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

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

data_D8_10140
_database_code_depnum_ccdc_archive 'CCDC 1477899'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT413_D8_10140            
;
PROBLEM: Short Inter XH3 .. XHn     H9B    ..  H1S2    ..       1.98 Ang.  
RESPONSE: Due to disordered solvent. H1S2 is a partially occupied hydrogen
atom from one of the components of the disordered THF molecule.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H31 I O P2'
_chemical_formula_weight         440.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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                   10.0682(2)
_cell_length_b                   13.5159(2)
_cell_length_c                   14.7514(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.3520(10)
_cell_angle_gamma                90
_cell_volume                     2005.69(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      4.40
_cell_measurement_theta_max      69.04

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    14.023
_shelx_estimated_absorpt_T_min   0.127
_shelx_estimated_absorpt_T_max   0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1274
_exptl_absorpt_correction_T_max  0.5407
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'

_exptl_special_details           
; 
 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube, graphite'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            37624
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.395
_diffrn_reflns_theta_max         65.824
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             3398
_reflns_number_gt                2973
_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       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_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          
; 
 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+6.4044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3398
_refine_ls_number_parameters     241
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.069
_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
I1 I 0.07873(3) 0.45154(3) 0.21113(2) 0.03841(14) Uani 1 1 d . . . . .
C9 C 0.1552(5) 0.7477(4) 0.2048(3) 0.0357(11) Uani 1 1 d . . . . .
H9A H 0.1220 0.7937 0.2500 0.054 Uiso 1 1 calc R U . . .
H9B H 0.2419 0.7704 0.1853 0.054 Uiso 1 1 calc R U . . .
H9C H 0.1643 0.6816 0.2316 0.054 Uiso 1 1 calc R U . . .
P1 P 0.01374(12) 0.88449(9) 0.03857(7) 0.0284(3) Uani 1 1 d . . . . .
P2 P 0.04043(12) 0.74305(9) 0.10888(7) 0.0280(3) Uani 1 1 d . . . . .
C1 C -0.1716(4) 0.8750(4) 0.0301(3) 0.0311(10) Uani 1 1 d . . . . .
H1A H -0.2064 0.8920 0.0900 0.037 Uiso 1 1 calc R U . . .
H1B H -0.2055 0.9253 -0.0137 0.037 Uiso 1 1 calc R U . . .
C2 C -0.2276(5) 0.7758(4) 0.0016(3) 0.0340(11) Uani 1 1 d . . . . .
C21 C -0.3006(5) 0.7759(5) -0.0902(3) 0.0405(12) Uani 1 1 d . . . . .
H21A H -0.3285 0.7084 -0.1058 0.061 Uiso 1 1 calc R U . . .
H21B H -0.2415 0.8008 -0.1362 0.061 Uiso 1 1 calc R U . . .
H21C H -0.3790 0.8187 -0.0880 0.061 Uiso 1 1 calc R U . . .
C31 C -0.2604(5) 0.5931(4) 0.0331(4) 0.0409(12) Uani 1 1 d . . . . .
H31A H -0.3395 0.5803 0.0678 0.061 Uiso 1 1 calc R U . . .
H31B H -0.1912 0.5448 0.0501 0.061 Uiso 1 1 calc R U . . .
H31C H -0.2833 0.5875 -0.0319 0.061 Uiso 1 1 calc R U . . .
C3 C -0.2097(5) 0.6962(4) 0.0538(3) 0.0314(10) Uani 1 1 d . . . . .
C4 C -0.1237(5) 0.7047(4) 0.1409(3) 0.0323(11) Uani 1 1 d . . . . .
H4A H -0.1188 0.6401 0.1726 0.039 Uiso 1 1 calc R U . . .
H4B H -0.1618 0.7541 0.1821 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1101(5) 0.6589(4) 0.0274(3) 0.0308(10) Uani 1 1 d . . . . .
H5A H 0.1393 0.5968 0.0577 0.037 Uiso 1 1 calc R U . . .
H5B H 0.0429 0.6426 -0.0212 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2281(5) 0.7117(4) -0.0121(3) 0.0313(10) Uani 1 1 d . . . . .
C61 C 0.3627(5) 0.6679(4) 0.0119(4) 0.0411(12) Uani 1 1 d . . . . .
H61A H 0.4322 0.7118 -0.0097 0.062 Uiso 1 1 calc R U . . .
H61B H 0.3700 0.6029 -0.0169 0.062 Uiso 1 1 calc R U . . .
H61C H 0.3733 0.6606 0.0779 0.062 Uiso 1 1 calc R U . . .
C71 C 0.3152(5) 0.8586(4) -0.0959(3) 0.0344(11) Uani 1 1 d . . . . .
H71A H 0.2757 0.9097 -0.1357 0.052 Uiso 1 1 calc R U . . .
H71B H 0.3754 0.8175 -0.1303 0.052 Uiso 1 1 calc R U . . .
H71C H 0.3651 0.8901 -0.0452 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2069(5) 0.7950(4) -0.0596(3) 0.0308(10) Uani 1 1 d . . . . .
C8 C 0.0660(5) 0.8345(4) -0.0726(3) 0.0309(10) Uani 1 1 d . . . . .
H8A H 0.0052 0.7808 -0.0933 0.037 Uiso 1 1 calc R U . . .
H8B H 0.0630 0.8875 -0.1190 0.037 Uiso 1 1 calc R U . . .
O1S O -0.5101(16) 0.6037(14) -0.3714(8) 0.085(4) Uani 0.497(17) 1 d D U P A 1
C1S C -0.6350(19) 0.5619(17) -0.3702(11) 0.051(5) Uani 0.497(17) 1 d D U P A 1
H1S1 H -0.6443 0.5068 -0.4142 0.062 Uiso 0.497(17) 1 calc R U P A 1
H1S2 H -0.7050 0.6117 -0.3843 0.062 Uiso 0.497(17) 1 calc R U P A 1
C2S C -0.6422(18) 0.5255(12) -0.2752(11) 0.056(4) Uani 0.497(17) 1 d D U P A 1
H2S1 H -0.6056 0.4576 -0.2698 0.067 Uiso 0.497(17) 1 calc R U P A 1
H2S2 H -0.7354 0.5246 -0.2564 0.067 Uiso 0.497(17) 1 calc R U P A 1
C3S C -0.5613(16) 0.5956(11) -0.2177(7) 0.051(3) Uani 0.497(17) 1 d D U P A 1
H3S1 H -0.5095 0.5601 -0.1693 0.061 Uiso 0.497(17) 1 calc R U P A 1
H3S2 H -0.6182 0.6458 -0.1897 0.061 Uiso 0.497(17) 1 calc R U P A 1
C4S C -0.4675(14) 0.6441(13) -0.2874(10) 0.047(3) Uani 0.497(17) 1 d D U P A 1
H4S1 H -0.4771 0.7170 -0.2876 0.057 Uiso 0.497(17) 1 calc R U P A 1
H4S2 H -0.3734 0.6271 -0.2727 0.057 Uiso 0.497(17) 1 calc R U P A 1
O1P O -0.5668(13) 0.6314(8) -0.3531(8) 0.060(3) Uani 0.503(17) 1 d D U P A 2
C1P C -0.491(3) 0.6493(15) -0.2725(14) 0.092(7) Uani 0.503(17) 1 d D U P A 2
H1P1 H -0.5334 0.7010 -0.2360 0.110 Uiso 0.503(17) 1 calc R U P A 2
H1P2 H -0.4003 0.6711 -0.2862 0.110 Uiso 0.503(17) 1 calc R U P A 2
C2P C -0.4870(19) 0.5490(13) -0.2209(9) 0.070(4) Uani 0.503(17) 1 d D U P A 2
H2P1 H -0.4034 0.5130 -0.2312 0.085 Uiso 0.503(17) 1 calc R U P A 2
H2P2 H -0.4954 0.5592 -0.1549 0.085 Uiso 0.503(17) 1 calc R U P A 2
C3P C -0.6029(19) 0.4950(13) -0.2605(12) 0.063(4) Uani 0.503(17) 1 d D U P A 2
H3P1 H -0.6835 0.5083 -0.2263 0.076 Uiso 0.503(17) 1 calc R U P A 2
H3P2 H -0.5862 0.4228 -0.2611 0.076 Uiso 0.503(17) 1 calc R U P A 2
C4P C -0.617(2) 0.5357(13) -0.3560(12) 0.053(4) Uani 0.503(17) 1 d D U P A 2
H4P1 H -0.5667 0.4945 -0.3981 0.064 Uiso 0.503(17) 1 calc R U P A 2
H4P2 H -0.7117 0.5363 -0.3771 0.064 Uiso 0.503(17) 1 calc R U P A 2


_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
C9 P2 1.791(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
P1 C8 1.869(4) . ?
P1 C1 1.869(5) . ?
P1 P2 2.1862(17) . ?
P2 C4 1.813(5) . ?
P2 C5 1.817(5) . ?
C1 C2 1.508(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.331(7) . ?
C2 C21 1.514(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 C3 1.510(7) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C3 C4 1.525(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.522(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.339(7) . ?
C6 C61 1.507(7) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C71 C7 1.504(6) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C7 C8 1.520(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O1S C1S 1.379(14) . ?
O1S C4S 1.405(13) . ?
C1S C2S 1.490(14) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S C3S 1.491(15) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?
C3S C4S 1.568(14) . ?
C3S H3S1 0.9900 . ?
C3S H3S2 0.9900 . ?
C4S H4S1 0.9900 . ?
C4S H4S2 0.9900 . ?
O1P C4P 1.389(13) . ?
O1P C1P 1.406(13) . ?
C1P C2P 1.554(15) . ?
C1P H1P1 0.9900 . ?
C1P H1P2 0.9900 . ?
C2P C3P 1.476(16) . ?
C2P H2P1 0.9900 . ?
C2P H2P2 0.9900 . ?
C3P C4P 1.514(14) . ?
C3P H3P1 0.9900 . ?
C3P H3P2 0.9900 . ?
C4P H4P1 0.9900 . ?
C4P H4P2 0.9900 . ?

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
P2 C9 H9A 109.5 . . ?
P2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
P2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 P1 C1 103.5(2) . . ?
C8 P1 P2 93.81(16) . . ?
C1 P1 P2 94.28(17) . . ?
C9 P2 C4 111.7(2) . . ?
C9 P2 C5 106.9(2) . . ?
C4 P2 C5 112.0(2) . . ?
C9 P2 P1 114.01(19) . . ?
C4 P2 P1 106.15(18) . . ?
C5 P2 P1 106.08(16) . . ?
C2 C1 P1 116.1(3) . . ?
C2 C1 H1A 108.3 . . ?
P1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
P1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 C21 124.5(5) . . ?
C1 C2 C21 114.3(5) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C2 C3 C31 126.4(5) . . ?
C2 C3 C4 119.1(5) . . ?
C31 C3 C4 114.5(4) . . ?
C3 C4 P2 107.1(3) . . ?
C3 C4 H4A 110.3 . . ?
P2 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
P2 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
C6 C5 P2 106.7(3) . . ?
C6 C5 H5A 110.4 . . ?
P2 C5 H5A 110.4 . . ?
C6 C5 H5B 110.4 . . ?
P2 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C7 C6 C61 125.1(4) . . ?
C7 C6 C5 119.0(4) . . ?
C61 C6 C5 115.7(4) . . ?
C6 C61 H61A 109.5 . . ?
C6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C7 C71 H71A 109.5 . . ?
C7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C6 C7 C71 124.4(5) . . ?
C6 C7 C8 119.3(4) . . ?
C71 C7 C8 116.2(4) . . ?
C7 C8 P1 108.1(3) . . ?
C7 C8 H8A 110.1 . . ?
P1 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
P1 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C1S O1S C4S 113.2(12) . . ?
O1S C1S C2S 103.1(11) . . ?
O1S C1S H1S1 111.1 . . ?
C2S C1S H1S1 111.1 . . ?
O1S C1S H1S2 111.1 . . ?
C2S C1S H1S2 111.1 . . ?
H1S1 C1S H1S2 109.1 . . ?
C1S C2S C3S 106.2(9) . . ?
C1S C2S H2S1 110.5 . . ?
C3S C2S H2S1 110.5 . . ?
C1S C2S H2S2 110.5 . . ?
C3S C2S H2S2 110.5 . . ?
H2S1 C2S H2S2 108.7 . . ?
C2S C3S C4S 102.9(9) . . ?
C2S C3S H3S1 111.2 . . ?
C4S C3S H3S1 111.2 . . ?
C2S C3S H3S2 111.2 . . ?
C4S C3S H3S2 111.2 . . ?
H3S1 C3S H3S2 109.1 . . ?
O1S C4S C3S 104.2(9) . . ?
O1S C4S H4S1 110.9 . . ?
C3S C4S H4S1 110.9 . . ?
O1S C4S H4S2 110.9 . . ?
C3S C4S H4S2 110.9 . . ?
H4S1 C4S H4S2 108.9 . . ?
C4P O1P C1P 111.7(11) . . ?
O1P C1P C2P 105.6(10) . . ?
O1P C1P H1P1 110.6 . . ?
C2P C1P H1P1 110.6 . . ?
O1P C1P H1P2 110.6 . . ?
C2P C1P H1P2 110.6 . . ?
H1P1 C1P H1P2 108.8 . . ?
C3P C2P C1P 103.4(10) . . ?
C3P C2P H2P1 111.1 . . ?
C1P C2P H2P1 111.1 . . ?
C3P C2P H2P2 111.1 . . ?
C1P C2P H2P2 111.1 . . ?
H2P1 C2P H2P2 109.0 . . ?
C2P C3P C4P 103.4(11) . . ?
C2P C3P H3P1 111.1 . . ?
C4P C3P H3P1 111.1 . . ?
C2P C3P H3P2 111.1 . . ?
C4P C3P H3P2 111.1 . . ?
H3P1 C3P H3P2 109.0 . . ?
O1P C4P C3P 106.8(10) . . ?
O1P C4P H4P1 110.4 . . ?
C3P C4P H4P1 110.4 . . ?
O1P C4P H4P2 110.4 . . ?
C3P C4P H4P2 110.4 . . ?
H4P1 C4P H4P2 108.6 . . ?

_refine_diff_density_max         1.850
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-4

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

data_D8_12021
_database_code_depnum_ccdc_archive 'CCDC 1477900'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H26 P2'
_chemical_formula_weight         256.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.4848(2)
_cell_length_b                   12.9532(3)
_cell_length_c                   14.0671(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.0400(10)
_cell_angle_gamma                90
_cell_volume                     1493.09(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      69.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.421
_shelx_estimated_absorpt_T_min   0.377
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3774
_exptl_absorpt_correction_T_max  0.8885
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'

_exptl_special_details           
; 
 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube, graphite'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            30850
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.717
_diffrn_reflns_theta_max         69.789
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2805
_reflns_number_gt                2519
_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       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_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          
; 
 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+0.7064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2805
_refine_ls_number_parameters     175
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_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 0.17191(4) 0.26704(3) 0.77450(3) 0.01750(15) Uani 1 1 d . . . . .
P2 P -0.24818(4) 0.27325(3) 0.99877(3) 0.01807(15) Uani 1 1 d . . . . .
C1 C 0.22783(19) 0.39541(13) 0.73702(12) 0.0236(3) Uani 1 1 d . . . . .
H1A H 0.1975 0.4001 0.6650 0.035 Uiso 1 1 calc R U . . .
H1B H 0.3458 0.4056 0.7621 0.035 Uiso 1 1 calc R U . . .
H1C H 0.1699 0.4488 0.7640 0.035 Uiso 1 1 calc R U . . .
C2 C -0.3070(2) 0.40269(13) 1.03160(12) 0.0254(4) Uani 1 1 d . . . . .
H2A H -0.2786 0.4098 1.1034 0.038 Uiso 1 1 calc R U . . .
H2B H -0.4249 0.4120 1.0052 0.038 Uiso 1 1 calc R U . . .
H2C H -0.2488 0.4552 1.0037 0.038 Uiso 1 1 calc R U . . .
C11 C -0.05285(18) 0.28578(12) 0.73576(12) 0.0198(3) Uani 1 1 d D . . . .
C12 C -0.15609(17) 0.19607(12) 0.75043(11) 0.0176(3) Uani 1 1 d . . . . .
C13 C -0.26344(17) 0.19877(12) 0.80594(11) 0.0171(3) Uani 1 1 d . . . . .
C14 C -0.29265(19) 0.29238(13) 0.86313(11) 0.0200(3) Uani 1 1 d D . . . .
C15 C -0.02332(18) 0.29349(13) 1.03740(12) 0.0208(3) Uani 1 1 d D . . . .
C16 C 0.07931(18) 0.20145(12) 1.02598(11) 0.0189(3) Uani 1 1 d . . . . .
C17 C 0.18548(18) 0.20056(12) 0.96975(11) 0.0190(3) Uani 1 1 d . . . . .
C18 C 0.21564(19) 0.29140(13) 0.90931(12) 0.0217(3) Uani 1 1 d D . . . .
C121 C -0.1316(2) 0.10117(12) 0.69302(12) 0.0232(3) Uani 1 1 d . . . . .
H12A H -0.2016 0.0452 0.7053 0.035 Uiso 1 1 calc R U . . .
H12B H -0.0171 0.0795 0.7141 0.035 Uiso 1 1 calc R U . . .
H12C H -0.1602 0.1174 0.6226 0.035 Uiso 1 1 calc R U . . .
C131 C -0.37533(19) 0.11032(12) 0.81362(12) 0.0223(3) Uani 1 1 d . . . . .
H13A H -0.3527 0.0516 0.7753 0.033 Uiso 1 1 calc R U . . .
H13B H -0.4891 0.1320 0.7878 0.033 Uiso 1 1 calc R U . . .
H13C H -0.3568 0.0900 0.8827 0.033 Uiso 1 1 calc R U . . .
C161 C 0.05605(19) 0.11159(13) 1.08958(12) 0.0233(3) Uani 1 1 d . . . . .
H16A H 0.1221 0.0530 1.0784 0.035 Uiso 1 1 calc R U . . .
H16B H -0.0593 0.0917 1.0726 0.035 Uiso 1 1 calc R U . . .
H16C H 0.0903 0.1318 1.1590 0.035 Uiso 1 1 calc R U . . .
C171 C 0.29363(19) 0.10938(13) 0.96332(12) 0.0239(4) Uani 1 1 d . . . . .
H17A H 0.2732 0.0536 1.0057 0.036 Uiso 1 1 calc R U . . .
H17B H 0.4083 0.1304 0.9850 0.036 Uiso 1 1 calc R U . . .
H17C H 0.2694 0.0850 0.8951 0.036 Uiso 1 1 calc R U . . .
H18B H 0.3343(18) 0.3058(15) 0.9250(14) 0.029 Uiso 1 1 d D U . . .
H14A H -0.234(2) 0.3548(13) 0.8532(14) 0.029 Uiso 1 1 d D U . . .
H11B H -0.069(2) 0.2977(15) 0.6660(11) 0.029 Uiso 1 1 d D U . . .
H14B H -0.4109(18) 0.3099(15) 0.8434(14) 0.029 Uiso 1 1 d D U . . .
H15B H -0.004(2) 0.3075(16) 1.1072(11) 0.029 Uiso 1 1 d D U . . .
H11A H -0.075(2) 0.3486(13) 0.7675(14) 0.029 Uiso 1 1 d D U . . .
H18A H 0.154(2) 0.3548(13) 0.9169(14) 0.029 Uiso 1 1 d D U . . .
H15A H -0.003(3) 0.3573(13) 1.0024(14) 0.029 Uiso 1 1 d D 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 C1 1.8433(16) . ?
P1 C11 1.8583(16) . ?
P1 C18 1.8624(16) . ?
P2 C2 1.8421(17) . ?
P2 C15 1.8617(16) . ?
P2 C14 1.8630(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C11 C12 1.501(2) . ?
C11 H11B 0.967(15) . ?
C11 H11A 0.970(15) . ?
C12 C13 1.345(2) . ?
C12 C121 1.514(2) . ?
C13 C131 1.510(2) . ?
C13 C14 1.511(2) . ?
C14 H14A 0.980(15) . ?
C14 H14B 0.995(15) . ?
C15 C16 1.509(2) . ?
C15 H15B 0.970(14) . ?
C15 H15A 0.999(15) . ?
C16 C17 1.344(2) . ?
C16 C161 1.512(2) . ?
C17 C18 1.512(2) . ?
C17 C171 1.513(2) . ?
C18 H18B 0.991(15) . ?
C18 H18A 0.995(15) . ?
C121 H12A 0.9800 . ?
C121 H12B 0.9800 . ?
C121 H12C 0.9800 . ?
C131 H13A 0.9800 . ?
C131 H13B 0.9800 . ?
C131 H13C 0.9800 . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?
C171 H17A 0.9800 . ?
C171 H17B 0.9800 . ?
C171 H17C 0.9800 . ?

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 C11 96.84(7) . . ?
C1 P1 C18 98.07(7) . . ?
C11 P1 C18 101.22(7) . . ?
C2 P2 C15 97.03(8) . . ?
C2 P2 C14 98.02(7) . . ?
C15 P2 C14 101.54(7) . . ?
P1 C1 H1A 109.5 . . ?
P1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
P1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
P2 C2 H2A 109.5 . . ?
P2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
P2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 C11 P1 116.72(11) . . ?
C12 C11 H11B 109.2(12) . . ?
P1 C11 H11B 100.5(12) . . ?
C12 C11 H11A 113.4(12) . . ?
P1 C11 H11A 106.4(12) . . ?
H11B C11 H11A 109.8(17) . . ?
C13 C12 C11 124.52(14) . . ?
C13 C12 C121 122.54(14) . . ?
C11 C12 C121 112.91(13) . . ?
C12 C13 C131 123.71(14) . . ?
C12 C13 C14 124.01(14) . . ?
C131 C13 C14 112.20(13) . . ?
C13 C14 P2 114.90(11) . . ?
C13 C14 H14A 115.2(11) . . ?
P2 C14 H14A 106.3(12) . . ?
C13 C14 H14B 109.1(12) . . ?
P2 C14 H14B 103.8(11) . . ?
H14A C14 H14B 106.7(16) . . ?
C16 C15 P2 115.69(11) . . ?
C16 C15 H15B 107.9(12) . . ?
P2 C15 H15B 102.1(12) . . ?
C16 C15 H15A 115.0(12) . . ?
P2 C15 H15A 105.5(12) . . ?
H15B C15 H15A 109.8(17) . . ?
C17 C16 C15 124.23(15) . . ?
C17 C16 C161 123.50(15) . . ?
C15 C16 C161 112.19(13) . . ?
C16 C17 C18 124.14(15) . . ?
C16 C17 C171 123.46(15) . . ?
C18 C17 C171 112.35(13) . . ?
C17 C18 P1 115.00(11) . . ?
C17 C18 H18B 109.4(12) . . ?
P1 C18 H18B 100.4(12) . . ?
C17 C18 H18A 114.4(11) . . ?
P1 C18 H18A 106.1(11) . . ?
H18B C18 H18A 110.7(16) . . ?
C12 C121 H12A 109.5 . . ?
C12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
C12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C13 C131 H13A 109.5 . . ?
C13 C131 H13B 109.5 . . ?
H13A C131 H13B 109.5 . . ?
C13 C131 H13C 109.5 . . ?
H13A C131 H13C 109.5 . . ?
H13B C131 H13C 109.5 . . ?
C16 C161 H16A 109.5 . . ?
C16 C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
C16 C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?
C17 C171 H17A 109.5 . . ?
C17 C171 H17B 109.5 . . ?
H17A C171 H17B 109.5 . . ?
C17 C171 H17C 109.5 . . ?
H17A C171 H17C 109.5 . . ?
H17B C171 H17C 109.5 . . ?

_refine_diff_density_max         0.805
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

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

data_X8_12021
_database_code_depnum_ccdc_archive 'CCDC 1477901'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT434_X8_12021            
;
PROBLEM: Short Inter HL..HL Contact I1     ..  I2      ..       3.42 Ang.  
RESPONSE: This short I1-I2 distance is consistent with our description
of this molecule as a diphosphane-iodine adduct, in which I1 is interacting
with both P1 and I2 or I2A (minor disordered component). 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cl6 I2 P2'
_chemical_formula_weight         718.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   23.5655(16)
_cell_length_b                   10.2998(7)
_cell_length_c                   20.9628(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.051(2)
_cell_angle_gamma                90
_cell_volume                     5037.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9304
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      30.85

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_F_000             2752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.259
_shelx_estimated_absorpt_T_min   0.356
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3556
_exptl_absorpt_correction_T_max  0.8540
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'

_exptl_special_details           
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            53977
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7692
_reflns_number_gt                6922
_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       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_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          
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0208P)²+7.9204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7692
_refine_ls_number_parameters     287
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0503
_refine_ls_wR_factor_gt          0.0482
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.004
_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
I1 I 0.22436(2) 1.65056(2) 0.14255(2) 0.01867(3) Uani 1 1 d . . . . .
I2 I 0.23194(7) 1.31987(11) 0.15367(10) 0.0227(3) Uani 0.71(4) 1 d . . P A 1
I2A I 0.23050(15) 1.3188(2) 0.1563(2) 0.0183(6) Uani 0.29(4) 1 d . . P A 2
P1 P 0.22532(2) 1.88155(5) 0.12409(2) 0.01633(9) Uani 1 1 d . . . . .
P2 P 0.22894(2) 1.92216(5) 0.02212(2) 0.01778(9) Uani 1 1 d . . . . .
C1 C 0.28973(8) 1.94872(19) 0.16945(9) 0.0199(3) Uani 1 1 d . . . . .
H1A H 0.2879 2.0448 0.1691 0.024 Uiso 1 1 calc R U . . .
H1B H 0.2938 1.9187 0.2147 0.024 Uiso 1 1 calc R U . . .
C2 C 0.34026(8) 1.90226(19) 0.13756(9) 0.0202(4) Uani 1 1 d . . . . .
C21 C 0.38259(9) 1.8188(2) 0.17988(11) 0.0270(4) Uani 1 1 d . . . . .
H21A H 0.4111 1.7843 0.1544 0.041 Uiso 1 1 calc R U . . .
H21B H 0.3623 1.7467 0.1972 0.041 Uiso 1 1 calc R U . . .
H21C H 0.4019 1.8711 0.2155 0.041 Uiso 1 1 calc R U . . .
C31 C 0.38944(9) 1.8919(2) 0.03802(10) 0.0262(4) Uani 1 1 d . . . . .
H31A H 0.4180 1.8406 0.0658 0.039 Uiso 1 1 calc R U . . .
H31B H 0.4080 1.9682 0.0221 0.039 Uiso 1 1 calc R U . . .
H31C H 0.3725 1.8388 0.0015 0.039 Uiso 1 1 calc R U . . .
C3 C 0.34318(8) 1.93516(19) 0.07600(9) 0.0206(4) Uani 1 1 d . . . . .
C4 C 0.29635(8) 2.01839(19) 0.03928(9) 0.0212(4) Uani 1 1 d . . . . .
H4A H 0.3084 2.0481 -0.0017 0.025 Uiso 1 1 calc R U . . .
H4B H 0.2897 2.0959 0.0651 0.025 Uiso 1 1 calc R U . . .
C5 C 0.17032(8) 2.04519(19) 0.01731(9) 0.0204(4) Uani 1 1 d . . . . .
H5A H 0.1796 2.1127 0.0507 0.024 Uiso 1 1 calc R U . . .
H5B H 0.1648 2.0875 -0.0255 0.024 Uiso 1 1 calc R U . . .
C6 C 0.11661(8) 1.97205(18) 0.02819(9) 0.0199(4) Uani 1 1 d . . . . .
C61 C 0.07383(9) 1.9514(2) -0.03110(10) 0.0264(4) Uani 1 1 d . . . . .
H61A H 0.0430 1.8948 -0.0207 0.040 Uiso 1 1 calc R U . . .
H61B H 0.0929 1.9109 -0.0647 0.040 Uiso 1 1 calc R U . . .
H61C H 0.0577 2.0353 -0.0466 0.040 Uiso 1 1 calc R U . . .
C71 C 0.06282(9) 1.8451(2) 0.10391(10) 0.0259(4) Uani 1 1 d . . . . .
H71A H 0.0350 1.8313 0.0652 0.039 Uiso 1 1 calc R U . . .
H71B H 0.0442 1.8899 0.1366 0.039 Uiso 1 1 calc R U . . .
H71C H 0.0775 1.7610 0.1208 0.039 Uiso 1 1 calc R U . . .
C7 C 0.11158(8) 1.92619(18) 0.08727(9) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.15911(8) 1.9535(2) 0.14277(9) 0.0200(4) Uani 1 1 d . . . . .
H8A H 0.1490 1.9159 0.1831 0.024 Uiso 1 1 calc R U . . .
H8B H 0.1640 2.0484 0.1488 0.024 Uiso 1 1 calc R U . . .
C1S C -0.06730(9) 0.6850(2) -0.12827(11) 0.0265(4) Uani 1 1 d . U . . .
H1S H -0.1086 0.6763 -0.1469 0.032 Uiso 1 1 calc R U . B 1
Cl1 Cl -0.0303(3) 0.5429(6) -0.1473(4) 0.0331(8) Uani 0.65(4) 1 d . U P C 1
Cl2 Cl -0.0629(6) 0.7132(12) -0.0448(5) 0.0321(8) Uani 0.65(4) 1 d . U P C 1
Cl3 Cl -0.0373(4) 0.8236(9) -0.1651(4) 0.0265(7) Uani 0.65(4) 1 d . U P C 1
Cl1A Cl -0.0376(8) 0.5349(14) -0.1395(8) 0.045(2) Uani 0.35(4) 1 d . U P C 2
Cl2A Cl -0.0561(12) 0.706(2) -0.0437(10) 0.039(3) Uani 0.35(4) 1 d . U P C 2
Cl3A Cl -0.0422(7) 0.8057(17) -0.1685(8) 0.0316(17) Uani 0.35(4) 1 d . U P C 2
C2S C 0.10696(9) 0.7782(2) 0.32125(10) 0.0242(4) Uani 1 1 d . U . . .
H2S H 0.1489 0.7894 0.3359 0.029 Uiso 1 1 calc R U . D 1
Cl4 Cl 0.0738(5) 0.7158(10) 0.3852(6) 0.0350(12) Uani 0.58(4) 1 d . U P E 1
Cl5 Cl 0.0969(3) 0.6699(6) 0.2574(3) 0.0446(10) Uani 0.58(4) 1 d . U P E 1
Cl6 Cl 0.0758(7) 0.9318(9) 0.2983(4) 0.0366(12) Uani 0.58(4) 1 d . U P E 1
Cl4A Cl 0.0846(7) 0.7237(13) 0.3922(6) 0.0306(14) Uani 0.42(4) 1 d . U P E 2
Cl5A Cl 0.0887(7) 0.6661(9) 0.2582(5) 0.0580(18) Uani 0.42(4) 1 d . U P E 2
Cl6A Cl 0.0845(10) 0.9334(13) 0.2984(6) 0.040(2) Uani 0.42(4) 1 d . U P E 2


_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
I1 P1 2.4110(5) . ?
I1 I2 3.4169(12) . ?
I1 I2A 3.431(2) . ?
P1 C1 1.8118(19) . ?
P1 C8 1.8190(19) . ?
P1 P2 2.1913(7) . ?
P2 C4 1.864(2) . ?
P2 C5 1.8668(19) . ?
C1 C2 1.522(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.345(3) . ?
C2 C21 1.508(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 C3 1.505(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C3 C4 1.519(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.346(3) . ?
C6 C61 1.502(3) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C71 C7 1.501(3) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C7 C8 1.524(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C1S Cl3A 1.657(18) . ?
C1S Cl1A 1.727(12) . ?
C1S Cl2 1.762(11) . ?
C1S Cl2A 1.77(2) . ?
C1S Cl1 1.777(6) . ?
C1S Cl3 1.814(9) . ?
C1S H1S 1.0000 . ?
C2S Cl6A 1.730(13) . ?
C2S Cl5 1.733(6) . ?
C2S Cl4A 1.739(14) . ?
C2S Cl5A 1.762(9) . ?
C2S Cl4 1.765(10) . ?
C2S Cl6 1.782(9) . ?
C2S H2S 1.0000 . ?

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
P1 I1 I2 173.21(4) . . ?
P1 I1 I2A 174.36(9) . . ?
C1 P1 C8 114.34(9) . . ?
C1 P1 P2 107.15(7) . . ?
C8 P1 P2 106.49(7) . . ?
C1 P1 I1 108.58(6) . . ?
C8 P1 I1 109.88(7) . . ?
P2 P1 I1 110.33(2) . . ?
C4 P2 C5 104.69(9) . . ?
C4 P2 P1 93.55(6) . . ?
C5 P2 P1 93.02(6) . . ?
C2 C1 P1 107.38(13) . . ?
C2 C1 H1A 110.2 . . ?
P1 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
P1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C3 C2 C21 126.13(18) . . ?
C3 C2 C1 119.36(17) . . ?
C21 C2 C1 114.50(17) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C2 C3 C31 124.82(18) . . ?
C2 C3 C4 119.82(17) . . ?
C31 C3 C4 115.33(17) . . ?
C3 C4 P2 109.68(13) . . ?
C3 C4 H4A 109.7 . . ?
P2 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
P2 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 P2 106.35(13) . . ?
C6 C5 H5A 110.5 . . ?
P2 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
P2 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C7 C6 C61 125.20(18) . . ?
C7 C6 C5 119.69(17) . . ?
C61 C6 C5 115.03(17) . . ?
C6 C61 H61A 109.5 . . ?
C6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C7 C71 H71A 109.5 . . ?
C7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C6 C7 C71 125.32(18) . . ?
C6 C7 C8 119.18(17) . . ?
C71 C7 C8 115.48(17) . . ?
C7 C8 P1 108.73(13) . . ?
C7 C8 H8A 109.9 . . ?
P1 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
P1 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
Cl3A C1S Cl1A 114.9(9) . . ?
Cl3A C1S Cl2A 113.9(10) . . ?
Cl1A C1S Cl2A 103.8(11) . . ?
Cl2 C1S Cl1 113.3(5) . . ?
Cl2 C1S Cl3 108.7(5) . . ?
Cl1 C1S Cl3 108.7(4) . . ?
Cl2 C1S H1S 108.7 . . ?
Cl1 C1S H1S 108.7 . . ?
Cl3 C1S H1S 108.7 . . ?
Cl6A C2S Cl4A 114.7(7) . . ?
Cl6A C2S Cl5A 111.3(6) . . ?
Cl4A C2S Cl5A 111.0(5) . . ?
Cl5 C2S Cl4 109.0(4) . . ?
Cl5 C2S Cl6 110.9(4) . . ?
Cl4 C2S Cl6 108.6(6) . . ?
Cl5 C2S H2S 109.5 . . ?
Cl4 C2S H2S 109.5 . . ?
Cl6 C2S H2S 109.5 . . ?

_refine_diff_density_max         1.451
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.090

_shelxl_version_number           2013-4

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

data_X8_15156
_database_code_depnum_ccdc_archive 'CCDC 1477902'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H46 Ni O2 P2'
_chemical_formula_weight         523.29

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'
Ni Ni 0.3393 1.1124 '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                   9.6408(9)
_cell_length_b                   12.6202(12)
_cell_length_c                   22.256(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2707.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.16

_exptl_crystal_description       needle
_exptl_crystal_colour            gold
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.856
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6035
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'

_exptl_special_details           
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            10744
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.830
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_point_group_measured_fraction_full 0.830
_reflns_number_total             4926
_reflns_number_gt                4051
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.435
_reflns_Friedel_fraction_max     0.545
_reflns_Friedel_fraction_full    0.626

_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       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_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          
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²] 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 x determined using 1151 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.013(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4926
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
Ni1 Ni 0.38086(6) 0.51500(5) 0.66283(3) 0.03020(19) Uani 1 1 d . . . . .
P1 P 0.41058(13) 0.43769(10) 0.75279(6) 0.0277(3) Uani 1 1 d . . . . .
P2 P 0.58505(13) 0.47239(9) 0.63567(6) 0.0273(3) Uani 1 1 d . . . . .
O1 O 0.1982(4) 0.5568(3) 0.68428(17) 0.0362(9) Uani 1 1 d . . . . .
O2 O 0.0068(4) 0.6223(3) 0.6441(2) 0.0448(11) Uani 1 1 d . . . . .
C1 C 0.1212(6) 0.5810(4) 0.6393(3) 0.0356(12) Uani 1 1 d . . . . .
C2 C 0.1772(6) 0.5466(5) 0.5783(3) 0.0525(17) Uani 1 1 d . . . . .
H2A H 0.1538 0.4715 0.5705 0.063 Uiso 1 1 calc R U . . .
H2B H 0.1367 0.5907 0.5459 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3291(6) 0.5608(5) 0.5806(3) 0.0459(15) Uani 1 1 d . . . . .
H3A H 0.3545 0.6359 0.5739 0.055 Uiso 1 1 calc R U . . .
H3B H 0.3756 0.5164 0.5500 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4214(5) 0.2930(3) 0.7391(2) 0.0322(12) Uani 1 1 d . . . . .
H11A H 0.5188 0.2696 0.7439 0.039 Uiso 1 1 calc R U . . .
H11B H 0.3647 0.2553 0.7694 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3708(6) 0.2635(3) 0.6764(3) 0.0340(13) Uani 1 1 d . . . . .
C13 C 0.4492(5) 0.2778(4) 0.6279(3) 0.0333(13) Uani 1 1 d . . . . .
C14 C 0.5935(5) 0.3256(4) 0.6325(3) 0.0310(12) Uani 1 1 d . . . . .
H14A H 0.6492 0.3038 0.5972 0.037 Uiso 1 1 calc R U . . .
H14B H 0.6400 0.2986 0.6690 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2216(6) 0.2270(5) 0.6750(3) 0.0423(15) Uani 1 1 d . . . . .
H15A H 0.1601 0.2879 0.6809 0.063 Uiso 1 1 calc R U . . .
H15B H 0.2061 0.1753 0.7072 0.063 Uiso 1 1 calc R U . . .
H15C H 0.2018 0.1940 0.6361 0.063 Uiso 1 1 calc R U . . .
C16 C 0.4014(6) 0.2579(4) 0.5641(3) 0.0431(14) Uani 1 1 d . . . . .
H16A H 0.3100 0.2239 0.5647 0.065 Uiso 1 1 calc R U . . .
H16B H 0.4680 0.2115 0.5438 0.065 Uiso 1 1 calc R U . . .
H16C H 0.3952 0.3255 0.5425 0.065 Uiso 1 1 calc R U . . .
C21 C 0.5602(5) 0.4658(4) 0.8023(2) 0.0280(11) Uani 1 1 d . . . . .
H21A H 0.5778 0.5430 0.8020 0.034 Uiso 1 1 calc R U . . .
H21B H 0.5352 0.4456 0.8439 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6925(5) 0.4095(4) 0.7854(2) 0.0280(12) Uani 1 1 d . . . . .
C23 C 0.7645(5) 0.4329(4) 0.7352(2) 0.0249(11) Uani 1 1 d . . . . .
C24 C 0.7154(5) 0.5167(4) 0.6920(2) 0.0266(10) Uani 1 1 d . . . . .
H24A H 0.7969 0.5450 0.6703 0.032 Uiso 1 1 calc R U . . .
H24B H 0.6749 0.5757 0.7155 0.032 Uiso 1 1 calc R U . . .
C25 C 0.7350(5) 0.3245(4) 0.8291(2) 0.0319(12) Uani 1 1 d . . . . .
H25A H 0.8141 0.2851 0.8128 0.048 Uiso 1 1 calc R U . . .
H25B H 0.6572 0.2759 0.8356 0.048 Uiso 1 1 calc R U . . .
H25C H 0.7614 0.3571 0.8674 0.048 Uiso 1 1 calc R U . . .
C26 C 0.8971(5) 0.3795(4) 0.7159(2) 0.0303(11) Uani 1 1 d . . . . .
H26A H 0.9193 0.3221 0.7439 0.045 Uiso 1 1 calc R U . . .
H26B H 0.9728 0.4314 0.7157 0.045 Uiso 1 1 calc R U . . .
H26C H 0.8855 0.3503 0.6754 0.045 Uiso 1 1 calc R U . . .
C31 C 0.2590(5) 0.4602(4) 0.8021(3) 0.0323(13) Uani 1 1 d . . . . .
H31 H 0.1747 0.4507 0.7764 0.039 Uiso 1 1 calc R U . . .
C32 C 0.2584(5) 0.5762(4) 0.8232(3) 0.0327(13) Uani 1 1 d . . . . .
H32A H 0.3387 0.5889 0.8500 0.039 Uiso 1 1 calc R U . . .
H32B H 0.2672 0.6238 0.7880 0.039 Uiso 1 1 calc R U . . .
C33 C 0.1243(6) 0.6007(4) 0.8567(3) 0.0428(14) Uani 1 1 d . . . . .
H33A H 0.1264 0.6749 0.8711 0.051 Uiso 1 1 calc R U . . .
H33B H 0.0447 0.5932 0.8289 0.051 Uiso 1 1 calc R U . . .
C34 C 0.1051(6) 0.5269(5) 0.9097(3) 0.0458(14) Uani 1 1 d . . . . .
H34A H 0.0152 0.5421 0.9295 0.055 Uiso 1 1 calc R U . . .
H34B H 0.1798 0.5393 0.9394 0.055 Uiso 1 1 calc R U . . .
C35 C 0.1083(6) 0.4109(4) 0.8895(3) 0.0442(14) Uani 1 1 d . . . . .
H35A H 0.1006 0.3641 0.9250 0.053 Uiso 1 1 calc R U . . .
H35B H 0.0279 0.3967 0.8630 0.053 Uiso 1 1 calc R U . . .
C36 C 0.2418(6) 0.3857(4) 0.8558(3) 0.0402(14) Uani 1 1 d . . . . .
H36A H 0.2395 0.3114 0.8417 0.048 Uiso 1 1 calc R U . . .
H36B H 0.3220 0.3938 0.8833 0.048 Uiso 1 1 calc R U . . .
C41 C 0.6581(5) 0.5214(4) 0.5643(2) 0.0297(11) Uani 1 1 d . . . . .
H41 H 0.5909 0.5028 0.5317 0.036 Uiso 1 1 calc R U . . .
C42 C 0.6687(6) 0.6432(4) 0.5664(2) 0.0330(13) Uani 1 1 d . . . . .
H42A H 0.5765 0.6732 0.5760 0.040 Uiso 1 1 calc R U . . .
H42B H 0.7335 0.6641 0.5988 0.040 Uiso 1 1 calc R U . . .
C43 C 0.7187(6) 0.6884(4) 0.5075(3) 0.0363(13) Uani 1 1 d . . . . .
H43A H 0.7264 0.7664 0.5108 0.044 Uiso 1 1 calc R U . . .
H43B H 0.6508 0.6719 0.4754 0.044 Uiso 1 1 calc R U . . .
C44 C 0.8587(6) 0.6419(4) 0.4912(3) 0.0347(13) Uani 1 1 d . . . . .
H44A H 0.9279 0.6624 0.5219 0.042 Uiso 1 1 calc R U . . .
H44B H 0.8894 0.6709 0.4521 0.042 Uiso 1 1 calc R U . . .
C45 C 0.8511(5) 0.5219(4) 0.4873(2) 0.0353(12) Uani 1 1 d . . . . .
H45A H 0.9442 0.4932 0.4780 0.042 Uiso 1 1 calc R U . . .
H45B H 0.7875 0.5014 0.4544 0.042 Uiso 1 1 calc R U . . .
C46 C 0.7992(6) 0.4742(4) 0.5467(2) 0.0340(12) Uani 1 1 d . . . . .
H46A H 0.8675 0.4885 0.5788 0.041 Uiso 1 1 calc R U . . .
H46B H 0.7904 0.3964 0.5423 0.041 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
Ni1 O1 1.899(4) . ?
Ni1 C3 1.982(6) . ?
Ni1 P2 2.1283(15) . ?
Ni1 P1 2.2454(15) . ?
P1 C21 1.849(5) . ?
P1 C31 1.849(5) . ?
P1 C11 1.855(5) . ?
P2 C41 1.844(5) . ?
P2 C14 1.855(5) . ?
P2 C24 1.861(5) . ?
O1 C1 1.283(6) . ?
O2 C1 1.225(6) . ?
C1 C2 1.524(9) . ?
C2 C3 1.476(8) . ?
C11 C12 1.524(7) . ?
C12 C13 1.330(7) . ?
C12 C15 1.511(7) . ?
C13 C16 1.513(8) . ?
C13 C14 1.520(7) . ?
C21 C22 1.507(7) . ?
C22 C23 1.349(7) . ?
C22 C25 1.506(7) . ?
C23 C24 1.505(7) . ?
C23 C26 1.507(7) . ?
C31 C36 1.531(7) . ?
C31 C32 1.538(7) . ?
C32 C33 1.524(7) . ?
C33 C34 1.516(7) . ?
C34 C35 1.532(8) . ?
C35 C36 1.523(8) . ?
C41 C46 1.536(7) . ?
C41 C42 1.541(7) . ?
C42 C43 1.509(8) . ?
C43 C44 1.516(7) . ?
C44 C45 1.518(7) . ?
C45 C46 1.535(7) . ?

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 Ni1 C3 85.3(2) . . ?
O1 Ni1 P2 177.63(12) . . ?
C3 Ni1 P2 92.56(19) . . ?
O1 Ni1 P1 90.86(12) . . ?
C3 Ni1 P1 168.99(18) . . ?
P2 Ni1 P1 91.46(5) . . ?
C21 P1 C31 103.5(2) . . ?
C21 P1 C11 104.0(2) . . ?
C31 P1 C11 107.0(2) . . ?
C21 P1 Ni1 123.18(17) . . ?
C31 P1 Ni1 111.16(19) . . ?
C11 P1 Ni1 106.78(18) . . ?
C41 P2 C14 106.5(2) . . ?
C41 P2 C24 102.8(2) . . ?
C14 P2 C24 107.2(2) . . ?
C41 P2 Ni1 120.88(17) . . ?
C14 P2 Ni1 107.68(18) . . ?
C24 P2 Ni1 110.93(17) . . ?
C1 O1 Ni1 114.0(3) . . ?
O2 C1 O1 123.7(5) . . ?
O2 C1 C2 121.2(5) . . ?
O1 C1 C2 115.0(5) . . ?
C3 C2 C1 106.6(5) . . ?
C2 C3 Ni1 104.3(4) . . ?
C12 C11 P1 111.9(3) . . ?
C13 C12 C15 124.5(5) . . ?
C13 C12 C11 121.9(5) . . ?
C15 C12 C11 113.5(5) . . ?
C12 C13 C16 124.5(5) . . ?
C12 C13 C14 121.3(5) . . ?
C16 C13 C14 114.0(5) . . ?
C13 C14 P2 111.0(3) . . ?
C22 C21 P1 114.9(3) . . ?
C23 C22 C25 123.4(5) . . ?
C23 C22 C21 122.6(5) . . ?
C25 C22 C21 113.9(4) . . ?
C22 C23 C24 121.4(4) . . ?
C22 C23 C26 125.1(5) . . ?
C24 C23 C26 113.5(4) . . ?
C23 C24 P2 115.6(3) . . ?
C36 C31 C32 110.2(5) . . ?
C36 C31 P1 117.0(4) . . ?
C32 C31 P1 109.3(3) . . ?
C33 C32 C31 110.2(4) . . ?
C34 C33 C32 111.1(4) . . ?
C33 C34 C35 110.9(5) . . ?
C36 C35 C34 111.1(5) . . ?
C35 C36 C31 110.3(4) . . ?
C46 C41 C42 109.6(4) . . ?
C46 C41 P2 115.4(3) . . ?
C42 C41 P2 109.5(4) . . ?
C43 C42 C41 111.8(4) . . ?
C42 C43 C44 110.2(4) . . ?
C43 C44 C45 110.9(4) . . ?
C44 C45 C46 111.0(5) . . ?
C45 C46 C41 110.9(4) . . ?

_refine_diff_density_max         1.163
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4

