# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201408174
_database_code_depnum_ccdc_archive 'CCDC 1024974'
_audit_update_record             
;
2014-09-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_date             2014-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H19 O P Si'
_chemical_formula_sum            'C22 H19 O P Si'
_chemical_formula_weight         358.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4P1Si1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.2464(4)
_cell_length_b                   12.4270(6)
_cell_length_c                   17.6262(7)
_cell_angle_alpha                84.434(3)
_cell_angle_beta                 76.892(3)
_cell_angle_gamma                77.143(4)
_cell_volume                     2128.52(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7025
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.2780
_cell_measurement_theta_min      4.3580
_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15415
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -72.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -73.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega   -2.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   30.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega    8.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 12 omega   13.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   19.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 13 omega   13.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega   32.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
 15 omega  128.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 16 omega   89.00  115.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   64.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   98.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 19 omega   93.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 20 omega   68.00  114.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 21 omega   40.00  105.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
 22 omega   92.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
 23 omega   42.00   87.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 24 omega  111.00  139.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 25 omega   48.00   81.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 26 omega   41.00   98.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
 27 omega   44.00   95.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 28 omega   60.00  103.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
 29 omega   62.00  106.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 30 omega   39.00   64.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   70.00  115.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 32 omega   93.00  174.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
 33 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 34 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 35 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
 36 omega   26.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -180.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0446266000
_diffrn_orient_matrix_UB_12      0.1095666000
_diffrn_orient_matrix_UB_13      -0.0302874000
_diffrn_orient_matrix_UB_21      -0.0847778000
_diffrn_orient_matrix_UB_22      0.0542914000
_diffrn_orient_matrix_UB_23      0.0755846000
_diffrn_orient_matrix_UB_31      0.1253714000
_diffrn_orient_matrix_UB_32      -0.0354328000
_diffrn_orient_matrix_UB_33      0.0379782000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6273
_reflns_number_total             7602
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0730P)²+0.0682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1231
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C1'(H1'), C2'(H2'), C3'(H3'),
  C4'(H4'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'), C18'(H18'),
 C19'(H19'), C20'(H20'), C21'(H21'), C22'(H22')
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C15'(H15D,H15E,H15F), C16'(H16D,
 H16E,H16F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
P1 P 0.16279(5) 0.76992(4) 0.45368(3) 0.04620(13) Uani 1 d . . .
Si1 Si 0.29114(5) 0.67554(4) 0.21387(3) 0.04743(14) Uani 1 d . . .
O1 O 0.01967(14) 0.78168(12) 0.49826(8) 0.0613(4) Uani 1 d . . .
C1 C 0.31862(18) 0.94734(15) 0.27017(11) 0.0499(4) Uani 1 d . . .
H1 H 0.3574 0.9324 0.2183 0.060 Uiso 1 calc . . R
C2 C 0.3083(2) 1.05148(15) 0.29746(13) 0.0556(5) Uani 1 d . . .
H2 H 0.3415 1.1058 0.2633 0.067 Uiso 1 calc . . R
C3 C 0.2499(2) 1.07508(16) 0.37389(13) 0.0568(5) Uani 1 d . . .
H3 H 0.2418 1.1455 0.3905 0.068 Uiso 1 calc . . R
C4 C 0.20286(19) 0.99377(15) 0.42667(12) 0.0506(4) Uani 1 d . . .
H4 H 0.1640 1.0091 0.4785 0.061 Uiso 1 calc . . R
C5 C 0.21520(17) 0.89049(14) 0.40038(10) 0.0440(4) Uani 1 d . . .
C6 C 0.27003(17) 0.86692(14) 0.32191(11) 0.0437(4) Uani 1 d . . .
C7 C 0.26416(18) 0.75425(14) 0.30370(10) 0.0447(4) Uani 1 d . . .
C8 C 0.21089(18) 0.69340(15) 0.36610(10) 0.0451(4) Uani 1 d . . .
C9 C 0.19488(18) 0.58197(14) 0.35354(11) 0.0465(4) Uani 1 d . . .
C10 C 0.2325(2) 0.55522(15) 0.27462(12) 0.0505(4) Uani 1 d . . .
C11 C 0.2207(2) 0.45243(17) 0.25625(14) 0.0638(5) Uani 1 d . . .
H11 H 0.2454 0.4327 0.2046 0.077 Uiso 1 calc . . R
C12 C 0.1721(3) 0.37840(17) 0.31442(16) 0.0708(6) Uani 1 d . . .
H12 H 0.1634 0.3101 0.3011 0.085 Uiso 1 calc . . R
C13 C 0.1368(2) 0.40495(17) 0.39124(15) 0.0658(6) Uani 1 d . . .
H13 H 0.1053 0.3544 0.4296 0.079 Uiso 1 calc . . R
C14 C 0.1481(2) 0.50701(16) 0.41188(13) 0.0553(5) Uani 1 d . . .
H14 H 0.1247 0.5251 0.4639 0.066 Uiso 1 calc . . R
C15 C 0.4694(2) 0.64001(19) 0.15782(15) 0.0734(7) Uani 1 d . . .
H15A H 0.4966 0.7057 0.1322 0.110 Uiso 1 calc . . GR
H15B H 0.4753 0.5882 0.1196 0.110 Uiso 1 calc . . GR
H15C H 0.5288 0.6076 0.1926 0.110 Uiso 1 calc . . GR
C16 C 0.1731(3) 0.7476(2) 0.15064(14) 0.0747(6) Uani 1 d . . .
H16A H 0.0809 0.7620 0.1808 0.112 Uiso 1 calc . . GR
H16B H 0.1792 0.7020 0.1085 0.112 Uiso 1 calc . . GR
H16C H 0.1982 0.8163 0.1299 0.112 Uiso 1 calc . . GR
C17 C 0.2887(2) 0.70967(16) 0.51168(12) 0.0560(5) Uani 1 d . . .
C18 C 0.4272(3) 0.7012(2) 0.48157(16) 0.0825(8) Uani 1 d . . .
H18 H 0.4572 0.7287 0.4311 0.099 Uiso 1 calc . . R
C19 C 0.5212(3) 0.6520(3) 0.5262(2) 0.1032(10) Uani 1 d . . .
H19 H 0.6143 0.6468 0.5058 0.124 Uiso 1 calc . . R
C20 C 0.4775(4) 0.6107(3) 0.6005(2) 0.0978(10) Uani 1 d . . .
H20 H 0.5412 0.5783 0.6304 0.117 Uiso 1 calc . . R
C21 C 0.3426(4) 0.6170(2) 0.63025(17) 0.0951(9) Uani 1 d . . .
H21 H 0.3139 0.5877 0.6803 0.114 Uiso 1 calc . . R
C22 C 0.2451(3) 0.6679(2) 0.58593(14) 0.0745(7) Uani 1 d . . .
H22 H 0.1521 0.6731 0.6067 0.089 Uiso 1 calc . . R
P1' P 0.35282(4) 0.05438(4) 0.90167(3) 0.04378(13) Uani 1 d . . .
Si1' Si 0.24777(6) 0.02867(6) 0.67974(3) 0.06284(18) Uani 1 d . . .
O1' O 0.47167(13) 0.09970(12) 0.90949(8) 0.0533(3) Uani 1 d . . .
C1' C 0.3788(2) -0.2174(2) 0.79460(16) 0.0724(6) Uani 1 d . . .
H1' H 0.3611 -0.2307 0.7473 0.087 Uiso 1 calc . . R
C2' C 0.4270(3) -0.3047(2) 0.8435(2) 0.0889(8) Uani 1 d . . .
H2' H 0.4404 -0.3769 0.8287 0.107 Uiso 1 calc . . R
C3' C 0.4552(3) -0.2863(2) 0.91308(19) 0.0851(8) Uani 1 d . . .
H3' H 0.4875 -0.3460 0.9447 0.102 Uiso 1 calc . . R
C4' C 0.4360(2) -0.18005(19) 0.93658(14) 0.0641(5) Uani 1 d . . .
H4' H 0.4554 -0.1675 0.9836 0.077 Uiso 1 calc . . R
C5' C 0.38713(18) -0.09265(16) 0.88876(11) 0.0494(4) Uani 1 d . . .
C6' C 0.35779(18) -0.11078(17) 0.81755(12) 0.0526(4) Uani 1 d . . .
C7' C 0.30434(18) -0.00861(18) 0.77510(11) 0.0523(4) Uani 1 d . . .
C8' C 0.29367(18) 0.08527(17) 0.81109(11) 0.0495(4) Uani 1 d . . .
C9' C 0.24162(19) 0.19160(18) 0.77201(12) 0.0567(5) Uani 1 d . . .
C10' C 0.2105(2) 0.1791(2) 0.69954(13) 0.0653(6) Uani 1 d . . .
C11' C 0.1587(3) 0.2742(3) 0.65809(16) 0.0844(8) Uani 1 d . . .
H11' H 0.1368 0.2682 0.6105 0.101 Uiso 1 calc . . R
C12' C 0.1397(3) 0.3768(3) 0.6869(2) 0.0976(10) Uani 1 d . . .
H12' H 0.1062 0.4396 0.6583 0.117 Uiso 1 calc . . R
C13' C 0.1696(3) 0.3876(2) 0.7577(2) 0.0901(9) Uani 1 d . . .
H13' H 0.1551 0.4574 0.7767 0.108 Uiso 1 calc . . R
C14' C 0.2215(2) 0.2946(2) 0.80088(15) 0.0694(6) Uani 1 d . . .
H14' H 0.2422 0.3018 0.8486 0.083 Uiso 1 calc . . R
C15' C 0.0934(2) -0.0234(3) 0.67547(16) 0.0833(8) Uani 1 d . . .
H15D H 0.1157 -0.1027 0.6753 0.125 Uiso 1 calc . . GR
H15E H 0.0624 0.0061 0.6288 0.125 Uiso 1 calc . . GR
H15F H 0.0223 -0.0007 0.7201 0.125 Uiso 1 calc . . GR
C16' C 0.3888(3) -0.0098(3) 0.59388(15) 0.1032(11) Uani 1 d . . .
H16D H 0.4672 0.0172 0.5986 0.155 Uiso 1 calc . . GR
H16E H 0.3594 0.0222 0.5472 0.155 Uiso 1 calc . . GR
H16F H 0.4126 -0.0888 0.5914 0.155 Uiso 1 calc . . GR
C17' C 0.20877(18) 0.08758(16) 0.98153(11) 0.0474(4) Uani 1 d . . .
C18' C 0.2335(2) 0.0774(2) 1.05606(13) 0.0762(7) Uani 1 d . . .
H18' H 0.3225 0.0529 1.0636 0.091 Uiso 1 calc . . R
C19' C 0.1269(3) 0.1035(3) 1.11926(14) 0.0978(11) Uani 1 d . . .
H19' H 0.1439 0.0958 1.1694 0.117 Uiso 1 calc . . R
C20' C -0.0048(2) 0.1408(3) 1.10824(14) 0.0827(8) Uani 1 d . . .
H20' H -0.0762 0.1598 1.1509 0.099 Uiso 1 calc . . R
C21' C -0.0311(2) 0.1502(2) 1.03525(15) 0.0717(6) Uani 1 d . . .
H21' H -0.1204 0.1743 1.0282 0.086 Uiso 1 calc . . R
C22' C 0.0756(2) 0.12364(19) 0.97168(12) 0.0595(5) Uani 1 d . . .
H22' H 0.0576 0.1301 0.9219 0.071 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4811(14) . ?
P1 C5 1.8089(18) . ?
P1 C8 1.8059(19) . ?
P1 C17 1.8141(19) . ?
Si1 C7 1.8766(19) . ?
Si1 C10 1.8817(19) . ?
Si1 C15 1.848(2) . ?
Si1 C16 1.855(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.398(3) . ?
C1 C6 1.385(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C5 C6 1.403(3) . ?
C6 C7 1.483(2) . ?
C7 C8 1.353(3) . ?
C8 C9 1.473(3) . ?
C9 C10 1.408(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.381(3) . ?
C17 C22 1.374(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.350(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.409(4) . ?
C22 H22 0.9300 . ?
P1' O1' 1.4885(13) . ?
P1' C5' 1.809(2) . ?
P1' C8' 1.8110(18) . ?
P1' C17' 1.7972(18) . ?
Si1' C7' 1.8834(19) . ?
Si1' C10' 1.873(3) . ?
Si1' C15' 1.856(3) . ?
Si1' C16' 1.857(2) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.392(4) . ?
C1' C6' 1.379(3) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.373(4) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.381(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.383(3) . ?
C5' C6' 1.405(3) . ?
C6' C7' 1.471(3) . ?
C7' C8' 1.353(3) . ?
C8' C9' 1.477(3) . ?
C9' C10' 1.415(3) . ?
C9' C14' 1.379(3) . ?
C10' C11' 1.393(3) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.376(4) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.374(4) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.392(3) . ?
C14' H14' 0.9300 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C17' C18' 1.382(3) . ?
C17' C22' 1.383(3) . ?
C18' H18' 0.9300 . ?
C18' C19' 1.378(3) . ?
C19' H19' 0.9300 . ?
C19' C20' 1.377(3) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.362(3) . ?
C21' H21' 0.9300 . ?
C21' C22' 1.384(3) . ?
C22' H22' 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
O1 P1 C5 118.28(8) . . ?
O1 P1 C8 117.66(9) . . ?
O1 P1 C17 113.35(10) . . ?
C5 P1 C17 107.41(9) . . ?
C8 P1 C5 91.57(8) . . ?
C8 P1 C17 106.04(9) . . ?
C7 Si1 C10 90.82(8) . . ?
C15 Si1 C7 116.01(10) . . ?
C15 Si1 C10 113.17(10) . . ?
C15 Si1 C16 111.36(12) . . ?
C16 Si1 C7 110.24(10) . . ?
C16 Si1 C10 113.84(11) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.72(18) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.24(18) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.30(18) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.63(18) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 P1 128.93(15) . . ?
C4 C5 C6 121.40(17) . . ?
C6 C5 P1 109.63(13) . . ?
C1 C6 C5 119.64(17) . . ?
C1 C6 C7 127.00(17) . . ?
C5 C6 C7 113.33(15) . . ?
C6 C7 Si1 136.97(13) . . ?
C8 C7 Si1 108.46(14) . . ?
C8 C7 C6 114.05(16) . . ?
C7 C8 P1 111.36(14) . . ?
C7 C8 C9 118.28(17) . . ?
C9 C8 P1 130.30(14) . . ?
C10 C9 C8 113.42(16) . . ?
C14 C9 C8 125.42(18) . . ?
C14 C9 C10 121.15(18) . . ?
C9 C10 Si1 108.87(13) . . ?
C11 C10 Si1 132.96(17) . . ?
C11 C10 C9 118.16(18) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 120.5 . . ?
C13 C14 C9 119.1(2) . . ?
C13 C14 H14 120.5 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 P1 121.30(17) . . ?
C22 C17 P1 118.97(18) . . ?
C22 C17 C18 119.7(2) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.3(3) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
O1' P1' C5' 115.80(8) . . ?
O1' P1' C8' 117.77(8) . . ?
O1' P1' C17' 112.39(9) . . ?
C5' P1' C8' 91.68(9) . . ?
C17' P1' C5' 108.48(9) . . ?
C17' P1' C8' 108.76(8) . . ?
C10' Si1' C7' 90.51(9) . . ?
C15' Si1' C7' 113.23(11) . . ?
C15' Si1' C10' 113.54(12) . . ?
C15' Si1' C16' 111.87(13) . . ?
C16' Si1' C7' 112.77(11) . . ?
C16' Si1' C10' 113.35(15) . . ?
C2' C1' H1' 120.6 . . ?
C6' C1' H1' 120.6 . . ?
C6' C1' C2' 118.9(2) . . ?
C1' C2' H2' 119.4 . . ?
C3' C2' C1' 121.2(2) . . ?
C3' C2' H2' 119.4 . . ?
C2' C3' H3' 119.7 . . ?
C2' C3' C4' 120.6(2) . . ?
C4' C3' H3' 119.7 . . ?
C3' C4' H4' 120.7 . . ?
C3' C4' C5' 118.6(2) . . ?
C5' C4' H4' 120.7 . . ?
C4' C5' P1' 129.65(17) . . ?
C4' C5' C6' 121.1(2) . . ?
C6' C5' P1' 109.29(14) . . ?
C1' C6' C5' 119.6(2) . . ?
C1' C6' C7' 126.8(2) . . ?
C5' C6' C7' 113.65(18) . . ?
C6' C7' Si1' 136.49(16) . . ?
C8' C7' Si1' 108.95(15) . . ?
C8' C7' C6' 114.54(17) . . ?
C7' C8' P1' 110.79(15) . . ?
C7' C8' C9' 117.93(18) . . ?
C9' C8' P1' 131.26(16) . . ?
C10' C9' C8' 113.1(2) . . ?
C14' C9' C8' 125.7(2) . . ?
C14' C9' C10' 121.2(2) . . ?
C9' C10' Si1' 109.51(16) . . ?
C11' C10' Si1' 132.5(2) . . ?
C11' C10' C9' 118.0(3) . . ?
C10' C11' H11' 119.7 . . ?
C12' C11' C10' 120.6(3) . . ?
C12' C11' H11' 119.7 . . ?
C11' C12' H12' 119.6 . . ?
C13' C12' C11' 120.8(2) . . ?
C13' C12' H12' 119.6 . . ?
C12' C13' H13' 119.8 . . ?
C12' C13' C14' 120.4(3) . . ?
C14' C13' H13' 119.8 . . ?
C9' C14' C13' 119.1(3) . . ?
C9' C14' H14' 120.4 . . ?
C13' C14' H14' 120.4 . . ?
Si1' C15' H15D 109.5 . . ?
Si1' C15' H15E 109.5 . . ?
Si1' C15' H15F 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
Si1' C16' H16D 109.5 . . ?
Si1' C16' H16E 109.5 . . ?
Si1' C16' H16F 109.5 . . ?
H16D C16' H16E 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C18' C17' P1' 117.93(14) . . ?
C18' C17' C22' 118.93(18) . . ?
C22' C17' P1' 123.14(15) . . ?
C17' C18' H18' 119.9 . . ?
C19' C18' C17' 120.3(2) . . ?
C19' C18' H18' 119.9 . . ?
C18' C19' H19' 120.0 . . ?
C20' C19' C18' 120.0(2) . . ?
C20' C19' H19' 120.0 . . ?
C19' C20' H20' 119.8 . . ?
C21' C20' C19' 120.4(2) . . ?
C21' C20' H20' 119.8 . . ?
C20' C21' H21' 120.1 . . ?
C20' C21' C22' 119.8(2) . . ?
C22' C21' H21' 120.1 . . ?
C17' C22' C21' 120.6(2) . . ?
C17' C22' H22' 119.7 . . ?
C21' C22' H22' 119.7 . . ?

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
P1 C5 C6 C1 -179.19(13) . . . . ?
P1 C5 C6 C7 2.69(18) . . . . ?
P1 C8 C9 C10 173.70(14) . . . . ?
P1 C8 C9 C14 -6.5(3) . . . . ?
P1 C17 C18 C19 -178.1(2) . . . . ?
P1 C17 C22 C21 177.5(2) . . . . ?
Si1 C7 C8 P1 -173.19(8) . . . . ?
Si1 C7 C8 C9 4.1(2) . . . . ?
Si1 C10 C11 C12 -179.47(18) . . . . ?
O1 P1 C5 C4 52.6(2) . . . . ?
O1 P1 C5 C6 -125.10(13) . . . . ?
O1 P1 C8 C7 124.64(14) . . . . ?
O1 P1 C8 C9 -52.29(19) . . . . ?
O1 P1 C17 C18 -174.4(2) . . . . ?
O1 P1 C17 C22 8.2(2) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C1 C6 C7 Si1 -9.3(3) . . . . ?
C1 C6 C7 C8 -179.75(18) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 176.19(17) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 P1 -179.26(14) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C4 C5 C6 C1 2.9(3) . . . . ?
C4 C5 C6 C7 -175.19(16) . . . . ?
C5 P1 C8 C7 1.31(14) . . . . ?
C5 P1 C8 C9 -175.62(17) . . . . ?
C5 P1 C17 C18 -41.9(2) . . . . ?
C5 P1 C17 C22 140.73(19) . . . . ?
C5 C6 C7 Si1 168.68(15) . . . . ?
C5 C6 C7 C8 -1.8(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C7 C8 P1 0.0(2) . . . . ?
C6 C7 C8 C9 177.32(14) . . . . ?
C7 Si1 C10 C9 1.63(14) . . . . ?
C7 Si1 C10 C11 -178.5(2) . . . . ?
C7 C8 C9 C10 -3.1(2) . . . . ?
C7 C8 C9 C14 176.75(18) . . . . ?
C8 P1 C5 C4 175.39(17) . . . . ?
C8 P1 C5 C6 -2.28(13) . . . . ?
C8 P1 C17 C18 55.0(2) . . . . ?
C8 P1 C17 C22 -122.37(19) . . . . ?
C8 C9 C10 Si1 0.24(19) . . . . ?
C8 C9 C10 C11 -179.66(17) . . . . ?
C8 C9 C14 C13 179.33(18) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 Si1 C7 C6 -174.05(19) . . . . ?
C10 Si1 C7 C8 -3.21(14) . . . . ?
C10 C9 C14 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C14 C9 C10 Si1 -179.58(15) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C15 Si1 C7 C6 69.5(2) . . . . ?
C15 Si1 C7 C8 -119.62(15) . . . . ?
C15 Si1 C10 C9 120.52(15) . . . . ?
C15 Si1 C10 C11 -59.6(2) . . . . ?
C16 Si1 C7 C6 -58.2(2) . . . . ?
C16 Si1 C7 C8 112.65(15) . . . . ?
C16 Si1 C10 C9 -110.99(15) . . . . ?
C16 Si1 C10 C11 68.9(2) . . . . ?
C17 P1 C5 C4 -77.25(18) . . . . ?
C17 P1 C5 C6 105.08(14) . . . . ?
C17 P1 C8 C7 -107.31(15) . . . . ?
C17 P1 C8 C9 75.76(18) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C17 C22 C21 0.1(4) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
C19 C20 C21 C22 -1.2(5) . . . . ?
C20 C21 C22 C17 0.9(4) . . . . ?
C22 C17 C18 C19 -0.7(4) . . . . ?
P1' C5' C6' C1' 178.82(16) . . . . ?
P1' C5' C6' C7' -1.9(2) . . . . ?
P1' C8' C9' C10' 177.83(15) . . . . ?
P1' C8' C9' C14' -3.1(3) . . . . ?
P1' C17' C18' C19' 179.0(2) . . . . ?
P1' C17' C22' C21' -178.67(18) . . . . ?
Si1' C7' C8' P1' -177.92(8) . . . . ?
Si1' C7' C8' C9' 0.7(2) . . . . ?
Si1' C10' C11' C12' 179.3(2) . . . . ?
O1' P1' C5' C4' 59.0(2) . . . . ?
O1' P1' C5' C6' -120.14(13) . . . . ?
O1' P1' C8' C7' 118.81(14) . . . . ?
O1' P1' C8' C9' -59.6(2) . . . . ?
O1' P1' C17' C18' -43.2(2) . . . . ?
O1' P1' C17' C22' 136.09(18) . . . . ?
C1' C2' C3' C4' 0.2(5) . . . . ?
C1' C6' C7' Si1' -1.7(3) . . . . ?
C1' C6' C7' C8' 179.9(2) . . . . ?
C2' C1' C6' C5' 0.9(3) . . . . ?
C2' C1' C6' C7' -178.3(2) . . . . ?
C2' C3' C4' C5' 0.3(4) . . . . ?
C3' C4' C5' P1' -179.27(19) . . . . ?
C3' C4' C5' C6' -0.2(3) . . . . ?
C4' C5' C6' C1' -0.4(3) . . . . ?
C4' C5' C6' C7' 178.88(18) . . . . ?
C5' P1' C8' C7' -1.70(15) . . . . ?
C5' P1' C8' C9' 179.87(18) . . . . ?
C5' P1' C17' C18' 86.1(2) . . . . ?
C5' P1' C17' C22' -94.56(19) . . . . ?
C5' C6' C7' Si1' 179.08(15) . . . . ?
C5' C6' C7' C8' 0.6(2) . . . . ?
C6' C1' C2' C3' -0.8(4) . . . . ?
C6' C7' C8' P1' 1.0(2) . . . . ?
C6' C7' C8' C9' 179.62(16) . . . . ?
C7' Si1' C10' C9' 0.33(15) . . . . ?
C7' Si1' C10' C11' -178.6(2) . . . . ?
C7' C8' C9' C10' -0.5(3) . . . . ?
C7' C8' C9' C14' 178.5(2) . . . . ?
C8' P1' C5' C4' -178.8(2) . . . . ?
C8' P1' C5' C6' 2.00(14) . . . . ?
C8' P1' C17' C18' -175.46(19) . . . . ?
C8' P1' C17' C22' 3.9(2) . . . . ?
C8' C9' C10' Si1' 0.0(2) . . . . ?
C8' C9' C10' C11' 179.13(19) . . . . ?
C8' C9' C14' C13' -179.0(2) . . . . ?
C9' C10' C11' C12' 0.4(4) . . . . ?
C10' Si1' C7' C6' -179.1(2) . . . . ?
C10' Si1' C7' C8' -0.60(15) . . . . ?
C10' C9' C14' C13' -0.1(3) . . . . ?
C10' C11' C12' C13' -0.9(4) . . . . ?
C11' C12' C13' C14' 0.8(5) . . . . ?
C12' C13' C14' C9' -0.4(4) . . . . ?
C14' C9' C10' Si1' -179.10(17) . . . . ?
C14' C9' C10' C11' 0.0(3) . . . . ?
C15' Si1' C7' C6' 64.9(2) . . . . ?
C15' Si1' C7' C8' -116.60(17) . . . . ?
C15' Si1' C10' C9' 116.05(16) . . . . ?
C15' Si1' C10' C11' -62.9(3) . . . . ?
C16' Si1' C7' C6' -63.4(3) . . . . ?
C16' Si1' C7' C8' 115.10(18) . . . . ?
C16' Si1' C10' C9' -114.85(16) . . . . ?
C16' Si1' C10' C11' 66.2(3) . . . . ?
C17' P1' C5' C4' -68.4(2) . . . . ?
C17' P1' C5' C6' 112.43(14) . . . . ?
C17' P1' C8' C7' -111.88(15) . . . . ?
C17' P1' C8' C9' 69.7(2) . . . . ?
C17' C18' C19' C20' -0.6(5) . . . . ?
C18' C17' C22' C21' 0.6(4) . . . . ?
C18' C19' C20' C21' 1.3(5) . . . . ?
C19' C20' C21' C22' -1.0(5) . . . . ?
C20' C21' C22' C17' 0.1(4) . . . . ?
C22' C17' C18' C19' -0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_details          
;
 ?
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.500 0.000 266.2 41.4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1470227'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 Br2 P'
_chemical_formula_sum            'C20 H13 Br2 P'
_chemical_formula_weight         444.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   9.4831(3)
_cell_length_b                   10.0989(3)
_cell_length_c                   10.6905(4)
_cell_angle_alpha                100.8520(10)
_cell_angle_beta                 108.6600(10)
_cell_angle_gamma                110.1360(10)
_cell_volume                     857.93(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7711
_cell_measurement_theta_min      4.6343
_cell_measurement_theta_max      68.3421

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    6.827
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.337
_exptl_absorpt_correction_T_max  0.359
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9719
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.63
_diffrn_reflns_theta_max         68.36
_reflns_number_total             3130
_reflns_number_gt                2964
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0285P)²+0.5108P] 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         3130
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0557
_refine_ls_wR_factor_gt          0.0549
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.23418(3) 0.61960(2) 0.83690(2) 0.02742(8) Uani 1 1 d . . .
Br2 Br 0.03052(3) 0.69616(2) 0.49670(2) 0.02931(8) Uani 1 1 d . . .
P1 P 0.54472(6) 0.85176(5) 0.63523(5) 0.01906(11) Uani 1 1 d . . .
C6 C 0.4826(2) 0.6216(2) 0.73043(19) 0.0207(4) Uani 1 1 d . . .
C4 C 0.6905(3) 0.6425(2) 0.6408(2) 0.0249(4) Uani 1 1 d . . .
H4 H 0.7597 0.6926 0.6007 0.030 Uiso 1 1 calc R . .
C5 C 0.5868(2) 0.6977(2) 0.67391(19) 0.0204(4) Uani 1 1 d . . .
C8 C 0.4015(2) 0.8202(2) 0.71982(19) 0.0200(4) Uani 1 1 d . . .
C15 C 0.8092(3) 1.0263(2) 0.9040(2) 0.0240(4) Uani 1 1 d . . .
H15 H 0.7792 0.9383 0.9287 0.029 Uiso 1 1 calc R . .
C14 C 0.1567(2) 0.8813(2) 0.6477(2) 0.0220(4) Uani 1 1 d . . .
C18 C 0.8975(3) 1.2834(2) 0.8335(2) 0.0276(4) Uani 1 1 d . . .
H18 H 0.9276 1.3719 0.8096 0.033 Uiso 1 1 calc R . .
C7 C 0.3823(2) 0.6967(2) 0.7551(2) 0.0205(4) Uani 1 1 d . . .
C19 C 0.7680(2) 1.1505(2) 0.7337(2) 0.0231(4) Uani 1 1 d . . .
H19 H 0.7103 1.1480 0.6418 0.028 Uiso 1 1 calc R . .
C16 C 0.9381(3) 1.1593(2) 1.0027(2) 0.0287(4) Uani 1 1 d . . .
H16 H 0.9960 1.1624 1.0947 0.034 Uiso 1 1 calc R . .
C17 C 0.9825(3) 1.2877(2) 0.9671(2) 0.0285(4) Uani 1 1 d . . .
H17 H 1.0713 1.3787 1.0344 0.034 Uiso 1 1 calc R . .
C10 C 0.4059(3) 1.0574(2) 0.8443(2) 0.0247(4) Uani 1 1 d . . .
H10 H 0.5169 1.0866 0.9065 0.030 Uiso 1 1 calc R . .
C13 C 0.0825(3) 0.9759(2) 0.6646(2) 0.0272(4) Uani 1 1 d . . .
H13 H -0.0286 0.9474 0.6029 0.033 Uiso 1 1 calc R . .
C20 C 0.7235(2) 1.0210(2) 0.7690(2) 0.0190(4) Uani 1 1 d . . .
C3 C 0.6917(3) 0.5128(2) 0.6671(2) 0.0294(5) Uani 1 1 d . . .
H3 H 0.7639 0.4754 0.6467 0.035 Uiso 1 1 calc R . .
C1 C 0.4827(3) 0.4908(2) 0.7545(2) 0.0265(4) Uani 1 1 d . . .
H1 H 0.4115 0.4387 0.7921 0.032 Uiso 1 1 calc R . .
C12 C 0.1717(3) 1.1125(2) 0.7724(2) 0.0302(5) Uani 1 1 d . . .
H12 H 0.1219 1.1782 0.7849 0.036 Uiso 1 1 calc R . .
C11 C 0.3333(3) 1.1531(2) 0.8617(2) 0.0285(4) Uani 1 1 d . . .
H11 H 0.3946 1.2469 0.9354 0.034 Uiso 1 1 calc R . .
C9 C 0.3186(2) 0.9184(2) 0.7366(2) 0.0204(4) Uani 1 1 d . . .
C2 C 0.5883(3) 0.4379(2) 0.7227(2) 0.0312(5) Uani 1 1 d . . .
H2 H 0.5897 0.3491 0.7393 0.037 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.9060(19) . ?
Br2 C14 1.903(2) . ?
P1 C5 1.8208(19) . ?
P1 C8 1.833(2) . ?
P1 C20 1.837(2) . ?
C6 C1 1.392(3) . ?
C6 C5 1.403(3) . ?
C6 C7 1.460(3) . ?
C4 C5 1.388(3) . ?
C4 C3 1.394(3) . ?
C4 H4 0.9500 . ?
C8 C7 1.340(3) . ?
C8 C9 1.482(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.391(3) . ?
C15 H15 0.9500 . ?
C14 C13 1.386(3) . ?
C14 C9 1.392(3) . ?
C18 C17 1.380(3) . ?
C18 C19 1.391(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(3) . ?
C19 H19 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C10 C11 1.383(3) . ?
C10 C9 1.401(3) . ?
C10 H10 0.9500 . ?
C13 C12 1.386(3) . ?
C13 H13 0.9500 . ?
C3 C2 1.385(3) . ?
C3 H3 0.9500 . ?
C1 C2 1.386(3) . ?
C1 H1 0.9500 . ?
C12 C11 1.383(3) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C2 H2 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
C5 P1 C8 90.02(9) . . ?
C5 P1 C20 104.52(9) . . ?
C8 P1 C20 101.03(9) . . ?
C1 C6 C5 120.43(19) . . ?
C1 C6 C7 128.30(19) . . ?
C5 C6 C7 111.26(17) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.12(18) . . ?
C4 C5 P1 128.41(16) . . ?
C6 C5 P1 111.05(14) . . ?
C7 C8 C9 128.06(18) . . ?
C7 C8 P1 109.90(15) . . ?
C9 C8 P1 121.98(14) . . ?
C16 C15 C20 120.35(19) . . ?
C16 C15 H15 119.8 . . ?
C20 C15 H15 119.8 . . ?
C13 C14 C9 122.05(19) . . ?
C13 C14 Br2 117.96(16) . . ?
C9 C14 Br2 120.00(15) . . ?
C17 C18 C19 120.51(19) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C8 C7 C6 117.22(18) . . ?
C8 C7 Br1 122.89(15) . . ?
C6 C7 Br1 119.88(14) . . ?
C20 C19 C18 119.69(19) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.93(19) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C11 C10 C9 121.18(19) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C19 C20 C15 119.51(18) . . ?
C19 C20 P1 117.47(15) . . ?
C15 C20 P1 122.95(15) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C13 C12 C11 119.85(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C14 C9 C10 117.24(18) . . ?
C14 C9 C8 123.13(17) . . ?
C10 C9 C8 119.61(18) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C5 C6 -1.3(3) . . . . ?
C3 C4 C5 P1 -173.18(15) . . . . ?
C1 C6 C5 C4 0.4(3) . . . . ?
C7 C6 C5 C4 -178.97(17) . . . . ?
C1 C6 C5 P1 173.56(15) . . . . ?
C7 C6 C5 P1 -5.8(2) . . . . ?
C8 P1 C5 C4 179.28(19) . . . . ?
C20 P1 C5 C4 -79.32(19) . . . . ?
C8 P1 C5 C6 6.79(14) . . . . ?
C20 P1 C5 C6 108.19(14) . . . . ?
C5 P1 C8 C7 -6.14(15) . . . . ?
C20 P1 C8 C7 -110.95(15) . . . . ?
C5 P1 C8 C9 176.39(16) . . . . ?
C20 P1 C8 C9 71.59(17) . . . . ?
C9 C8 C7 C6 -178.53(18) . . . . ?
P1 C8 C7 C6 4.2(2) . . . . ?
C9 C8 C7 Br1 0.6(3) . . . . ?
P1 C8 C7 Br1 -176.67(10) . . . . ?
C1 C6 C7 C8 -178.3(2) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C1 C6 C7 Br1 2.6(3) . . . . ?
C5 C6 C7 Br1 -178.15(13) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C20 C15 C16 C17 -0.2(3) . . . . ?
C19 C18 C17 C16 -0.5(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C9 C14 C13 C12 0.5(3) . . . . ?
Br2 C14 C13 C12 -179.13(15) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C18 C19 C20 P1 176.86(16) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C16 C15 C20 P1 -176.73(16) . . . . ?
C5 P1 C20 C19 150.89(16) . . . . ?
C8 P1 C20 C19 -116.19(16) . . . . ?
C5 P1 C20 C15 -32.40(19) . . . . ?
C8 P1 C20 C15 60.52(18) . . . . ?
C5 C4 C3 C2 1.4(3) . . . . ?
C5 C6 C1 C2 0.5(3) . . . . ?
C7 C6 C1 C2 179.67(19) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C13 C12 C11 C10 -0.3(3) . . . . ?
C13 C14 C9 C10 -0.7(3) . . . . ?
Br2 C14 C9 C10 178.92(14) . . . . ?
C13 C14 C9 C8 -179.23(18) . . . . ?
Br2 C14 C9 C8 0.4(3) . . . . ?
C11 C10 C9 C14 0.4(3) . . . . ?
C11 C10 C9 C8 178.96(18) . . . . ?
C7 C8 C9 C14 -77.4(3) . . . . ?
P1 C8 C9 C14 99.6(2) . . . . ?
C7 C8 C9 C10 104.1(2) . . . . ?
P1 C8 C9 C10 -78.9(2) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        68.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.077
