# Electronic Supplementary Material (ESI) for ChemComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1058665'
_audit_update_record             
;
2015-04-09 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H30 Al Cl6 P3'
_chemical_formula_iupac          ?
_chemical_formula_weight         807.20

_chemical_melting_point          ?

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

_cell_length_a                   10.7482(3)
_cell_length_b                   11.7146(3)
_cell_length_c                   16.2326(5)
_cell_angle_alpha                108.1778(13)
_cell_angle_beta                 100.8287(13)
_cell_angle_gamma                99.8863(13)
_cell_volume                     1848.28(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9274
_cell_measurement_theta_min      2.6665
_cell_measurement_theta_max      31.0430
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            54649
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         31.15
_diffrn_reflns_theta_full        31.15
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             11898
_reflns_number_gt                9903
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0845
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_number_reflns         11898
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.8901P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.886
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Al Al 0.0645 0.0514 '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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Al Al1 0.63469(4) 0.41584(4) 0.25750(3) 0.01521(8) Uani d . . . 1 . .
C C1 0.21415(12) 0.94656(11) 0.29991(8) 0.0107(2) Uani d . . . 1 . .
C C2 -0.03592(12) 0.88072(12) 0.15504(9) 0.0134(2) Uani d . . . 1 . .
C C3 -0.11067(14) 0.90944(14) 0.08685(10) 0.0199(3) Uani d . . . 1 . .
H H3 -0.0719 0.9716 0.0669 0.024 Uiso calc U . R 1 . .
C C4 -0.24115(14) 0.84691(15) 0.04864(10) 0.0237(3) Uani d . . . 1 . .
H H4 -0.2915 0.866 0.0023 0.028 Uiso calc U . R 1 . .
C C5 -0.29842(14) 0.75633(15) 0.07804(10) 0.0224(3) Uani d . . . 1 . .
H H5 -0.3879 0.7139 0.052 0.027 Uiso calc U . R 1 . .
C C6 -0.22528(14) 0.72800(14) 0.14516(10) 0.0193(3) Uani d . . . 1 . .
H H6 -0.2645 0.6657 0.1648 0.023 Uiso calc U . R 1 . .
C C7 -0.09418(13) 0.79050(12) 0.18418(9) 0.0151(2) Uani d . . . 1 . .
H H7 -0.0446 0.7713 0.2308 0.018 Uiso calc U . R 1 . .
C C8 0.12515(13) 1.12512(12) 0.22571(9) 0.0136(2) Uani d . . . 1 . .
C C9 0.21952(14) 1.21140(13) 0.21267(10) 0.0181(3) Uani d . . . 1 . .
H H9 0.2864 1.1856 0.1862 0.022 Uiso calc U . R 1 . .
C C10 0.21482(16) 1.33501(14) 0.23867(11) 0.0234(3) Uani d . . . 1 . .
H H10 0.2782 1.3939 0.2296 0.028 Uiso calc U . R 1 . .
C C11 0.11734(16) 1.37261(14) 0.27803(11) 0.0235(3) Uani d . . . 1 . .
H H11 0.1166 1.4578 0.298 0.028 Uiso calc U . R 1 . .
C C12 0.02149(15) 1.28683(14) 0.28826(10) 0.0217(3) Uani d . . . 1 . .
H H12 -0.0464 1.3128 0.3135 0.026 Uiso calc U . R 1 . .
C C13 0.02421(14) 1.16289(13) 0.26178(9) 0.0169(3) Uani d . . . 1 . .
H H13 -0.0423 1.1038 0.2681 0.02 Uiso calc U . R 1 . .
C C14 0.21859(13) 0.92346(12) 0.11637(9) 0.0128(2) Uani d . . . 1 . .
C C15 0.15494(14) 0.84503(13) 0.02827(9) 0.0172(3) Uani d . . . 1 . .
H H15 0.0628 0.8134 0.0113 0.021 Uiso calc U . R 1 . .
C C16 0.22710(16) 0.81343(14) -0.03443(10) 0.0214(3) Uani d . . . 1 . .
H H16 0.184 0.7607 -0.0945 0.026 Uiso calc U . R 1 . .
C C17 0.36229(16) 0.85886(14) -0.00945(10) 0.0220(3) Uani d . . . 1 . .
H H17 0.4114 0.8356 -0.0522 0.026 Uiso calc U . R 1 . .
C C18 0.42553(14) 0.93778(13) 0.07746(10) 0.0187(3) Uani d . . . 1 . .
H H18 0.5177 0.9694 0.0941 0.022 Uiso calc U . R 1 . .
C C19 0.35406(13) 0.97070(12) 0.14043(9) 0.0143(2) Uani d . . . 1 . .
H H19 0.3974 1.0254 0.1999 0.017 Uiso calc U . R 1 . .
C C20 0.22758(12) 0.68909(12) 0.19597(8) 0.0123(2) Uani d . . . 1 . .
C C21 0.11445(13) 0.59991(12) 0.18352(9) 0.0151(2) Uani d . . . 1 . .
H H21 0.065 0.6129 0.2269 0.018 Uiso calc U . R 1 . .
C C22 0.07408(15) 0.49243(13) 0.10803(10) 0.0209(3) Uani d . . . 1 . .
H H22 -0.0031 0.4321 0.0997 0.025 Uiso calc U . R 1 . .
C C23 0.14626(15) 0.47309(14) 0.04479(10) 0.0217(3) Uani d . . . 1 . .
H H23 0.1192 0.3989 -0.0064 0.026 Uiso calc U . R 1 . .
C C24 0.25775(15) 0.56164(14) 0.05599(10) 0.0199(3) Uani d . . . 1 . .
H H24 0.3062 0.5484 0.012 0.024 Uiso calc U . R 1 . .
C C25 0.29905(14) 0.66973(13) 0.13116(9) 0.0158(2) Uani d . . . 1 . .
H H25 0.3755 0.7303 0.1386 0.019 Uiso calc U . R 1 . .
C C26 0.46136(12) 0.86269(12) 0.31997(8) 0.0122(2) Uani d . . . 1 . .
C C27 0.52899(13) 0.76898(13) 0.30965(9) 0.0155(2) Uani d . . . 1 . .
H H27 0.482 0.6846 0.2886 0.019 Uiso calc U . R 1 . .
C C28 0.66428(13) 0.79941(14) 0.33012(10) 0.0180(3) Uani d . . . 1 . .
H H28 0.7102 0.7361 0.3254 0.022 Uiso calc U . R 1 . .
C C29 0.73301(13) 0.92257(14) 0.35756(10) 0.0186(3) Uani d . . . 1 . .
H H29 0.8257 0.9429 0.37 0.022 Uiso calc U . R 1 . .
C C30 0.66704(13) 1.01570(13) 0.36689(9) 0.0171(3) Uani d . . . 1 . .
H H30 0.7144 1.0996 0.3855 0.021 Uiso calc U . R 1 . .
C C31 0.53104(13) 0.98621(12) 0.34897(9) 0.0137(2) Uani d . . . 1 . .
H H31 0.4859 1.0502 0.3565 0.016 Uiso calc U . R 1 . .
C C32 0.24708(13) 0.76423(12) 0.38557(8) 0.0125(2) Uani d . . . 1 . .
C C33 0.12314(13) 0.75742(13) 0.40168(9) 0.0156(2) Uani d . . . 1 . .
H H33 0.0635 0.7937 0.3737 0.019 Uiso calc U . R 1 . .
C C34 0.08688(14) 0.69760(13) 0.45857(10) 0.0191(3) Uani d . . . 1 . .
H H34 0.0022 0.6922 0.4688 0.023 Uiso calc U . R 1 . .
C C35 0.17442(16) 0.64591(14) 0.50029(10) 0.0214(3) Uani d . . . 1 . .
H H35 0.1491 0.6037 0.5381 0.026 Uiso calc U . R 1 . .
C C36 0.29870(16) 0.65578(14) 0.48688(10) 0.0224(3) Uani d . . . 1 . .
H H36 0.3592 0.6222 0.5169 0.027 Uiso calc U . R 1 . .
C C37 0.33549(14) 0.71458(13) 0.42980(9) 0.0178(3) Uani d . . . 1 . .
H H37 0.4209 0.721 0.4209 0.021 Uiso calc U . R 1 . .
Cl Cl1 0.07810(3) 1.07927(3) 0.43829(2) 0.01968(7) Uani d . . . 1 . .
Cl Cl2 0.33582(3) 1.22376(3) 0.41736(2) 0.01871(7) Uani d . . . 1 . .
Cl Cl3 0.56827(5) 0.50530(4) 0.37010(3) 0.03297(10) Uani d . . . 1 . .
Cl Cl4 0.63622(4) 0.23050(3) 0.24882(3) 0.02443(8) Uani d . . . 1 . .
Cl Cl5 0.82839(4) 0.51230(4) 0.26914(4) 0.03755(11) Uani d . . . 1 . .
Cl Cl6 0.51029(4) 0.41786(4) 0.13928(3) 0.03304(10) Uani d . . . 1 . .
P P1 0.13335(3) 0.96621(3) 0.20294(2) 0.01054(6) Uani d . . . 1 . .
P P2 0.28565(3) 0.82215(3) 0.29919(2) 0.00984(6) Uani d . . . 1 . .
P P3 0.25505(3) 1.04799(3) 0.41373(2) 0.01252(7) Uani 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Al1 Cl3 . 2.1215(6) ?
Al1 Cl6 . 2.1322(5) ?
Al1 Cl4 . 2.1346(5) ?
Al1 Cl5 . 2.1349(6) ?
C1 P1 . 1.7509(13) ?
C1 P2 . 1.7585(12) ?
C1 P3 . 1.7789(13) ?
C2 C7 . 1.3887(18) ?
C2 C3 . 1.4054(18) ?
C2 P1 . 1.8096(13) ?
C3 C4 . 1.387(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.391(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.381(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.3943(19) ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C8 C13 . 1.3991(19) ?
C8 C9 . 1.3991(19) ?
C8 P1 . 1.8025(13) ?
C9 C10 . 1.389(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.391(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.383(2) ?
C11 H11 . 0.95 ?
C12 C13 . 1.387(2) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C19 . 1.3978(18) ?
C14 C15 . 1.3978(18) ?
C14 P1 . 1.8075(13) ?
C15 C16 . 1.391(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.392(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.385(2) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3909(19) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C20 C21 . 1.3965(18) ?
C20 C25 . 1.4011(19) ?
C20 P2 . 1.8083(13) ?
C21 C22 . 1.3876(19) ?
C21 H21 . 0.95 ?
C22 C23 . 1.386(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.385(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.3888(19) ?
C24 H24 . 0.95 ?
C25 H25 . 0.95 ?
C26 C31 . 1.3952(18) ?
C26 C27 . 1.4024(18) ?
C26 P2 . 1.8051(13) ?
C27 C28 . 1.3852(19) ?
C27 H27 . 0.95 ?
C28 C29 . 1.391(2) ?
C28 H28 . 0.95 ?
C29 C30 . 1.385(2) ?
C29 H29 . 0.95 ?
C30 C31 . 1.3946(18) ?
C30 H30 . 0.95 ?
C31 H31 . 0.95 ?
C32 C37 . 1.3966(18) ?
C32 C33 . 1.3989(18) ?
C32 P2 . 1.8205(13) ?
C33 C34 . 1.3932(19) ?
C33 H33 . 0.95 ?
C34 C35 . 1.387(2) ?
C34 H34 . 0.95 ?
C35 C36 . 1.385(2) ?
C35 H35 . 0.95 ?
C36 C37 . 1.3898(19) ?
C36 H36 . 0.95 ?
C37 H37 . 0.95 ?
Cl1 P3 . 2.0842(5) ?
Cl2 P3 . 2.0708(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl3 Al1 Cl6 . . 108.95(3) ?
Cl3 Al1 Cl4 . . 110.07(2) ?
Cl6 Al1 Cl4 . . 110.98(3) ?
Cl3 Al1 Cl5 . . 110.53(3) ?
Cl6 Al1 Cl5 . . 107.85(3) ?
Cl4 Al1 Cl5 . . 108.43(2) ?
P1 C1 P2 . . 124.00(7) ?
P1 C1 P3 . . 129.34(7) ?
P2 C1 P3 . . 106.41(6) ?
C7 C2 C3 . . 119.43(12) ?
C7 C2 P1 . . 122.59(10) ?
C3 C2 P1 . . 117.96(10) ?
C4 C3 C2 . . 119.96(14) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.15(13) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.05(13) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C7 . . 120.27(14) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C2 C7 C6 . . 120.14(13) ?
C2 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C13 C8 C9 . . 119.91(12) ?
C13 C8 P1 . . 117.98(10) ?
C9 C8 P1 . . 122.03(10) ?
C10 C9 C8 . . 119.59(13) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 120.05(14) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C12 C11 C10 . . 120.43(14) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 120.11(14) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 119.82(13) ?
C12 C13 H13 . . 120.1 ?
C8 C13 H13 . . 120.1 ?
C19 C14 C15 . . 119.70(12) ?
C19 C14 P1 . . 117.50(10) ?
C15 C14 P1 . . 122.79(10) ?
C16 C15 C14 . . 119.75(13) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.18(13) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C18 C17 C16 . . 120.26(13) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C19 . . 119.96(13) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C18 C19 C14 . . 120.13(13) ?
C18 C19 H19 . . 119.9 ?
C14 C19 H19 . . 119.9 ?
C21 C20 C25 . . 119.47(12) ?
C21 C20 P2 . . 119.35(10) ?
C25 C20 P2 . . 121.03(10) ?
C22 C21 C20 . . 120.20(13) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
C23 C22 C21 . . 120.03(13) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C24 C23 C22 . . 120.21(13) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 120.32(13) ?
C23 C24 H24 . . 119.8 ?
C25 C24 H24 . . 119.8 ?
C24 C25 C20 . . 119.77(13) ?
C24 C25 H25 . . 120.1 ?
C20 C25 H25 . . 120.1 ?
C31 C26 C27 . . 119.59(12) ?
C31 C26 P2 . . 120.91(10) ?
C27 C26 P2 . . 119.47(10) ?
C28 C27 C26 . . 120.04(12) ?
C28 C27 H27 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C27 C28 C29 . . 120.03(13) ?
C27 C28 H28 . . 120.0 ?
C29 C28 H28 . . 120.0 ?
C30 C29 C28 . . 120.34(12) ?
C30 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C29 C30 C31 . . 119.99(13) ?
C29 C30 H30 . . 120.0 ?
C31 C30 H30 . . 120.0 ?
C30 C31 C26 . . 119.96(12) ?
C30 C31 H31 . . 120.0 ?
C26 C31 H31 . . 120.0 ?
C37 C32 C33 . . 119.22(12) ?
C37 C32 P2 . . 120.45(10) ?
C33 C32 P2 . . 120.01(10) ?
C34 C33 C32 . . 120.23(13) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C35 C34 C33 . . 119.96(13) ?
C35 C34 H34 . . 120.0 ?
C33 C34 H34 . . 120.0 ?
C36 C35 C34 . . 120.09(13) ?
C36 C35 H35 . . 120.0 ?
C34 C35 H35 . . 120.0 ?
C35 C36 C37 . . 120.36(14) ?
C35 C36 H36 . . 119.8 ?
C37 C36 H36 . . 119.8 ?
C36 C37 C32 . . 120.09(13) ?
C36 C37 H37 . . 120.0 ?
C32 C37 H37 . . 120.0 ?
C1 P1 C8 . . 110.90(6) ?
C1 P1 C14 . . 110.08(6) ?
C8 P1 C14 . . 108.73(6) ?
C1 P1 C2 . . 116.12(6) ?
C8 P1 C2 . . 103.19(6) ?
C14 P1 C2 . . 107.40(6) ?
C1 P2 C26 . . 113.69(6) ?
C1 P2 C20 . . 114.81(6) ?
C26 P2 C20 . . 105.67(6) ?
C1 P2 C32 . . 109.56(6) ?
C26 P2 C32 . . 107.46(6) ?
C20 P2 C32 . . 105.06(6) ?
C1 P3 Cl2 . . 107.21(4) ?
C1 P3 Cl1 . . 105.08(4) ?
Cl2 P3 Cl1 . . 97.48(2) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1058666'
_audit_update_record             
;
2015-04-09 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 Cl2 F6 N4 P Sb'
_chemical_formula_iupac          ?
_chemical_formula_weight         642.01

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   11.6300(9)
_cell_length_b                   19.1931(14)
_cell_length_c                   21.1940(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4730.8(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5316
_cell_measurement_theta_min      2.8082
_cell_measurement_theta_max      21.5006
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2528

_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            69640
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             4854
_reflns_number_gt                2742
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.2044
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.066
_refine_ls_number_reflns         4854
_refine_ls_number_parameters     359
_refine_ls_number_restraints     166
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0863P)²+22.1672P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.703
_refine_diff_density_min         -1.035
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.6978(3) 0.9393(2) 0.74866(15) 0.0493(9) Uani d U P D 0.711(3) A 1
Cl Cl1 0.5279(3) 0.9658(3) 0.7341(2) 0.0619(12) Uani d U P D 0.711(3) A 1
Cl Cl2 0.7498(4) 1.0346(3) 0.78997(19) 0.0806(14) Uani d U P D 0.711(3) A 1
P P1A 0.6792(12) 0.8987(8) 0.7453(6) 0.058(3) Uani d U P D 0.194(3) A 2
Cl Cl1A 0.5160(13) 0.9314(10) 0.7227(9) 0.064(4) Uani d U P D 0.194(3) A 2
Cl Cl2A 0.7240(14) 0.9832(11) 0.8062(7) 0.082(4) Uani d U P D 0.194(3) A 2
P P1B 0.6373(17) 0.9644(13) 0.7222(9) 0.059(3) Uani d U P D 0.094(2) A 3
Cl Cl1B 0.514(2) 0.8867(16) 0.7244(13) 0.066(5) Uani d U P D 0.094(2) A 3
Cl Cl2B 0.724(2) 0.9363(17) 0.8065(11) 0.068(5) Uani d U P D 0.094(2) A 3
C C1 0.7485(7) 0.9305(5) 0.6703(4) 0.051(2) Uani d . . D 1.0 . .
C C2 0.8424(7) 0.8841(4) 0.6629(3) 0.0428(19) Uani d . . . 1.0 . .
C C3 0.9643(7) 0.9612(4) 0.5938(4) 0.047(2) Uani d . . . 1.0 . .
H H3A 1.048 0.9653 0.5899 0.07 Uiso calc U . R 1.0 . .
H H3B 0.9347 1.0 0.6191 0.07 Uiso calc U . R 1.0 . .
H H3C 0.9294 0.9625 0.5517 0.07 Uiso calc U . R 1.0 . .
C C4 0.7722(10) 0.7816(6) 0.7263(4) 0.078(4) Uani d . . . 1.0 . .
H H4A 0.7826 0.7925 0.7712 0.118 Uiso calc U . R 1.0 . .
H H4B 0.7818 0.7314 0.7198 0.118 Uiso calc U . R 1.0 . .
H H4C 0.6949 0.7956 0.713 0.118 Uiso calc U . R 1.0 . .
C C5 1.0098(7) 0.8392(4) 0.6270(3) 0.0408(19) Uani d . . . 1.0 . .
C C6 1.1107(7) 0.8252(4) 0.5950(4) 0.046(2) Uani d . . . 1.0 . .
H H6 1.1419 0.8571 0.5654 0.055 Uiso calc U . R 1.0 . .
C C7 1.1646(8) 0.7620(5) 0.6083(4) 0.056(2) Uani d . . . 1.0 . .
H H7 1.2347 0.7504 0.5878 0.067 Uiso calc U . R 1.0 . .
C C8 1.1151(10) 0.7152(5) 0.6523(4) 0.062(3) Uani d . . . 1.0 . .
H H8 1.1527 0.6721 0.6602 0.074 Uiso calc U . R 1.0 . .
C C9 1.0167(9) 0.7294(5) 0.6836(4) 0.058(3) Uani d . . . 1.0 . .
H H9 0.9867 0.6983 0.7143 0.07 Uiso calc U . R 1.0 . .
C C10 0.9610(8) 0.7918(5) 0.6689(4) 0.044(2) Uani d . . . 1.0 . .
C C11 0.7086(7) 0.9671(5) 0.6155(4) 0.047(2) Uani d . . . 1.0 . .
C C12 0.7079(8) 0.8621(4) 0.5438(4) 0.048(2) Uani d . . . 1.0 . .
H H12A 0.7875 0.8511 0.5324 0.073 Uiso calc U . R 1.0 . .
H H12B 0.657 0.8505 0.5085 0.073 Uiso calc U . R 1.0 . .
H H12C 0.6857 0.8349 0.581 0.073 Uiso calc U . R 1.0 . .
C C13 0.6887(10) 1.0900(6) 0.6572(6) 0.092(4) Uani d . . . 1.0 . .
H H13A 0.7124 1.1341 0.6378 0.138 Uiso calc U . R 1.0 . .
H H13B 0.7458 1.0759 0.6887 0.138 Uiso calc U . R 1.0 . .
H H13C 0.6138 1.096 0.6777 0.138 Uiso calc U . R 1.0 . .
C C14 0.6663(8) 0.9855(5) 0.5139(4) 0.051(2) Uani d . . . 1.0 . .
C C15 0.6481(9) 0.9824(6) 0.4493(5) 0.075(3) Uani d . . . 1.0 . .
H H15 0.6601 0.9404 0.4265 0.089 Uiso calc U . R 1.0 . .
C C16 0.6120(10) 1.0422(7) 0.4191(6) 0.078(3) Uani d . . . 1.0 . .
H H16 0.5952 1.0407 0.3753 0.094 Uiso calc U . R 1.0 . .
C C17 0.6002(10) 1.1017(7) 0.4502(7) 0.089(4) Uani d . . . 1.0 . .
H H17 0.5798 1.1421 0.4269 0.107 Uiso calc U . R 1.0 . .
C C18 0.6160(8) 1.1081(5) 0.5145(7) 0.081(4) Uani d . . . 1.0 . .
H H18 0.6034 1.1506 0.5364 0.097 Uiso calc U . R 1.0 . .
C C19 0.6524(8) 1.0464(5) 0.5454(5) 0.059(2) Uani d . . . 1.0 . .
F F1 -0.0624(7) 0.1065(3) 0.5478(3) 0.0837(19) Uani d . . . 1.0 . .
F F2 -0.1509(6) 0.2157(3) 0.6010(3) 0.098(2) Uani d . . . 1.0 . .
F F3 0.0375(5) 0.2290(3) 0.5293(2) 0.0684(16) Uani d . . . 1.0 . .
F F4 0.0458(8) 0.2484(3) 0.6513(3) 0.102(2) Uani d . . . 1.0 . .
F F5 0.1396(5) 0.1354(4) 0.5967(3) 0.091(2) Uani d . . . 1.0 . .
F F6 -0.0426(5) 0.1231(3) 0.6707(2) 0.0673(15) Uani d . . . 1.0 . .
N N1 0.9355(6) 0.8950(3) 0.6246(3) 0.0405(16) Uani d . . . 1.0 . .
N N2 0.8579(6) 0.8194(4) 0.6891(3) 0.0500(19) Uani d . . . 1.0 . .
N N3 0.6984(6) 0.9358(3) 0.5579(3) 0.0396(15) Uani d . . . 1.0 . .
N N4 0.6797(6) 1.0348(4) 0.6073(4) 0.055(2) Uani d . . . 1.0 . .
Sb Sb1 -0.00345(5) 0.17601(3) 0.60000(3) 0.0460(2) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 . 1.772(8) ?
P1 Cl1 . 2.063(5) ?
P1 Cl2 . 2.117(6) ?
P1A C1 . 1.885(14) ?
P1A Cl1A . 2.055(15) ?
P1A Cl2A . 2.136(17) ?
P1B C1 . 1.820(17) ?
P1B Cl1B . 2.073(18) ?
P1B Cl2B . 2.122(18) ?
C1 C2 . 1.418(11) ?
C1 C11 . 1.433(12) ?
C2 N1 . 1.368(10) ?
C2 N2 . 1.371(10) ?
C3 N1 . 1.469(10) ?
C4 N2 . 1.465(11) ?
C5 N1 . 1.377(10) ?
C5 C6 . 1.381(11) ?
C5 C10 . 1.392(11) ?
C6 C7 . 1.393(12) ?
C7 C8 . 1.419(14) ?
C8 C9 . 1.350(14) ?
C9 C10 . 1.396(13) ?
C10 N2 . 1.379(11) ?
C11 N4 . 1.353(11) ?
C11 N3 . 1.366(10) ?
C12 N3 . 1.450(10) ?
C13 N4 . 1.501(11) ?
C14 C19 . 1.356(12) ?
C14 N3 . 1.386(10) ?
C14 C15 . 1.387(13) ?
C15 C16 . 1.378(14) ?
C16 C17 . 1.325(17) ?
C17 C18 . 1.381(17) ?
C18 C19 . 1.417(14) ?
C19 N4 . 1.367(12) ?
F1 Sb1 . 1.865(5) ?
F2 Sb1 . 1.877(6) ?
F3 Sb1 . 1.874(5) ?
F4 Sb1 . 1.855(5) ?
F5 Sb1 . 1.838(6) ?
F6 Sb1 . 1.867(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 P1 Cl1 . . 101.7(3) ?
C1 P1 Cl2 . . 112.0(4) ?
Cl1 P1 Cl2 . . 97.0(2) ?
C1 P1A Cl1A . . 95.7(8) ?
C1 P1A Cl2A . . 99.2(9) ?
Cl1A P1A Cl2A . . 97.7(8) ?
C1 P1B Cl1B . . 104.4(13) ?
C1 P1B Cl2B . . 94.6(12) ?
Cl1B P1B Cl2B . . 97.5(12) ?
C2 C1 C11 . . 117.9(7) ?
C2 C1 P1 . . 114.8(7) ?
C11 C1 P1 . . 127.2(7) ?
C2 C1 P1B . . 147.0(10) ?
C11 C1 P1B . . 94.8(9) ?
C2 C1 P1A . . 102.7(7) ?
C11 C1 P1A . . 134.7(7) ?
N1 C2 N2 . . 105.9(7) ?
N1 C2 C1 . . 125.4(8) ?
N2 C2 C1 . . 128.7(8) ?
N1 C5 C6 . . 131.8(8) ?
N1 C5 C10 . . 106.0(7) ?
C6 C5 C10 . . 122.2(8) ?
C5 C6 C7 . . 116.9(8) ?
C6 C7 C8 . . 120.1(9) ?
C9 C8 C7 . . 122.6(9) ?
C8 C9 C10 . . 117.2(9) ?
N2 C10 C5 . . 107.5(8) ?
N2 C10 C9 . . 131.6(8) ?
C5 C10 C9 . . 120.9(9) ?
N4 C11 N3 . . 106.6(8) ?
N4 C11 C1 . . 131.0(8) ?
N3 C11 C1 . . 122.4(8) ?
C19 C14 N3 . . 107.1(8) ?
C19 C14 C15 . . 120.3(9) ?
N3 C14 C15 . . 132.6(9) ?
C16 C15 C14 . . 118.0(11) ?
C17 C16 C15 . . 121.2(12) ?
C16 C17 C18 . . 123.6(11) ?
C17 C18 C19 . . 115.0(11) ?
C14 C19 N4 . . 107.7(8) ?
C14 C19 C18 . . 121.8(11) ?
N4 C19 C18 . . 130.5(11) ?
C2 N1 C5 . . 110.9(7) ?
C2 N1 C3 . . 125.2(7) ?
C5 N1 C3 . . 123.1(7) ?
C2 N2 C10 . . 109.7(7) ?
C2 N2 C4 . . 125.3(8) ?
C10 N2 C4 . . 124.6(8) ?
C11 N3 C14 . . 108.8(7) ?
C11 N3 C12 . . 127.4(7) ?
C14 N3 C12 . . 123.6(7) ?
C11 N4 C19 . . 109.8(7) ?
C11 N4 C13 . . 124.7(9) ?
C19 N4 C13 . . 125.2(9) ?
F5 Sb1 F4 . . 93.5(4) ?
F5 Sb1 F1 . . 90.4(3) ?
F4 Sb1 F1 . . 176.1(4) ?
F5 Sb1 F6 . . 91.2(3) ?
F4 Sb1 F6 . . 90.7(2) ?
F1 Sb1 F6 . . 89.9(2) ?
F5 Sb1 F3 . . 88.3(3) ?
F4 Sb1 F3 . . 89.0(2) ?
F1 Sb1 F3 . . 90.4(2) ?
F6 Sb1 F3 . . 179.4(3) ?
F5 Sb1 F2 . . 178.1(3) ?
F4 Sb1 F2 . . 88.3(4) ?
F1 Sb1 F2 . . 87.8(3) ?
F6 Sb1 F2 . . 89.3(3) ?
F3 Sb1 F2 . . 91.2(3) ?

