# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1047184'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Br Cl'
_chemical_formula_weight         281.57

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'
Cl Cl 0.3639 0.7018 '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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   16.0522(6)
_cell_length_b                   14.3181(6)
_cell_length_c                   4.6148(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1060.65(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1452
_cell_measurement_theta_min      6.32
_cell_measurement_theta_max      65.07

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    7.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1551
_exptl_absorpt_correction_T_max  0.7603
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            3251
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         6.18
_diffrn_reflns_theta_max         65.10
_reflns_number_total             1310
_reflns_number_gt                1094
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.4200P] 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     SHELXL
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_number_reflns         1310
_refine_ls_number_parameters     137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.50811(3) 0.88783(3) 0.5246(4) 0.0292(2) Uani 1 1 d . . .
Cl1 Cl 0.38898(7) 0.67767(9) 0.4997(6) 0.0240(4) Uani 1 1 d . . .
C1 C 0.4765(4) 0.6823(4) 0.2532(16) 0.0195(15) Uani 1 1 d . . .
H1A H 0.4662 0.6401 0.0871 0.023 Uiso 1 1 calc R . .
H1B H 0.4827 0.7466 0.1773 0.023 Uiso 1 1 calc R . .
C2 C 0.5555(4) 0.6535(4) 0.4053(14) 0.0157(15) Uani 1 1 d . . .
C3 C 0.5819(4) 0.5635(4) 0.3574(16) 0.0199(14) Uani 1 1 d . . .
H3 H 0.5508 0.5262 0.2260 0.024 Uiso 1 1 calc R . .
C4 C 0.6529(4) 0.5227(4) 0.492(2) 0.0219(15) Uani 1 1 d . . .
H4 H 0.6682 0.4598 0.4539 0.026 Uiso 1 1 calc R . .
C5 C 0.6980(4) 0.5760(4) 0.6764(16) 0.0185(15) Uani 1 1 d . . .
C6 C 0.7744(4) 0.5542(4) 0.8536(16) 0.0215(15) Uani 1 1 d . . .
H6A H 0.8211 0.5348 0.7271 0.026 Uiso 1 1 calc R . .
H6B H 0.7628 0.5036 0.9942 0.026 Uiso 1 1 calc R . .
C7 C 0.6032(3) 0.7113(4) 0.5966(14) 0.0145(15) Uani 1 1 d . . .
C8 C 0.6724(4) 0.6694(4) 0.7289(16) 0.0170(14) Uani 1 1 d . . .
C9 C 0.7264(4) 0.7128(4) 0.9266(15) 0.0238(19) Uani 1 1 d . . .
C10 C 0.7106(3) 0.8032(4) 1.005(2) 0.0213(13) Uani 1 1 d . . .
H10 H 0.7446 0.8341 1.1435 0.026 Uiso 1 1 calc R . .
C11 C 0.6436(4) 0.8490(4) 0.8768(17) 0.0228(16) Uani 1 1 d . . .
H11 H 0.6333 0.9122 0.9283 0.027 Uiso 1 1 calc R . .
C12 C 0.5919(4) 0.8072(4) 0.6801(16) 0.0198(15) Uani 1 1 d . . .
C13 C 0.7954(3) 0.6465(4) 1.013(3) 0.0205(12) Uani 1 1 d . . .
H13A H 0.7962 0.6370 1.2253 0.025 Uiso 1 1 calc R . .
H13B H 0.8503 0.6707 0.9506 0.025 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 C12 1.912(6) . ?
Cl1 C1 1.809(7) . ?
C1 C2 1.508(9) . ?
C2 C3 1.374(8) . ?
C2 C7 1.431(8) . ?
C3 C4 1.424(9) . ?
C4 C5 1.352(10) . ?
C5 C8 1.421(8) . ?
C5 C6 1.506(9) . ?
C6 C13 1.548(9) . ?
C7 C8 1.403(9) . ?
C7 C12 1.438(8) . ?
C8 C9 1.404(9) . ?
C9 C10 1.368(8) . ?
C9 C13 1.512(8) . ?
C10 C11 1.392(9) . ?
C11 C12 1.368(9) . ?

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
C2 C1 Cl1 110.5(5) . . ?
C3 C2 C7 118.5(6) . . ?
C3 C2 C1 116.2(5) . . ?
C7 C2 C1 125.3(5) . . ?
C2 C3 C4 124.1(6) . . ?
C5 C4 C3 118.1(5) . . ?
C4 C5 C8 119.0(6) . . ?
C4 C5 C6 131.3(5) . . ?
C8 C5 C6 109.7(5) . . ?
C5 C6 C13 105.0(5) . . ?
C8 C7 C2 116.4(5) . . ?
C8 C7 C12 113.0(6) . . ?
C2 C7 C12 130.6(5) . . ?
C7 C8 C9 125.7(6) . . ?
C7 C8 C5 123.9(6) . . ?
C9 C8 C5 110.4(6) . . ?
C10 C9 C8 118.4(6) . . ?
C10 C9 C13 131.4(6) . . ?
C8 C9 C13 110.2(6) . . ?
C9 C10 C11 118.6(7) . . ?
C12 C11 C10 123.0(6) . . ?
C11 C12 C7 121.3(6) . . ?
C11 C12 Br1 114.3(4) . . ?
C7 C12 Br1 124.4(5) . . ?
C9 C13 C6 104.6(6) . . ?

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        65.00
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1047185'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br Cl'
_chemical_formula_weight         255.53

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0594(3)
_cell_length_b                   28.0000(10)
_cell_length_c                   8.3318(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.1380(10)
_cell_angle_gamma                90
_cell_volume                     1880.18(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    4.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2543
_exptl_absorpt_correction_T_max  0.3391
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15297
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.527
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measured_fraction_theta_full 0.884
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_Laue_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.884
_reflns_number_total             3403
_reflns_number_gt                3081
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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/[σ²(Fo²)+(0.0270P)²+3.0000P] 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         3403
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_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 0.48645(3) 0.14171(2) -0.13684(4) 0.02246(9) Uani 1 1 d . . . . .
Br1' Br 0.38648(3) -0.10762(2) 0.73543(3) 0.02081(8) Uani 1 1 d . . . . .
Cl1' Cl 0.28179(8) -0.00328(2) 0.92768(8) 0.02200(15) Uani 1 1 d . . . . .
Cl1 Cl 0.68810(8) 0.24833(2) -0.07089(8) 0.02133(15) Uani 1 1 d . . . . .
C1 C 0.4942(3) 0.25370(10) -0.1815(3) 0.0172(6) Uani 1 1 d . . . . .
H1A H 0.4970 0.2831 -0.2473 0.021 Uiso 1 1 calc R U . . .
H1B H 0.4826 0.2261 -0.2551 0.021 Uiso 1 1 calc R U . . .
C1' C 0.4138(3) 0.00462(9) 0.7537(3) 0.0169(6) Uani 1 1 d . . . . .
H1'A H 0.4775 0.0347 0.7652 0.020 Uiso 1 1 calc R U . . .
H1'B H 0.4940 -0.0221 0.7479 0.020 Uiso 1 1 calc R U . . .
C2' C 0.3138(3) 0.00636(9) 0.6010(3) 0.0150(5) Uani 1 1 d . . . . .
C2 C 0.3465(3) 0.25546(9) -0.0717(3) 0.0159(5) Uani 1 1 d . . . . .
C3 C 0.2544(3) 0.21498(9) -0.0129(3) 0.0137(5) Uani 1 1 d . . . . .
C3' C 0.2593(3) -0.03436(9) 0.5096(3) 0.0132(5) Uani 1 1 d . . . . .
C4 C 0.2906(3) 0.16518(9) -0.0357(3) 0.0173(6) Uani 1 1 d . . . . .
C4' C 0.2850(3) -0.08407(9) 0.5434(3) 0.0159(5) Uani 1 1 d . . . . .
C5' C 0.2332(3) -0.11978(9) 0.4421(3) 0.0194(6) Uani 1 1 d . . . . .
H5'A H 0.2534 -0.1522 0.4697 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1873(4) 0.12977(10) 0.0176(3) 0.0207(6) Uani 1 1 d . . . . .
H5A H 0.2159 0.0973 -0.0011 0.025 Uiso 1 1 calc R U . . .
C6' C 0.1504(3) -0.10884(10) 0.2974(3) 0.0199(6) Uani 1 1 d . . . . .
H6'A H 0.1184 -0.1336 0.2257 0.024 Uiso 1 1 calc R U . . .
C6 C 0.0376(3) 0.14065(9) 0.1007(3) 0.0173(6) Uani 1 1 d . . . . .
H6A H -0.0358 0.1160 0.1335 0.021 Uiso 1 1 calc R U . . .
C7 C 0.0028(3) 0.18711(10) 0.1319(3) 0.0196(6) Uani 1 1 d . . . . .
H7A H -0.0939 0.1948 0.1915 0.023 Uiso 1 1 calc R U . . .
C7' C 0.1168(3) -0.06234(10) 0.2615(3) 0.0184(6) Uani 1 1 d . . . . .
H7'A H 0.0570 -0.0550 0.1662 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1072(3) 0.22453(9) 0.0776(3) 0.0161(6) Uani 1 1 d . . . . .
C8' C 0.1691(3) -0.02488(9) 0.3632(3) 0.0152(5) Uani 1 1 d . . . . .
C9 C 0.0618(3) 0.27224(10) 0.1157(3) 0.0190(6) Uani 1 1 d . . . . .
H9A H -0.0342 0.2781 0.1787 0.023 Uiso 1 1 calc R U . . .
C9' C 0.1317(3) 0.02279(9) 0.3177(3) 0.0174(6) Uani 1 1 d . . . . .
H9'A H 0.0690 0.0285 0.2229 0.021 Uiso 1 1 calc R U . . .
C10 C 0.1550(3) 0.30954(9) 0.0625(3) 0.0202(6) Uani 1 1 d . . . . .
H10A H 0.1249 0.3413 0.0897 0.024 Uiso 1 1 calc R U . . .
C10' C 0.1844(3) 0.06034(10) 0.4077(3) 0.0188(6) Uani 1 1 d . . . . .
H10B H 0.1596 0.0921 0.3758 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2957(3) 0.30111(10) -0.0327(3) 0.0200(6) Uani 1 1 d . . . . .
H11A H 0.3576 0.3276 -0.0714 0.024 Uiso 1 1 calc R U . . .
C11' C 0.2760(3) 0.05166(9) 0.5483(3) 0.0179(6) Uani 1 1 d . . . . .
H11B H 0.3134 0.0782 0.6097 0.022 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
Br1 C4 1.908(3) . ?
Br1' C4' 1.913(2) . ?
Cl1' C1' 1.814(3) . ?
Cl1 C1 1.818(2) . ?
C1 C2 1.504(4) . ?
C1' C2' 1.505(3) . ?
C2' C11' 1.376(4) . ?
C2' C3' 1.439(3) . ?
C2 C11 1.381(4) . ?
C2 C3 1.442(4) . ?
C3 C8 1.433(4) . ?
C3 C4 1.437(4) . ?
C3' C4' 1.435(3) . ?
C3' C8' 1.443(3) . ?
C4 C5 1.370(4) . ?
C4' C5' 1.373(4) . ?
C5' C6' 1.411(4) . ?
C5 C6 1.425(4) . ?
C6' C7' 1.363(4) . ?
C6 C7 1.356(4) . ?
C7 C8 1.418(4) . ?
C7' C8' 1.412(4) . ?
C8 C9 1.421(4) . ?
C8' C9' 1.420(4) . ?
C9 C10 1.362(4) . ?
C9' C10' 1.359(4) . ?
C10 C11 1.405(4) . ?
C10' C11' 1.405(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl1 112.03(18) . . ?
C2' C1' Cl1' 111.44(18) . . ?
C11' C2' C3' 119.6(2) . . ?
C11' C2' C1' 114.7(2) . . ?
C3' C2' C1' 125.7(2) . . ?
C11 C2 C3 119.6(3) . . ?
C11 C2 C1 114.2(2) . . ?
C3 C2 C1 126.2(2) . . ?
C8 C3 C4 114.8(2) . . ?
C8 C3 C2 117.4(2) . . ?
C4 C3 C2 127.8(3) . . ?
C4' C3' C2' 128.4(2) . . ?
C4' C3' C8' 114.6(2) . . ?
C2' C3' C8' 117.0(2) . . ?
C5 C4 C3 122.4(3) . . ?
C5 C4 Br1 113.5(2) . . ?
C3 C4 Br1 124.1(2) . . ?
C5' C4' C3' 122.9(2) . . ?
C5' C4' Br1' 113.07(19) . . ?
C3' C4' Br1' 124.03(19) . . ?
C4' C5' C6' 120.7(2) . . ?
C4 C5 C6 121.2(3) . . ?
C7' C6' C5' 119.2(2) . . ?
C7 C6 C5 118.3(2) . . ?
C6 C7 C8 121.6(3) . . ?
C6' C7' C8' 121.3(2) . . ?
C7 C8 C9 118.0(3) . . ?
C7 C8 C3 121.5(2) . . ?
C9 C8 C3 120.5(2) . . ?
C7' C8' C9' 118.4(2) . . ?
C7' C8' C3' 121.3(2) . . ?
C9' C8' C3' 120.3(2) . . ?
C10 C9 C8 120.4(3) . . ?
C10' C9' C8' 121.0(2) . . ?
C9 C10 C11 120.1(3) . . ?
C9' C10' C11' 119.3(2) . . ?
C2 C11 C10 121.9(3) . . ?
C2' C11' C10' 122.8(2) . . ?

_refine_diff_density_max         1.098
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1047186'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Br O2 P'
_chemical_formula_weight         429.28

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   18.9410(7)
_cell_length_b                   17.6865(6)
_cell_length_c                   5.6269(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1885.01(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7106
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            9974
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.41
_reflns_number_total             3251
_reflns_number_gt                3055
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0240P)²+0.2246P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3251
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_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 0.307580(16) 0.716584(15) 0.50798(7) 0.02862(10) Uani 1 1 d . . .
P1 P 0.10000(4) 0.77446(4) 0.61692(12) 0.01273(17) Uani 1 1 d . . .
O1 O 0.11720(11) 0.78677(11) 0.3640(4) 0.0176(5) Uani 1 1 d . . .
O2 O 0.07225(9) 0.69184(10) 0.6814(3) 0.0137(4) Uani 1 1 d . . .
C1 C 0.03001(14) 0.83698(15) 0.7114(5) 0.0137(6) Uani 1 1 d . . .
C2 C 0.01176(13) 0.89713(15) 0.5662(4) 0.0162(6) Uani 1 1 d . . .
H2A H 0.0360 0.9049 0.4245 0.019 Uiso 1 1 calc R . .
C3 C -0.04241(14) 0.94593(16) 0.6308(5) 0.0204(6) Uani 1 1 d . . .
H3A H -0.0539 0.9867 0.5339 0.024 Uiso 1 1 calc R . .
C4 C -0.07889(15) 0.93372(16) 0.8384(5) 0.0188(6) Uani 1 1 d . . .
H4A H -0.1158 0.9658 0.8796 0.023 Uiso 1 1 calc R . .
C5 C -0.06138(13) 0.87425(15) 0.9867(6) 0.0198(6) Uani 1 1 d . . .
H5A H -0.0862 0.8665 1.1271 0.024 Uiso 1 1 calc R . .
C6 C -0.00611(14) 0.82586(17) 0.9241(5) 0.0188(6) Uani 1 1 d . . .
H6A H 0.0065 0.7863 1.0243 0.023 Uiso 1 1 calc R . .
C7 C -0.03090(15) 0.61550(18) 0.7144(5) 0.0242(7) Uani 1 1 d . . .
H7A H -0.0482 0.6485 0.8365 0.036 Uiso 1 1 calc R . .
H7B H -0.0028 0.5763 0.7849 0.036 Uiso 1 1 calc R . .
H7C H -0.0700 0.5933 0.6314 0.036 Uiso 1 1 calc R . .
C8 C 0.01381(13) 0.66024(15) 0.5415(5) 0.0171(6) Uani 1 1 d . . .
H8A H -0.0144 0.7016 0.4748 0.021 Uiso 1 1 calc R . .
C9 C 0.04354(15) 0.61310(17) 0.3426(5) 0.0240(7) Uani 1 1 d . . .
H9A H 0.0713 0.6445 0.2395 0.036 Uiso 1 1 calc R . .
H9B H 0.0056 0.5909 0.2538 0.036 Uiso 1 1 calc R . .
H9C H 0.0727 0.5738 0.4075 0.036 Uiso 1 1 calc R . .
C10 C 0.17298(14) 0.78381(14) 0.8203(5) 0.0130(6) Uani 1 1 d . . .
H10A H 0.1561 0.7817 0.9829 0.016 Uiso 1 1 calc R . .
H10B H 0.2062 0.7428 0.7967 0.016 Uiso 1 1 calc R . .
C11 C 0.20868(14) 0.85886(16) 0.7743(4) 0.0131(6) Uani 1 1 d . . .
C12 C 0.25829(13) 0.87226(15) 0.5863(5) 0.0140(6) Uani 1 1 d . . .
C13 C 0.29695(14) 0.82196(16) 0.4381(5) 0.0166(7) Uani 1 1 d . . .
C14 C 0.33632(15) 0.84652(16) 0.2477(5) 0.0180(6) Uani 1 1 d . . .
H14A H 0.3586 0.8110 0.1516 0.022 Uiso 1 1 calc R . .
C15 C 0.34384(14) 0.92347(16) 0.1943(5) 0.0197(6) Uani 1 1 d . . .
H15A H 0.3687 0.9388 0.0602 0.024 Uiso 1 1 calc R . .
C16 C 0.31408(13) 0.97534(17) 0.3424(5) 0.0157(6) Uani 1 1 d . . .
C17 C 0.27238(13) 0.94947(14) 0.5336(5) 0.0142(6) Uani 1 1 d . . .
C18 C 0.24471(14) 1.01052(15) 0.6654(5) 0.0150(6) Uani 1 1 d . . .
C19 C 0.20203(14) 0.99608(16) 0.8544(5) 0.0178(6) Uani 1 1 d . . .
H19A H 0.1850 1.0353 0.9486 0.021 Uiso 1 1 calc R . .
C20 C 0.18407(14) 0.91986(16) 0.9045(5) 0.0157(6) Uani 1 1 d . . .
H20A H 0.1541 0.9103 1.0319 0.019 Uiso 1 1 calc R . .
C21 C 0.31562(15) 1.06085(18) 0.3429(5) 0.0227(7) Uani 1 1 d . . .
H21A H 0.2962 1.0808 0.1962 0.027 Uiso 1 1 calc R . .
H21B H 0.3636 1.0793 0.3611 0.027 Uiso 1 1 calc R . .
C22 C 0.26977(15) 1.08427(15) 0.5572(5) 0.0204(7) Uani 1 1 d . . .
H22A H 0.2973 1.1130 0.6710 0.025 Uiso 1 1 calc R . .
H22B H 0.2300 1.1147 0.5059 0.025 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 C13 1.915(3) . ?
P1 O1 1.476(2) . ?
P1 O2 1.5947(19) . ?
P1 C10 1.802(3) . ?
P1 C1 1.806(3) . ?
O2 C8 1.469(3) . ?
C1 C2 1.385(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.374(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.397(4) . ?
C7 C8 1.513(4) . ?
C8 C9 1.505(4) . ?
C10 C11 1.512(4) . ?
C11 C20 1.385(4) . ?
C11 C12 1.434(4) . ?
C12 C13 1.423(4) . ?
C12 C17 1.423(4) . ?
C13 C14 1.376(4) . ?
C14 C15 1.401(4) . ?
C15 C16 1.362(4) . ?
C16 C17 1.411(4) . ?
C16 C21 1.513(4) . ?
C17 C18 1.411(4) . ?
C18 C19 1.360(4) . ?
C18 C22 1.516(4) . ?
C19 C20 1.419(4) . ?
C21 C22 1.543(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 115.28(11) . . ?
O1 P1 C10 115.44(13) . . ?
O2 P1 C10 101.10(11) . . ?
O1 P1 C1 110.82(13) . . ?
O2 P1 C1 104.60(11) . . ?
C10 P1 C1 108.65(12) . . ?
C8 O2 P1 118.39(16) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 P1 118.7(2) . . ?
C6 C1 P1 121.8(2) . . ?
C1 C2 C3 120.5(3) . . ?
C4 C3 C2 119.7(3) . . ?
C3 C4 C5 120.8(3) . . ?
C4 C5 C6 119.6(3) . . ?
C1 C6 C5 119.9(3) . . ?
O2 C8 C9 109.1(2) . . ?
O2 C8 C7 106.1(2) . . ?
C9 C8 C7 113.4(2) . . ?
C11 C10 P1 108.34(17) . . ?
C20 C11 C12 118.8(3) . . ?
C20 C11 C10 116.3(2) . . ?
C12 C11 C10 124.4(2) . . ?
C13 C12 C17 112.4(2) . . ?
C13 C12 C11 131.8(3) . . ?
C17 C12 C11 115.8(2) . . ?
C14 C13 C12 122.6(3) . . ?
C14 C13 Br1 114.2(2) . . ?
C12 C13 Br1 122.83(19) . . ?
C13 C14 C15 121.9(3) . . ?
C16 C15 C14 118.8(3) . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 C21 131.8(3) . . ?
C17 C16 C21 109.5(2) . . ?
C16 C17 C18 111.1(2) . . ?
C16 C17 C12 125.1(3) . . ?
C18 C17 C12 123.7(3) . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 C22 131.4(3) . . ?
C17 C18 C22 109.3(2) . . ?
C18 C19 C20 118.5(3) . . ?
C11 C20 C19 123.7(3) . . ?
C16 C21 C22 105.0(2) . . ?
C18 C22 C21 105.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_Ph-11
_database_code_depnum_ccdc_archive 'CCDC 1047187'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 Br P'
_chemical_formula_weight         355.20

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.217(3)
_cell_length_b                   6.9781(19)
_cell_length_c                   10.816(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.873(3)
_cell_angle_gamma                90.00
_cell_volume                     754.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6268
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5284
_exptl_absorpt_correction_T_max  0.7580
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11849
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.93
_reflns_number_total             3365
_reflns_number_gt                2979
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(19)
_refine_ls_number_reflns         3365
_refine_ls_number_parameters     194
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.49803(3) 0.75799(7) 0.26581(3) 0.02573(12) Uani 1 1 d . . .
P1 P 0.65892(11) 0.43606(16) 0.49373(9) 0.0242(2) Uani 1 1 d D . .
H1 H 0.733(4) 0.566(5) 0.460(4) 0.036 Uiso 1 1 d D . .
C1 C 0.6602(4) 0.3248(5) 0.2389(3) 0.0190(8) Uani 1 1 d . . .
C2 C 0.7358(4) 0.1651(6) 0.2267(4) 0.0217(8) Uani 1 1 d . . .
H2A H 0.7376 0.0637 0.2857 0.026 Uiso 1 1 calc R . .
C3 C 0.8111(4) 0.1433(6) 0.1307(4) 0.0217(9) Uani 1 1 d . . .
H3A H 0.8621 0.0307 0.1263 0.026 Uiso 1 1 calc R . .
C4 C 0.8087(3) 0.2861(7) 0.0459(3) 0.0224(9) Uani 1 1 d . . .
C5 C 0.7339(4) 0.4525(6) 0.0573(3) 0.0204(8) Uani 1 1 d . . .
C6 C 0.6608(3) 0.4813(6) 0.1535(3) 0.0199(8) Uani 1 1 d . . .
C7 C 0.5957(4) 0.6642(6) 0.1449(4) 0.0214(8) Uani 1 1 d . . .
C8 C 0.6014(4) 0.7913(6) 0.0503(3) 0.0245(10) Uani 1 1 d . . .
H8A H 0.5546 0.9093 0.0484 0.029 Uiso 1 1 calc R . .
C9 C 0.6738(3) 0.7541(9) -0.0444(3) 0.0235(7) Uani 1 1 d . . .
H9A H 0.6760 0.8445 -0.1096 0.028 Uiso 1 1 calc R . .
C10 C 0.7410(4) 0.5845(6) -0.0399(3) 0.0221(8) Uani 1 1 d . . .
C11 C 0.8255(4) 0.5023(6) -0.1255(4) 0.0264(9) Uani 1 1 d . . .
H11A H 0.9028 0.5868 -0.1282 0.032 Uiso 1 1 calc R . .
H11B H 0.7723 0.4867 -0.2123 0.032 Uiso 1 1 calc R . .
C12 C 0.8734(4) 0.3054(7) -0.0673(4) 0.0323(12) Uani 1 1 d . . .
H12A H 0.8442 0.2009 -0.1286 0.039 Uiso 1 1 calc R . .
H12B H 0.9721 0.3020 -0.0411 0.039 Uiso 1 1 calc R . .
C13 C 0.5798(4) 0.3217(6) 0.3420(3) 0.0208(8) Uani 1 1 d . . .
H13A H 0.5601 0.1865 0.3591 0.025 Uiso 1 1 calc R . .
H13B H 0.4932 0.3862 0.3096 0.025 Uiso 1 1 calc R . .
C14 C 0.7915(3) 0.2650(8) 0.5562(3) 0.0209(7) Uani 1 1 d . . .
C15 C 0.9237(4) 0.3273(6) 0.5976(3) 0.0246(9) Uani 1 1 d . . .
H15A H 0.9465 0.4566 0.5843 0.029 Uiso 1 1 calc R . .
C16 C 1.0211(4) 0.2022(6) 0.6577(4) 0.0277(11) Uani 1 1 d . . .
H16A H 1.1102 0.2461 0.6867 0.033 Uiso 1 1 calc R . .
C17 C 0.9893(4) 0.0141(7) 0.6755(4) 0.0293(10) Uani 1 1 d . . .
H17A H 1.0567 -0.0719 0.7160 0.035 Uiso 1 1 calc R . .
C18 C 0.8590(4) -0.0508(7) 0.6345(4) 0.0280(9) Uani 1 1 d . . .
H18A H 0.8370 -0.1809 0.6461 0.034 Uiso 1 1 calc R . .
C19 C 0.7612(4) 0.0773(6) 0.5764(4) 0.0261(9) Uani 1 1 d . . .
H19A H 0.6717 0.0340 0.5500 0.031 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 1.916(4) . ?
P1 C14 1.827(5) . ?
P1 C13 1.854(4) . ?
P1 H1 1.285(19) . ?
C1 C2 1.378(5) . ?
C1 C6 1.432(5) . ?
C1 C13 1.515(5) . ?
C2 C3 1.422(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.350(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.410(6) . ?
C4 C12 1.513(5) . ?
C5 C10 1.411(6) . ?
C5 C6 1.414(5) . ?
C6 C7 1.433(5) . ?
C7 C8 1.364(6) . ?
C8 C9 1.406(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.364(7) . ?
C9 H9A 0.9500 . ?
C10 C11 1.504(5) . ?
C11 C12 1.548(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.373(7) . ?
C14 C15 1.402(5) . ?
C15 C16 1.382(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.376(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.389(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.390(6) . ?
C18 H18A 0.9500 . ?
C19 H19A 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
C14 P1 C13 101.60(17) . . ?
C14 P1 H1 98(2) . . ?
C13 P1 H1 103.0(19) . . ?
C2 C1 C6 118.6(3) . . ?
C2 C1 C13 117.3(3) . . ?
C6 C1 C13 124.1(3) . . ?
C1 C2 C3 123.7(4) . . ?
C1 C2 H2A 118.2 . . ?
C3 C2 H2A 118.2 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C12 131.7(4) . . ?
C5 C4 C12 109.4(4) . . ?
C4 C5 C10 111.2(3) . . ?
C4 C5 C6 124.0(4) . . ?
C10 C5 C6 124.8(4) . . ?
C5 C6 C1 116.1(4) . . ?
C5 C6 C7 112.8(4) . . ?
C1 C6 C7 131.1(3) . . ?
C8 C7 C6 122.5(4) . . ?
C8 C7 Br1 113.5(3) . . ?
C6 C7 Br1 124.1(3) . . ?
C7 C8 C9 122.4(4) . . ?
C7 C8 H8A 118.8 . . ?
C9 C8 H8A 118.8 . . ?
C10 C9 C8 118.1(4) . . ?
C10 C9 H9A 121.0 . . ?
C8 C9 H9A 121.0 . . ?
C9 C10 C5 119.4(3) . . ?
C9 C10 C11 131.1(4) . . ?
C5 C10 C11 109.5(4) . . ?
C10 C11 C12 105.2(3) . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11A 110.7 . . ?
C10 C11 H11B 110.7 . . ?
C12 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C4 C12 C11 104.7(3) . . ?
C4 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C4 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C1 C13 P1 116.2(2) . . ?
C1 C13 H13A 108.2 . . ?
P1 C13 H13A 108.2 . . ?
C1 C13 H13B 108.2 . . ?
P1 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C19 C14 C15 118.6(4) . . ?
C19 C14 P1 120.5(3) . . ?
C15 C14 P1 120.5(4) . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C19 C18 C17 119.1(4) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C14 C19 C18 121.4(4) . . ?
C14 C19 H19A 119.3 . . ?
C18 C19 H19A 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_18a
_database_code_depnum_ccdc_archive 'CCDC 1047188'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H48 F6 P4 Pt'
_chemical_formula_weight         997.78

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'
F F 0.0171 0.0103 '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'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   12.5232(4)
_cell_length_b                   15.3824(5)
_cell_length_c                   20.9494(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4035.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9332
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    3.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3342
_exptl_absorpt_correction_T_max  0.3844
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            50401
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         26.43
_reflns_number_total             8283
_reflns_number_gt                7835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+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     SHELXL
_refine_ls_extinction_coef       0.00025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8283
_refine_ls_number_parameters     488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_ref         0.0394
_refine_ls_wR_factor_gt          0.0387
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.911
_refine_ls_shift/su_max          0.007
_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
Pt1 Pt 0.758649(8) 0.151234(6) 0.683745(5) 0.00943(3) Uani 1 1 d . . .
P1 P 0.79742(6) 0.18191(5) 0.57953(4) 0.01147(17) Uani 1 1 d . . .
P2 P 0.72044(6) 0.29511(5) 0.69411(3) 0.01107(16) Uani 1 1 d . . .
P3 P 0.81029(6) 0.00793(5) 0.69147(4) 0.01219(16) Uani 1 1 d . . .
F1 F 0.65235(17) 0.29098(14) 0.27008(11) 0.0392(6) Uani 1 1 d . . .
F2 F 0.84169(16) 0.38183(15) 0.34668(10) 0.0378(6) Uani 1 1 d . . .
F3 F 0.83217(18) 0.28258(16) 0.26789(10) 0.0431(7) Uani 1 1 d . . .
F4 F 0.7506(2) 0.41216(11) 0.25579(8) 0.0366(5) Uani 1 1 d . . .
F5 F 0.74466(19) 0.26043(11) 0.36034(8) 0.0340(5) Uani 1 1 d . . .
F6 F 0.66259(17) 0.39086(15) 0.34875(11) 0.0438(7) Uani 1 1 d . . .
C1 C 0.7701(2) 0.29709(18) 0.56566(12) 0.0108(6) Uani 1 1 d . . .
C2 C 0.7819(2) 0.33571(19) 0.50519(13) 0.0147(7) Uani 1 1 d . . .
H2A H 0.8056 0.3018 0.4701 0.018 Uiso 1 1 calc R . .
C3 C 0.7591(2) 0.42274(18) 0.49674(13) 0.0176(6) Uani 1 1 d . . .
H3A H 0.7664 0.4486 0.4558 0.021 Uiso 1 1 calc R . .
C4 C 0.7256(2) 0.47223(18) 0.54808(13) 0.0182(7) Uani 1 1 d . . .
H4A H 0.7096 0.5321 0.5421 0.022 Uiso 1 1 calc R . .
C5 C 0.7151(2) 0.43574(19) 0.60768(13) 0.0154(7) Uani 1 1 d . . .
H5A H 0.6934 0.4706 0.6428 0.018 Uiso 1 1 calc R . .
C6 C 0.7364(2) 0.34762(18) 0.61663(12) 0.0122(6) Uani 1 1 d . . .
C7 C 0.5913(2) 0.32802(19) 0.72882(14) 0.0152(7) Uani 1 1 d . . .
H7A H 0.5651 0.2773 0.7543 0.018 Uiso 1 1 calc R . .
C8 C 0.5047(2) 0.3486(2) 0.68072(15) 0.0231(7) Uani 1 1 d . . .
H8A H 0.4390 0.3646 0.7032 0.035 Uiso 1 1 calc R . .
H8B H 0.4913 0.2974 0.6541 0.035 Uiso 1 1 calc R . .
H8C H 0.5277 0.3971 0.6537 0.035 Uiso 1 1 calc R . .
C9 C 0.6200(3) 0.3999(2) 0.77728(15) 0.0213(8) Uani 1 1 d . . .
H9A H 0.6229 0.4572 0.7557 0.026 Uiso 1 1 calc R . .
H9B H 0.5655 0.4027 0.8115 0.026 Uiso 1 1 calc R . .
C10 C 0.7286(3) 0.37735(19) 0.80537(13) 0.0223(7) Uani 1 1 d . . .
H10A H 0.7223 0.3263 0.8339 0.027 Uiso 1 1 calc R . .
H10B H 0.7563 0.4269 0.8306 0.027 Uiso 1 1 calc R . .
C11 C 0.8049(2) 0.3569(2) 0.75015(13) 0.0176(7) Uani 1 1 d . . .
H11A H 0.8228 0.4133 0.7291 0.021 Uiso 1 1 calc R . .
C12 C 0.9098(2) 0.3127(2) 0.76666(16) 0.0224(8) Uani 1 1 d . . .
H12A H 0.9501 0.3493 0.7964 0.034 Uiso 1 1 calc R . .
H12B H 0.9516 0.3040 0.7276 0.034 Uiso 1 1 calc R . .
H12C H 0.8953 0.2563 0.7866 0.034 Uiso 1 1 calc R . .
C13 C 0.9273(2) 0.1554(2) 0.54285(15) 0.0251(8) Uani 1 1 d . . .
H13A H 0.9571 0.1059 0.5681 0.030 Uiso 1 1 calc R . .
C14 C 1.0107(3) 0.2259(3) 0.5447(2) 0.0512(13) Uani 1 1 d . . .
H14A H 1.0761 0.2051 0.5241 0.077 Uiso 1 1 calc R . .
H14B H 1.0260 0.2413 0.5891 0.077 Uiso 1 1 calc R . .
H14C H 0.9842 0.2773 0.5220 0.077 Uiso 1 1 calc R . .
C15 C 0.8999(3) 0.1187(3) 0.47717(16) 0.0460(12) Uani 1 1 d . . .
H15A H 0.8890 0.1665 0.4462 0.055 Uiso 1 1 calc R . .
H15B H 0.9586 0.0812 0.4615 0.055 Uiso 1 1 calc R . .
C16 C 0.7979(3) 0.0659(2) 0.48457(16) 0.0422(11) Uani 1 1 d . . .
H16A H 0.8123 0.0124 0.5094 0.051 Uiso 1 1 calc R . .
H16B H 0.7701 0.0489 0.4421 0.051 Uiso 1 1 calc R . .
C17 C 0.7167(3) 0.1223(2) 0.51927(14) 0.0224(9) Uani 1 1 d . . .
H17A H 0.6893 0.1660 0.4880 0.027 Uiso 1 1 calc R . .
C18 C 0.6202(3) 0.0743(3) 0.54654(18) 0.0450(12) Uani 1 1 d . . .
H18A H 0.5821 0.0447 0.5119 0.068 Uiso 1 1 calc R . .
H18B H 0.5723 0.1160 0.5673 0.068 Uiso 1 1 calc R . .
H18C H 0.6443 0.0313 0.5779 0.068 Uiso 1 1 calc R . .
C19 C 0.6862(2) 0.12876(18) 0.77184(14) 0.0118(7) Uani 1 1 d . . .
C20 C 0.7321(3) 0.13352(16) 0.83206(12) 0.0162(7) Uani 1 1 d . . .
H20A H 0.8065 0.1448 0.8356 0.019 Uiso 1 1 calc R . .
C21 C 0.6725(3) 0.1222(2) 0.88729(15) 0.0221(8) Uani 1 1 d . . .
H21A H 0.7063 0.1268 0.9278 0.026 Uiso 1 1 calc R . .
C22 C 0.5644(3) 0.1045(2) 0.88395(15) 0.0207(8) Uani 1 1 d . . .
H22A H 0.5239 0.0961 0.9218 0.025 Uiso 1 1 calc R . .
C23 C 0.5161(2) 0.09909(19) 0.82464(15) 0.0197(7) Uani 1 1 d . . .
H23A H 0.4419 0.0869 0.8216 0.024 Uiso 1 1 calc R . .
C24 C 0.5760(2) 0.11144(19) 0.76969(14) 0.0151(7) Uani 1 1 d . . .
H24A H 0.5415 0.1081 0.7294 0.018 Uiso 1 1 calc R . .
C25 C 0.6950(2) -0.06833(19) 0.69251(14) 0.0171(7) Uani 1 1 d . . .
H25A H 0.6844 -0.0923 0.7359 0.020 Uiso 1 1 calc R . .
H25B H 0.6288 -0.0380 0.6793 0.020 Uiso 1 1 calc R . .
C26 C 0.7217(2) -0.14027(19) 0.64595(13) 0.0131(6) Uani 1 1 d . . .
C27 C 0.6657(2) -0.2139(2) 0.63188(15) 0.0181(7) Uani 1 1 d . . .
H27A H 0.5981 -0.2232 0.6512 0.022 Uiso 1 1 calc R . .
C28 C 0.7072(3) -0.2780(2) 0.58820(15) 0.0192(8) Uani 1 1 d . . .
H28A H 0.6664 -0.3284 0.5785 0.023 Uiso 1 1 calc R . .
C29 C 0.8042(3) -0.2665(2) 0.56093(15) 0.0187(8) Uani 1 1 d . . .
C30 C 0.8747(3) -0.3187(2) 0.51534(16) 0.0274(9) Uani 1 1 d . . .
H30A H 0.8408 -0.3234 0.4728 0.033 Uiso 1 1 calc R . .
H30B H 0.8872 -0.3780 0.5322 0.033 Uiso 1 1 calc R . .
C31 C 0.9810(3) -0.2672(2) 0.51120(17) 0.0276(9) Uani 1 1 d . . .
H31A H 1.0406 -0.3020 0.5288 0.033 Uiso 1 1 calc R . .
H31B H 0.9976 -0.2524 0.4663 0.033 Uiso 1 1 calc R . .
C32 C 0.9644(2) -0.1861(2) 0.54991(15) 0.0175(7) Uani 1 1 d . . .
C33 C 1.0258(2) -0.1157(2) 0.56595(13) 0.0149(7) Uani 1 1 d . . .
H33A H 1.0959 -0.1106 0.5490 0.018 Uiso 1 1 calc R . .
C34 C 0.9862(2) -0.0499(2) 0.60762(13) 0.0142(7) Uani 1 1 d . . .
H34A H 1.0302 -0.0018 0.6183 0.017 Uiso 1 1 calc R . .
C35 C 0.8845(2) -0.0554(2) 0.63263(14) 0.0124(7) Uani 1 1 d . . .
C36 C 0.8217(2) -0.12767(19) 0.61722(13) 0.0124(7) Uani 1 1 d . . .
C37 C 0.8613(2) -0.1911(2) 0.57573(14) 0.0152(7) Uani 1 1 d . . .
C38 C 0.8883(2) -0.0058(2) 0.76376(14) 0.0145(7) Uani 1 1 d . . .
C39 C 0.9729(2) 0.0507(2) 0.77377(15) 0.0200(7) Uani 1 1 d . . .
H39A H 0.9891 0.0934 0.7425 0.024 Uiso 1 1 calc R . .
C40 C 1.0339(2) 0.0458(2) 0.82835(15) 0.0267(8) Uani 1 1 d . . .
H40A H 1.0917 0.0847 0.8348 0.032 Uiso 1 1 calc R . .
C41 C 1.0097(3) -0.0169(3) 0.87388(16) 0.0302(9) Uani 1 1 d . . .
H41A H 1.0507 -0.0206 0.9120 0.036 Uiso 1 1 calc R . .
C42 C 0.9267(3) -0.0734(2) 0.86377(16) 0.0295(9) Uani 1 1 d . . .
H42A H 0.9105 -0.1161 0.8950 0.035 Uiso 1 1 calc R . .
C43 C 0.8667(2) -0.0689(2) 0.80899(15) 0.0224(7) Uani 1 1 d . . .
H43A H 0.8104 -0.1092 0.8022 0.027 Uiso 1 1 calc R . .
P4 P 0.74703(6) 0.33643(5) 0.30795(3) 0.01986(16) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pt1 C19 2.086(3) . ?
Pt1 P2 2.2747(7) . ?
Pt1 P1 2.2859(7) . ?
Pt1 P3 2.3030(7) . ?
P1 C1 1.828(3) . ?
P1 C13 1.844(3) . ?
P1 C17 1.859(3) . ?
P2 C6 1.824(3) . ?
P2 C11 1.844(3) . ?
P2 C7 1.845(3) . ?
P3 C38 1.815(3) . ?
P3 C35 1.825(3) . ?
P3 C25 1.861(3) . ?
F1 P4 1.589(2) . ?
F2 P4 1.597(2) . ?
F3 P4 1.590(2) . ?
F4 P4 1.5979(17) . ?
F5 P4 1.6038(17) . ?
F6 P4 1.597(2) . ?
C1 C6 1.387(4) . ?
C1 C2 1.407(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.375(4) . ?
C5 C6 1.394(4) . ?
C7 C8 1.514(4) . ?
C7 C9 1.544(4) . ?
C9 C10 1.523(4) . ?
C10 C11 1.533(4) . ?
C11 C12 1.519(4) . ?
C13 C14 1.506(5) . ?
C13 C15 1.527(5) . ?
C15 C16 1.521(5) . ?
C16 C17 1.521(5) . ?
C17 C18 1.527(5) . ?
C19 C20 1.388(4) . ?
C19 C24 1.406(4) . ?
C20 C21 1.388(4) . ?
C21 C22 1.383(5) . ?
C22 C23 1.384(4) . ?
C23 C24 1.387(4) . ?
C25 C26 1.513(4) . ?
C26 C27 1.365(4) . ?
C26 C36 1.403(4) . ?
C27 C28 1.442(4) . ?
C28 C29 1.354(4) . ?
C29 C37 1.398(4) . ?
C29 C30 1.529(4) . ?
C30 C31 1.552(4) . ?
C31 C32 1.502(4) . ?
C32 C33 1.370(4) . ?
C32 C37 1.402(4) . ?
C33 C34 1.425(4) . ?
C34 C35 1.379(4) . ?
C35 C36 1.400(4) . ?
C36 C37 1.398(4) . ?
C38 C43 1.383(4) . ?
C38 C39 1.386(4) . ?
C39 C40 1.377(4) . ?
C40 C41 1.390(5) . ?
C41 C42 1.371(5) . ?
C42 C43 1.374(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 Pt1 P2 89.16(8) . . ?
C19 Pt1 P1 166.38(8) . . ?
P2 Pt1 P1 86.27(3) . . ?
C19 Pt1 P3 84.34(8) . . ?
P2 Pt1 P3 169.63(3) . . ?
P1 Pt1 P3 101.83(3) . . ?
C1 P1 C13 108.22(15) . . ?
C1 P1 C17 105.57(13) . . ?
C13 P1 C17 95.04(15) . . ?
C1 P1 Pt1 108.19(9) . . ?
C13 P1 Pt1 122.66(11) . . ?
C17 P1 Pt1 115.55(11) . . ?
C6 P2 C11 106.01(13) . . ?
C6 P2 C7 108.99(13) . . ?
C11 P2 C7 96.35(14) . . ?
C6 P2 Pt1 108.83(9) . . ?
C11 P2 Pt1 116.20(10) . . ?
C7 P2 Pt1 119.28(10) . . ?
C38 P3 C35 103.15(13) . . ?
C38 P3 C25 109.56(14) . . ?
C35 P3 C25 93.81(13) . . ?
C38 P3 Pt1 108.72(10) . . ?
C35 P3 Pt1 127.33(10) . . ?
C25 P3 Pt1 112.73(10) . . ?
C6 C1 C2 119.2(3) . . ?
C6 C1 P1 118.6(2) . . ?
C2 C1 P1 122.2(2) . . ?
C3 C2 C1 120.2(3) . . ?
C2 C3 C4 119.8(3) . . ?
C5 C4 C3 120.7(3) . . ?
C4 C5 C6 120.1(3) . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 P2 118.1(2) . . ?
C5 C6 P2 122.0(2) . . ?
C8 C7 C9 117.0(3) . . ?
C8 C7 P2 115.0(2) . . ?
C9 C7 P2 104.6(2) . . ?
C10 C9 C7 107.4(2) . . ?
C9 C10 C11 108.2(2) . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 P2 114.2(2) . . ?
C10 C11 P2 103.2(2) . . ?
C14 C13 C15 116.5(3) . . ?
C14 C13 P1 116.2(3) . . ?
C15 C13 P1 105.0(2) . . ?
C16 C15 C13 107.1(3) . . ?
C15 C16 C17 107.8(3) . . ?
C16 C17 C18 115.6(3) . . ?
C16 C17 P1 104.0(2) . . ?
C18 C17 P1 114.5(2) . . ?
C20 C19 C24 116.5(3) . . ?
C20 C19 Pt1 127.9(2) . . ?
C24 C19 Pt1 115.5(2) . . ?
C21 C20 C19 121.9(3) . . ?
C22 C21 C20 120.6(3) . . ?
C21 C22 C23 119.0(3) . . ?
C22 C23 C24 120.1(3) . . ?
C23 C24 C19 122.0(3) . . ?
C26 C25 P3 106.39(19) . . ?
C27 C26 C36 118.7(3) . . ?
C27 C26 C25 129.3(3) . . ?
C36 C26 C25 111.9(3) . . ?
C26 C27 C28 121.3(3) . . ?
C29 C28 C27 120.1(3) . . ?
C28 C29 C37 118.3(3) . . ?
C28 C29 C30 135.5(3) . . ?
C37 C29 C30 106.2(3) . . ?
C29 C30 C31 105.2(3) . . ?
C32 C31 C30 106.0(3) . . ?
C33 C32 C37 117.7(3) . . ?
C33 C32 C31 135.4(3) . . ?
C37 C32 C31 106.8(3) . . ?
C32 C33 C34 121.1(3) . . ?
C35 C34 C33 120.7(3) . . ?
C34 C35 C36 118.7(3) . . ?
C34 C35 P3 133.9(2) . . ?
C36 C35 P3 107.1(2) . . ?
C37 C36 C35 119.9(3) . . ?
C37 C36 C26 119.2(3) . . ?
C35 C36 C26 120.8(3) . . ?
C36 C37 C29 122.3(3) . . ?
C36 C37 C32 122.0(3) . . ?
C29 C37 C32 115.5(3) . . ?
C43 C38 C39 119.1(3) . . ?
C43 C38 P3 123.2(3) . . ?
C39 C38 P3 117.7(2) . . ?
C40 C39 C38 121.0(3) . . ?
C39 C40 C41 119.2(3) . . ?
C42 C41 C40 119.9(3) . . ?
C41 C42 C43 120.8(3) . . ?
C42 C43 C38 120.0(3) . . ?
F1 P4 F3 90.43(11) . . ?
F1 P4 F6 90.22(13) . . ?
F3 P4 F6 179.33(13) . . ?
F1 P4 F2 179.43(13) . . ?
F3 P4 F2 89.90(12) . . ?
F6 P4 F2 89.44(11) . . ?
F1 P4 F4 90.02(12) . . ?
F3 P4 F4 89.99(12) . . ?
F6 P4 F4 90.15(12) . . ?
F2 P4 F4 90.44(12) . . ?
F1 P4 F5 90.41(12) . . ?
F3 P4 F5 89.65(12) . . ?
F6 P4 F5 90.21(12) . . ?
F2 P4 F5 89.13(12) . . ?
F4 P4 F5 179.44(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1047189'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_audit_creation_date             2013-11-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.11.04 svn.r2830 for OlexSys, GUI svn.r4690)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        GWr99
_chemical_formula_moiety         'C19 H18 B P'
_chemical_formula_sum            'C19 H18 B P'
_chemical_formula_weight         288.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.795(3)
_cell_length_b                   6.3966(7)
_cell_length_c                   17.4407(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.000(7)
_cell_angle_gamma                90
_cell_volume                     3100.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2983
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.143
_cell_measurement_theta_min      2.736
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0552 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.9166.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         2.736
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2897
_reflns_number_total             3852
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker Saint'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+1.8404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1123
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All B(H,H,H) groups
2. Restrained distances
 B1-H1C = B1-H1B = B1-H1A
 1.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C13M) = Uanis(C13)
Uanis(C1M) = Uanis(C1)
Uanis(C2M) = Uanis(C2)
Uanis(C3M) = Uanis(C3)
Uanis(C4M) = Uanis(C4)
Uanis(C5M) = Uanis(C5)
Uanis(C6M) = Uanis(C6)
Uanis(C7M) = Uanis(C7)
Uanis(C8M) = Uanis(C8)
Uanis(C9M) = Uanis(C9)
Uanis(C10M) = Uanis(C10)
Uanis(C11M) = Uanis(C11)
Uanis(C12M) = Uanis(C12)
Uanis(B1M) = Uanis(B1)
Uanis(P1M) = Uanis(P1)
4. Same fragment restrains
{C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13}
as
{C1M, C2M, C3M, C4M, C5M, C6M, C7M, C8M, C9M, C10M, C11M, C12M, C13M}
5. Others
 Sof(P1M)=Sof(C1M)=Sof(C2M)=Sof(H2M)=Sof(C3M)=Sof(H3M)=Sof(C4M)=Sof(C5M)=
 Sof(H5MA)=Sof(H5MB)=Sof(C6M)=Sof(H6MA)=Sof(H6MB)=Sof(C7M)=Sof(C8M)=Sof(H8M)=
 Sof(C9M)=Sof(H9M)=Sof(C10M)=Sof(C11M)=Sof(C12M)=Sof(C13M)=Sof(H13C)=Sof(H13D)=
 Sof(B1M)=Sof(H1MA)=Sof(H1MB)=Sof(H1MC)=1-FVAR(1)
 Sof(P1)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5A)=
 Sof(H5B)=Sof(C6)=Sof(H6B)=Sof(H6A)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=
 Sof(C10)=Sof(C11)=Sof(C12)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(B1)=Sof(H1A)=
 Sof(H1B)=Sof(H1C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6B,H6A), C13(H13A,H13B), C5M(H5MA,H5MB), C6M(H6MA,H6MB),
 C13M(H13C,H13D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C2M(H2M), C3M(H3M), C8M(H8M), C9M(H9M),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
6.c Idealised Me refined as rotating group:
 B1M(H1MA,H1MB,H1MC)
;
_atom_sites_solution_hydrogens   mixed
_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_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 0.40051(2) 0.26085(9) 0.85256(3) 0.01951(14) Uani 0.8061(11) 1 d . . P A 1
C1 C 0.36086(6) 0.4491(3) 0.80734(10) 0.0205(3) Uani 0.8061(11) 1 d . . P A 1
C2 C 0.33790(7) 0.6269(3) 0.83236(13) 0.0279(4) Uani 0.8061(11) 1 d . . P A 1
H2 H 0.3440 0.6762 0.8830 0.033 Uiso 0.8061(11) 1 calc R . P A 1
C3 C 0.3050(2) 0.7385(9) 0.7830(3) 0.0334(7) Uani 0.8061(11) 1 d . . P A 1
H3 H 0.2892 0.8597 0.8014 0.040 Uiso 0.8061(11) 1 calc R . P A 1
C4 C 0.29644(7) 0.6715(3) 0.71010(13) 0.0301(5) Uani 0.8061(11) 1 d . . P A 1
C5 C 0.26470(7) 0.7447(3) 0.64335(13) 0.0382(5) Uani 0.8061(11) 1 d . . P A 1
H5A H 0.2732 0.8891 0.6283 0.046 Uiso 0.8061(11) 1 calc R . P A 1
H5B H 0.2304 0.7416 0.6575 0.046 Uiso 0.8061(11) 1 calc R . P A 1
C6 C 0.27431(9) 0.5882(5) 0.57575(17) 0.0377(7) Uani 0.8061(11) 1 d . . P A 1
H6B H 0.2440 0.5219 0.5577 0.045 Uiso 0.8061(11) 1 calc R . P A 1
H6A H 0.2893 0.6609 0.5321 0.045 Uiso 0.8061(11) 1 calc R . P A 1
C7 C 0.30849(6) 0.4260(3) 0.61025(10) 0.0274(4) Uani 0.8061(11) 1 d . . P A 1
C8 C 0.32858(7) 0.2452(4) 0.58365(12) 0.0311(4) Uani 0.8061(11) 1 d . . P A 1
H8 H 0.3214 0.1981 0.5331 0.037 Uiso 0.8061(11) 1 calc R . P A 1
C9 C 0.36062(10) 0.1265(5) 0.63282(13) 0.0278(6) Uani 0.8061(11) 1 d . . P A 1
H9 H 0.3737 -0.0009 0.6145 0.033 Uiso 0.8061(11) 1 calc R . P A 1
C10 C 0.37276(7) 0.1929(3) 0.70555(10) 0.0217(4) Uani 0.8061(11) 1 d . . P A 1
C11 C 0.35119(7) 0.3782(3) 0.73227(10) 0.0201(4) Uani 0.8061(11) 1 d . . P A 1
C12 C 0.31968(10) 0.4880(4) 0.68464(15) 0.0237(5) Uani 0.8061(11) 1 d . . P A 1
C13 C 0.40664(7) 0.0965(3) 0.76497(10) 0.0240(4) Uani 0.8061(11) 1 d . . P A 1
H13A H 0.4402 0.0987 0.7469 0.029 Uiso 0.8061(11) 1 calc R . P A 1
H13B H 0.3974 -0.0500 0.7756 0.029 Uiso 0.8061(11) 1 calc R . P A 1
B1 B 0.3744(3) 0.1185(13) 0.9399(5) 0.0256(10) Uani 0.8061(11) 1 d D . P A 1
H1A H 0.3376(6) 0.053(3) 0.9184(11) 0.029(5) Uiso 0.8061(11) 1 d D . P A 1
H1B H 0.3702(8) 0.247(3) 0.9862(12) 0.044(6) Uiso 0.8061(11) 1 d D . P A 1
H1C H 0.4021(8) -0.015(3) 0.9568(12) 0.038(7) Uiso 0.8061(11) 1 d D . P A 1
P1M P 0.39179(8) 0.3137(4) 0.87725(14) 0.01951(14) Uani 0.1939(11) 1 d . . P A
2
C1M C 0.3769(2) 0.2670(10) 0.7763(4) 0.0205(3) Uani 0.1939(11) 1 d . . P A 2
C2M C 0.3882(3) 0.1144(14) 0.7258(6) 0.0279(4) Uani 0.1939(11) 1 d . . P A 2
H2M H 0.4089 0.0031 0.7411 0.033 Uiso 0.1939(11) 1 calc R . P A 2
C3M C 0.3685(6) 0.122(2) 0.6483(9) 0.0334(7) Uani 0.1939(11) 1 d . . P A 2
H3M H 0.3777 0.0176 0.6128 0.040 Uiso 0.1939(11) 1 calc R . P A 2
C4M C 0.3378(3) 0.2723(13) 0.6252(5) 0.0301(5) Uani 0.1939(11) 1 d . . P A 2
C5M C 0.3107(3) 0.3276(13) 0.5525(6) 0.0382(5) Uani 0.1939(11) 1 d . . P A 2
H5MA H 0.2876 0.2158 0.5380 0.046 Uiso 0.1939(11) 1 calc R . P A 2
H5MB H 0.3330 0.3507 0.5098 0.046 Uiso 0.1939(11) 1 calc R . P A 2
C6M C 0.2841(5) 0.531(2) 0.5731(8) 0.0377(7) Uani 0.1939(11) 1 d . . P A 2
H6MA H 0.2948 0.6461 0.5395 0.045 Uiso 0.1939(11) 1 calc R . P A 2
H6MB H 0.2490 0.5122 0.5650 0.045 Uiso 0.1939(11) 1 calc R . P A 2
C7M C 0.2945(3) 0.5838(12) 0.6542(4) 0.0274(4) Uani 0.1939(11) 1 d . . P A 2
C8M C 0.2808(3) 0.7326(16) 0.7018(5) 0.0311(4) Uani 0.1939(11) 1 d . . P A 2
H8M H 0.2580 0.8347 0.6853 0.037 Uiso 0.1939(11) 1 calc R . P A 2
C9M C 0.3011(10) 0.739(4) 0.7812(9) 0.0278(6) Uani 0.1939(11) 1 d . . P A 2
H9M H 0.2929 0.8507 0.8146 0.033 Uiso 0.1939(11) 1 calc R . P A 2
C10M C 0.3316(3) 0.5850(14) 0.8059(5) 0.0217(4) Uani 0.1939(11) 1 d . . P A 2
C11M C 0.3464(4) 0.4249(15) 0.7556(5) 0.0201(4) Uani 0.1939(11) 1 d . . P A 2
C12M C 0.3270(5) 0.433(2) 0.6820(7) 0.0237(5) Uani 0.1939(11) 1 d . . P A 2
C13M C 0.3534(3) 0.5462(12) 0.8859(4) 0.0240(4) Uani 0.1939(11) 1 d . . P A 2
H13C H 0.3278 0.5214 0.9235 0.029 Uiso 0.1939(11) 1 calc R . P A 2
H13D H 0.3727 0.6682 0.9029 0.029 Uiso 0.1939(11) 1 calc R . P A 2
B1M B 0.3797(15) 0.094(7) 0.945(3) 0.0256(10) Uani 0.1939(11) 1 d . . P A 2
H1MA H 0.3853 0.1422 0.9979 0.038 Uiso 0.1939(11) 1 calc GR . P A 2
H1MB H 0.4013 -0.0227 0.9342 0.038 Uiso 0.1939(11) 1 calc GR . P A 2
H1MC H 0.3462 0.0488 0.9388 0.038 Uiso 0.1939(11) 1 calc GR . P A 2
C14 C 0.45761(5) 0.3844(2) 0.87311(8) 0.0265(3) Uani 1 1 d . . . . .
C15 C 0.49144(6) 0.2742(3) 0.91719(9) 0.0342(4) Uani 1 1 d . . . . .
H15 H 0.4833 0.1424 0.9384 0.041 Uiso 1 1 calc R . . . .
C16 C 0.53680(6) 0.3566(3) 0.93006(9) 0.0381(4) Uani 1 1 d . . . . .
H16 H 0.5598 0.2805 0.9597 0.046 Uiso 1 1 calc R . . . .
C17 C 0.54873(6) 0.5473(3) 0.90040(10) 0.0412(4) Uani 1 1 d . . . . .
H17 H 0.5801 0.6024 0.9090 0.049 Uiso 1 1 calc R . . . .
C18 C 0.51544(7) 0.6590(3) 0.85824(12) 0.0526(5) Uani 1 1 d . . . . .
H18 H 0.5237 0.7924 0.8384 0.063 Uiso 1 1 calc R . . . .
C19 C 0.46979(6) 0.5779(3) 0.84445(11) 0.0424(5) Uani 1 1 d . . . . .
H19 H 0.4469 0.6558 0.8152 0.051 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 C1 1.8046(17) . ?
P1 C13 1.8647(19) . ?
P1 B1 1.927(10) . ?
P1 C14 1.8033(15) . ?
C1 C2 1.379(3) . ?
C1 C11 1.407(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.434(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.360(5) . ?
C4 C5 1.522(3) . ?
C4 C12 1.415(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.573(4) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 C7 1.523(3) . ?
C7 C8 1.369(3) . ?
C7 C12 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.441(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(3) . ?
C10 C11 1.411(3) . ?
C10 C13 1.519(2) . ?
C11 C12 1.387(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
B1 H1A 1.162(15) . ?
B1 H1B 1.161(16) . ?
B1 H1C 1.182(16) . ?
P1M C1M 1.826(7) . ?
P1M C13M 1.838(8) . ?
P1M B1M 1.87(4) . ?
P1M C14 1.887(3) . ?
C1M C2M 1.355(9) . ?
C1M C11M 1.364(10) . ?
C2M H2M 0.9500 . ?
C2M C3M 1.450(13) . ?
C3M H3M 0.9500 . ?
C3M C4M 1.344(12) . ?
C4M C5M 1.505(10) . ?
C4M C12M 1.463(12) . ?
C5M H5MA 0.9900 . ?
C5M H5MB 0.9900 . ?
C5M C6M 1.542(13) . ?
C6M H6MA 0.9900 . ?
C6M H6MB 0.9900 . ?
C6M C7M 1.479(13) . ?
C7M C8M 1.324(11) . ?
C7M C12M 1.400(10) . ?
C8M H8M 0.9500 . ?
C8M C9M 1.487(16) . ?
C9M H9M 0.9500 . ?
C9M C10M 1.366(16) . ?
C10M C11M 1.415(10) . ?
C10M C13M 1.531(9) . ?
C11M C12M 1.384(12) . ?
C13M H13C 0.9900 . ?
C13M H13D 0.9900 . ?
B1M H1MA 0.9800 . ?
B1M H1MB 0.9800 . ?
B1M H1MC 0.9800 . ?
C14 C15 1.395(2) . ?
C14 C19 1.379(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.368(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(2) . ?
C19 H19 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
C1 P1 C13 94.71(8) . . ?
C1 P1 B1 115.2(2) . . ?
C13 P1 B1 115.0(3) . . ?
C14 P1 C1 108.85(8) . . ?
C14 P1 C13 108.50(8) . . ?
C14 P1 B1 113.1(3) . . ?
C2 C1 P1 134.01(15) . . ?
C2 C1 C11 118.59(17) . . ?
C11 C1 P1 107.26(13) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 135.1(2) . . ?
C3 C4 C12 118.8(2) . . ?
C12 C4 C5 106.1(2) . . ?
C4 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C4 C5 C6 105.88(17) . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C5 C6 H6B 110.9 . . ?
C5 C6 H6A 110.9 . . ?
H6B C6 H6A 108.9 . . ?
C7 C6 C5 104.49(19) . . ?
C7 C6 H6B 110.9 . . ?
C7 C6 H6A 110.9 . . ?
C8 C7 C6 134.2(2) . . ?
C8 C7 C12 118.20(18) . . ?
C12 C7 C6 107.6(2) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 117.7(2) . . ?
C9 C10 C13 130.1(2) . . ?
C11 C10 C13 112.19(15) . . ?
C1 C11 C10 120.18(17) . . ?
C12 C11 C1 120.15(19) . . ?
C12 C11 C10 119.66(18) . . ?
C7 C12 C4 115.75(19) . . ?
C7 C12 C11 122.98(19) . . ?
C11 C12 C4 121.3(2) . . ?
P1 C13 H13A 110.7 . . ?
P1 C13 H13B 110.7 . . ?
C10 C13 P1 105.40(12) . . ?
C10 C13 H13A 110.7 . . ?
C10 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
P1 B1 H1A 104.9(10) . . ?
P1 B1 H1B 105.0(13) . . ?
P1 B1 H1C 106.5(11) . . ?
H1A B1 H1B 112.5(16) . . ?
H1A B1 H1C 112.7(14) . . ?
H1B B1 H1C 114.2(16) . . ?
C1M P1M C13M 95.1(3) . . ?
C1M P1M B1M 116.6(14) . . ?
C1M P1M C14 101.8(2) . . ?
C13M P1M B1M 116.4(14) . . ?
C13M P1M C14 111.9(3) . . ?
B1M P1M C14 112.9(12) . . ?
C2M C1M P1M 133.9(6) . . ?
C2M C1M C11M 120.7(8) . . ?
C11M C1M P1M 105.3(5) . . ?
C1M C2M H2M 120.2 . . ?
C1M C2M C3M 119.6(10) . . ?
C3M C2M H2M 120.2 . . ?
C2M C3M H3M 118.9 . . ?
C4M C3M C2M 122.1(13) . . ?
C4M C3M H3M 118.9 . . ?
C3M C4M C5M 136.6(10) . . ?
C3M C4M C12M 115.9(10) . . ?
C12M C4M C5M 107.4(7) . . ?
C4M C5M H5MA 111.0 . . ?
C4M C5M H5MB 111.0 . . ?
C4M C5M C6M 103.7(8) . . ?
H5MA C5M H5MB 109.0 . . ?
C6M C5M H5MA 111.0 . . ?
C6M C5M H5MB 111.0 . . ?
C5M C6M H6MA 109.9 . . ?
C5M C6M H6MB 109.9 . . ?
H6MA C6M H6MB 108.3 . . ?
C7M C6M C5M 109.2(8) . . ?
C7M C6M H6MA 109.9 . . ?
C7M C6M H6MB 109.9 . . ?
C8M C7M C6M 135.2(8) . . ?
C8M C7M C12M 118.0(8) . . ?
C12M C7M C6M 106.8(8) . . ?
C7M C8M H8M 120.1 . . ?
C7M C8M C9M 119.7(10) . . ?
C9M C8M H8M 120.1 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M C8M 119.8(14) . . ?
C10M C9M H9M 120.1 . . ?
C9M C10M C11M 120.8(10) . . ?
C9M C10M C13M 129.7(9) . . ?
C11M C10M C13M 109.4(7) . . ?
C1M C11M C10M 123.9(8) . . ?
C1M C11M C12M 120.4(8) . . ?
C12M C11M C10M 115.7(8) . . ?
C7M C12M C4M 112.8(8) . . ?
C11M C12M C4M 121.2(8) . . ?
C11M C12M C7M 125.9(9) . . ?
P1M C13M H13C 110.5 . . ?
P1M C13M H13D 110.5 . . ?
C10M C13M P1M 106.1(5) . . ?
C10M C13M H13C 110.5 . . ?
C10M C13M H13D 110.5 . . ?
H13C C13M H13D 108.7 . . ?
P1M B1M H1MA 109.5 . . ?
P1M B1M H1MB 109.5 . . ?
P1M B1M H1MC 109.5 . . ?
H1MA B1M H1MB 109.5 . . ?
H1MA B1M H1MC 109.5 . . ?
H1MB B1M H1MC 109.5 . . ?
C15 C14 P1 118.06(12) . . ?
C15 C14 P1M 120.14(14) . . ?
C19 C14 P1 122.82(12) . . ?
C19 C14 P1M 118.25(13) . . ?
C19 C14 C15 119.07(14) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.08(16) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.35(16) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.10(16) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.24(18) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.14(16) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?

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
P1 C1 C2 C3 -175.3(4) . . . . ?
P1 C1 C11 C10 -1.7(2) . . . . ?
P1 C1 C11 C12 177.1(2) . . . . ?
P1 C14 C15 C16 175.65(13) . . . . ?
P1 C14 C19 C18 -175.86(15) . . . . ?
C1 P1 C13 C10 -4.70(13) . . . . ?
C1 P1 C14 P1M 70.2(2) . . . . ?
C1 P1 C14 C15 171.76(13) . . . . ?
C1 P1 C14 C19 -11.11(17) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C1 C11 C12 C4 -0.4(4) . . . . ?
C1 C11 C12 C7 -179.8(2) . . . . ?
C2 C1 C11 C10 -177.87(18) . . . . ?
C2 C1 C11 C12 0.9(3) . . . . ?
C2 C3 C4 C5 179.3(3) . . . . ?
C2 C3 C4 C12 1.4(8) . . . . ?
C3 C4 C5 C6 179.4(5) . . . . ?
C3 C4 C12 C7 178.6(4) . . . . ?
C3 C4 C12 C11 -0.8(5) . . . . ?
C4 C5 C6 C7 3.8(3) . . . . ?
C5 C4 C12 C7 0.2(3) . . . . ?
C5 C4 C12 C11 -179.2(2) . . . . ?
C5 C6 C7 C8 176.2(2) . . . . ?
C5 C6 C7 C12 -3.8(3) . . . . ?
C6 C7 C8 C9 179.6(3) . . . . ?
C6 C7 C12 C4 2.4(3) . . . . ?
C6 C7 C12 C11 -178.2(3) . . . . ?
C7 C8 C9 C10 -1.8(4) . . . . ?
C8 C7 C12 C4 -177.6(2) . . . . ?
C8 C7 C12 C11 1.8(4) . . . . ?
C8 C9 C10 C11 2.6(4) . . . . ?
C8 C9 C10 C13 -177.9(2) . . . . ?
C9 C10 C11 C1 177.5(2) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C9 C10 C13 P1 -175.0(2) . . . . ?
C10 C11 C12 C4 178.4(2) . . . . ?
C10 C11 C12 C7 -1.0(4) . . . . ?
C11 C1 C2 C3 -0.3(5) . . . . ?
C11 C10 C13 P1 4.53(19) . . . . ?
C12 C4 C5 C6 -2.6(3) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C13 P1 C1 C2 179.11(19) . . . . ?
C13 P1 C1 C11 3.73(14) . . . . ?
C13 P1 C14 P1M 172.1(2) . . . . ?
C13 P1 C14 C15 -86.37(14) . . . . ?
C13 P1 C14 C19 90.75(16) . . . . ?
C13 C10 C11 C1 -2.1(2) . . . . ?
C13 C10 C11 C12 179.1(2) . . . . ?
B1 P1 C1 C2 58.7(4) . . . . ?
B1 P1 C1 C11 -116.7(3) . . . . ?
B1 P1 C13 C10 115.9(3) . . . . ?
B1 P1 C14 P1M -59.1(4) . . . . ?
B1 P1 C14 C15 42.4(3) . . . . ?
B1 P1 C14 C19 -140.4(3) . . . . ?
P1M C1M C2M C3M 178.0(10) . . . . ?
P1M C1M C11M C10M 0.2(12) . . . . ?
P1M C1M C11M C12M -178.3(11) . . . . ?
P1M C14 C15 C16 -163.18(16) . . . . ?
P1M C14 C19 C18 163.19(18) . . . . ?
C1M P1M C13M C10M -2.5(6) . . . . ?
C1M P1M C14 P1 -36.1(3) . . . . ?
C1M P1M C14 C15 -124.9(3) . . . . ?
C1M P1M C14 C19 73.3(3) . . . . ?
C1M C2M C3M C4M -3(2) . . . . ?
C1M C11M C12M C4M 1(2) . . . . ?
C1M C11M C12M C7M 178.5(12) . . . . ?
C2M C1M C11M C10M 177.5(9) . . . . ?
C2M C1M C11M C12M -1.0(15) . . . . ?
C2M C3M C4M C5M -179.3(10) . . . . ?
C2M C3M C4M C12M 3(2) . . . . ?
C3M C4M C5M C6M -178.1(15) . . . . ?
C3M C4M C12M C7M -179.6(12) . . . . ?
C3M C4M C12M C11M -2(2) . . . . ?
C4M C5M C6M C7M -1.7(13) . . . . ?
C5M C4M C12M C7M 1.8(15) . . . . ?
C5M C4M C12M C11M 179.4(12) . . . . ?
C5M C6M C7M C8M -177.6(9) . . . . ?
C5M C6M C7M C12M 2.8(15) . . . . ?
C6M C7M C8M C9M -177.6(19) . . . . ?
C6M C7M C12M C4M -2.9(16) . . . . ?
C6M C7M C12M C11M 179.7(15) . . . . ?
C7M C8M C9M C10M -4(3) . . . . ?
C8M C7M C12M C4M 177.5(9) . . . . ?
C8M C7M C12M C11M 0(2) . . . . ?
C8M C9M C10M C11M 4(3) . . . . ?
C8M C9M C10M C13M -174.0(14) . . . . ?
C9M C10M C11M C1M 179.6(18) . . . . ?
C9M C10M C11M C12M -2(2) . . . . ?
C9M C10M C13M P1M -179.1(19) . . . . ?
C10M C11M C12M C4M -177.4(11) . . . . ?
C10M C11M C12M C7M 0(2) . . . . ?
C11M C1M C2M C3M 1.6(14) . . . . ?
C11M C10M C13M P1M 2.9(9) . . . . ?
C12M C4M C5M C6M 0.0(12) . . . . ?
C12M C7M C8M C9M 2(2) . . . . ?
C13M P1M C1M C2M -175.3(8) . . . . ?
C13M P1M C1M C11M 1.5(7) . . . . ?
C13M P1M C14 P1 -136.6(4) . . . . ?
C13M P1M C14 C15 134.5(3) . . . . ?
C13M P1M C14 C19 -27.2(3) . . . . ?
C13M C10M C11M C1M -2.2(13) . . . . ?
C13M C10M C11M C12M 176.4(11) . . . . ?
B1M P1M C1M C2M -52.4(16) . . . . ?
B1M P1M C1M C11M 124.4(15) . . . . ?
B1M P1M C13M C10M -125.7(16) . . . . ?
B1M P1M C14 P1 89.7(16) . . . . ?
B1M P1M C14 C15 0.9(16) . . . . ?
B1M P1M C14 C19 -160.8(16) . . . . ?
C14 P1 C1 C2 -69.5(2) . . . . ?
C14 P1 C1 C11 115.12(13) . . . . ?
C14 P1 C13 C10 -116.38(12) . . . . ?
C14 P1M C1M C2M 71.0(8) . . . . ?
C14 P1M C1M C11M -112.2(6) . . . . ?
C14 P1M C13M C10M 102.4(5) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C14 C19 C18 1.2(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C19 C14 C15 C16 -1.6(3) . . . . ?

####################################################################### 
# 
# 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_18a.THF
_database_code_depnum_ccdc_archive 'CCDC 1047190'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            GW
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H56 F6 O P4 Pt'
_chemical_formula_weight         1069.88

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'
F F 0.0171 0.0103 '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'
Pt Pt -1.7033 8.3905 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.5207(4)
_cell_length_b                   17.2787(5)
_cell_length_c                   22.7156(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4521.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             2152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    3.305
_shelx_estimated_absorpt_T_min   0.437
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_T_max  0.666
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43409
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             11027
_reflns_number_gt                9907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.993

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0600P)²+7.3000P] 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_abs_structure_details 
; 
 Flack x determined using 3845 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.000(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11027
_refine_ls_number_parameters     597
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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
Pt1 Pt 0.26199(2) 0.36736(2) 0.82432(2) 0.01640(6) Uani 1 1 d D . . . .
P1 P 0.20090(13) 0.24558(10) 0.80269(7) 0.0167(3) Uani 1 1 d . . . . .
P2 P 0.31368(14) 0.31871(10) 0.91451(7) 0.0178(3) Uani 1 1 d . . . . .
P3 P 0.29005(19) 0.49811(12) 0.83857(9) 0.0188(5) Uani 0.819(4) 1 d D . P A .
P3' P 0.3557(9) 0.4915(5) 0.8340(4) 0.0188(5) Uani 0.181(4) 1 d D . P A 2
P4B P 0.7871(5) 0.4378(4) 0.8503(3) 0.0680(18) Uani 0.5 1 d D U P B 2
F1B F 0.7526(13) 0.4997(6) 0.8990(5) 0.111(4) Uani 0.5 1 d D U P B 2
F2B F 0.6590(6) 0.4077(7) 0.8383(5) 0.075(4) Uani 0.5 1 d D U P B 2
F3B F 0.7741(13) 0.4946(7) 0.7957(5) 0.105(4) Uani 0.5 1 d D U P B 2
F4B F 0.9165(6) 0.4668(8) 0.8598(5) 0.136(6) Uani 0.5 1 d D U P B 2
F5B F 0.8024(9) 0.3740(6) 0.9001(4) 0.103(4) Uani 0.5 1 d D U P B 2
F6B F 0.8316(8) 0.3758(6) 0.8038(4) 0.079(3) Uani 0.5 1 d D U P B 2
O1 O 0.2184(6) 0.8652(5) 0.8983(4) 0.088(3) Uani 1 1 d . . . . .
C1 C -0.0363(6) 0.2171(5) 0.8360(4) 0.040(2) Uani 1 1 d . . . . .
H1A H -0.1171 0.2204 0.8228 0.060 Uiso 1 1 calc R U . . .
H1B H -0.0238 0.2534 0.8685 0.060 Uiso 1 1 calc R U . . .
H1C H -0.0197 0.1643 0.8493 0.060 Uiso 1 1 calc R U . . .
C2 C 0.0443(5) 0.2377(5) 0.7851(3) 0.0273(16) Uani 1 1 d . . . . .
H2 H 0.0195 0.2898 0.7708 0.033 Uiso 1 1 calc R U . . .
C3 C 0.0391(7) 0.1838(5) 0.7322(3) 0.039(2) Uani 1 1 d . . . . .
H3A H -0.0319 0.1940 0.7089 0.046 Uiso 1 1 calc R U . . .
H3B H 0.0375 0.1292 0.7453 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1468(7) 0.1988(5) 0.6949(3) 0.041(2) Uani 1 1 d . . . . .
H4A H 0.1432 0.2509 0.6769 0.049 Uiso 1 1 calc R U . . .
H4B H 0.1530 0.1599 0.6630 0.049 Uiso 1 1 calc R U . . .
C5 C 0.2512(7) 0.1928(4) 0.7366(2) 0.0275(15) Uani 1 1 d . . . . .
H5 H 0.2594 0.1371 0.7478 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3673(7) 0.2187(5) 0.7108(4) 0.038(2) Uani 1 1 d . . . . .
H6A H 0.3893 0.1839 0.6786 0.057 Uiso 1 1 calc R U . . .
H6B H 0.4270 0.2173 0.7415 0.057 Uiso 1 1 calc R U . . .
H6C H 0.3600 0.2716 0.6956 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2345(5) 0.1830(3) 0.8646(2) 0.0175(12) Uani 1 1 d . . . . .
C8 C 0.2058(5) 0.1032(4) 0.8635(3) 0.0248(15) Uani 1 1 d . . . . .
H8 H 0.1681 0.0816 0.8302 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2328(7) 0.0568(4) 0.9112(3) 0.0318(16) Uani 1 1 d . . . . .
H9 H 0.2155 0.0031 0.9101 0.038 Uiso 1 1 calc R U . . .
C10 C 0.2844(7) 0.0882(4) 0.9597(3) 0.0323(18) Uani 1 1 d . . . . .
H10 H 0.3028 0.0557 0.9922 0.039 Uiso 1 1 calc R U . . .
C11 C 0.3102(6) 0.1659(4) 0.9626(3) 0.0265(16) Uani 1 1 d . . . . .
H11 H 0.3446 0.1865 0.9972 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2861(5) 0.2153(4) 0.9148(3) 0.0182(14) Uani 1 1 d . . . . .
C13 C 0.1377(8) 0.3994(5) 0.9781(4) 0.056(3) Uani 1 1 d . . . . .
H13A H 0.0977 0.4014 1.0161 0.083 Uiso 1 1 calc R U . . .
H13B H 0.0867 0.3753 0.9488 0.083 Uiso 1 1 calc R U . . .
H13C H 0.1575 0.4520 0.9655 0.083 Uiso 1 1 calc R U . . .
C14 C 0.2486(8) 0.3515(4) 0.9842(3) 0.0383(18) Uani 1 1 d . . . . .
H14 H 0.2267 0.3037 1.0064 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3460(8) 0.3895(6) 1.0188(3) 0.055(3) Uani 1 1 d . . . . .
H15A H 0.3537 0.4445 1.0073 0.065 Uiso 1 1 calc R U . . .
H15B H 0.3291 0.3872 1.0615 0.065 Uiso 1 1 calc R U . . .
C16 C 0.4570(8) 0.3466(6) 1.0055(3) 0.054(3) Uani 1 1 d . . . . .
H16A H 0.4569 0.2957 1.0255 0.064 Uiso 1 1 calc R U . . .
H16B H 0.5246 0.3767 1.0198 0.064 Uiso 1 1 calc R U . . .
C17 C 0.4651(6) 0.3355(5) 0.9391(3) 0.0359(19) Uani 1 1 d . . . . .
H17 H 0.4892 0.3866 0.9223 0.043 Uiso 1 1 calc R U . . .
C18 C 0.5532(6) 0.2760(5) 0.9172(5) 0.052(3) Uani 1 1 d . . . . .
H18A H 0.6317 0.2929 0.9277 0.079 Uiso 1 1 calc R U . . .
H18B H 0.5471 0.2712 0.8743 0.079 Uiso 1 1 calc R U . . .
H18C H 0.5372 0.2258 0.9355 0.079 Uiso 1 1 calc R U . . .
C19 C 0.3642(7) 0.5431(5) 0.7752(4) 0.0348(18) Uani 1 1 d . . . . .
C20 C 0.4727(7) 0.5171(5) 0.7617(4) 0.042(2) Uani 1 1 d . . . C 1
H20 H 0.5098 0.4801 0.7863 0.050 Uiso 1 1 calc R U . C 1
C21 C 0.5286(7) 0.5446(6) 0.7120(5) 0.057(3) Uani 1 1 d . . . . .
H21 H 0.6048 0.5269 0.7033 0.069 Uiso 1 1 calc R U . C 1
C22 C 0.4755(7) 0.5976(5) 0.6745(5) 0.051(2) Uani 1 1 d . . . . .
H22 H 0.5137 0.6149 0.6399 0.061 Uiso 1 1 calc R U . . .
C23 C 0.3664(7) 0.6244(5) 0.6888(4) 0.043(2) Uani 1 1 d . . . . .
H23 H 0.3288 0.6613 0.6643 0.052 Uiso 1 1 calc R U . . .
C24 C 0.3123(7) 0.5970(5) 0.7391(3) 0.0358(18) Uani 1 1 d . . . . .
H24 H 0.2373 0.6158 0.7489 0.043 Uiso 1 1 calc R U . . .
C25 C 0.1468(7) 0.5441(5) 0.8539(4) 0.047(2) Uani 1 1 d . . . . .
H25A H 0.1240 0.5775 0.8204 0.056 Uiso 1 1 calc R U . A .
H25B H 0.0867 0.5037 0.8589 0.056 Uiso 1 1 calc R U . . .
C26 C 0.1562(7) 0.5903(5) 0.9073(4) 0.045(2) Uani 1 1 d . . . . .
C27 C 0.0765(9) 0.6307(6) 0.9366(5) 0.066(3) Uani 1 1 d . . . . .
H27 H -0.0010 0.6320 0.9223 0.079 Uiso 1 1 calc R U . . .
C28 C 0.1063(13) 0.6735(7) 0.9906(6) 0.085(4) Uani 1 1 d . . . . .
H28 H 0.0471 0.7002 1.0115 0.102 Uiso 1 1 calc R U . . .
C29 C 0.2112(13) 0.6752(6) 1.0099(4) 0.069(4) Uani 1 1 d . . . . .
C30 C 0.2708(13) 0.7154(6) 1.0581(4) 0.080(4) Uani 1 1 d . . . . .
H30A H 0.2362 0.7009 1.0965 0.096 Uiso 1 1 calc R U . . .
H30B H 0.2642 0.7722 1.0532 0.096 Uiso 1 1 calc R U . . .
C31 C 0.4020(14) 0.6897(7) 1.0555(5) 0.095(5) Uani 1 1 d . . . . .
H31A H 0.4535 0.7350 1.0501 0.114 Uiso 1 1 calc R U . . .
H31B H 0.4247 0.6622 1.0920 0.114 Uiso 1 1 calc R U . . .
C32 C 0.4085(11) 0.6371(6) 1.0036(4) 0.069(3) Uani 1 1 d . . . . .
C33 C 0.4989(8) 0.5944(6) 0.9745(4) 0.052(3) Uani 1 1 d . . . . .
H33 H 0.5764 0.5955 0.9887 0.062 Uiso 1 1 calc R U . . .
C34 C 0.4688(7) 0.5501(5) 0.9235(4) 0.041(2) Uani 1 1 d . . . . .
H34 H 0.5282 0.5219 0.9039 0.050 Uiso 1 1 calc R U . . .
C35 C 0.3578(7) 0.5466(5) 0.9017(4) 0.041(2) Uani 1 1 d . . . . .
C36 C 0.2966(7) 0.6332(5) 0.9766(3) 0.045(2) Uani 1 1 d . . . . .
C37 C 0.2731(9) 0.5891(5) 0.9288(3) 0.046(2) Uani 1 1 d . . . . .
C38 C 0.0835(6) 0.4293(5) 0.7403(4) 0.0362(19) Uani 1 1 d . . . . .
H38 H 0.0360 0.4225 0.7741 0.043 Uiso 1 1 calc R U . . .
C39 C 0.0347(8) 0.4619(5) 0.6901(4) 0.056(3) Uani 1 1 d . . . . .
H39 H -0.0449 0.4762 0.6894 0.067 Uiso 1 1 calc R U . . .
C40 C 0.1022(10) 0.4729(6) 0.6421(5) 0.061(3) Uani 1 1 d . . . . .
H40 H 0.0695 0.4954 0.6077 0.073 Uiso 1 1 calc R U . . .
C41 C 0.2182(9) 0.4520(5) 0.6421(3) 0.051(3) Uani 1 1 d . . . . .
H41 H 0.2648 0.4601 0.6082 0.061 Uiso 1 1 calc R U . . .
C42 C 0.2665(8) 0.4184(4) 0.6932(3) 0.0365(18) Uani 1 1 d . . . . .
H42 H 0.3461 0.4040 0.6933 0.044 Uiso 1 1 calc R U . . .
C48 C 0.2097(13) 0.8221(10) 0.8460(8) 0.139(7) Uani 1 1 d . . . . .
H48A H 0.1617 0.7756 0.8535 0.166 Uiso 1 1 calc R U . . .
H48B H 0.1694 0.8538 0.8159 0.166 Uiso 1 1 calc R U . . .
C43 C 0.2006(6) 0.4060(4) 0.7430(3) 0.0241(15) Uani 1 1 d . . . . .
C47 C 0.3179(14) 0.7989(10) 0.8237(7) 0.139(7) Uani 1 1 d . . . . .
H47A H 0.3375 0.8276 0.7873 0.167 Uiso 1 1 calc R U . . .
H47B H 0.3189 0.7427 0.8152 0.167 Uiso 1 1 calc R U . . .
C46 C 0.3975(11) 0.8181(11) 0.8712(6) 0.123(6) Uani 1 1 d . . . . .
H46A H 0.4387 0.7711 0.8848 0.148 Uiso 1 1 calc R U . . .
H46B H 0.4559 0.8561 0.8574 0.148 Uiso 1 1 calc R U . . .
C45 C 0.3291(9) 0.8507(7) 0.9187(5) 0.071(3) Uani 1 1 d . . . . .
H45A H 0.3260 0.8140 0.9521 0.085 Uiso 1 1 calc R U . . .
H45B H 0.3650 0.8994 0.9326 0.085 Uiso 1 1 calc R U . . .
P4A P 0.7943(6) 0.4684(5) 0.8525(3) 0.0680(18) Uani 0.5 1 d D U P D 1
F6A F 0.8865(13) 0.4026(9) 0.8608(9) 0.118(5) Uani 0.5 1 d D U P D 1
F4A F 0.8595(14) 0.5167(10) 0.9007(7) 0.113(5) Uani 0.5 1 d D U P D 1
F5A F 0.7160(9) 0.4319(8) 0.9044(5) 0.072(3) Uani 0.5 1 d D U P D 1
F2A F 0.7139(15) 0.4299(11) 0.8059(7) 0.122(5) Uani 0.5 1 d D U P D 1
F3A F 0.8745(10) 0.5101(7) 0.8076(7) 0.086(4) Uani 0.5 1 d D U P D 1
F1 F 0.7017(8) 0.5386(7) 0.8456(6) 0.081(4) Uani 0.5 1 d D U P D 1


_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
Pt1 C43 2.087(6) . ?
Pt1 P1 2.2726(17) . ?
Pt1 P2 2.2933(16) . ?
Pt1 P3 2.305(2) . ?
Pt1 P3' 2.412(9) . ?
P1 C7 1.817(6) . ?
P1 C5 1.850(6) . ?
P1 C2 1.853(6) . ?
P2 C12 1.815(7) . ?
P2 C14 1.841(7) . ?
P2 C17 1.854(7) . ?
P3 P3' 0.772(10) . ?
P3 C35 1.835(9) . ?
P3 C19 1.846(8) . ?
P3 C25 1.864(8) . ?
P3' C19 1.609(12) . ?
P3' C35 1.808(13) . ?
P4B F4B 1.5878(12) . ?
P4B F6B 1.5886(12) . ?
P4B F2B 1.5887(12) . ?
P4B F1B 1.5890(12) . ?
P4B F3B 1.5893(12) . ?
P4B F5B 1.5895(12) . ?
O1 C45 1.379(12) . ?
O1 C48 1.405(15) . ?
C1 C2 1.524(10) . ?
C2 C3 1.522(10) . ?
C3 C4 1.525(11) . ?
C4 C5 1.534(10) . ?
C5 C6 1.528(10) . ?
C7 C12 1.400(8) . ?
C7 C8 1.418(9) . ?
C8 C9 1.381(9) . ?
C9 C10 1.364(10) . ?
C10 C11 1.377(10) . ?
C11 C12 1.410(9) . ?
C13 C14 1.528(12) . ?
C14 C15 1.519(11) . ?
C15 C16 1.508(13) . ?
C16 C17 1.524(11) . ?
C17 C18 1.529(12) . ?
C19 C20 1.363(11) . ?
C19 C24 1.377(10) . ?
C20 C21 1.383(12) . ?
C21 C22 1.392(13) . ?
C22 C23 1.378(11) . ?
C23 C24 1.386(10) . ?
C25 C26 1.457(12) . ?
C26 C27 1.331(12) . ?
C26 C37 1.432(13) . ?
C27 C28 1.474(16) . ?
C28 C29 1.286(17) . ?
C29 C36 1.438(14) . ?
C29 C30 1.468(14) . ?
C30 C31 1.577(19) . ?
C31 C32 1.489(15) . ?
C32 C36 1.429(14) . ?
C32 C33 1.438(15) . ?
C33 C34 1.431(12) . ?
C34 C35 1.373(11) . ?
C35 C37 1.369(12) . ?
C36 C37 1.352(11) . ?
C38 C39 1.392(11) . ?
C38 C43 1.410(10) . ?
C39 C40 1.352(14) . ?
C40 C41 1.385(14) . ?
C41 C42 1.411(11) . ?
C42 C43 1.379(9) . ?
C48 C47 1.405(19) . ?
C47 C46 1.454(19) . ?
C46 C45 1.450(15) . ?
P4A F3A 1.554(11) . ?
P4A F2A 1.555(14) . ?
P4A F6A 1.568(13) . ?
P4A F4A 1.568(14) . ?
P4A F5A 1.613(10) . ?
P4A F1 1.622(12) . ?

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
C43 Pt1 P1 90.0(2) . . ?
C43 Pt1 P2 174.72(19) . . ?
P1 Pt1 P2 86.23(6) . . ?
C43 Pt1 P3 81.8(2) . . ?
P1 Pt1 P3 168.91(6) . . ?
P2 Pt1 P3 101.38(7) . . ?
C43 Pt1 P3' 87.0(3) . . ?
P1 Pt1 P3' 169.1(3) . . ?
P2 Pt1 P3' 97.4(2) . . ?
P3 Pt1 P3' 18.7(2) . . ?
C7 P1 C5 105.6(3) . . ?
C7 P1 C2 109.3(3) . . ?
C5 P1 C2 95.4(3) . . ?
C7 P1 Pt1 108.5(2) . . ?
C5 P1 Pt1 122.3(2) . . ?
C2 P1 Pt1 114.6(3) . . ?
C12 P2 C14 103.3(3) . . ?
C12 P2 C17 108.6(3) . . ?
C14 P2 C17 94.3(4) . . ?
C12 P2 Pt1 108.5(2) . . ?
C14 P2 Pt1 123.3(3) . . ?
C17 P2 Pt1 117.1(3) . . ?
P3' P3 C35 75.8(8) . . ?
P3' P3 C19 60.3(8) . . ?
C35 P3 C19 102.7(4) . . ?
P3' P3 C25 162.8(8) . . ?
C35 P3 C25 92.1(4) . . ?
C19 P3 C25 112.0(4) . . ?
P3' P3 Pt1 88.5(7) . . ?
C35 P3 Pt1 128.1(3) . . ?
C19 P3 Pt1 111.6(3) . . ?
C25 P3 Pt1 108.6(3) . . ?
P3 P3' C19 95.1(9) . . ?
P3 P3' C35 79.7(8) . . ?
C19 P3' C35 114.5(6) . . ?
P3 P3' Pt1 72.8(7) . . ?
C19 P3' Pt1 116.4(5) . . ?
C35 P3' Pt1 123.5(6) . . ?
F4B P4B F6B 90.01(9) . . ?
F4B P4B F2B 177.7(7) . . ?
F6B P4B F2B 88.0(7) . . ?
F4B P4B F1B 85.9(7) . . ?
F6B P4B F1B 175.5(7) . . ?
F2B P4B F1B 96.2(8) . . ?
F4B P4B F3B 89.97(9) . . ?
F6B P4B F3B 85.9(8) . . ?
F2B P4B F3B 88.9(7) . . ?
F1B P4B F3B 96.0(7) . . ?
F4B P4B F5B 91.0(7) . . ?
F6B P4B F5B 88.3(6) . . ?
F2B P4B F5B 89.92(9) . . ?
F1B P4B F5B 89.93(9) . . ?
F3B P4B F5B 174.1(7) . . ?
C45 O1 C48 104.7(9) . . ?
C3 C2 C1 115.6(6) . . ?
C3 C2 P1 104.7(5) . . ?
C1 C2 P1 116.5(5) . . ?
C2 C3 C4 107.6(6) . . ?
C3 C4 C5 106.4(6) . . ?
C6 C5 C4 115.4(6) . . ?
C6 C5 P1 116.2(5) . . ?
C4 C5 P1 102.9(5) . . ?
C12 C7 C8 120.1(6) . . ?
C12 C7 P1 118.8(4) . . ?
C8 C7 P1 121.1(4) . . ?
C9 C8 C7 119.8(6) . . ?
C10 C9 C8 120.1(7) . . ?
C9 C10 C11 121.3(7) . . ?
C10 C11 C12 120.8(7) . . ?
C7 C12 C11 117.9(6) . . ?
C7 C12 P2 117.7(4) . . ?
C11 C12 P2 124.3(5) . . ?
C15 C14 C13 115.6(7) . . ?
C15 C14 P2 106.1(5) . . ?
C13 C14 P2 115.4(5) . . ?
C16 C15 C14 108.1(7) . . ?
C15 C16 C17 108.1(7) . . ?
C16 C17 C18 116.6(7) . . ?
C16 C17 P2 105.1(6) . . ?
C18 C17 P2 114.9(5) . . ?
C20 C19 C24 119.1(8) . . ?
C24 C19 P3' 147.4(8) . . ?
C20 C19 P3 117.4(6) . . ?
C24 C19 P3 123.2(6) . . ?
P3' C19 P3 24.6(4) . . ?
C19 C20 C21 119.8(8) . . ?
C20 C21 C22 121.4(8) . . ?
C23 C22 C21 118.6(9) . . ?
C22 C23 C24 119.3(8) . . ?
C19 C24 C23 121.8(8) . . ?
C26 C25 P3 108.8(6) . . ?
C27 C26 C37 119.0(9) . . ?
C27 C26 C25 130.7(9) . . ?
C37 C26 C25 110.3(7) . . ?
C26 C27 C28 121.3(10) . . ?
C29 C28 C27 120.9(11) . . ?
C28 C29 C36 116.9(10) . . ?
C28 C29 C30 134.8(12) . . ?
C36 C29 C30 108.1(11) . . ?
C29 C30 C31 106.7(10) . . ?
C32 C31 C30 104.5(10) . . ?
C36 C32 C33 115.5(8) . . ?
C36 C32 C31 108.9(11) . . ?
C33 C32 C31 135.5(11) . . ?
C34 C33 C32 118.2(8) . . ?
C35 C34 C33 122.8(9) . . ?
C37 C35 C34 118.6(9) . . ?
C37 C35 P3' 131.0(8) . . ?
C34 C35 P3' 110.0(8) . . ?
C37 C35 P3 107.1(6) . . ?
C34 C35 P3 134.3(8) . . ?
P3' C35 P3 24.5(3) . . ?
C37 C36 C32 123.5(9) . . ?
C37 C36 C29 124.7(9) . . ?
C32 C36 C29 111.5(9) . . ?
C36 C37 C35 121.4(9) . . ?
C36 C37 C26 117.0(9) . . ?
C35 C37 C26 121.6(8) . . ?
C39 C38 C43 122.6(8) . . ?
C40 C39 C38 119.0(9) . . ?
C39 C40 C41 121.2(8) . . ?
C40 C41 C42 119.2(8) . . ?
C43 C42 C41 121.5(8) . . ?
C47 C48 O1 113.1(12) . . ?
C42 C43 C38 116.5(7) . . ?
C42 C43 Pt1 126.1(6) . . ?
C38 C43 Pt1 117.0(5) . . ?
C48 C47 C46 103.1(12) . . ?
C45 C46 C47 107.3(11) . . ?
O1 C45 C46 108.9(11) . . ?
F3A P4A F2A 96.1(10) . . ?
F3A P4A F6A 90.7(7) . . ?
F2A P4A F6A 100.1(12) . . ?
F3A P4A F4A 85.8(10) . . ?
F2A P4A F4A 171.0(12) . . ?
F6A P4A F4A 88.6(11) . . ?
F3A P4A F5A 173.7(10) . . ?
F2A P4A F5A 89.8(9) . . ?
F6A P4A F5A 90.4(9) . . ?
F4A P4A F5A 88.1(8) . . ?
F3A P4A F1 89.0(7) . . ?
F2A P4A F1 82.1(9) . . ?
F6A P4A F1 177.7(12) . . ?
F4A P4A F1 89.1(9) . . ?
F5A P4A F1 89.7(7) . . ?

_refine_diff_density_max         1.412
_refine_diff_density_min         -1.456
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1047191'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 B Br2 P'
_chemical_formula_weight         614.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.116(3)
_cell_length_b                   10.2016(12)
_cell_length_c                   12.0731(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.709(4)
_cell_angle_gamma                90
_cell_volume                     2599.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6076
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.10

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.201
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_T_max  0.818
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28486
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.930
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_full        25.000
_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             5329
_reflns_number_gt                4082
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0496P)²+3.0753P] 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         5329
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_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 0.24805(4) 0.62336(9) 0.64209(7) 0.0158(2) Uani 1 1 d . . . . .
B1 B 0.2564(2) 0.6287(4) 0.4838(3) 0.0201(9) Uani 1 1 d . . . . .
H1AA H 0.3009 0.6157 0.4658 0.030 Uiso 1 1 calc R U . . .
H1AB H 0.2420 0.7141 0.4556 0.030 Uiso 1 1 calc R U . . .
H1AC H 0.2306 0.5592 0.4494 0.030 Uiso 1 1 calc R U . . .
Br1 Br 0.34533(2) 0.92898(4) 0.54357(3) 0.02536(12) Uani 1 1 d . . . . .
Br2 Br 0.09348(2) 0.50960(4) 0.53785(3) 0.02761(12) Uani 1 1 d . . . . .
C1 C 0.31364(16) 0.7002(4) 0.7216(3) 0.0177(8) Uani 1 1 d . . . . .
H1A H 0.3136 0.7954 0.7060 0.021 Uiso 1 1 calc R U . . .
H1B H 0.3063 0.6887 0.8017 0.021 Uiso 1 1 calc R U . . .
C2 C 0.37826(17) 0.6449(3) 0.6961(3) 0.0170(8) Uani 1 1 d . . . . .
C3 C 0.39617(18) 0.5295(4) 0.7484(3) 0.0189(8) Uani 1 1 d . . . . .
H3A H 0.3662 0.4895 0.7949 0.023 Uiso 1 1 calc R U . . .
C4 C 0.45479(17) 0.4665(4) 0.7388(3) 0.0191(8) Uani 1 1 d . . . . .
H4A H 0.4634 0.3860 0.7757 0.023 Uiso 1 1 calc R U . . .
C5 C 0.49920(17) 0.5243(3) 0.6748(3) 0.0172(8) Uani 1 1 d . . . . .
C6 C 0.48231(17) 0.6409(3) 0.6171(3) 0.0150(7) Uani 1 1 d . . . . .
C7 C 0.42243(17) 0.7031(3) 0.6238(3) 0.0161(7) Uani 1 1 d . . . . .
C8 C 0.41831(18) 0.8172(3) 0.5542(3) 0.0189(8) Uani 1 1 d . . . . .
C9 C 0.46626(19) 0.8557(4) 0.4881(3) 0.0221(8) Uani 1 1 d . . . . .
H9A H 0.4601 0.9309 0.4427 0.027 Uiso 1 1 calc R U . . .
C10 C 0.52442(18) 0.7886(4) 0.4846(3) 0.0209(8) Uani 1 1 d . . . . .
H10A H 0.5570 0.8172 0.4376 0.025 Uiso 1 1 calc R U . . .
C11 C 0.53247(17) 0.6813(4) 0.5506(3) 0.0185(8) Uani 1 1 d . . . . .
C12 C 0.58774(17) 0.5906(4) 0.5655(3) 0.0214(8) Uani 1 1 d . . . . .
H12A H 0.6255 0.6385 0.5943 0.026 Uiso 1 1 calc R U . . .
H12B H 0.5980 0.5485 0.4944 0.026 Uiso 1 1 calc R U . . .
C13 C 0.56591(18) 0.4871(4) 0.6505(3) 0.0215(8) Uani 1 1 d . . . . .
H13A H 0.5676 0.3978 0.6187 0.026 Uiso 1 1 calc R U . . .
H13B H 0.5931 0.4899 0.7187 0.026 Uiso 1 1 calc R U . . .
C14 C 0.17721(17) 0.7000(4) 0.6996(3) 0.0192(8) Uani 1 1 d . . . . .
H14A H 0.1442 0.6317 0.7066 0.023 Uiso 1 1 calc R U . . .
H14B H 0.1883 0.7318 0.7752 0.023 Uiso 1 1 calc R U . . .
C15 C 0.14919(17) 0.8124(4) 0.6340(3) 0.0181(8) Uani 1 1 d . . . . .
C16 C 0.16245(18) 0.9374(4) 0.6707(3) 0.0232(8) Uani 1 1 d . . . . .
H16A H 0.1878 0.9466 0.7366 0.028 Uiso 1 1 calc R U . . .
C17 C 0.14104(18) 1.0525(4) 0.6174(3) 0.0238(9) Uani 1 1 d . . . . .
H17A H 0.1507 1.1361 0.6482 0.029 Uiso 1 1 calc R U . . .
C18 C 0.10613(17) 1.0420(4) 0.5205(3) 0.0205(8) Uani 1 1 d . . . . .
C19 C 0.09161(16) 0.9151(3) 0.4801(3) 0.0164(7) Uani 1 1 d . . . . .
C20 C 0.11022(16) 0.7976(4) 0.5345(3) 0.0160(7) Uani 1 1 d . . . . .
C21 C 0.08601(17) 0.6833(3) 0.4797(3) 0.0187(8) Uani 1 1 d . . . . .
C22 C 0.05078(17) 0.6896(4) 0.3823(3) 0.0193(8) Uani 1 1 d . . . . .
H22A H 0.0362 0.6104 0.3490 0.023 Uiso 1 1 calc R U . . .
C23 C 0.03566(18) 0.8095(4) 0.3303(3) 0.0208(8) Uani 1 1 d . . . . .
H23A H 0.0125 0.8116 0.2616 0.025 Uiso 1 1 calc R U . . .
C24 C 0.05514(17) 0.9221(4) 0.3808(3) 0.0192(8) Uani 1 1 d . . . . .
C25 C 0.04530(19) 1.0636(4) 0.3489(3) 0.0247(9) Uani 1 1 d . . . . .
H25A H -0.0004 1.0843 0.3414 0.030 Uiso 1 1 calc R U . . .
H25B H 0.0656 1.0832 0.2779 0.030 Uiso 1 1 calc R U . . .
C26 C 0.07693(19) 1.1434(4) 0.4450(3) 0.0237(9) Uani 1 1 d . . . . .
H26A H 0.1097 1.2032 0.4168 0.028 Uiso 1 1 calc R U . . .
H26B H 0.0450 1.1957 0.4841 0.028 Uiso 1 1 calc R U . . .
C27 C 0.24857(16) 0.4596(4) 0.6995(3) 0.0180(8) Uani 1 1 d . . . . .
C28 C 0.23086(17) 0.4370(4) 0.8085(3) 0.0241(9) Uani 1 1 d . . . . .
H28A H 0.2140 0.5065 0.8509 0.029 Uiso 1 1 calc R U . . .
C29 C 0.23777(19) 0.3135(4) 0.8548(3) 0.0297(10) Uani 1 1 d . . . . .
H29A H 0.2256 0.2985 0.9288 0.036 Uiso 1 1 calc R U . . .
C30 C 0.2622(2) 0.2128(4) 0.7942(4) 0.0335(11) Uani 1 1 d . . . . .
H30A H 0.2669 0.1284 0.8265 0.040 Uiso 1 1 calc R U . . .
C31 C 0.28006(19) 0.2334(4) 0.6860(4) 0.0301(10) Uani 1 1 d . . . . .
H31A H 0.2974 0.1635 0.6446 0.036 Uiso 1 1 calc R U . . .
C32 C 0.27253(18) 0.3564(4) 0.6385(3) 0.0233(9) Uani 1 1 d . . . . .
H32A H 0.2838 0.3701 0.5638 0.028 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
P1 C27 1.808(4) . ?
P1 C1 1.837(4) . ?
P1 C14 1.842(4) . ?
P1 B1 1.925(4) . ?
B1 H1AA 0.9800 . ?
B1 H1AB 0.9800 . ?
B1 H1AC 0.9800 . ?
Br1 C8 1.918(4) . ?
Br2 C21 1.911(4) . ?
C1 C2 1.517(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.383(5) . ?
C2 C7 1.426(5) . ?
C3 C4 1.403(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.366(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.418(5) . ?
C5 C13 1.496(5) . ?
C6 C11 1.409(5) . ?
C6 C7 1.420(5) . ?
C7 C8 1.437(5) . ?
C8 C9 1.365(5) . ?
C9 C10 1.408(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.362(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.496(5) . ?
C12 C13 1.552(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.505(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.376(5) . ?
C15 C20 1.444(5) . ?
C16 C17 1.407(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.368(5) . ?
C17 H17A 0.9500 . ?
C18 C19 1.414(5) . ?
C18 C26 1.499(5) . ?
C19 C24 1.407(5) . ?
C19 C20 1.417(5) . ?
C20 C21 1.428(5) . ?
C21 C22 1.374(5) . ?
C22 C23 1.407(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.359(5) . ?
C23 H23A 0.9500 . ?
C24 C25 1.506(5) . ?
C25 C26 1.552(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C32 1.389(5) . ?
C27 C28 1.397(5) . ?
C28 C29 1.384(5) . ?
C28 H28A 0.9500 . ?
C29 C30 1.370(6) . ?
C29 H29A 0.9500 . ?
C30 C31 1.386(6) . ?
C30 H30A 0.9500 . ?
C31 C32 1.387(6) . ?
C31 H31A 0.9500 . ?
C32 H32A 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
C27 P1 C1 101.40(16) . . ?
C27 P1 C14 104.07(17) . . ?
C1 P1 C14 103.28(17) . . ?
C27 P1 B1 114.03(19) . . ?
C1 P1 B1 114.62(18) . . ?
C14 P1 B1 117.52(18) . . ?
P1 B1 H1AA 109.5 . . ?
P1 B1 H1AB 109.5 . . ?
H1AA B1 H1AB 109.5 . . ?
P1 B1 H1AC 109.5 . . ?
H1AA B1 H1AC 109.5 . . ?
H1AB B1 H1AC 109.5 . . ?
C2 C1 P1 113.8(2) . . ?
C2 C1 H1A 108.8 . . ?
P1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C7 117.3(3) . . ?
C3 C2 C1 117.3(3) . . ?
C7 C2 C1 125.3(3) . . ?
C2 C3 C4 125.6(4) . . ?
C2 C3 H3A 117.2 . . ?
C4 C3 H3A 117.2 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 C13 131.9(3) . . ?
C6 C5 C13 109.9(3) . . ?
C11 C6 C5 110.1(3) . . ?
C11 C6 C7 126.0(3) . . ?
C5 C6 C7 123.9(3) . . ?
C6 C7 C2 116.6(3) . . ?
C6 C7 C8 111.6(3) . . ?
C2 C7 C8 131.8(3) . . ?
C9 C8 C7 122.8(3) . . ?
C9 C8 Br1 113.5(3) . . ?
C7 C8 Br1 123.7(3) . . ?
C8 C9 C10 122.8(4) . . ?
C8 C9 H9A 118.6 . . ?
C10 C9 H9A 118.6 . . ?
C11 C10 C9 117.8(4) . . ?
C11 C10 H10A 121.1 . . ?
C9 C10 H10A 121.1 . . ?
C10 C11 C6 119.1(3) . . ?
C10 C11 C12 130.6(4) . . ?
C6 C11 C12 110.3(3) . . ?
C11 C12 C13 104.7(3) . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C5 C13 C12 104.9(3) . . ?
C5 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C5 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C15 C14 P1 115.8(3) . . ?
C15 C14 H14A 108.3 . . ?
P1 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
P1 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C20 118.1(3) . . ?
C16 C15 C14 117.6(3) . . ?
C20 C15 C14 124.3(3) . . ?
C15 C16 C17 124.5(3) . . ?
C15 C16 H16A 117.8 . . ?
C17 C16 H16A 117.8 . . ?
C18 C17 C16 118.9(3) . . ?
C18 C17 H17A 120.5 . . ?
C16 C17 H17A 120.5 . . ?
C17 C18 C19 118.2(3) . . ?
C17 C18 C26 131.8(3) . . ?
C19 C18 C26 109.9(3) . . ?
C24 C19 C18 110.8(3) . . ?
C24 C19 C20 125.1(3) . . ?
C18 C19 C20 124.1(3) . . ?
C19 C20 C21 112.7(3) . . ?
C19 C20 C15 116.1(3) . . ?
C21 C20 C15 131.1(3) . . ?
C22 C21 C20 122.3(3) . . ?
C22 C21 Br2 113.2(3) . . ?
C20 C21 Br2 124.3(3) . . ?
C21 C22 C23 122.2(3) . . ?
C21 C22 H22A 118.9 . . ?
C23 C22 H22A 118.9 . . ?
C24 C23 C22 118.2(3) . . ?
C24 C23 H23A 120.9 . . ?
C22 C23 H23A 120.9 . . ?
C23 C24 C19 119.3(3) . . ?
C23 C24 C25 131.1(3) . . ?
C19 C24 C25 109.5(3) . . ?
C24 C25 C26 105.0(3) . . ?
C24 C25 H25A 110.7 . . ?
C26 C25 H25A 110.7 . . ?
C24 C25 H25B 110.7 . . ?
C26 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?
C18 C26 C25 104.6(3) . . ?
C18 C26 H26A 110.8 . . ?
C25 C26 H26A 110.8 . . ?
C18 C26 H26B 110.8 . . ?
C25 C26 H26B 110.8 . . ?
H26A C26 H26B 108.9 . . ?
C32 C27 C28 119.1(3) . . ?
C32 C27 P1 119.7(3) . . ?
C28 C27 P1 121.0(3) . . ?
C29 C28 C27 120.2(4) . . ?
C29 C28 H28A 119.9 . . ?
C27 C28 H28A 119.9 . . ?
C30 C29 C28 120.2(4) . . ?
C30 C29 H29A 119.9 . . ?
C28 C29 H29A 119.9 . . ?
C29 C30 C31 120.5(4) . . ?
C29 C30 H30A 119.8 . . ?
C31 C30 H30A 119.8 . . ?
C30 C31 C32 119.7(4) . . ?
C30 C31 H31A 120.2 . . ?
C32 C31 H31A 120.2 . . ?
C31 C32 C27 120.4(4) . . ?
C31 C32 H32A 119.8 . . ?
C27 C32 H32A 119.8 . . ?

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
C27 P1 C1 C2 67.7(3) . . . . ?
C14 P1 C1 C2 175.3(3) . . . . ?
B1 P1 C1 C2 -55.6(3) . . . . ?
P1 C1 C2 C3 -81.7(3) . . . . ?
P1 C1 C2 C7 99.4(4) . . . . ?
C7 C2 C3 C4 1.7(5) . . . . ?
C1 C2 C3 C4 -177.3(3) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C3 C4 C5 C6 -3.3(5) . . . . ?
C3 C4 C5 C13 177.5(4) . . . . ?
C4 C5 C6 C11 -176.4(3) . . . . ?
C13 C5 C6 C11 3.0(4) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C13 C5 C6 C7 -179.0(3) . . . . ?
C11 C6 C7 C2 179.5(3) . . . . ?
C5 C6 C7 C2 1.9(5) . . . . ?
C11 C6 C7 C8 -0.8(5) . . . . ?
C5 C6 C7 C8 -178.4(3) . . . . ?
C3 C2 C7 C6 -3.4(5) . . . . ?
C1 C2 C7 C6 175.6(3) . . . . ?
C3 C2 C7 C8 177.0(3) . . . . ?
C1 C2 C7 C8 -4.1(6) . . . . ?
C6 C7 C8 C9 1.9(5) . . . . ?
C2 C7 C8 C9 -178.4(4) . . . . ?
C6 C7 C8 Br1 -178.7(2) . . . . ?
C2 C7 C8 Br1 0.9(5) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
Br1 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C6 1.4(5) . . . . ?
C9 C10 C11 C12 180.0(3) . . . . ?
C5 C6 C11 C10 177.1(3) . . . . ?
C7 C6 C11 C10 -0.9(5) . . . . ?
C5 C6 C11 C12 -1.8(4) . . . . ?
C7 C6 C11 C12 -179.8(3) . . . . ?
C10 C11 C12 C13 -178.7(4) . . . . ?
C6 C11 C12 C13 0.0(4) . . . . ?
C4 C5 C13 C12 176.4(4) . . . . ?
C6 C5 C13 C12 -2.9(4) . . . . ?
C11 C12 C13 C5 1.7(4) . . . . ?
C27 P1 C14 C15 -156.0(3) . . . . ?
C1 P1 C14 C15 98.5(3) . . . . ?
B1 P1 C14 C15 -28.8(4) . . . . ?
P1 C14 C15 C16 -101.1(4) . . . . ?
P1 C14 C15 C20 78.0(4) . . . . ?
C20 C15 C16 C17 -0.6(6) . . . . ?
C14 C15 C16 C17 178.6(4) . . . . ?
C15 C16 C17 C18 -2.0(6) . . . . ?
C16 C17 C18 C19 1.8(6) . . . . ?
C16 C17 C18 C26 180.0(4) . . . . ?
C17 C18 C19 C24 179.4(3) . . . . ?
C26 C18 C19 C24 0.9(4) . . . . ?
C17 C18 C19 C20 0.9(6) . . . . ?
C26 C18 C19 C20 -177.6(3) . . . . ?
C24 C19 C20 C21 -2.1(5) . . . . ?
C18 C19 C20 C21 176.2(3) . . . . ?
C24 C19 C20 C15 178.3(3) . . . . ?
C18 C19 C20 C15 -3.4(5) . . . . ?
C16 C15 C20 C19 3.1(5) . . . . ?
C14 C15 C20 C19 -176.0(3) . . . . ?
C16 C15 C20 C21 -176.4(4) . . . . ?
C14 C15 C20 C21 4.5(6) . . . . ?
C19 C20 C21 C22 2.5(5) . . . . ?
C15 C20 C21 C22 -177.9(4) . . . . ?
C19 C20 C21 Br2 -172.8(3) . . . . ?
C15 C20 C21 Br2 6.8(6) . . . . ?
C20 C21 C22 C23 -0.6(6) . . . . ?
Br2 C21 C22 C23 175.2(3) . . . . ?
C21 C22 C23 C24 -2.1(6) . . . . ?
C22 C23 C24 C19 2.6(5) . . . . ?
C22 C23 C24 C25 -178.1(4) . . . . ?
C18 C19 C24 C23 -179.0(3) . . . . ?
C20 C19 C24 C23 -0.4(6) . . . . ?
C18 C19 C24 C25 1.6(4) . . . . ?
C20 C19 C24 C25 -179.9(3) . . . . ?
C23 C24 C25 C26 177.3(4) . . . . ?
C19 C24 C25 C26 -3.3(4) . . . . ?
C17 C18 C26 C25 178.8(4) . . . . ?
C19 C18 C26 C25 -2.9(4) . . . . ?
C24 C25 C26 C18 3.7(4) . . . . ?
C1 P1 C27 C32 -105.1(3) . . . . ?
C14 P1 C27 C32 147.9(3) . . . . ?
B1 P1 C27 C32 18.6(4) . . . . ?
C1 P1 C27 C28 68.7(3) . . . . ?
C14 P1 C27 C28 -38.2(3) . . . . ?
B1 P1 C27 C28 -167.5(3) . . . . ?
C32 C27 C28 C29 0.6(5) . . . . ?
P1 C27 C28 C29 -173.3(3) . . . . ?
C27 C28 C29 C30 0.2(6) . . . . ?
C28 C29 C30 C31 -0.1(6) . . . . ?
C29 C30 C31 C32 -0.7(6) . . . . ?
C30 C31 C32 C27 1.5(6) . . . . ?
C28 C27 C32 C31 -1.4(5) . . . . ?
P1 C27 C32 C31 172.5(3) . . . . ?

_refine_diff_density_max         1.134
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_16-0.5H2O
_database_code_depnum_ccdc_archive 'CCDC 1047192'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 O2 P'
_chemical_formula_weight         307.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.5181(6)
_cell_length_b                   9.0445(4)
_cell_length_c                   22.9130(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.5400(10)
_cell_angle_gamma                90
_cell_volume                     2898.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9328
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29611
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_full        25.000
_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             3460
_reflns_number_gt                3202
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0478P)²+3.7851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3460
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
P1 P 0.05761(2) 0.53580(3) 0.37481(2) 0.01074(10) Uani 1 1 d . . . . .
O1 O 0.08930(7) 0.38058(10) 0.36917(4) 0.0139(2) Uani 1 1 d . . . . .
O2 O 0.05210(9) 0.25350(14) 0.25899(5) 0.0333(3) Uani 1 1 d . . . . .
H16 H 0.0617(17) 0.295(3) 0.2957(11) 0.050 Uiso 1 1 d . U . . .
C12 C -0.08882(10) 0.92042(15) 0.55865(6) 0.0158(3) Uani 1 1 d . . . . .
H12A H -0.1304 0.8845 0.5835 0.019 Uiso 1 1 calc R U . . .
H12B H -0.0999 1.0277 0.5514 0.019 Uiso 1 1 calc R U . . .
C11 C -0.10878(9) 0.83651(14) 0.49907(6) 0.0140(3) Uani 1 1 d . . . . .
C19 C -0.02415(9) 0.76423(14) 0.49735(6) 0.0125(3) Uani 1 1 d . . . . .
C18 C -0.01626(9) 0.68004(14) 0.44824(6) 0.0119(2) Uani 1 1 d . . . . .
C17 C 0.07204(9) 0.61360(14) 0.44895(6) 0.0122(2) Uani 1 1 d . . . . .
C1 C 0.11672(9) 0.66074(14) 0.33549(6) 0.0115(2) Uani 1 1 d . . . . .
C6 C 0.19904(9) 0.61198(14) 0.32079(6) 0.0127(3) Uani 1 1 d . . . . .
H6A H 0.2215 0.5140 0.3305 0.015 Uiso 1 1 calc R U . . .
C5 C 0.24823(10) 0.70694(16) 0.29188(6) 0.0162(3) Uani 1 1 d . . . . .
H5A H 0.3042 0.6739 0.2818 0.019 Uiso 1 1 calc R U . . .
C4 C 0.21513(11) 0.84986(16) 0.27782(6) 0.0194(3) Uani 1 1 d . . . . .
H4A H 0.2486 0.9144 0.2580 0.023 Uiso 1 1 calc R U . . .
C13 C 0.01933(10) 0.88882(15) 0.59112(6) 0.0154(3) Uani 1 1 d . . . . .
H13A H 0.0568 0.9817 0.5974 0.018 Uiso 1 1 calc R U . . .
H13B H 0.0260 0.8411 0.6309 0.018 Uiso 1 1 calc R U . . .
C14 C 0.05321(9) 0.78571(14) 0.54860(6) 0.0133(3) Uani 1 1 d . . . . .
C15 C 0.13888(9) 0.71789(15) 0.54985(6) 0.0146(3) Uani 1 1 d . . . . .
H15A H 0.1919 0.7284 0.5844 0.017 Uiso 1 1 calc R U . . .
C16 C 0.14842(9) 0.63200(15) 0.49951(6) 0.0144(3) Uani 1 1 d . . . . .
H16A H 0.2080 0.5869 0.5008 0.017 Uiso 1 1 calc R U . . .
C7 C -0.07221(9) 0.56991(15) 0.34848(6) 0.0143(3) Uani 1 1 d . . . . .
H7A H -0.0886 0.6223 0.3091 0.017 Uiso 1 1 calc R U . . .
H7B H -0.1080 0.4756 0.3437 0.017 Uiso 1 1 calc R U . . .
C8 C -0.09590(9) 0.66486(14) 0.39713(6) 0.0136(3) Uani 1 1 d . . . . .
C10 C -0.18692(10) 0.81977(15) 0.44995(6) 0.0161(3) Uani 1 1 d . . . . .
H10A H -0.2458 0.8656 0.4500 0.019 Uiso 1 1 calc R U . . .
C9 C -0.18009(9) 0.73346(15) 0.39866(6) 0.0147(3) Uani 1 1 d . . . . .
H9A H -0.2347 0.7234 0.3651 0.018 Uiso 1 1 calc R U . . .
C3 C 0.13359(11) 0.89983(16) 0.29244(7) 0.0219(3) Uani 1 1 d . . . . .
H3A H 0.1115 0.9980 0.2827 0.026 Uiso 1 1 calc R U . . .
C2 C 0.08447(10) 0.80524(15) 0.32146(6) 0.0178(3) Uani 1 1 d . . . . .
H2A H 0.0289 0.8390 0.3318 0.021 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
P1 O1 1.4937(9) . ?
P1 C17 1.7982(13) . ?
P1 C1 1.7999(13) . ?
P1 C7 1.8445(13) . ?
O2 O2 1.457(2) 2 ?
C12 C11 1.5205(18) . ?
C12 C13 1.5731(19) . ?
C11 C10 1.3755(19) . ?
C11 C19 1.4016(18) . ?
C19 C18 1.3885(18) . ?
C19 C14 1.4041(18) . ?
C18 C17 1.4121(17) . ?
C18 C8 1.4147(18) . ?
C17 C16 1.3825(18) . ?
C1 C2 1.3964(18) . ?
C1 C6 1.3971(17) . ?
C6 C5 1.3928(18) . ?
C5 C4 1.387(2) . ?
C4 C3 1.389(2) . ?
C13 C14 1.5224(18) . ?
C14 C15 1.3802(19) . ?
C15 C16 1.4279(18) . ?
C7 C8 1.5177(18) . ?
C8 C9 1.3795(18) . ?
C10 C9 1.4363(19) . ?
C3 C2 1.3917(19) . ?

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 C17 119.26(6) . . ?
O1 P1 C1 110.34(6) . . ?
C17 P1 C1 106.06(6) . . ?
O1 P1 C7 116.13(6) . . ?
C17 P1 C7 95.38(6) . . ?
C1 P1 C7 108.29(6) . . ?
C11 C12 C13 105.06(10) . . ?
C10 C11 C19 117.56(12) . . ?
C10 C11 C12 134.95(12) . . ?
C19 C11 C12 107.48(11) . . ?
C18 C19 C11 122.80(12) . . ?
C18 C19 C14 122.17(12) . . ?
C11 C19 C14 115.01(12) . . ?
C19 C18 C17 119.72(12) . . ?
C19 C18 C8 119.84(12) . . ?
C17 C18 C8 120.42(12) . . ?
C16 C17 C18 118.71(12) . . ?
C16 C17 P1 134.67(10) . . ?
C18 C17 P1 106.26(9) . . ?
C2 C1 C6 119.72(12) . . ?
C2 C1 P1 121.83(10) . . ?
C6 C1 P1 118.42(10) . . ?
C5 C6 C1 120.05(12) . . ?
C4 C5 C6 119.70(13) . . ?
C5 C4 C3 120.79(12) . . ?
C14 C13 C12 105.15(11) . . ?
C15 C14 C19 118.06(12) . . ?
C15 C14 C13 134.65(12) . . ?
C19 C14 C13 107.27(11) . . ?
C14 C15 C16 120.45(12) . . ?
C17 C16 C15 120.86(12) . . ?
C8 C7 P1 105.49(9) . . ?
C9 C8 C18 117.93(12) . . ?
C9 C8 C7 130.53(12) . . ?
C18 C8 C7 111.54(11) . . ?
C11 C10 C9 120.44(12) . . ?
C8 C9 C10 121.41(12) . . ?
C4 C3 C2 119.60(13) . . ?
C3 C2 C1 120.14(13) . . ?

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_21
_database_code_depnum_ccdc_archive 'CCDC 1047193'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            GWr154
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H48 F6 P4 Pt'
_chemical_formula_weight         997.78

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'
F F 0.0171 0.0103 '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'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.698(3)
_cell_length_b                   17.675(3)
_cell_length_c                   19.808(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4095.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9691
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             1992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.232
_exptl_absorpt_coefficient_mu    3.640
_shelx_estimated_absorpt_T_min   0.278
_shelx_estimated_absorpt_T_max   0.486
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.250
_exptl_absorpt_correction_T_max  0.500
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23377
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             9979
_reflns_number_gt                8598
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.972

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)] 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_abs_structure_details 
; 
 Flack x determined using 3278 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.003(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9979
_refine_ls_number_parameters     491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.888
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Pt1 Pt 0.56458(3) 0.43191(2) 0.22968(2) 0.01092(8) Uani 1 1 d . . . . .
P1 P 0.37527(19) 0.45814(12) 0.24625(9) 0.0129(4) Uani 1 1 d . . . . .
P2 P 0.58508(18) 0.45172(11) 0.11481(9) 0.0118(4) Uani 1 1 d . . . . .
P3 P 0.75216(19) 0.38981(12) 0.22323(10) 0.0162(4) Uani 1 1 d . . . . .
C1 C 0.7840(7) 0.3681(5) 0.1350(4) 0.0158(17) Uani 1 1 d . . . . .
C2 C 0.8829(8) 0.3301(5) 0.1160(4) 0.0200(19) Uani 1 1 d . . . . .
H02 H 0.9347 0.3125 0.1495 0.024 Uiso 1 1 calc R U . . .
C3 C 0.9060(8) 0.3180(5) 0.0479(4) 0.0203(19) Uani 1 1 d . . . . .
H03 H 0.9720 0.2905 0.0346 0.024 Uiso 1 1 calc R U . . .
C4 C 0.8315(8) 0.3466(5) -0.0005(4) 0.022(2) Uani 1 1 d . . . . .
H04 H 0.8476 0.3390 -0.0470 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7360(8) 0.3852(6) 0.0178(4) 0.023(2) Uani 1 1 d . . . . .
H05 H 0.6860 0.4036 -0.0162 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7097(8) 0.3985(5) 0.0864(4) 0.0162(18) Uani 1 1 d . . . . .
C7 C 0.4707(7) 0.4339(5) 0.0527(3) 0.0164(16) Uani 1 1 d . . . . .
H07 H 0.3984 0.4497 0.0755 0.020 Uiso 1 1 calc R U . . .
C8 C 0.4518(9) 0.3529(5) 0.0322(4) 0.024(2) Uani 1 1 d . . . . .
H08A H 0.5169 0.3354 0.0051 0.036 Uiso 1 1 calc R U . . .
H08B H 0.3816 0.3491 0.0053 0.036 Uiso 1 1 calc R U . . .
H08C H 0.4447 0.3213 0.0726 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4899(8) 0.4926(5) -0.0045(4) 0.0196(19) Uani 1 1 d . . . . .
H09A H 0.5502 0.4749 -0.0358 0.023 Uiso 1 1 calc R U . . .
H09B H 0.4185 0.5002 -0.0305 0.023 Uiso 1 1 calc R U . . .
C10 C 0.5266(7) 0.5670(6) 0.0297(3) 0.0208(18) Uani 1 1 d . . . . .
H10A H 0.4584 0.5931 0.0480 0.025 Uiso 1 1 calc R U . . .
H10B H 0.5627 0.6007 -0.0040 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6124(7) 0.5508(4) 0.0878(3) 0.0136(17) Uani 1 1 d . . . . .
H11 H 0.6918 0.5540 0.0692 0.016 Uiso 1 1 calc R U . . .
C12 C 0.6006(9) 0.6086(5) 0.1453(4) 0.023(2) Uani 1 1 d . . . . .
H12A H 0.5226 0.6070 0.1633 0.034 Uiso 1 1 calc R U . . .
H12B H 0.6167 0.6595 0.1281 0.034 Uiso 1 1 calc R U . . .
H12C H 0.6550 0.5962 0.1813 0.034 Uiso 1 1 calc R U . . .
C13 C 0.8073(8) 0.3084(5) 0.2728(5) 0.0243(18) Uani 1 1 d . . . . .
H13 H 0.8473 0.2743 0.2401 0.029 Uiso 1 1 calc R U . . .
C14 C 0.7189(9) 0.2604(5) 0.3086(5) 0.031(2) Uani 1 1 d . . . . .
H14A H 0.6882 0.2884 0.3472 0.047 Uiso 1 1 calc R U . . .
H14B H 0.7545 0.2135 0.3244 0.047 Uiso 1 1 calc R U . . .
H14C H 0.6567 0.2483 0.2772 0.047 Uiso 1 1 calc R U . . .
C15 C 0.8996(8) 0.3414(6) 0.3187(4) 0.028(2) Uani 1 1 d . . . . .
H15A H 0.9558 0.3017 0.3306 0.034 Uiso 1 1 calc R U . . .
H15B H 0.8646 0.3605 0.3609 0.034 Uiso 1 1 calc R U . . .
C16 C 0.9591(8) 0.4059(5) 0.2813(4) 0.029(2) Uani 1 1 d . . . . .
H16A H 1.0104 0.3850 0.2463 0.034 Uiso 1 1 calc R U . . .
H16B H 1.0060 0.4356 0.3134 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8694(9) 0.4572(5) 0.2485(4) 0.023(2) Uani 1 1 d . . . . .
H17 H 0.8385 0.4916 0.2841 0.027 Uiso 1 1 calc R U . . .
C18 C 0.9158(9) 0.5057(5) 0.1918(4) 0.028(2) Uani 1 1 d . . . . .
H18A H 0.9498 0.4732 0.1571 0.042 Uiso 1 1 calc R U . . .
H18B H 0.9742 0.5401 0.2097 0.042 Uiso 1 1 calc R U . . .
H18C H 0.8534 0.5353 0.1720 0.042 Uiso 1 1 calc R U . . .
C19 C 0.5606(8) 0.4167(4) 0.3352(3) 0.0125(16) Uani 1 1 d . . . . .
C20 C 0.6505(7) 0.4483(5) 0.3723(4) 0.0176(19) Uani 1 1 d . . . . .
H20 H 0.7012 0.4818 0.3496 0.021 Uiso 1 1 calc R U . . .
C21 C 0.6705(7) 0.4336(6) 0.4415(3) 0.0191(17) Uani 1 1 d . . . . .
H21 H 0.7323 0.4573 0.4643 0.023 Uiso 1 1 calc R U . . .
C22 C 0.6005(7) 0.3854(5) 0.4748(4) 0.0167(18) Uani 1 1 d . . . . .
C23 C 0.5957(8) 0.3591(5) 0.5485(4) 0.023(2) Uani 1 1 d . . . . .
H23A H 0.5762 0.4016 0.5789 0.028 Uiso 1 1 calc R U . . .
H23B H 0.6697 0.3371 0.5627 0.028 Uiso 1 1 calc R U . . .
C24 C 0.5000(8) 0.2984(5) 0.5486(4) 0.0173(18) Uani 1 1 d . . . . .
H24B H 0.5330 0.2468 0.5503 0.021 Uiso 1 1 calc R U . . .
H24A H 0.4485 0.3052 0.5877 0.021 Uiso 1 1 calc R U . . .
C25 C 0.4358(9) 0.3108(4) 0.4826(3) 0.0162(16) Uani 1 1 d . . . . .
C26 C 0.5045(8) 0.3558(5) 0.4404(4) 0.0139(17) Uani 1 1 d . . . . .
C27 C 0.4779(7) 0.3744(4) 0.3724(4) 0.0121(16) Uani 1 1 d . . . . .
C28 C 0.3657(7) 0.3498(5) 0.3514(3) 0.0135(17) Uani 1 1 d . . . . .
C29 C 0.2968(8) 0.3092(5) 0.3938(4) 0.0167(17) Uani 1 1 d . . . . .
H29 H 0.2223 0.2958 0.3788 0.020 Uiso 1 1 calc R U . . .
C30 C 0.3322(8) 0.2863(5) 0.4592(4) 0.0177(18) Uani 1 1 d . . . . .
H30 H 0.2851 0.2546 0.4862 0.021 Uiso 1 1 calc R U . . .
C31 C 0.3161(8) 0.3714(5) 0.2829(4) 0.0203(19) Uani 1 1 d . . . . .
H31A H 0.2324 0.3776 0.2877 0.024 Uiso 1 1 calc R U . . .
H31B H 0.3294 0.3292 0.2510 0.024 Uiso 1 1 calc R U . . .
C32 C 0.2809(7) 0.4760(5) 0.1754(4) 0.0154(17) Uani 1 1 d . . . . .
C33 C 0.2249(7) 0.4176(5) 0.1419(4) 0.0192(19) Uani 1 1 d . . . . .
H33 H 0.2271 0.3677 0.1595 0.023 Uiso 1 1 calc R U . . .
C34 C 0.1649(7) 0.4327(7) 0.0818(4) 0.026(2) Uani 1 1 d . . . . .
H34 H 0.1255 0.3928 0.0596 0.031 Uiso 1 1 calc R U . . .
C35 C 0.1625(8) 0.5035(6) 0.0551(4) 0.026(2) Uani 1 1 d . . . . .
H35 H 0.1244 0.5126 0.0136 0.031 Uiso 1 1 calc R U . . .
C36 C 0.2164(7) 0.5630(6) 0.0891(4) 0.024(2) Uani 1 1 d . . . . .
H36 H 0.2135 0.6127 0.0710 0.029 Uiso 1 1 calc R U . . .
C37 C 0.2738(8) 0.5497(5) 0.1490(4) 0.022(2) Uani 1 1 d . . . . .
H37 H 0.3087 0.5906 0.1723 0.026 Uiso 1 1 calc R U . . .
C38 C 0.3496(8) 0.5384(5) 0.3024(4) 0.0182(18) Uani 1 1 d . . . . .
C39 C 0.2394(8) 0.5557(6) 0.3234(4) 0.025(2) Uani 1 1 d . . . . .
H39 H 0.1772 0.5246 0.3100 0.030 Uiso 1 1 calc R U . . .
C40 C 0.2204(9) 0.6185(6) 0.3641(4) 0.030(2) Uani 1 1 d . . . . .
H40 H 0.1453 0.6297 0.3794 0.035 Uiso 1 1 calc R U . . .
C41 C 0.3115(9) 0.6653(6) 0.3827(4) 0.029(2) Uani 1 1 d . . . . .
H41 H 0.2985 0.7079 0.4109 0.035 Uiso 1 1 calc R U . . .
C42 C 0.4206(10) 0.6494(5) 0.3599(4) 0.031(2) Uani 1 1 d . . . . .
H42 H 0.4820 0.6819 0.3718 0.037 Uiso 1 1 calc R U . . .
C43 C 0.4416(9) 0.5858(5) 0.3196(4) 0.0225(18) Uani 1 1 d . . . . .
H43 H 0.5167 0.5748 0.3042 0.027 Uiso 1 1 calc R U . . .
P4 P 0.8445(2) 0.68603(15) 0.31970(12) 0.0263(6) Uani 1 1 d . . . . .
F1 F 0.8062(7) 0.6567(4) 0.2490(3) 0.060(2) Uani 1 1 d . . . . .
F2 F 0.8875(6) 0.7639(3) 0.2861(3) 0.0431(16) Uani 1 1 d . . . . .
F3 F 0.9683(6) 0.6509(4) 0.3081(4) 0.062(2) Uani 1 1 d . . . . .
F4 F 0.8840(7) 0.7173(4) 0.3916(3) 0.054(2) Uani 1 1 d . . . . .
F5 F 0.8005(8) 0.6105(4) 0.3551(3) 0.064(2) Uani 1 1 d . . . . .
F6 F 0.7218(6) 0.7241(4) 0.3324(3) 0.0486(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pt1 C19 2.107(6) . ?
Pt1 P1 2.286(2) . ?
Pt1 P2 2.3146(18) . ?
Pt1 P3 2.321(2) . ?
P1 C32 1.813(8) . ?
P1 C38 1.828(9) . ?
P1 C31 1.832(9) . ?
P2 C6 1.824(9) . ?
P2 C7 1.845(7) . ?
P2 C11 1.859(8) . ?
P3 C1 1.827(8) . ?
P3 C13 1.858(8) . ?
P3 C17 1.884(10) . ?
C1 C2 1.389(12) . ?
C1 C6 1.405(11) . ?
C2 C3 1.394(11) . ?
C3 C4 1.390(12) . ?
C4 C5 1.358(13) . ?
C5 C6 1.413(10) . ?
C7 C8 1.505(12) . ?
C7 C9 1.553(11) . ?
C9 C10 1.541(13) . ?
C10 C11 1.553(11) . ?
C11 C12 1.537(10) . ?
C13 C14 1.514(13) . ?
C13 C15 1.526(13) . ?
C15 C16 1.527(13) . ?
C16 C17 1.531(13) . ?
C17 C18 1.514(11) . ?
C19 C20 1.399(11) . ?
C19 C27 1.427(11) . ?
C20 C21 1.416(10) . ?
C21 C22 1.353(12) . ?
C22 C26 1.414(12) . ?
C22 C23 1.532(10) . ?
C23 C24 1.552(12) . ?
C24 C25 1.523(11) . ?
C25 C30 1.367(13) . ?
C25 C26 1.407(11) . ?
C26 C27 1.422(10) . ?
C27 C28 1.444(11) . ?
C28 C29 1.368(11) . ?
C28 C31 1.525(10) . ?
C29 C30 1.421(11) . ?
C32 C33 1.391(12) . ?
C32 C37 1.407(12) . ?
C33 C34 1.406(11) . ?
C34 C35 1.359(15) . ?
C35 C36 1.398(14) . ?
C36 C37 1.383(11) . ?
C38 C39 1.388(12) . ?
C38 C43 1.406(12) . ?
C39 C40 1.390(13) . ?
C40 C41 1.398(15) . ?
C41 C42 1.383(15) . ?
C42 C43 1.400(12) . ?
P4 F1 1.559(6) . ?
P4 F3 1.592(8) . ?
P4 F5 1.593(7) . ?
P4 F4 1.597(6) . ?
P4 F6 1.605(7) . ?
P4 F2 1.610(6) . ?

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
C19 Pt1 P1 82.1(2) . . ?
C19 Pt1 P2 175.1(3) . . ?
P1 Pt1 P2 102.17(7) . . ?
C19 Pt1 P3 92.0(2) . . ?
P1 Pt1 P3 171.44(7) . . ?
P2 Pt1 P3 84.06(7) . . ?
C32 P1 C38 103.7(4) . . ?
C32 P1 C31 102.8(4) . . ?
C38 P1 C31 110.3(4) . . ?
C32 P1 Pt1 120.9(3) . . ?
C38 P1 Pt1 113.8(3) . . ?
C31 P1 Pt1 104.7(3) . . ?
C6 P2 C7 106.6(4) . . ?
C6 P2 C11 105.0(4) . . ?
C7 P2 C11 95.4(4) . . ?
C6 P2 Pt1 108.0(3) . . ?
C7 P2 Pt1 123.7(2) . . ?
C11 P2 Pt1 116.3(2) . . ?
C1 P3 C13 105.8(4) . . ?
C1 P3 C17 103.8(4) . . ?
C13 P3 C17 95.5(4) . . ?
C1 P3 Pt1 108.2(3) . . ?
C13 P3 Pt1 123.2(3) . . ?
C17 P3 Pt1 118.1(3) . . ?
C2 C1 C6 121.0(7) . . ?
C2 C1 P3 122.0(6) . . ?
C6 C1 P3 116.7(6) . . ?
C1 C2 C3 119.9(8) . . ?
C4 C3 C2 119.3(8) . . ?
C5 C4 C3 121.0(8) . . ?
C4 C5 C6 121.3(8) . . ?
C1 C6 C5 117.4(8) . . ?
C1 C6 P2 118.7(6) . . ?
C5 C6 P2 123.9(7) . . ?
C8 C7 C9 117.4(6) . . ?
C8 C7 P2 116.7(6) . . ?
C9 C7 P2 105.5(6) . . ?
C10 C9 C7 106.9(6) . . ?
C9 C10 C11 110.4(7) . . ?
C12 C11 C10 111.7(7) . . ?
C12 C11 P2 113.4(5) . . ?
C10 C11 P2 106.0(6) . . ?
C14 C13 C15 114.8(8) . . ?
C14 C13 P3 116.3(7) . . ?
C15 C13 P3 105.3(6) . . ?
C13 C15 C16 108.6(7) . . ?
C15 C16 C17 109.6(8) . . ?
C18 C17 C16 113.9(8) . . ?
C18 C17 P3 115.0(6) . . ?
C16 C17 P3 103.7(6) . . ?
C20 C19 C27 116.6(6) . . ?
C20 C19 Pt1 116.9(6) . . ?
C27 C19 Pt1 126.4(6) . . ?
C19 C20 C21 124.0(8) . . ?
C22 C21 C20 119.2(8) . . ?
C21 C22 C26 118.6(7) . . ?
C21 C22 C23 132.6(8) . . ?
C26 C22 C23 108.5(7) . . ?
C22 C23 C24 103.7(6) . . ?
C25 C24 C23 104.8(6) . . ?
C30 C25 C26 119.0(7) . . ?
C30 C25 C24 133.0(7) . . ?
C26 C25 C24 108.0(8) . . ?
C25 C26 C22 112.2(7) . . ?
C25 C26 C27 124.7(8) . . ?
C22 C26 C27 123.0(7) . . ?
C26 C27 C19 117.5(7) . . ?
C26 C27 C28 113.7(7) . . ?
C19 C27 C28 128.7(7) . . ?
C29 C28 C27 121.2(7) . . ?
C29 C28 C31 116.9(8) . . ?
C27 C28 C31 121.8(7) . . ?
C28 C29 C30 122.6(8) . . ?
C25 C30 C29 118.5(8) . . ?
C28 C31 P1 114.7(6) . . ?
C33 C32 C37 118.8(7) . . ?
C33 C32 P1 121.9(7) . . ?
C37 C32 P1 119.0(7) . . ?
C32 C33 C34 119.9(9) . . ?
C35 C34 C33 120.9(9) . . ?
C34 C35 C36 119.7(8) . . ?
C37 C36 C35 120.3(9) . . ?
C36 C37 C32 120.4(9) . . ?
C39 C38 C43 120.5(8) . . ?
C39 C38 P1 120.4(7) . . ?
C43 C38 P1 118.9(7) . . ?
C38 C39 C40 119.9(9) . . ?
C39 C40 C41 120.2(9) . . ?
C42 C41 C40 119.8(8) . . ?
C41 C42 C43 120.8(9) . . ?
C42 C43 C38 118.8(9) . . ?
F1 P4 F3 90.1(4) . . ?
F1 P4 F5 91.4(4) . . ?
F3 P4 F5 91.8(5) . . ?
F1 P4 F4 179.1(4) . . ?
F3 P4 F4 90.0(4) . . ?
F5 P4 F4 89.4(4) . . ?
F1 P4 F6 91.3(4) . . ?
F3 P4 F6 178.0(4) . . ?
F5 P4 F6 89.6(4) . . ?
F4 P4 F6 88.5(4) . . ?
F1 P4 F2 90.2(4) . . ?
F3 P4 F2 89.4(4) . . ?
F5 P4 F2 178.0(4) . . ?
F4 P4 F2 89.0(3) . . ?
F6 P4 F2 89.2(4) . . ?

_refine_diff_density_max         1.117
_refine_diff_density_min         -1.113
_refine_diff_density_rms         0.153

_shelxl_version_number           2013-3

