0.7089(3) 0.0395(7) Uani 1 1 d . . . . .
C24 C 0.3730(4) 0.51571(16) 0.7063(3) 0.0467(8) Uani 1 1 d . . . . .
H24 H 0.4559 0.5352 0.6992 0.056 Uiso 1 1 calc R U . . .
C25 C 0.2575(4) 0.55172(19) 0.7146(3) 0.0553(10) Uani 1 1 d . . . . .
H25 H 0.2628 0.5956 0.7126 0.066 Uiso 1 1 calc R U . . .
C26 C 0.1343(4) 0.5228(2) 0.7258(3) 0.0583(11) Uani 1 1 d . . . . .
H26 H 0.0569 0.5471 0.7300 0.070 Uiso 1 1 calc R U . . .
C27 C 0.1264(4) 0.4582(2) 0.7306(3) 0.0560(10) Uani 1 1 d . . . . .
H27 H 0.0438 0.4390 0.7401 0.067 Uiso 1 1 calc R U . . .
C28 C 0.2399(4) 0.42108(19) 0.7217(3) 0.0499(9) Uani 1 1 d . . . . .
H28 H 0.2337 0.3773 0.7242 0.060 Uiso 1 1 calc R U . . .
C29 C 0.4328(6) 0.2582(3) 0.2450(5) 0.0975(18) Uani 1 1 d . . . . .
H29A H 0.4036 0.2944 0.2833 0.117 Uiso 1 1 calc R U . . .
H29B H 0.3670 0.2516 0.1861 0.117 Uiso 1 1 calc R U . . .


_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
Cl1 C29 1.706(6) . ?
Cl2 C29 1.738(5) . ?
P1 C17 1.797(3) . ?
P1 C23 1.800(3) . ?
P1 C1 1.812(3) . ?
P1 C10 1.818(3) . ?
C1 C2 1.379(5) . ?
C1 C6 1.405(5) . ?
C2 C3 1.395(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(5) . ?
C7 C8 1.514(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.531(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.514(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.382(5) . ?
C11 C16 1.391(5) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.386(5) . ?
C17 C22 1.390(5) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.390(5) . ?
C23 C24 1.394(5) . ?
C24 C25 1.386(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.371(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 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
C17 P1 C23 111.59(15) . . ?
C17 P1 C1 110.95(16) . . ?
C23 P1 C1 107.71(16) . . ?
C17 P1 C10 107.01(15) . . ?
C23 P1 C10 106.20(16) . . ?
C1 P1 C10 113.33(16) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 P1 117.0(3) . . ?
C6 C1 P1 122.4(3) . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 122.2(4) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 C7 117.7(3) . . ?
C1 C6 C7 125.1(3) . . ?
C8 C7 C6 113.4(3) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 112.6(4) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 P1 117.5(2) . . ?
C11 C10 H10A 107.9 . . ?
P1 C10 H10A 107.9 . . ?
C11 C10 H10B 107.9 . . ?
P1 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 C10 121.4(3) . . ?
C16 C11 C10 119.6(3) . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C18 C17 C22 120.1(3) . . ?
C18 C17 P1 119.0(3) . . ?
C22 C17 P1 120.5(3) . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.3(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 119.5(4) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C28 C23 C24 120.3(3) . . ?
C28 C23 P1 122.3(3) . . ?
C24 C23 P1 117.4(3) . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 120.1(4) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.7(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C23 119.3(4) . . ?
C27 C28 H28 120.3 . . ?
C23 C28 H28 120.3 . . ?
Cl1 C29 Cl2 112.4(3) . . ?
Cl1 C29 H29A 109.1 . . ?
Cl2 C29 H29A 109.1 . . ?
Cl1 C29 H29B 109.1 . . ?
Cl2 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?

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
C17 P1 C1 C2 126.4(3) . . . . ?
C23 P1 C1 C2 -111.2(3) . . . . ?
C10 P1 C1 C2 6.0(3) . . . . ?
C17 P1 C1 C6 -56.5(3) . . . . ?
C23 P1 C1 C6 65.9(3) . . . . ?
C10 P1 C1 C6 -176.9(3) . . . . ?
C6 C1 C2 C3 2.5(6) . . . . ?
P1 C1 C2 C3 179.7(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -1.9(6) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C1 2.0(6) . . . . ?
C4 C5 C6 C7 -176.1(4) . . . . ?
C2 C1 C6 C5 -3.6(5) . . . . ?
P1 C1 C6 C5 179.4(3) . . . . ?
C2 C1 C6 C7 174.4(4) . . . . ?
P1 C1 C6 C7 -2.6(5) . . . . ?
C5 C6 C7 C8 64.8(5) . . . . ?
C1 C6 C7 C8 -113.2(5) . . . . ?
C6 C7 C8 C9 177.0(5) . . . . ?
C17 P1 C10 C11 -54.4(3) . . . . ?
C23 P1 C10 C11 -173.7(3) . . . . ?
C1 P1 C10 C11 68.2(3) . . . . ?
P1 C10 C11 C12 73.8(4) . . . . ?
P1 C10 C11 C16 -111.6(3) . . . . ?
C16 C11 C12 C13 2.2(6) . . . . ?
C10 C11 C12 C13 176.8(4) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
C12 C13 C14 C15 -1.5(7) . . . . ?
C13 C14 C15 C16 1.6(7) . . . . ?
C14 C15 C16 C11 0.3(7) . . . . ?
C12 C11 C16 C15 -2.1(6) . . . . ?
C10 C11 C16 C15 -176.9(4) . . . . ?
C23 P1 C17 C18 52.5(3) . . . . ?
C1 P1 C17 C18 172.6(3) . . . . ?
C10 P1 C17 C18 -63.3(3) . . . . ?
C23 P1 C17 C22 -135.1(3) . . . . ?
C1 P1 C17 C22 -15.0(3) . . . . ?
C10 P1 C17 C22 109.1(3) . . . . ?
C22 C17 C18 C19 0.8(5) . . . . ?
P1 C17 C18 C19 173.2(3) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
C18 C19 C20 C21 0.1(6) . . . . ?
C19 C20 C21 C22 -0.3(6) . . . . ?
C20 C21 C22 C17 0.7(6) . . . . ?
C18 C17 C22 C21 -1.0(5) . . . . ?
P1 C17 C22 C21 -173.3(3) . . . . ?
C17 P1 C23 C28 10.7(4) . . . . ?
C1 P1 C23 C28 -111.3(3) . . . . ?
C10 P1 C23 C28 127.0(3) . . . . ?
C17 P1 C23 C24 -170.8(3) . . . . ?
C1 P1 C23 C24 67.2(3) . . . . ?
C10 P1 C23 C24 -54.6(3) . . . . ?
C28 C23 C24 C25 -1.3(5) . . . . ?
P1 C23 C24 C25 -179.8(3) . . . . ?
C23 C24 C25 C26 0.4(6) . . . . ?
C24 C25 C26 C27 1.2(6) . . . . ?
C25 C26 C27 C28 -1.7(6) . . . . ?
C26 C27 C28 C23 0.8(6) . . . . ?
C24 C23 C28 C27 0.8(6) . . . . ?
P1 C23 C28 C27 179.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 Br1 0.93 3.09 3.766(4) 131.1 2_656
C10 H10A Br1 0.97 2.95 3.908(4) 170.0 4_565
C10 H10B Br1 0.97 2.81 3.773(3) 172.2 2_656
C18 H18 Br1 0.93 2.94 3.754(4) 146.5 4_565
C24 H24 Br1 0.93 3.06 3.975(4) 169.2 2_656
C29 H29A Br1 0.97 2.79 3.753(6) 171.1 4_565

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 992105'
#######################################################################
#
#                 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_cd213470

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 Br O P'
_chemical_formula_weight         477.36

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)/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                   10.419(6)
_cell_length_b                   12.707(8)
_cell_length_c                   18.309(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.667(13)
_cell_angle_gamma                90.00
_cell_volume                     2355(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4110
_cell_measurement_theta_min      4.579
_cell_measurement_theta_max      49.636

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.42515
_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            13933
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4627
_reflns_number_gt                3766
_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)+(0.0586P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4627
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.20116(2) 0.663034(19) 0.068764(13) 0.04745(11) Uani 1 1 d . . .
P1 P 0.23125(6) 0.31650(4) 0.08914(3) 0.03773(15) Uani 1 1 d . . .
O1 O 0.51075(17) 0.21881(15) 0.07759(11) 0.0624(5) Uani 1 1 d . . .
C1 C 0.2776(2) 0.36296(17) 0.00581(13) 0.0399(5) Uani 1 1 d . . .
C2 C 0.1755(2) 0.3957(2) -0.05363(13) 0.0483(6) Uani 1 1 d . . .
H2 H 0.0891 0.3951 -0.0481 0.058 Uiso 1 1 calc R . .
C3 C 0.2010(3) 0.4289(2) -0.12025(15) 0.0586(7) Uani 1 1 d . . .
H3 H 0.1320 0.4502 -0.1596 0.070 Uiso 1 1 calc R . .
C4 C 0.3276(3) 0.4304(2) -0.12849(15) 0.0613(7) Uani 1 1 d . . .
H4 H 0.3453 0.4536 -0.1733 0.074 Uiso 1 1 calc R . .
C5 C 0.4299(3) 0.3973(2) -0.06999(15) 0.0567(7) Uani 1 1 d . . .
H5 H 0.5157 0.3983 -0.0765 0.068 Uiso 1 1 calc R . .
C6 C 0.4084(2) 0.36304(18) -0.00255(14) 0.0452(5) Uani 1 1 d . . .
C7 C 0.5248(2) 0.3250(2) 0.05743(16) 0.0558(7) Uani 1 1 d . . .
H7A H 0.6047 0.3320 0.0393 0.067 Uiso 1 1 calc R . .
H7B H 0.5342 0.3690 0.1017 0.067 Uiso 1 1 calc R . .
C8 C 0.5356(4) 0.1484(3) 0.0234(2) 0.0879(11) Uani 1 1 d . . .
H8A H 0.4680 0.1556 -0.0221 0.132 Uiso 1 1 calc R . .
H8B H 0.5358 0.0777 0.0418 0.132 Uiso 1 1 calc R . .
H8C H 0.6200 0.1640 0.0134 0.132 Uiso 1 1 calc R . .
C9 C 0.3491(2) 0.34941(19) 0.17510(14) 0.0461(6) Uani 1 1 d . . .
C10 C 0.3587(3) 0.4536(2) 0.19719(15) 0.0620(7) Uani 1 1 d . . .
H10 H 0.3095 0.5048 0.1665 0.074 Uiso 1 1 calc R . .
C11 C 0.4418(3) 0.4814(3) 0.26509(18) 0.0821(10) Uani 1 1 d . . .
H11 H 0.4468 0.5512 0.2806 0.098 Uiso 1 1 calc R . .
C12 C 0.5165(3) 0.4067(4) 0.3095(2) 0.0936(13) Uani 1 1 d . . .
H12 H 0.5720 0.4260 0.3552 0.112 Uiso 1 1 calc R . .
C13 C 0.5101(3) 0.3048(3) 0.28739(18) 0.0855(11) Uani 1 1 d . . .
H13 H 0.5627 0.2548 0.3175 0.103 Uiso 1 1 calc R . .
C14 C 0.4254(3) 0.2740(2) 0.21999(16) 0.0627(7) Uani 1 1 d . . .
H14 H 0.4201 0.2038 0.2053 0.075 Uiso 1 1 calc R . .
C15 C 0.0781(2) 0.38026(19) 0.09455(12) 0.0409(5) Uani 1 1 d . . .
H15A H 0.0944 0.4547 0.1040 0.049 Uiso 1 1 calc R . .
H15B H 0.0149 0.3731 0.0465 0.049 Uiso 1 1 calc R . .
C16 C 0.0195(2) 0.3350(2) 0.15515(14) 0.0500(6) Uani 1 1 d . . .
C17 C 0.0656(3) 0.3589(3) 0.23057(16) 0.0740(9) Uani 1 1 d . . .
H17 H 0.1342 0.4068 0.2458 0.089 Uiso 1 1 calc R . .
C18 C 0.0080(5) 0.3102(4) 0.28388(19) 0.0998(14) Uani 1 1 d . . .
H18 H 0.0402 0.3242 0.3348 0.120 Uiso 1 1 calc R . .
C19 C -0.0936(5) 0.2432(4) 0.2614(2) 0.1120(16) Uani 1 1 d . . .
H19 H -0.1313 0.2116 0.2972 0.134 Uiso 1 1 calc R . .
C20 C -0.1417(4) 0.2212(4) 0.1881(2) 0.1081(14) Uani 1 1 d . . .
H20 H -0.2127 0.1753 0.1735 0.130 Uiso 1 1 calc R . .
C21 C -0.0858(3) 0.2667(3) 0.13472(17) 0.0707(8) Uani 1 1 d . . .
H21 H -0.1195 0.2511 0.0842 0.085 Uiso 1 1 calc R . .
C22 C 0.2047(2) 0.17797(19) 0.08226(16) 0.0486(6) Uani 1 1 d . . .
C23 C 0.1825(3) 0.1215(2) 0.14392(18) 0.0651(7) Uani 1 1 d . . .
H23 H 0.1831 0.1557 0.1889 0.078 Uiso 1 1 calc R . .
C24 C 0.1600(3) 0.0151(3) 0.1370(3) 0.0865(12) Uani 1 1 d . . .
H24 H 0.1453 -0.0230 0.1776 0.104 Uiso 1 1 calc R . .
C25 C 0.1588(3) -0.0354(3) 0.0706(3) 0.0881(13) Uani 1 1 d . . .
H25 H 0.1456 -0.1078 0.0671 0.106 Uiso 1 1 calc R . .
C26 C 0.1766(3) 0.0189(2) 0.0103(2) 0.0812(11) Uani 1 1 d . . .
H26 H 0.1731 -0.0160 -0.0347 0.097 Uiso 1 1 calc R . .
C27 C 0.2002(2) 0.1268(2) 0.01527(18) 0.0604(7) Uani 1 1 d . . .
H27 H 0.2129 0.1640 -0.0262 0.072 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 C22 1.782(3) . ?
P1 C9 1.802(3) . ?
P1 C1 1.805(2) . ?
P1 C15 1.813(2) . ?
O1 C8 1.405(4) . ?
O1 C7 1.415(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.381(4) . ?
C9 C14 1.384(4) . ?
C10 C11 1.382(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.354(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.502(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.380(4) . ?
C16 C17 1.384(4) . ?
C17 C18 1.405(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.345(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.347(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.379(4) . ?
C22 C23 1.402(4) . ?
C23 C24 1.373(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.350(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.393(4) . ?
C26 H26 0.9300 . ?
C27 H27 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
C22 P1 C9 110.70(12) . . ?
C22 P1 C1 109.36(12) . . ?
C9 P1 C1 113.52(12) . . ?
C22 P1 C15 108.74(11) . . ?
C9 P1 C15 105.99(12) . . ?
C1 P1 C15 108.36(11) . . ?
C8 O1 C7 112.0(2) . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 P1 116.76(18) . . ?
C6 C1 P1 123.50(18) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 C7 118.7(2) . . ?
C1 C6 C7 123.6(2) . . ?
O1 C7 C6 112.3(2) . . ?
O1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
O1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 119.9(2) . . ?
C10 C9 P1 117.74(18) . . ?
C14 C9 P1 122.3(2) . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 119.1(3) . . ?
C9 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 P1 112.72(16) . . ?
C16 C15 H15A 109.0 . . ?
P1 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
P1 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C21 C16 C17 118.4(3) . . ?
C21 C16 C15 118.5(2) . . ?
C17 C16 C15 123.2(3) . . ?
C16 C17 C18 119.5(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C27 C22 C23 119.9(3) . . ?
C27 C22 P1 120.0(2) . . ?
C23 C22 P1 120.0(2) . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.7(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.4(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 119.4(3) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?

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
C22 P1 C1 C2 90.9(2) . . . . ?
C9 P1 C1 C2 -144.92(19) . . . . ?
C15 P1 C1 C2 -27.5(2) . . . . ?
C22 P1 C1 C6 -86.2(2) . . . . ?
C9 P1 C1 C6 37.9(2) . . . . ?
C15 P1 C1 C6 155.37(19) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
P1 C1 C2 C3 -177.7(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
P1 C1 C6 C5 177.85(19) . . . . ?
C2 C1 C6 C7 -177.5(2) . . . . ?
P1 C1 C6 C7 -0.4(3) . . . . ?
C8 O1 C7 C6 76.4(3) . . . . ?
C5 C6 C7 O1 -119.7(3) . . . . ?
C1 C6 C7 O1 58.6(3) . . . . ?
C22 P1 C9 C10 -165.8(2) . . . . ?
C1 P1 C9 C10 70.8(2) . . . . ?
C15 P1 C9 C10 -48.0(2) . . . . ?
C22 P1 C9 C14 11.9(3) . . . . ?
C1 P1 C9 C14 -111.5(2) . . . . ?
C15 P1 C9 C14 129.7(2) . . . . ?
C14 C9 C10 C11 -1.8(4) . . . . ?
P1 C9 C10 C11 175.9(2) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -1.4(6) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
P1 C9 C14 C13 -177.1(2) . . . . ?
C12 C13 C14 C9 1.1(5) . . . . ?
C22 P1 C15 C16 52.3(2) . . . . ?
C9 P1 C15 C16 -66.7(2) . . . . ?
C1 P1 C15 C16 171.13(17) . . . . ?
P1 C15 C16 C21 -102.4(2) . . . . ?
P1 C15 C16 C17 77.9(3) . . . . ?
C21 C16 C17 C18 2.5(4) . . . . ?
C15 C16 C17 C18 -177.8(3) . . . . ?
C16 C17 C18 C19 -1.9(5) . . . . ?
C17 C18 C19 C20 0.3(7) . . . . ?
C18 C19 C20 C21 0.7(7) . . . . ?
C19 C20 C21 C16 0.0(6) . . . . ?
C17 C16 C21 C20 -1.6(5) . . . . ?
C15 C16 C21 C20 178.7(3) . . . . ?
C9 P1 C22 C27 -135.9(2) . . . . ?
C1 P1 C22 C27 -10.1(2) . . . . ?
C15 P1 C22 C27 108.0(2) . . . . ?
C9 P1 C22 C23 46.8(2) . . . . ?
C1 P1 C22 C23 172.65(19) . . . . ?
C15 P1 C22 C23 -69.2(2) . . . . ?
C27 C22 C23 C24 1.7(4) . . . . ?
P1 C22 C23 C24 178.9(2) . . . . ?
C22 C23 C24 C25 -0.1(5) . . . . ?
C23 C24 C25 C26 -1.6(5) . . . . ?
C24 C25 C26 C27 1.8(5) . . . . ?
C23 C22 C27 C26 -1.4(4) . . . . ?
P1 C22 C27 C26 -178.7(2) . . . . ?
C25 C26 C27 C22 -0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 962019'
#######################################################################
#
#                 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_cd213438

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 Br O2 P'
_chemical_formula_weight         505.37

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                   10.9121(12)
_cell_length_b                   17.4195(19)
_cell_length_c                   12.6700(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.809(2)
_cell_angle_gamma                90.00
_cell_volume                     2365.6(5)
_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          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6578
_exptl_absorpt_correction_T_max  0.7711
_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            16472
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         28.36
_reflns_number_total             5874
_reflns_number_gt                3981
_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)+(0.0628P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5874
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.19875(3) 0.367264(15) 0.39412(2) 0.05602(12) Uani 1 1 d . . .
O1 O 0.23583(15) 0.41568(11) 1.00094(14) 0.0450(4) Uani 1 1 d . . .
O2 O 0.43951(17) 0.43212(12) 1.07239(14) 0.0524(5) Uani 1 1 d . . .
P1 P 0.16893(5) 0.47682(3) 0.74355(5) 0.02983(14) Uani 1 1 d . . .
C1 C 0.1412(2) 0.51090(14) 0.60556(18) 0.0368(5) Uani 1 1 d . . .
H1A H 0.1510 0.4676 0.5597 0.044 Uiso 1 1 calc R . .
H1B H 0.0548 0.5272 0.5872 0.044 Uiso 1 1 calc R . .
C2 C 0.2213(2) 0.57552(14) 0.57768(18) 0.0374(5) Uani 1 1 d . . .
C3 C 0.3432(3) 0.56347(17) 0.5639(2) 0.0493(7) Uani 1 1 d . . .
H3 H 0.3776 0.5145 0.5719 0.059 Uiso 1 1 calc R . .
C4 C 0.4130(3) 0.62446(19) 0.5383(3) 0.0599(8) Uani 1 1 d . . .
H4 H 0.4956 0.6167 0.5318 0.072 Uiso 1 1 calc R . .
C5 C 0.3618(3) 0.69657(18) 0.5224(2) 0.0628(9) Uani 1 1 d . . .
H5 H 0.4089 0.7370 0.5032 0.075 Uiso 1 1 calc R . .
C6 C 0.2418(3) 0.70880(16) 0.5346(2) 0.0601(8) Uani 1 1 d . . .
H6 H 0.2072 0.7576 0.5235 0.072 Uiso 1 1 calc R . .
C7 C 0.1710(3) 0.64881(15) 0.5638(2) 0.0480(7) Uani 1 1 d . . .
H7 H 0.0900 0.6578 0.5739 0.058 Uiso 1 1 calc R . .
C8 C 0.1677(2) 0.55816(12) 0.83109(18) 0.0319(5) Uani 1 1 d . . .
C9 C 0.2531(2) 0.61725(14) 0.8302(2) 0.0408(6) Uani 1 1 d . . .
H9 H 0.3088 0.6156 0.7829 0.049 Uiso 1 1 calc R . .
C10 C 0.2548(3) 0.67858(14) 0.9001(2) 0.0473(7) Uani 1 1 d . . .
H10 H 0.3108 0.7186 0.8988 0.057 Uiso 1 1 calc R . .
C11 C 0.1740(3) 0.68051(15) 0.9714(2) 0.0510(7) Uani 1 1 d . . .
H11 H 0.1767 0.7215 1.0188 0.061 Uiso 1 1 calc R . .
C12 C 0.0890(3) 0.62213(15) 0.9728(2) 0.0489(7) Uani 1 1 d . . .
H12 H 0.0342 0.6238 1.0209 0.059 Uiso 1 1 calc R . .
C13 C 0.0856(2) 0.56070(13) 0.9022(2) 0.0394(6) Uani 1 1 d . . .
H13 H 0.0282 0.5213 0.9027 0.047 Uiso 1 1 calc R . .
C14 C 0.3115(2) 0.42206(12) 0.77624(18) 0.0330(5) Uani 1 1 d . . .
C15 C 0.3456(2) 0.38198(14) 0.6912(2) 0.0419(6) Uani 1 1 d . . .
H15 H 0.3003 0.3890 0.6220 0.050 Uiso 1 1 calc R . .
C16 C 0.4456(3) 0.33192(16) 0.7076(2) 0.0492(7) Uani 1 1 d . . .
H16 H 0.4674 0.3058 0.6498 0.059 Uiso 1 1 calc R . .
C17 C 0.5127(3) 0.32080(16) 0.8093(2) 0.0524(7) Uani 1 1 d . . .
H17 H 0.5794 0.2867 0.8209 0.063 Uiso 1 1 calc R . .
C18 C 0.4804(2) 0.36062(15) 0.8947(2) 0.0482(7) Uani 1 1 d . . .
H18 H 0.5276 0.3535 0.9631 0.058 Uiso 1 1 calc R . .
C19 C 0.3802(2) 0.41072(13) 0.88137(18) 0.0337(5) Uani 1 1 d . . .
C20 C 0.3482(2) 0.44733(14) 0.98035(19) 0.0376(5) Uani 1 1 d . . .
H20 H 0.3388 0.5029 0.9697 0.045 Uiso 1 1 calc R . .
C21 C 0.2431(3) 0.4251(3) 1.1136(3) 0.0768(11) Uani 1 1 d . . .
H21A H 0.2099 0.3803 1.1440 0.092 Uiso 1 1 calc R . .
H21B H 0.1960 0.4698 1.1281 0.092 Uiso 1 1 calc R . .
C22 C 0.3779(3) 0.4350(2) 1.1603(2) 0.0678(9) Uani 1 1 d . . .
H22A H 0.3924 0.4839 1.1971 0.081 Uiso 1 1 calc R . .
H22B H 0.4068 0.3942 1.2109 0.081 Uiso 1 1 calc R . .
C23 C 0.0395(2) 0.41379(12) 0.74806(18) 0.0329(5) Uani 1 1 d . . .
C24 C 0.0584(2) 0.33632(14) 0.7720(2) 0.0420(6) Uani 1 1 d . . .
H24 H 0.1389 0.3170 0.7910 0.050 Uiso 1 1 calc R . .
C25 C -0.0429(3) 0.28835(15) 0.7674(2) 0.0527(7) Uani 1 1 d . . .
H25 H -0.0301 0.2364 0.7827 0.063 Uiso 1 1 calc R . .
C26 C -0.1620(3) 0.31603(17) 0.7408(2) 0.0523(7) Uani 1 1 d . . .
H26 H -0.2296 0.2833 0.7395 0.063 Uiso 1 1 calc R . .
C27 C -0.1814(2) 0.39279(17) 0.7157(2) 0.0480(6) Uani 1 1 d . . .
H27 H -0.2624 0.4114 0.6965 0.058 Uiso 1 1 calc R . .
C28 C -0.0819(2) 0.44190(14) 0.7190(2) 0.0383(5) Uani 1 1 d . . .
H28 H -0.0956 0.4935 0.7019 0.046 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
O1 C20 1.412(3) . ?
O1 C21 1.424(4) . ?
O2 C22 1.405(4) . ?
O2 C20 1.410(3) . ?
P1 C23 1.799(2) . ?
P1 C8 1.801(2) . ?
P1 C14 1.805(2) . ?
P1 C1 1.817(2) . ?
C1 C2 1.507(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.388(3) . ?
C2 C3 1.389(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.385(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.386(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.392(3) . ?
C14 C19 1.415(3) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.505(3) . ?
C20 H20 0.9800 . ?
C21 C22 1.489(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.390(3) . ?
C23 C28 1.396(3) . ?
C24 C25 1.378(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.367(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.377(4) . ?
C27 H27 0.9300 . ?
C28 H28 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
C20 O1 C21 104.7(2) . . ?
C22 O2 C20 106.2(2) . . ?
C23 P1 C8 111.35(11) . . ?
C23 P1 C14 108.55(11) . . ?
C8 P1 C14 112.35(10) . . ?
C23 P1 C1 103.89(11) . . ?
C8 P1 C1 108.44(11) . . ?
C14 P1 C1 111.97(11) . . ?
C2 C1 P1 118.05(16) . . ?
C2 C1 H1A 107.8 . . ?
P1 C1 H1A 107.8 . . ?
C2 C1 H1B 107.8 . . ?
P1 C1 H1B 107.8 . . ?
H1A C1 H1B 107.1 . . ?
C7 C2 C3 119.2(2) . . ?
C7 C2 C1 118.9(2) . . ?
C3 C2 C1 121.8(2) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 119.9(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C13 C8 C9 119.9(2) . . ?
C13 C8 P1 120.41(17) . . ?
C9 C8 P1 119.65(19) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 120.0(2) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C19 119.2(2) . . ?
C15 C14 P1 115.57(18) . . ?
C19 C14 P1 124.87(18) . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C14 118.0(2) . . ?
C18 C19 C20 117.8(2) . . ?
C14 C19 C20 124.1(2) . . ?
O2 C20 O1 106.1(2) . . ?
O2 C20 C19 111.78(19) . . ?
O1 C20 C19 109.50(19) . . ?
O2 C20 H20 109.8 . . ?
O1 C20 H20 109.8 . . ?
C19 C20 H20 109.8 . . ?
O1 C21 C22 106.0(3) . . ?
O1 C21 H21A 110.5 . . ?
C22 C21 H21A 110.5 . . ?
O1 C21 H21B 110.5 . . ?
C22 C21 H21B 110.5 . . ?
H21A C21 H21B 108.7 . . ?
O2 C22 C21 105.4(2) . . ?
O2 C22 H22A 110.7 . . ?
C21 C22 H22A 110.7 . . ?
O2 C22 H22B 110.7 . . ?
C21 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
C24 C23 C28 119.5(2) . . ?
C24 C23 P1 120.94(18) . . ?
C28 C23 P1 119.33(18) . . ?
C25 C24 C23 119.6(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 119.7(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C23 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
C23 C28 H28 120.2 . . ?

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
C23 P1 C1 C2 170.12(19) . . . . ?
C8 P1 C1 C2 51.6(2) . . . . ?
C14 P1 C1 C2 -72.9(2) . . . . ?
P1 C1 C2 C7 -103.9(2) . . . . ?
P1 C1 C2 C3 77.1(3) . . . . ?
C7 C2 C3 C4 1.0(4) . . . . ?
C1 C2 C3 C4 180.0(3) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C3 C2 C7 C6 1.0(4) . . . . ?
C1 C2 C7 C6 -177.9(2) . . . . ?
C5 C6 C7 C2 -1.7(4) . . . . ?
C23 P1 C8 C13 9.2(2) . . . . ?
C14 P1 C8 C13 -112.83(19) . . . . ?
C1 P1 C8 C13 122.87(19) . . . . ?
C23 P1 C8 C9 -173.42(17) . . . . ?
C14 P1 C8 C9 64.6(2) . . . . ?
C1 P1 C8 C9 -59.7(2) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
P1 C8 C9 C10 -177.86(18) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C9 C8 C13 C12 -0.2(4) . . . . ?
P1 C8 C13 C12 177.15(19) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C23 P1 C14 C15 83.8(2) . . . . ?
C8 P1 C14 C15 -152.66(18) . . . . ?
C1 P1 C14 C15 -30.3(2) . . . . ?
C23 P1 C14 C19 -88.8(2) . . . . ?
C8 P1 C14 C19 34.8(2) . . . . ?
C1 P1 C14 C19 157.08(19) . . . . ?
C19 C14 C15 C16 -0.4(4) . . . . ?
P1 C14 C15 C16 -173.5(2) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C17 C18 C19 C14 -1.4(4) . . . . ?
C17 C18 C19 C20 176.2(2) . . . . ?
C15 C14 C19 C18 0.9(3) . . . . ?
P1 C14 C19 C18 173.26(19) . . . . ?
C15 C14 C19 C20 -176.5(2) . . . . ?
P1 C14 C19 C20 -4.2(3) . . . . ?
C22 O2 C20 O1 -33.3(3) . . . . ?
C22 O2 C20 C19 -152.6(2) . . . . ?
C21 O1 C20 O2 33.4(3) . . . . ?
C21 O1 C20 C19 154.2(2) . . . . ?
C18 C19 C20 O2 8.5(3) . . . . ?
C14 C19 C20 O2 -174.1(2) . . . . ?
C18 C19 C20 O1 -108.8(2) . . . . ?
C14 C19 C20 O1 68.7(3) . . . . ?
C20 O1 C21 C22 -20.8(3) . . . . ?
C20 O2 C22 C21 19.4(3) . . . . ?
O1 C21 C22 O2 1.0(4) . . . . ?
C8 P1 C23 C24 -125.2(2) . . . . ?
C14 P1 C23 C24 -1.0(2) . . . . ?
C1 P1 C23 C24 118.3(2) . . . . ?
C8 P1 C23 C28 59.8(2) . . . . ?
C14 P1 C23 C28 -176.00(19) . . . . ?
C1 P1 C23 C28 -56.7(2) . . . . ?
C28 C23 C24 C25 -0.4(4) . . . . ?
P1 C23 C24 C25 -175.4(2) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
C24 C25 C26 C27 1.4(4) . . . . ?
C25 C26 C27 C28 -1.0(4) . . . . ?
C26 C27 C28 C23 -0.1(4) . . . . ?
C24 C23 C28 C27 0.9(4) . . . . ?
P1 C23 C28 C27 175.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 962015'
