# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

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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_uvic1217

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 P, Br'
_chemical_formula_sum            'C27 H22 Br P'
_chemical_formula_weight         457.33

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'
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   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8176(15)
_cell_length_b                   12.4498(18)
_cell_length_c                   18.455(3)
_cell_angle_alpha                98.278(3)
_cell_angle_beta                 94.561(3)
_cell_angle_gamma                107.751(3)
_cell_volume                     2322.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.41

_exptl_crystal_description       tablet
_exptl_crystal_colour            'light brown'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7946
_exptl_absorpt_correction_T_max  0.9390
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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  'Bruker APEX-I'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            47622
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.12
_diffrn_reflns_theta_max         26.41
_reflns_number_total             9517
_reflns_number_gt                7951
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II v2012-2.0'
_computing_cell_refinement       'Bruker SAINT v8.18C'
_computing_data_reduction        'Bruker SAINT v8.18C'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1310P)^2^+10.5522P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9517
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.2057
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.77064(4) -0.00819(4) 0.13317(2) 0.01649(15) Uani 1 1 d . . .
Br2 Br 0.54519(5) 0.42038(4) 0.26878(3) 0.02734(17) Uani 1 1 d . . .
P1 P 0.88338(17) 0.39375(14) 0.12470(10) 0.0386(4) Uani 1 1 d . . .
C1 C 0.8298(7) 0.3242(6) 0.2018(4) 0.0456(16) Uani 1 1 d . . .
H1A H 0.7474 0.3378 0.2133 0.055 Uiso 1 1 calc R . .
H1B H 0.8099 0.2406 0.1864 0.055 Uiso 1 1 calc R . .
C2 C 0.9266(7) 0.3632(6) 0.2713(4) 0.0436(15) Uani 1 1 d . . .
C3 C 0.9253(7) 0.4538(6) 0.3238(4) 0.0450(15) Uani 1 1 d . . .
H3 H 0.8646 0.4934 0.3154 0.054 Uiso 1 1 calc R . .
C4 C 1.0120(7) 0.4873(6) 0.3887(4) 0.0468(16) Uani 1 1 d . . .
H4 H 1.0082 0.5485 0.4248 0.056 Uiso 1 1 calc R . .
C5 C 1.1034(8) 0.4337(6) 0.4019(4) 0.0495(17) Uani 1 1 d . . .
C6 C 1.1048(10) 0.3411(8) 0.3492(5) 0.064(2) Uani 1 1 d . . .
H6 H 1.1667 0.3024 0.3570 0.077 Uiso 1 1 calc R . .
C7 C 1.0144(9) 0.3062(7) 0.2851(4) 0.058(2) Uani 1 1 d . . .
H7 H 1.0135 0.2417 0.2503 0.069 Uiso 1 1 calc R . .
C8 C 1.1943(8) 0.4687(7) 0.4686(4) 0.0556(19) Uani 1 1 d . . .
C9 C 1.2666(10) 0.4967(8) 0.5252(5) 0.068(2) Uani 1 1 d . . .
H9 H 1.3242 0.5190 0.5703 0.081 Uiso 1 1 calc R . .
C10 C 0.7475(7) 0.3482(6) 0.0529(4) 0.0423(15) Uani 1 1 d . . .
C11 C 0.6497(7) 0.2417(6) 0.0490(4) 0.0512(18) Uani 1 1 d . . .
H11 H 0.6537 0.1946 0.0847 0.061 Uiso 1 1 calc R . .
C12 C 0.5472(8) 0.2075(6) -0.0086(5) 0.0547(19) Uani 1 1 d . . .
H12 H 0.4822 0.1347 -0.0132 0.066 Uiso 1 1 calc R . .
C13 C 0.5379(8) 0.2765(7) -0.0588(5) 0.0557(19) Uani 1 1 d . . .
H13 H 0.4665 0.2514 -0.0974 0.067 Uiso 1 1 calc R . .
C14 C 0.6313(9) 0.3817(8) -0.0538(5) 0.067(2) Uani 1 1 d . . .
H14 H 0.6230 0.4304 -0.0878 0.081 Uiso 1 1 calc R . .
C15 C 0.7377(8) 0.4165(7) 0.0011(5) 0.058(2) Uani 1 1 d . . .
H15 H 0.8044 0.4877 0.0032 0.070 Uiso 1 1 calc R . .
C16 C 1.0192(7) 0.3546(6) 0.0933(4) 0.0454(16) Uani 1 1 d . . .
C17 C 1.0006(7) 0.2812(6) 0.0254(4) 0.0454(15) Uani 1 1 d . . .
H17 H 0.9185 0.2561 -0.0049 0.054 Uiso 1 1 calc R . .
C18 C 1.1030(8) 0.2457(7) 0.0031(5) 0.0541(18) Uani 1 1 d . . .
H18 H 1.0917 0.1971 -0.0433 0.065 Uiso 1 1 calc R . .
C19 C 1.2229(9) 0.2812(8) 0.0484(5) 0.060(2) Uani 1 1 d . . .
H19 H 1.2924 0.2557 0.0330 0.072 Uiso 1 1 calc R . .
C20 C 1.2411(8) 0.3524(7) 0.1148(5) 0.058(2) Uani 1 1 d . . .
H20 H 1.3237 0.3772 0.1446 0.070 Uiso 1 1 calc R . .
C21 C 1.1389(7) 0.3889(7) 0.1391(5) 0.0519(18) Uani 1 1 d . . .
H21 H 1.1506 0.4363 0.1860 0.062 Uiso 1 1 calc R . .
C22 C 0.9239(7) 0.5465(6) 0.1508(4) 0.0432(15) Uani 1 1 d . . .
C23 C 1.0471(8) 0.6234(6) 0.1488(4) 0.0499(17) Uani 1 1 d . . .
H23 H 1.1153 0.5956 0.1336 0.060 Uiso 1 1 calc R . .
C24 C 1.0706(9) 0.7392(7) 0.1688(5) 0.059(2) Uani 1 1 d . . .
H24 H 1.1552 0.7916 0.1680 0.071 Uiso 1 1 calc R . .
C25 C 0.9685(10) 0.7797(7) 0.1902(5) 0.062(2) Uani 1 1 d . . .
H25 H 0.9844 0.8596 0.2049 0.075 Uiso 1 1 calc R . .
C26 C 0.8474(9) 0.7047(7) 0.1900(5) 0.059(2) Uani 1 1 d . . .
H26 H 0.7778 0.7327 0.2024 0.071 Uiso 1 1 calc R . .
C27 C 0.8242(8) 0.5876(6) 0.1720(4) 0.0521(18) Uani 1 1 d . . .
H27 H 0.7401 0.5355 0.1741 0.063 Uiso 1 1 calc R . .
P2 P 0.44593(17) 0.03327(15) 0.30060(10) 0.0394(4) Uani 1 1 d . . .
C28 C 0.6126(7) 0.1159(6) 0.2943(4) 0.0440(15) Uani 1 1 d . . .
H28A H 0.6417 0.0777 0.2512 0.053 Uiso 1 1 calc R . .
H28B H 0.6135 0.1923 0.2845 0.053 Uiso 1 1 calc R . .
C29 C 0.7112(7) 0.1331(6) 0.3613(4) 0.0438(15) Uani 1 1 d . . .
C30 C 0.7149(8) 0.2091(6) 0.4242(5) 0.0526(18) Uani 1 1 d . . .
H30 H 0.6550 0.2513 0.4252 0.063 Uiso 1 1 calc R . .
C31 C 0.8016(7) 0.2247(7) 0.4842(5) 0.0534(18) Uani 1 1 d . . .
H31 H 0.8004 0.2769 0.5269 0.064 Uiso 1 1 calc R . .
C32 C 0.8917(8) 0.1677(8) 0.4859(4) 0.0564(19) Uani 1 1 d . . .
C33 C 0.8924(8) 0.0913(8) 0.4231(4) 0.0570(19) Uani 1 1 d . . .
H33 H 0.9536 0.0504 0.4230 0.068 Uiso 1 1 calc R . .
C34 C 0.8039(8) 0.0746(7) 0.3605(4) 0.0520(18) Uani 1 1 d . . .
H34 H 0.8059 0.0238 0.3173 0.062 Uiso 1 1 calc R . .
C35 C 0.9886(10) 0.1879(8) 0.5555(6) 0.067(2) Uani 1 1 d . . .
C36 C 1.0546(13) 0.2046(12) 0.6059(7) 0.101(4) Uani 1 1 d . . .
H36 H 1.1127 0.2193 0.6502 0.122 Uiso 1 1 calc R . .
C37 C 0.4248(7) -0.1151(6) 0.3026(4) 0.0431(15) Uani 1 1 d . . .
C38 C 0.3085(8) -0.1832(7) 0.3205(4) 0.0519(17) Uani 1 1 d . . .
H38 H 0.2438 -0.1499 0.3344 0.062 Uiso 1 1 calc R . .
C39 C 0.2852(9) -0.2981(7) 0.3183(5) 0.059(2) Uani 1 1 d . . .
H39 H 0.2046 -0.3440 0.3305 0.071 Uiso 1 1 calc R . .
C40 C 0.3786(9) -0.3476(7) 0.2983(5) 0.0565(19) Uani 1 1 d . . .
H40 H 0.3636 -0.4268 0.2986 0.068 Uiso 1 1 calc R . .
C41 C 0.4940(9) -0.2814(7) 0.2781(5) 0.061(2) Uani 1 1 d . . .
H41 H 0.5571 -0.3160 0.2630 0.073 Uiso 1 1 calc R . .
C42 C 0.5186(8) -0.1644(7) 0.2794(4) 0.0535(18) Uani 1 1 d . . .
H42 H 0.5974 -0.1190 0.2650 0.064 Uiso 1 1 calc R . .
C43 C 0.3452(7) 0.0377(6) 0.2196(4) 0.0431(15) Uani 1 1 d . . .
C44 C 0.2301(7) 0.0638(6) 0.2233(4) 0.0452(15) Uani 1 1 d . . .
H44 H 0.2044 0.0859 0.2697 0.054 Uiso 1 1 calc R . .
C45 C 0.1523(8) 0.0571(7) 0.1576(5) 0.0545(19) Uani 1 1 d . . .
H45 H 0.0735 0.0754 0.1596 0.065 Uiso 1 1 calc R . .
C46 C 0.1874(8) 0.0247(6) 0.0907(5) 0.0530(18) Uani 1 1 d . . .
H46 H 0.1328 0.0207 0.0468 0.064 Uiso 1 1 calc R . .
C47 C 0.3040(8) -0.0030(7) 0.0859(4) 0.0523(18) Uani 1 1 d . . .
H47 H 0.3277 -0.0263 0.0392 0.063 Uiso 1 1 calc R . .
C48 C 0.3841(8) 0.0042(7) 0.1509(4) 0.0509(17) Uani 1 1 d . . .
H48 H 0.4636 -0.0131 0.1489 0.061 Uiso 1 1 calc R . .
C49 C 0.3985(7) 0.0977(6) 0.3832(4) 0.0460(16) Uani 1 1 d . . .
C50 C 0.3903(7) 0.2068(7) 0.3855(4) 0.0498(17) Uani 1 1 d . . .
H50 H 0.3942 0.2395 0.3419 0.060 Uiso 1 1 calc R . .
C51 C 0.3763(9) 0.2689(8) 0.4519(5) 0.062(2) Uani 1 1 d . . .
H51 H 0.3748 0.3453 0.4545 0.074 Uiso 1 1 calc R . .
C52 C 0.3646(10) 0.2167(10) 0.5146(5) 0.074(3) Uani 1 1 d . . .
H52 H 0.3505 0.2568 0.5594 0.088 Uiso 1 1 calc R . .
C53 C 0.3733(9) 0.1092(9) 0.5122(5) 0.069(2) Uani 1 1 d . . .
H53 H 0.3683 0.0761 0.5556 0.082 Uiso 1 1 calc R . .
C54 C 0.3895(8) 0.0473(7) 0.4457(4) 0.0532(18) Uani 1 1 d . . .
H54 H 0.3942 -0.0280 0.4436 0.064 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0158(2) 0.0150(2) 0.0170(2) -0.00086(16) 0.00192(16) 0.00428(17)
Br2 0.0285(3) 0.0280(3) 0.0295(3) 0.0119(2) 0.0028(2) 0.0120(2)
P1 0.0417(9) 0.0315(8) 0.0380(9) 0.0056(7) 0.0037(7) 0.0058(7)
C1 0.057(4) 0.031(3) 0.048(4) 0.010(3) 0.010(3) 0.010(3)
C2 0.058(4) 0.032(3) 0.039(3) 0.008(3) 0.007(3) 0.010(3)
C3 0.050(4) 0.042(4) 0.045(4) 0.008(3) 0.007(3) 0.017(3)
C4 0.056(4) 0.044(4) 0.040(4) 0.002(3) 0.009(3) 0.019(3)
C5 0.066(5) 0.046(4) 0.041(4) 0.009(3) 0.011(3) 0.023(4)
C6 0.088(6) 0.062(5) 0.050(4) 0.000(4) -0.004(4) 0.042(5)
C7 0.088(6) 0.051(4) 0.041(4) 0.004(3) -0.001(4) 0.037(4)
C8 0.066(5) 0.058(5) 0.047(4) 0.004(4) 0.005(4) 0.030(4)
C9 0.080(6) 0.072(6) 0.055(5) -0.008(4) -0.010(4) 0.044(5)
C10 0.042(4) 0.042(4) 0.041(3) 0.006(3) 0.005(3) 0.013(3)
C11 0.051(4) 0.039(4) 0.058(4) 0.012(3) -0.002(3) 0.006(3)
C12 0.049(4) 0.041(4) 0.062(5) 0.005(3) -0.005(4) 0.003(3)
C13 0.045(4) 0.055(5) 0.057(5) 0.010(4) -0.002(3) 0.004(3)
C14 0.064(5) 0.063(5) 0.062(5) 0.028(4) -0.011(4) 0.000(4)
C15 0.055(5) 0.047(4) 0.058(5) 0.017(4) 0.000(4) -0.006(3)
C16 0.041(4) 0.040(4) 0.050(4) 0.013(3) 0.003(3) 0.004(3)
C17 0.045(4) 0.043(4) 0.049(4) 0.011(3) 0.006(3) 0.013(3)
C18 0.061(5) 0.053(4) 0.056(5) 0.019(4) 0.016(4) 0.023(4)
C19 0.057(5) 0.063(5) 0.071(6) 0.027(4) 0.016(4) 0.027(4)
C20 0.042(4) 0.060(5) 0.077(6) 0.030(4) 0.002(4) 0.016(4)
C21 0.048(4) 0.050(4) 0.054(4) 0.010(3) -0.002(3) 0.012(3)
C22 0.056(4) 0.032(3) 0.037(3) 0.005(3) 0.004(3) 0.009(3)
C23 0.054(4) 0.044(4) 0.043(4) 0.008(3) 0.000(3) 0.005(3)
C24 0.069(5) 0.039(4) 0.057(5) 0.013(3) -0.001(4) 0.001(4)
C25 0.086(6) 0.039(4) 0.060(5) 0.008(4) 0.011(4) 0.016(4)
C26 0.078(6) 0.040(4) 0.061(5) 0.012(4) 0.016(4) 0.018(4)
C27 0.058(4) 0.041(4) 0.058(4) 0.011(3) 0.012(4) 0.013(3)
P2 0.0425(9) 0.0395(9) 0.0400(9) 0.0115(7) 0.0103(7) 0.0153(7)
C28 0.049(4) 0.043(4) 0.044(4) 0.014(3) 0.014(3) 0.015(3)
C29 0.043(4) 0.042(4) 0.046(4) 0.012(3) 0.010(3) 0.010(3)
C30 0.048(4) 0.044(4) 0.062(5) -0.001(3) 0.007(4) 0.013(3)
C31 0.043(4) 0.060(5) 0.052(4) -0.001(4) 0.004(3) 0.015(3)
C32 0.048(4) 0.065(5) 0.049(4) 0.011(4) 0.002(3) 0.009(4)
C33 0.061(5) 0.070(5) 0.051(4) 0.009(4) 0.010(4) 0.036(4)
C34 0.056(4) 0.059(5) 0.047(4) 0.008(3) 0.009(3) 0.027(4)
C35 0.065(5) 0.068(6) 0.065(6) 0.003(4) 0.012(5) 0.019(4)
C36 0.093(8) 0.139(12) 0.064(7) -0.014(7) -0.010(6) 0.047(8)
C37 0.047(4) 0.040(3) 0.045(4) 0.013(3) 0.006(3) 0.015(3)
C38 0.051(4) 0.049(4) 0.056(4) 0.017(3) 0.008(3) 0.014(3)
C39 0.065(5) 0.045(4) 0.061(5) 0.015(4) 0.010(4) 0.007(4)
C40 0.074(5) 0.037(4) 0.059(5) 0.014(3) 0.006(4) 0.019(4)
C41 0.075(6) 0.046(4) 0.069(5) 0.013(4) 0.022(4) 0.027(4)
C42 0.062(5) 0.048(4) 0.056(4) 0.012(3) 0.016(4) 0.021(4)
C43 0.046(4) 0.043(4) 0.041(4) 0.013(3) 0.009(3) 0.012(3)
C44 0.041(4) 0.043(4) 0.051(4) 0.009(3) 0.005(3) 0.013(3)
C45 0.043(4) 0.046(4) 0.075(6) 0.012(4) 0.002(4) 0.016(3)
C46 0.054(4) 0.045(4) 0.055(4) 0.009(3) -0.004(4) 0.010(3)
C47 0.058(4) 0.054(4) 0.042(4) 0.014(3) 0.004(3) 0.013(4)
C48 0.053(4) 0.059(5) 0.044(4) 0.015(3) 0.007(3) 0.020(4)
C49 0.044(4) 0.053(4) 0.042(4) 0.011(3) 0.011(3) 0.015(3)
C50 0.053(4) 0.053(4) 0.049(4) 0.008(3) 0.008(3) 0.026(3)
C51 0.071(5) 0.068(5) 0.055(5) 0.004(4) 0.009(4) 0.036(5)
C52 0.086(7) 0.105(8) 0.047(5) 0.006(5) 0.021(4) 0.056(6)
C53 0.071(6) 0.090(7) 0.052(5) 0.020(5) 0.020(4) 0.031(5)
C54 0.058(5) 0.061(5) 0.046(4) 0.016(3) 0.016(3) 0.022(4)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C10 1.790(7) . ?
P1 C16 1.795(8) . ?
P1 C22 1.799(7) . ?
P1 C1 1.814(7) . ?
C1 C2 1.508(10) . ?
C2 C7 1.377(11) . ?
C2 C3 1.381(10) . ?
C3 C4 1.389(10) . ?
C4 C5 1.375(10) . ?
C5 C6 1.401(11) . ?
C5 C8 1.436(11) . ?
C6 C7 1.398(11) . ?
C8 C9 1.194(12) . ?
C10 C15 1.386(10) . ?
C10 C11 1.410(10) . ?
C11 C12 1.391(10) . ?
C12 C13 1.368(11) . ?
C13 C14 1.375(11) . ?
C14 C15 1.387(11) . ?
C16 C21 1.400(10) . ?
C16 C17 1.401(10) . ?
C17 C18 1.382(10) . ?
C18 C19 1.396(12) . ?
C19 C20 1.366(13) . ?
C20 C21 1.399(11) . ?
C22 C27 1.387(11) . ?
C22 C23 1.390(10) . ?
C23 C24 1.374(11) . ?
C24 C25 1.409(13) . ?
C25 C26 1.357(12) . ?
C26 C27 1.388(10) . ?
P2 C43 1.796(7) . ?
P2 C37 1.797(7) . ?
P2 C49 1.803(7) . ?
P2 C28 1.805(7) . ?
C28 C29 1.513(10) . ?
C29 C30 1.378(10) . ?
C29 C34 1.407(10) . ?
C30 C31 1.344(11) . ?
C31 C32 1.371(11) . ?
C32 C33 1.391(11) . ?
C32 C35 1.531(13) . ?
C33 C34 1.389(11) . ?
C35 C36 1.078(14) . ?
C37 C38 1.381(10) . ?
C37 C42 1.401(10) . ?
C38 C39 1.368(11) . ?
C39 C40 1.382(12) . ?
C40 C41 1.383(12) . ?
C41 C42 1.395(11) . ?
C43 C44 1.384(10) . ?
C43 C48 1.414(10) . ?
C44 C45 1.396(11) . ?
C45 C46 1.363(12) . ?
C46 C47 1.411(11) . ?
C47 C48 1.397(10) . ?
C49 C50 1.383(10) . ?
C49 C54 1.386(10) . ?
C50 C51 1.397(11) . ?
C51 C52 1.403(13) . ?
C52 C53 1.365(14) . ?
C53 C54 1.406(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C36 H36 0.9500 . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 P1 C16 110.6(3) . . ?
C10 P1 C22 106.8(3) . . ?
C16 P1 C22 111.7(3) . . ?
C10 P1 C1 107.5(3) . . ?
C16 P1 C1 110.1(3) . . ?
C22 P1 C1 110.1(3) . . ?
C2 C1 P1 115.1(5) . . ?
C7 C2 C3 118.6(7) . . ?
C7 C2 C1 120.6(6) . . ?
C3 C2 C1 120.7(7) . . ?
C2 C3 C4 120.6(7) . . ?
C5 C4 C3 121.3(7) . . ?
C4 C5 C6 118.6(7) . . ?
C4 C5 C8 121.6(7) . . ?
C6 C5 C8 119.8(7) . . ?
C7 C6 C5 119.4(8) . . ?
C2 C7 C6 121.4(7) . . ?
C9 C8 C5 178.0(10) . . ?
C15 C10 C11 119.8(7) . . ?
C15 C10 P1 120.6(5) . . ?
C11 C10 P1 119.6(5) . . ?
C12 C11 C10 118.1(7) . . ?
C13 C12 C11 121.4(7) . . ?
C12 C13 C14 120.4(7) . . ?
C13 C14 C15 119.7(8) . . ?
C10 C15 C14 120.5(7) . . ?
C21 C16 C17 120.4(7) . . ?
C21 C16 P1 120.2(6) . . ?
C17 C16 P1 119.2(5) . . ?
C18 C17 C16 119.3(7) . . ?
C17 C18 C19 120.1(8) . . ?
C20 C19 C18 120.6(8) . . ?
C19 C20 C21 120.5(8) . . ?
C20 C21 C16 119.0(8) . . ?
C27 C22 C23 119.6(7) . . ?
C27 C22 P1 116.9(5) . . ?
C23 C22 P1 123.5(6) . . ?
C24 C23 C22 120.3(8) . . ?
C23 C24 C25 119.5(8) . . ?
C26 C25 C24 120.1(8) . . ?
C25 C26 C27 120.6(9) . . ?
C22 C27 C26 119.9(7) . . ?
C43 P2 C37 106.9(3) . . ?
C43 P2 C49 111.1(3) . . ?
C37 P2 C49 110.0(3) . . ?
C43 P2 C28 107.9(3) . . ?
C37 P2 C28 113.1(3) . . ?
C49 P2 C28 107.7(3) . . ?
C29 C28 P2 116.1(5) . . ?
C30 C29 C34 118.2(7) . . ?
C30 C29 C28 120.6(7) . . ?
C34 C29 C28 121.1(7) . . ?
C31 C30 C29 121.2(8) . . ?
C30 C31 C32 122.2(8) . . ?
C31 C32 C33 118.4(7) . . ?
C31 C32 C35 120.4(8) . . ?
C33 C32 C35 121.2(8) . . ?
C34 C33 C32 120.2(8) . . ?
C33 C34 C29 119.8(7) . . ?
C36 C35 C32 177.4(12) . . ?
C38 C37 C42 119.9(7) . . ?
C38 C37 P2 118.9(6) . . ?
C42 C37 P2 120.9(6) . . ?
C39 C38 C37 120.8(8) . . ?
C38 C39 C40 120.2(8) . . ?
C39 C40 C41 119.8(7) . . ?
C40 C41 C42 120.6(8) . . ?
C41 C42 C37 118.6(7) . . ?
C44 C43 C48 121.1(7) . . ?
C44 C43 P2 122.3(5) . . ?
C48 C43 P2 116.4(6) . . ?
C43 C44 C45 118.8(7) . . ?
C46 C45 C44 121.3(7) . . ?
C45 C46 C47 120.7(7) . . ?
C48 C47 C46 119.1(7) . . ?
C47 C48 C43 119.0(7) . . ?
C50 C49 C54 120.9(7) . . ?
C50 C49 P2 117.3(5) . . ?
C54 C49 P2 121.2(6) . . ?
C49 C50 C51 119.9(8) . . ?
C50 C51 C52 118.9(8) . . ?
C53 C52 C51 120.9(8) . . ?
C52 C53 C54 120.2(8) . . ?
C49 C54 C53 119.1(8) . . ?
C2 C1 H1A 108.5 . . ?
P1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
P1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C9 H9 180.0 . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.5 . . ?
C16 C21 H21 120.5 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 H28A 108.3 . . ?
P2 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
P2 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 H31 118.9 . . ?
C32 C31 H31 118.9 . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 H34 120.1 . . ?
C29 C34 H34 120.1 . . ?
C35 C36 H36 180.0 . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 H42 120.7 . . ?
C37 C42 H42 120.7 . . ?
C43 C44 H44 120.6 . . ?
C45 C44 H44 120.6 . . ?
C46 C45 H45 119.4 . . ?
C44 C45 H45 119.4 . . ?
C45 C46 H46 119.7 . . ?
C47 C46 H46 119.7 . . ?
C48 C47 H47 120.4 . . ?
C46 C47 H47 120.4 . . ?
C47 C48 H48 120.5 . . ?
C43 C48 H48 120.5 . . ?
C49 C50 H50 120.0 . . ?
C51 C50 H50 120.0 . . ?
C50 C51 H51 120.5 . . ?
C52 C51 H51 120.5 . . ?
C53 C52 H52 119.6 . . ?
C51 C52 H52 119.6 . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C49 C54 H54 120.4 . . ?
C53 C54 H54 120.4 . . ?

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
C10 P1 C1 C2 -173.0(5) . . . . ?
C16 P1 C1 C2 66.4(6) . . . . ?
C22 P1 C1 C2 -57.1(6) . . . . ?
P1 C1 C2 C7 -92.8(8) . . . . ?
P1 C1 C2 C3 90.0(8) . . . . ?
C7 C2 C3 C4 0.8(11) . . . . ?
C1 C2 C3 C4 178.1(6) . . . . ?
C2 C3 C4 C5 1.6(11) . . . . ?
C3 C4 C5 C6 -2.1(12) . . . . ?
C3 C4 C5 C8 179.3(7) . . . . ?
C4 C5 C6 C7 0.2(13) . . . . ?
C8 C5 C6 C7 178.8(8) . . . . ?
C3 C2 C7 C6 -2.7(12) . . . . ?
C1 C2 C7 C6 -180.0(8) . . . . ?
C5 C6 C7 C2 2.2(14) . . . . ?
C4 C5 C8 C9 66(25) . . . . ?
C6 C5 C8 C9 -113(25) . . . . ?
C16 P1 C10 C15 -85.9(7) . . . . ?
C22 P1 C10 C15 35.8(7) . . . . ?
C1 P1 C10 C15 153.9(7) . . . . ?
C16 P1 C10 C11 94.1(6) . . . . ?
C22 P1 C10 C11 -144.2(6) . . . . ?
C1 P1 C10 C11 -26.1(7) . . . . ?
C15 C10 C11 C12 1.6(12) . . . . ?
P1 C10 C11 C12 -178.4(6) . . . . ?
C10 C11 C12 C13 -2.4(13) . . . . ?
C11 C12 C13 C14 0.6(14) . . . . ?
C12 C13 C14 C15 2.1(15) . . . . ?
C11 C10 C15 C14 1.0(13) . . . . ?
P1 C10 C15 C14 -179.0(7) . . . . ?
C13 C14 C15 C10 -2.9(15) . . . . ?
C10 P1 C16 C21 175.6(6) . . . . ?
C22 P1 C16 C21 56.8(7) . . . . ?
C1 P1 C16 C21 -65.8(7) . . . . ?
C10 P1 C16 C17 -9.9(7) . . . . ?
C22 P1 C16 C17 -128.7(6) . . . . ?
C1 P1 C16 C17 108.7(6) . . . . ?
C21 C16 C17 C18 -1.9(11) . . . . ?
P1 C16 C17 C18 -176.4(5) . . . . ?
C16 C17 C18 C19 1.1(11) . . . . ?
C17 C18 C19 C20 -0.8(12) . . . . ?
C18 C19 C20 C21 1.3(12) . . . . ?
C19 C20 C21 C16 -2.1(12) . . . . ?
C17 C16 C21 C20 2.4(11) . . . . ?
P1 C16 C21 C20 176.8(6) . . . . ?
C10 P1 C22 C27 55.3(6) . . . . ?
C16 P1 C22 C27 176.4(6) . . . . ?
C1 P1 C22 C27 -61.1(7) . . . . ?
C10 P1 C22 C23 -122.9(6) . . . . ?
C16 P1 C22 C23 -1.9(7) . . . . ?
C1 P1 C22 C23 120.7(6) . . . . ?
C27 C22 C23 C24 1.0(11) . . . . ?
P1 C22 C23 C24 179.2(6) . . . . ?
C22 C23 C24 C25 -0.9(12) . . . . ?
C23 C24 C25 C26 -1.1(13) . . . . ?
C24 C25 C26 C27 2.9(13) . . . . ?
C23 C22 C27 C26 0.8(11) . . . . ?
P1 C22 C27 C26 -177.5(6) . . . . ?
C25 C26 C27 C22 -2.8(13) . . . . ?
C43 P2 C28 C29 173.9(5) . . . . ?
C37 P2 C28 C29 -68.0(6) . . . . ?
C49 P2 C28 C29 53.8(6) . . . . ?
P2 C28 C29 C30 -74.9(8) . . . . ?
P2 C28 C29 C34 107.0(7) . . . . ?
C34 C29 C30 C31 -2.1(11) . . . . ?
C28 C29 C30 C31 179.7(7) . . . . ?
C29 C30 C31 C32 1.0(13) . . . . ?
C30 C31 C32 C33 -0.1(13) . . . . ?
C30 C31 C32 C35 -179.9(8) . . . . ?
C31 C32 C33 C34 0.4(13) . . . . ?
C35 C32 C33 C34 -179.8(8) . . . . ?
C32 C33 C34 C29 -1.6(13) . . . . ?
C30 C29 C34 C33 2.4(11) . . . . ?
C28 C29 C34 C33 -179.4(7) . . . . ?
C31 C32 C35 C36 5(30) . . . . ?
C33 C32 C35 C36 -175(29) . . . . ?
C43 P2 C37 C38 -72.8(7) . . . . ?
C49 P2 C37 C38 48.0(7) . . . . ?
C28 P2 C37 C38 168.6(6) . . . . ?
C43 P2 C37 C42 100.9(7) . . . . ?
C49 P2 C37 C42 -138.3(6) . . . . ?
C28 P2 C37 C42 -17.7(7) . . . . ?
C42 C37 C38 C39 2.3(12) . . . . ?
P2 C37 C38 C39 176.0(6) . . . . ?
C37 C38 C39 C40 0.2(13) . . . . ?
C38 C39 C40 C41 -2.2(13) . . . . ?
C39 C40 C41 C42 1.7(13) . . . . ?
C40 C41 C42 C37 0.7(13) . . . . ?
C38 C37 C42 C41 -2.7(12) . . . . ?
P2 C37 C42 C41 -176.4(6) . . . . ?
C37 P2 C43 C44 106.8(6) . . . . ?
C49 P2 C43 C44 -13.3(7) . . . . ?
C28 P2 C43 C44 -131.2(6) . . . . ?
C37 P2 C43 C48 -68.3(6) . . . . ?
C49 P2 C43 C48 171.6(6) . . . . ?
C28 P2 C43 C48 53.7(6) . . . . ?
C48 C43 C44 C45 -0.3(11) . . . . ?
P2 C43 C44 C45 -175.3(6) . . . . ?
C43 C44 C45 C46 0.5(11) . . . . ?
C44 C45 C46 C47 -0.1(12) . . . . ?
C45 C46 C47 C48 -0.6(12) . . . . ?
C46 C47 C48 C43 0.8(11) . . . . ?
C44 C43 C48 C47 -0.4(11) . . . . ?
P2 C43 C48 C47 174.9(6) . . . . ?
C43 P2 C49 C50 -52.4(7) . . . . ?
C37 P2 C49 C50 -170.6(6) . . . . ?
C28 P2 C49 C50 65.6(7) . . . . ?
C43 P2 C49 C54 136.8(6) . . . . ?
C37 P2 C49 C54 18.6(8) . . . . ?
C28 P2 C49 C54 -105.1(7) . . . . ?
C54 C49 C50 C51 1.8(12) . . . . ?
P2 C49 C50 C51 -169.0(6) . . . . ?
C49 C50 C51 C52 -3.0(13) . . . . ?
C50 C51 C52 C53 3.3(15) . . . . ?
C51 C52 C53 C54 -2.3(15) . . . . ?
C50 C49 C54 C53 -0.7(12) . . . . ?
P2 C49 C54 C53 169.7(7) . . . . ?
C52 C53 C54 C49 1.0(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.125
_refine_diff_density_min         -1.731
_refine_diff_density_rms         0.173
_database_code_depnum_ccdc_archive 'CCDC 937932'
#######################################################################
#
#                 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_uvic1304

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 I P'
_chemical_formula_weight         470.30

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'
I I -0.4742 1.8119 '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                   13.0516(10)
_cell_length_b                   12.5831(10)
_cell_length_c                   13.2499(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.207(4)
_cell_angle_gamma                90
_cell_volume                     2163.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.32

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    1.559
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8813
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_reflns_number            35698
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5405
_reflns_number_gt                4546
_reflns_threshold_expression     'I > 2\s(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 APEX-II v2012-10.0'
_computing_cell_refinement       'Bruker SAINT v8.18C'
_computing_data_reduction        'Bruker SAINT v8.18C'
_computing_structure_solution    'SHELXT-2012/2 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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/[\s^2^(Fo^2^)+(0.0268P)^2^+1.2216P]
 where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     vecmap
_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         5405
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0559
_refine_ls_wR_factor_gt          0.0521
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
P1 P 0.59437(4) 0.35145(4) 0.77633(4) 0.01489(10) Uani 1 1 d . . . . .
C1 C 0.58625(15) 0.34134(15) 0.91035(15) 0.0193(4) Uani 1 1 d . . . . .
H1A H 0.6124 0.4076 0.9442 0.023 Uiso 1 1 calc R U . . .
H1B H 0.5133 0.3323 0.9229 0.023 Uiso 1 1 calc R U . . .
C2 C 0.65005(16) 0.24609(16) 0.95519(15) 0.0224(4) Uani 1 1 d . . . . .
H2A H 0.6249 0.1803 0.9197 0.027 Uiso 1 1 calc R U . . .
H2B H 0.7231 0.2561 0.9436 0.027 Uiso 1 1 calc R U . . .
C3 C 0.64279(18) 0.23386(18) 1.06805(16) 0.0282(5) Uani 1 1 d . . . . .
H3A H 0.5708 0.2165 1.0789 0.034 Uiso 1 1 calc R U . . .
H3B H 0.6607 0.3024 1.1023 0.034 Uiso 1 1 calc R U . . .
C4 C 0.71426(18) 0.14714(18) 1.11623(17) 0.0311(5) Uani 1 1 d . . . . .
H4A H 0.7865 0.1666 1.1084 0.037 Uiso 1 1 calc R U . . .
H4B H 0.7072 0.1437 1.1898 0.037 Uiso 1 1 calc R U . . .
C5 C 0.69245(18) 0.0405(2) 1.07102(18) 0.0351(5) Uani 1 1 d . . . . .
C6 C 0.67377(19) -0.0383(2) 1.03465(18) 0.0353(5) Uani 1 1 d . . . . .
H6 H 0.6579 -0.1053 1.0037 0.042 Uiso 1 1 calc R U . . .
C7 C 0.72855(14) 0.35328(14) 0.75839(14) 0.0159(4) Uani 1 1 d . . . . .
C8 C 0.78310(15) 0.44387(16) 0.79383(16) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.7488 0.5003 0.8239 0.027 Uiso 1 1 calc R U . . .
C9 C 0.88741(16) 0.45062(17) 0.78475(17) 0.0277(5) Uani 1 1 d . . . . .
H9 H 0.9247 0.5123 0.8081 0.033 Uiso 1 1 calc R U . . .
C10 C 0.93784(16) 0.36803(18) 0.74190(17) 0.0282(5) Uani 1 1 d . . . . .
H10 H 1.0095 0.3734 0.7357 0.034 Uiso 1 1 calc R U . . .
C11 C 0.88443(16) 0.27791(17) 0.70810(17) 0.0257(4) Uani 1 1 d . . . . .
H11 H 0.9195 0.2212 0.6793 0.031 Uiso 1 1 calc R U . . .
C12 C 0.77930(15) 0.27011(15) 0.71609(15) 0.0202(4) Uani 1 1 d . . . . .
H12 H 0.7424 0.2082 0.6927 0.024 Uiso 1 1 calc R U . . .
C13 C 0.53804(14) 0.47189(14) 0.72400(14) 0.0166(4) Uani 1 1 d . . . . .
C14 C 0.44746(14) 0.51100(15) 0.75743(15) 0.0203(4) Uani 1 1 d . . . . .
H14 H 0.4195 0.4789 0.8133 0.024 Uiso 1 1 calc R U . . .
C15 C 0.39882(15) 0.59753(16) 0.70789(15) 0.0220(4) Uani 1 1 d . . . . .
H15 H 0.3372 0.6247 0.7301 0.026 Uiso 1 1 calc R U . . .
C16 C 0.43910(16) 0.64432(16) 0.62686(16) 0.0234(4) Uani 1 1 d . . . . .
H16 H 0.4050 0.7033 0.5935 0.028 Uiso 1 1 calc R U . . .
C17 C 0.52931(16) 0.60550(16) 0.59386(16) 0.0248(4) Uani 1 1 d . . . . .
H17 H 0.5571 0.6385 0.5383 0.030 Uiso 1 1 calc R U . . .
C18 C 0.57886(15) 0.51915(16) 0.64136(15) 0.0217(4) Uani 1 1 d . . . . .
H18 H 0.6401 0.4920 0.6182 0.026 Uiso 1 1 calc R U . . .
C19 C 0.52645(14) 0.24431(14) 0.70879(14) 0.0173(4) Uani 1 1 d . . . . .
C20 C 0.54421(15) 0.22521(15) 0.60839(15) 0.0213(4) Uani 1 1 d . . . . .
H20 H 0.5981 0.2615 0.5800 0.026 Uiso 1 1 calc R U . . .
C21 C 0.48296(18) 0.15309(16) 0.55023(17) 0.0265(5) Uani 1 1 d . . . . .
H21 H 0.4947 0.1407 0.4817 0.032 Uiso 1 1 calc R U . . .
C22 C 0.40499(15) 0.09917(16) 0.59120(17) 0.0263(4) Uani 1 1 d . . . . .
H22 H 0.3632 0.0501 0.5508 0.032 Uiso 1 1 calc R U . . .
C23 C 0.38776(15) 0.11668(16) 0.69143(18) 0.0266(5) Uani 1 1 d . . . . .
H23 H 0.3346 0.0789 0.7196 0.032 Uiso 1 1 calc R U . . .
C24 C 0.44817(14) 0.18958(16) 0.75110(16) 0.0224(4) Uani 1 1 d . . . . .
H24 H 0.4362 0.2018 0.8196 0.027 Uiso 1 1 calc R U . . .
I1 I 0.78749(2) 0.13419(2) 0.45604(2) 0.02227(5) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0150(2) 0.0133(2) 0.0165(2) 0.00100(17) 0.00227(17) -0.00001(17)
C1 0.0210(9) 0.0210(9) 0.0165(9) 0.0014(7) 0.0043(7) 0.0017(7)
C2 0.0242(10) 0.0256(10) 0.0179(10) 0.0034(8) 0.0039(8) 0.0046(8)
C3 0.0340(12) 0.0317(11) 0.0191(10) 0.0019(9) 0.0034(9) 0.0039(9)
C4 0.0361(12) 0.0358(13) 0.0199(10) 0.0072(9) -0.0042(9) 0.0023(10)
C5 0.0318(12) 0.0425(14) 0.0300(12) 0.0176(11) -0.0017(10) 0.0068(11)
C6 0.0385(13) 0.0339(13) 0.0309(13) 0.0076(10) -0.0079(10) -0.0082(11)
C7 0.0139(8) 0.0172(9) 0.0164(9) 0.0002(7) 0.0011(7) -0.0010(7)
C8 0.0226(10) 0.0191(9) 0.0267(11) -0.0056(8) 0.0018(8) -0.0001(8)
C9 0.0233(10) 0.0249(10) 0.0342(12) -0.0044(9) 0.0001(9) -0.0084(8)
C10 0.0149(9) 0.0399(12) 0.0301(11) -0.0018(10) 0.0037(8) -0.0028(9)
C11 0.0217(10) 0.0266(11) 0.0290(11) -0.0045(9) 0.0034(8) 0.0047(8)
C12 0.0200(9) 0.0186(9) 0.0217(10) -0.0034(7) 0.0011(8) -0.0001(7)
C13 0.0170(9) 0.0135(8) 0.0189(9) -0.0001(7) 0.0006(7) 0.0002(7)
C14 0.0195(9) 0.0199(9) 0.0220(10) 0.0020(8) 0.0048(8) -0.0005(8)
C15 0.0193(9) 0.0225(9) 0.0243(10) -0.0007(8) 0.0029(8) 0.0036(8)
C16 0.0260(10) 0.0191(10) 0.0241(10) 0.0024(8) -0.0013(8) 0.0049(8)
C17 0.0302(11) 0.0227(10) 0.0224(10) 0.0054(8) 0.0069(8) 0.0035(8)
C18 0.0220(10) 0.0215(10) 0.0225(10) 0.0009(8) 0.0058(8) 0.0031(8)
C19 0.0159(9) 0.0137(8) 0.0216(10) 0.0007(7) -0.0012(7) 0.0002(7)
C20 0.0247(10) 0.0181(9) 0.0202(10) 0.0029(7) -0.0012(8) -0.0053(8)
C21 0.0354(12) 0.0191(10) 0.0230(11) 0.0023(8) -0.0062(9) -0.0023(8)
C22 0.0206(10) 0.0175(9) 0.0381(12) -0.0006(9) -0.0085(9) -0.0006(8)
C23 0.0146(9) 0.0181(10) 0.0476(14) 0.0015(9) 0.0053(9) -0.0015(7)
C24 0.0166(9) 0.0195(10) 0.0321(11) -0.0003(8) 0.0068(8) 0.0016(8)
I1 0.02153(7) 0.01972(7) 0.02713(8) -0.00479(5) 0.00984(5) -0.00270(5)

_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 1.7911(19) . ?
P1 C7 1.7927(19) . ?
P1 C1 1.795(2) . ?
P1 C19 1.7979(19) . ?
C1 C2 1.541(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.516(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.484(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.118(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.389(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.396(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.396(3) . ?
C19 C24 1.399(3) . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 P1 C7 107.69(9) . . ?
C13 P1 C1 112.16(9) . . ?
C7 P1 C1 107.16(9) . . ?
C13 P1 C19 106.39(9) . . ?
C7 P1 C19 112.32(9) . . ?
C1 P1 C19 111.14(9) . . ?
C2 C1 P1 110.44(13) . . ?
C2 C1 H1A 109.6 . . ?
P1 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
P1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 111.73(17) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 112.57(18) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 113.24(19) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 177.7(3) . . ?
C5 C6 H6 180.0 . . ?
C12 C7 C8 120.15(17) . . ?
C12 C7 P1 124.00(14) . . ?
C8 C7 P1 115.80(14) . . ?
C9 C8 C7 119.44(18) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.39(19) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.27(19) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.07(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 119.67(18) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C18 120.33(17) . . ?
C14 C13 P1 120.11(14) . . ?
C18 C13 P1 119.13(14) . . ?
C15 C14 C13 119.06(18) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 120.66(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.21(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.31(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 119.42(18) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
C20 C19 C24 120.07(17) . . ?
C20 C19 P1 118.67(14) . . ?
C24 C19 P1 120.80(15) . . ?
C21 C20 C19 119.81(19) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.01(19) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.36(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 119.23(19) . . ?
C23 C24 H24 120.4 . . ?
C19 C24 H24 120.4 . . ?

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 C2 -171.15(13) . . . . ?
C7 P1 C1 C2 -53.16(16) . . . . ?
C19 P1 C1 C2 69.90(16) . . . . ?
P1 C1 C2 C3 -178.70(15) . . . . ?
C1 C2 C3 C4 -174.04(18) . . . . ?
C2 C3 C4 C5 -59.7(3) . . . . ?
C13 P1 C7 C12 -129.77(17) . . . . ?
C1 P1 C7 C12 109.37(17) . . . . ?
C19 P1 C7 C12 -13.0(2) . . . . ?
C13 P1 C7 C8 52.73(17) . . . . ?
C1 P1 C7 C8 -68.13(17) . . . . ?
C19 P1 C7 C8 169.55(15) . . . . ?
C12 C7 C8 C9 1.1(3) . . . . ?
P1 C7 C8 C9 178.72(16) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C8 C7 C12 C11 -0.7(3) . . . . ?
P1 C7 C12 C11 -178.12(16) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C7 P1 C13 C14 -156.87(15) . . . . ?
C1 P1 C13 C14 -39.20(18) . . . . ?
C19 P1 C13 C14 82.51(17) . . . . ?
C7 P1 C13 C18 30.58(18) . . . . ?
C1 P1 C13 C18 148.25(15) . . . . ?
C19 P1 C13 C18 -90.04(17) . . . . ?
C18 C13 C14 C15 -0.3(3) . . . . ?
P1 C13 C14 C15 -172.73(15) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 -0.8(3) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
P1 C13 C18 C17 173.20(16) . . . . ?
C13 P1 C19 C20 72.36(17) . . . . ?
C7 P1 C19 C20 -45.23(18) . . . . ?
C1 P1 C19 C20 -165.27(15) . . . . ?
C13 P1 C19 C24 -99.80(16) . . . . ?
C7 P1 C19 C24 142.61(15) . . . . ?
C1 P1 C19 C24 22.56(18) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
P1 C19 C20 C21 -171.19(15) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C19 -0.3(3) . . . . ?
C20 C19 C24 C23 -0.6(3) . . . . ?
P1 C19 C24 C23 171.46(15) . . . . ?

_refine_diff_density_max         0.656
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.074

_shelxl_version_number           2012-9

#==============END
_database_code_depnum_ccdc_archive 'CCDC 937933'