# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1414316'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 Cl2 P'
_chemical_formula_weight         221.05

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'

_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                   8.1445(3)
_cell_length_b                   7.1178(3)
_cell_length_c                   18.4060(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.8230(10)
_cell_angle_gamma                90
_cell_volume                     1044.38(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6458
_cell_measurement_theta_min      2.574
_cell_measurement_theta_max      30.088

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.719
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5786
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10452
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         30.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3026
_reflns_number_gt                2710
_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 SMART'
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0466P)²+0.6246P] 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         3026
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.97028(5) 0.67927(6) 0.18167(2) 0.02741(11) Uani 1 1 d . . . . .
Cl1 Cl 1.16895(5) 0.82670(6) 0.24506(2) 0.03354(12) Uani 1 1 d . . . . .
Cl2 Cl 1.07383(6) 0.60130(6) 0.09138(2) 0.03628(12) Uani 1 1 d . . . . .
C1 C 0.82681(18) 0.8661(2) 0.14277(8) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.6623(2) 0.8390(2) 0.15400(8) 0.0263(3) Uani 1 1 d . . . . .
C21 C 0.6130(3) 0.6749(3) 0.19734(12) 0.0408(4) Uani 1 1 d . . . . .
H21A H 0.4939 0.6764 0.1942 0.049 Uiso 1 1 calc R U . . .
H21B H 0.6695 0.6848 0.2484 0.049 Uiso 1 1 calc R U . . .
H21C H 0.6445 0.5594 0.1769 0.049 Uiso 1 1 calc R U . . .
C3 C 0.53883(19) 0.9700(2) 0.12561(9) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.4269 0.9510 0.1332 0.034 Uiso 1 1 calc R U . . .
C4 C 0.57278(19) 1.1272(2) 0.08666(8) 0.0263(3) Uani 1 1 d . . . . .
C41 C 0.4361(2) 1.2638(3) 0.05486(10) 0.0343(4) Uani 1 1 d . . . . .
H41A H 0.4847 1.3737 0.0375 0.041 Uiso 1 1 calc R U . . .
H41B H 0.3761 1.2989 0.0925 0.041 Uiso 1 1 calc R U . . .
H41C H 0.3603 1.2060 0.0142 0.041 Uiso 1 1 calc R U . . .
C5 C 0.73630(19) 1.1534(2) 0.07701(8) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.7613 1.2623 0.0505 0.030 Uiso 1 1 calc R U . . .
C6 C 0.86518(18) 1.0275(2) 0.10448(8) 0.0221(3) Uani 1 1 d . . . . .
C61 C 1.03860(19) 1.0761(2) 0.09386(9) 0.0270(3) Uani 1 1 d . . . . .
H61A H 1.0311 1.1694 0.0557 0.032 Uiso 1 1 calc R U . . .
H61B H 1.0917 0.9654 0.0797 0.032 Uiso 1 1 calc R U . . .
H61C H 1.1037 1.1244 0.1395 0.032 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 C1 1.8174(15) . ?
P1 Cl1 2.0753(6) . ?
P1 Cl2 2.0871(6) . ?
C1 C2 1.410(2) . ?
C1 C6 1.416(2) . ?
C2 C3 1.392(2) . ?
C2 C21 1.515(2) . ?
C21 H21A 0.9599 . ?
C21 H21B 0.9599 . ?
C21 H21C 0.9599 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9600 . ?
C4 C5 1.392(2) . ?
C4 C41 1.503(2) . ?
C41 H41A 0.9599 . ?
C41 H41B 0.9599 . ?
C41 H41C 0.9599 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9600 . ?
C6 C61 1.505(2) . ?
C61 H61A 0.9599 . ?
C61 H61B 0.9599 . ?
C61 H61C 0.9599 . ?

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 Cl1 102.47(5) . . ?
C1 P1 Cl2 102.29(5) . . ?
Cl1 P1 Cl2 100.75(3) . . ?
C2 C1 C6 119.80(13) . . ?
C2 C1 P1 113.33(11) . . ?
C6 C1 P1 126.87(11) . . ?
C3 C2 C1 119.25(14) . . ?
C3 C2 C21 117.74(15) . . ?
C1 C2 C21 123.00(15) . . ?
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 . . ?
C4 C3 C2 121.94(14) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.13(14) . . ?
C3 C4 C41 120.85(14) . . ?
C5 C4 C41 121.01(15) . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C4 C5 C6 122.46(14) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 118.40(13) . . ?
C5 C6 C61 117.52(13) . . ?
C1 C6 C61 124.04(13) . . ?
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 . . ?

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
Cl1 P1 C1 C2 -128.31(11) . . . . ?
Cl2 P1 C1 C2 127.59(11) . . . . ?
Cl1 P1 C1 C6 51.51(14) . . . . ?
Cl2 P1 C1 C6 -52.59(14) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
P1 C1 C2 C3 -178.70(12) . . . . ?
C6 C1 C2 C21 -177.17(16) . . . . ?
P1 C1 C2 C21 2.7(2) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C21 C2 C3 C4 178.53(16) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 C41 178.38(15) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C41 C4 C5 C6 -178.69(15) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C61 -176.99(14) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
P1 C1 C6 C5 178.44(11) . . . . ?
C2 C1 C6 C61 175.86(14) . . . . ?
P1 C1 C6 C61 -3.9(2) . . . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    'Air-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_sadp21n
_database_code_depnum_ccdc_archive 'CCDC 1414317'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 Cl P'
_chemical_formula_weight         266.73

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'

_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                   8.8446(5)
_cell_length_b                   13.6377(11)
_cell_length_c                   12.7896(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.263(3)
_cell_angle_gamma                90
_cell_volume                     1536.18(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.193
_cell_measurement_theta_max      30.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22519
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         30.105
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4504
_reflns_number_gt                3184
_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 SMART'
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0751P)²+0.8152P] 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         4504
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Cl1 Cl 0.70982(7) 0.72331(5) 0.30380(5) 0.04879(19) Uani 1 1 d . . . . .
P1 P 0.55050(6) 0.82377(4) 0.35393(4) 0.03258(16) Uani 1 1 d . . . . .
C1 C 0.4308(2) 0.74190(16) 0.41248(17) 0.0338(4) Uani 1 1 d . . . . .
C2 C 0.3321(2) 0.68984(15) 0.43857(17) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.2146(2) 0.62389(17) 0.47316(17) 0.0368(5) Uani 1 1 d . . . . .
C31 C 0.2802(4) 0.5609(3) 0.5643(3) 0.0788(10) Uani 1 1 d . . . . .
H31A H 0.3598 0.5204 0.5417 0.095 Uiso 1 1 calc R U . . .
H31B H 0.2017 0.5201 0.5880 0.095 Uiso 1 1 calc R U . . .
H31C H 0.3204 0.6023 0.6208 0.095 Uiso 1 1 calc R U . . .
C32 C 0.0861(4) 0.6850(3) 0.5105(3) 0.0825(11) Uani 1 1 d . . . . .
H32A H 0.1247 0.7255 0.5683 0.099 Uiso 1 1 calc R U . . .
H32B H 0.0089 0.6423 0.5328 0.099 Uiso 1 1 calc R U . . .
H32C H 0.0435 0.7257 0.4541 0.099 Uiso 1 1 calc R U . . .
C33 C 0.1561(5) 0.5597(3) 0.3825(3) 0.1092(17) Uani 1 1 d . . . . .
H33A H 0.1180 0.6000 0.3244 0.131 Uiso 1 1 calc R U . . .
H33B H 0.0758 0.5188 0.4034 0.131 Uiso 1 1 calc R U . . .
H33C H 0.2371 0.5193 0.3618 0.131 Uiso 1 1 calc R U . . .
C4 C 0.6625(2) 0.88224(14) 0.46362(14) 0.0254(4) Uani 1 1 d . . . . .
C5 C 0.7306(2) 0.83451(15) 0.55389(15) 0.0296(4) Uani 1 1 d . . . . .
C51 C 0.7037(3) 0.72805(16) 0.5785(2) 0.0425(5) Uani 1 1 d . . . . .
H51A H 0.7784 0.7066 0.6329 0.051 Uiso 1 1 calc R U . . .
H51B H 0.7115 0.6893 0.5166 0.051 Uiso 1 1 calc R U . . .
H51C H 0.6042 0.7206 0.6018 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8255(2) 0.88817(17) 0.62542(17) 0.0364(5) Uani 1 1 d . . . . .
H6 H 0.8737 0.8554 0.6860 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8529(2) 0.98701(18) 0.61230(17) 0.0383(5) Uani 1 1 d . . . . .
C71 C 0.9588(3) 1.0429(2) 0.6909(2) 0.0599(8) Uani 1 1 d . . . . .
H71A H 1.0433 1.0675 0.6568 0.072 Uiso 1 1 calc R U . . .
H71B H 0.9952 0.9999 0.7471 0.072 Uiso 1 1 calc R U . . .
H71C H 0.9051 1.0967 0.7187 0.072 Uiso 1 1 calc R U . . .
C8 C 0.7808(2) 1.03361(16) 0.52494(17) 0.0361(5) Uani 1 1 d . . . . .
H8 H 0.7966 1.1026 0.5161 0.043 Uiso 1 1 calc R U . . .
C9 C 0.6867(2) 0.98379(14) 0.45002(15) 0.0284(4) Uani 1 1 d . . . . .
C91 C 0.6143(3) 1.04090(16) 0.35726(18) 0.0401(5) Uani 1 1 d . . . . .
H91A H 0.6378 1.1093 0.3664 0.048 Uiso 1 1 calc R U . . .
H91B H 0.5062 1.0320 0.3524 0.048 Uiso 1 1 calc R U . . .
H91C H 0.6529 1.0177 0.2940 0.048 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
Cl1 P1 2.1070(8) . ?
P1 C1 1.753(2) . ?
P1 C4 1.8250(19) . ?
C1 C2 1.196(3) . ?
C2 C3 1.473(3) . ?
C3 C33 1.507(4) . ?
C3 C31 1.520(4) . ?
C3 C32 1.521(4) . ?
C31 H31A 0.9599 . ?
C31 H31B 0.9599 . ?
C31 H31C 0.9599 . ?
C32 H32A 0.9599 . ?
C32 H32B 0.9599 . ?
C32 H32C 0.9599 . ?
C33 H33A 0.9599 . ?
C33 H33B 0.9599 . ?
C33 H33C 0.9599 . ?
C4 C5 1.411(3) . ?
C4 C9 1.415(3) . ?
C5 C6 1.392(3) . ?
C5 C51 1.509(3) . ?
C51 H51A 0.9599 . ?
C51 H51B 0.9599 . ?
C51 H51C 0.9599 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9600 . ?
C7 C8 1.388(3) . ?
C7 C71 1.516(3) . ?
C71 H71A 0.9599 . ?
C71 H71B 0.9599 . ?
C71 H71C 0.9599 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9600 . ?
C9 C91 1.512(3) . ?
C91 H91A 0.9599 . ?
C91 H91B 0.9599 . ?
C91 H91C 0.9599 . ?

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 C4 104.85(9) . . ?
C1 P1 Cl1 99.36(8) . . ?
C4 P1 Cl1 100.78(6) . . ?
C2 C1 P1 169.1(2) . . ?
C1 C2 C3 178.0(2) . . ?
C2 C3 C33 109.0(2) . . ?
C2 C3 C31 110.21(19) . . ?
C33 C3 C31 110.0(3) . . ?
C2 C3 C32 109.2(2) . . ?
C33 C3 C32 110.3(3) . . ?
C31 C3 C32 108.2(3) . . ?
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 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C3 C33 H33A 109.5 . . ?
C3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C5 C4 C9 119.61(17) . . ?
C5 C4 P1 126.02(15) . . ?
C9 C4 P1 114.26(14) . . ?
C6 C5 C4 118.79(19) . . ?
C6 C5 C51 117.75(19) . . ?
C4 C5 C51 123.45(18) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C7 C6 C5 122.3(2) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 C7 C8 118.13(19) . . ?
C6 C7 C71 121.0(2) . . ?
C8 C7 C71 120.9(2) . . ?
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 . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C4 118.84(18) . . ?
C8 C9 C91 118.28(18) . . ?
C4 C9 C91 122.88(18) . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?

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
C4 P1 C1 C2 145.9(10) . . . . ?
Cl1 P1 C1 C2 -110.3(10) . . . . ?
C1 P1 C4 C5 43.72(19) . . . . ?
Cl1 P1 C4 C5 -59.09(17) . . . . ?
C1 P1 C4 C9 -140.00(14) . . . . ?
Cl1 P1 C4 C9 117.19(13) . . . . ?
C9 C4 C5 C6 -2.7(3) . . . . ?
P1 C4 C5 C6 173.43(15) . . . . ?
C9 C4 C5 C51 176.13(19) . . . . ?
P1 C4 C5 C51 -7.8(3) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
C51 C5 C6 C7 -177.4(2) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C5 C6 C7 C71 -179.1(2) . . . . ?
C6 C7 C8 C9 -1.8(3) . . . . ?
C71 C7 C8 C9 178.1(2) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C7 C8 C9 C91 -179.59(19) . . . . ?
C5 C4 C9 C8 1.7(3) . . . . ?
P1 C4 C9 C8 -174.81(15) . . . . ?
C5 C4 C9 C91 -178.15(18) . . . . ?
P1 C4 C9 C91 5.3(2) . . . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    'Air-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1414318'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-14 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 H30 N P'
_chemical_formula_weight         399.49

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.6369(3)
_cell_length_b                   9.9898(4)
_cell_length_c                   13.8908(6)
_cell_angle_alpha                76.3559(11)
_cell_angle_beta                 79.6790(11)
_cell_angle_gamma                80.8855(11)
_cell_volume                     1137.36(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.328
_cell_measurement_theta_max      30.041

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18334
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         30.041
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6566
_reflns_number_gt                5704
_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 SMART'
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0602P)²+0.4941P] 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         6566
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.58725(3) 0.94118(3) 0.28004(2) 0.01484(8) Uani 1 1 d . . . . .
C4 C 0.57899(13) 0.86766(11) 0.41441(8) 0.0152(2) Uani 1 1 d . . . . .
C6 C 0.66732(14) 0.78797(12) 0.57588(9) 0.0192(2) Uani 1 1 d . . . . .
H6 H 0.7463 0.7821 0.6178 0.023 Uiso 1 1 calc R U . . .
C9 C 0.43597(14) 0.81051(13) 0.45654(9) 0.0191(2) Uani 1 1 d . . . . .
C5 C 0.69577(13) 0.85699(12) 0.47558(8) 0.0163(2) Uani 1 1 d . . . . .
C8 C 0.41455(14) 0.74133(13) 0.55639(9) 0.0217(2) Uani 1 1 d . . . . .
H8 H 0.3176 0.7019 0.5840 0.026 Uiso 1 1 calc R U . . .
C7 C 0.52998(15) 0.72778(13) 0.61720(9) 0.0206(2) Uani 1 1 d . . . . .
C51 C 0.85341(14) 0.91169(14) 0.43984(9) 0.0223(2) Uani 1 1 d . . . . .
H51A H 0.9151 0.8884 0.4938 0.027 Uiso 1 1 calc R U . . .
H51B H 0.8368 1.0107 0.4175 0.027 Uiso 1 1 calc R U . . .
H51C H 0.9089 0.8709 0.3854 0.027 Uiso 1 1 calc R U . . .
C71 C 0.50690(18) 0.64772(16) 0.72407(10) 0.0301(3) Uani 1 1 d . . . . .
H71A H 0.5161 0.5504 0.7251 0.036 Uiso 1 1 calc R U . . .
H71B H 0.4036 0.6771 0.7566 0.036 Uiso 1 1 calc R U . . .
H71C H 0.5863 0.6647 0.7586 0.036 Uiso 1 1 calc R U . . .
C91 C 0.30485(16) 0.81805(17) 0.39593(11) 0.0291(3) Uani 1 1 d . . . . .
H91A H 0.2179 0.7747 0.4382 0.035 Uiso 1 1 calc R U . . .
H91B H 0.3438 0.7708 0.3421 0.035 Uiso 1 1 calc R U . . .
H91C H 0.2696 0.9134 0.3690 0.035 Uiso 1 1 calc R U . . .
C1 C 0.75208(14) 1.03487(12) 0.24097(8) 0.0179(2) Uani 1 1 d . . . . .
C2 C 0.85251(14) 1.10710(12) 0.19693(9) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.98625(15) 1.18625(13) 0.14802(9) 0.0214(2) Uani 1 1 d . . . . .
N1 N 0.65722(11) 0.79267(10) 0.23377(7) 0.01614(19) Uani 1 1 d . . . . .
C20 C 0.59963(13) 0.76771(11) 0.15160(8) 0.0148(2) Uani 1 1 d . . . . .
C21 C 0.66450(14) 0.65136(12) 0.11141(9) 0.0182(2) Uani 1 1 d . . . . .
H21 H 0.7491 0.5888 0.1397 0.022 Uiso 1 1 calc R U . . .
C25 C 0.47649(15) 0.85616(13) 0.10843(9) 0.0216(2) Uani 1 1 d . . . . .
H25 H 0.4301 0.9366 0.1345 0.026 Uiso 1 1 calc R U . . .
C22 C 0.60748(15) 0.62579(13) 0.03109(9) 0.0218(2) Uani 1 1 d . . . . .
H22 H 0.6534 0.5457 0.0044 0.026 Uiso 1 1 calc R U . . .
C23 C 0.48532(15) 0.71410(14) -0.01126(9) 0.0231(2) Uani 1 1 d . . . . .
H23 H 0.4464 0.6960 -0.0669 0.028 Uiso 1 1 calc R U . . .
C24 C 0.42048(15) 0.82899(14) 0.02832(10) 0.0240(3) Uani 1 1 d . . . . .
H24 H 0.3355 0.8908 -0.0001 0.029 Uiso 1 1 calc R U . . .
C10 C 0.79772(13) 0.70876(11) 0.26524(8) 0.0158(2) Uani 1 1 d . . . . .
C15 C 0.94603(14) 0.73410(13) 0.21147(9) 0.0196(2) Uani 1 1 d . . . . .
H15 H 0.9543 0.8060 0.1518 0.024 Uiso 1 1 calc R U . . .
C11 C 0.78554(14) 0.60312(12) 0.35088(9) 0.0191(2) Uani 1 1 d . . . . .
H11 H 0.6833 0.5838 0.3874 0.023 Uiso 1 1 calc R U . . .
C12 C 0.92274(16) 0.52569(13) 0.38318(10) 0.0239(3) Uani 1 1 d . . . . .
H12 H 0.9149 0.4534 0.4426 0.029 Uiso 1 1 calc R U . . .
C13 C 1.07048(16) 0.55221(14) 0.33010(11) 0.0261(3) Uani 1 1 d . . . . .
H13 H 1.1646 0.4990 0.3531 0.031 Uiso 1 1 calc R U . . .
C14 C 1.08230(15) 0.65582(14) 0.24366(10) 0.0243(3) Uani 1 1 d . . . . .
H14 H 1.1845 0.6733 0.2062 0.029 Uiso 1 1 calc R U . . .
C32 C 0.93262(17) 1.30854(15) 0.06754(12) 0.0341(3) Uani 1 1 d . . . . .
H32A H 0.8937 1.2750 0.0182 0.041 Uiso 1 1 calc R U . . .
H32B H 1.0206 1.3590 0.0361 0.041 Uiso 1 1 calc R U . . .
H32C H 0.8498 1.3687 0.0975 0.041 Uiso 1 1 calc R U . . .
C31 C 1.11478(19) 1.08947(17) 0.09735(16) 0.0452(5) Uani 1 1 d . . . . .
H31A H 1.1449 1.0085 0.1463 0.054 Uiso 1 1 calc R U . . .
H31B H 1.2057 1.1372 0.0683 0.054 Uiso 1 1 calc R U . . .
H31C H 1.0740 1.0623 0.0459 0.054 Uiso 1 1 calc R U . . .
C33 C 1.0500(3) 1.2351(3) 0.22639(15) 0.0716(8) Uani 1 1 d . . . . .
H33A H 0.9706 1.2993 0.2548 0.086 Uiso 1 1 calc R U . . .
H33B H 1.1425 1.2801 0.1961 0.086 Uiso 1 1 calc R U . . .
H33C H 1.0776 1.1569 0.2782 0.086 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 N1 1.7338(10) . ?
P1 C1 1.7615(12) . ?
P1 C4 1.8303(11) . ?
C4 C5 1.4074(15) . ?
C4 C9 1.4146(16) . ?
C6 C7 1.3847(17) . ?
C6 C5 1.3982(16) . ?
C6 H6 0.9600 . ?
C9 C8 1.3900(17) . ?
C9 C91 1.5105(17) . ?
C5 C51 1.5047(16) . ?
C8 C7 1.3895(18) . ?
C8 H8 0.9600 . ?
C7 C71 1.5058(17) . ?
C51 H51A 0.9599 . ?
C51 H51B 0.9599 . ?
C51 H51C 0.9599 . ?
C71 H71A 0.9599 . ?
C71 H71B 0.9599 . ?
C71 H71C 0.9599 . ?
C91 H91A 0.9599 . ?
C91 H91B 0.9599 . ?
C91 H91C 0.9599 . ?
C1 C2 1.2030(17) . ?
C2 C3 1.4750(17) . ?
C3 C33 1.509(2) . ?
C3 C32 1.5227(19) . ?
C3 C31 1.537(2) . ?
N1 C20 1.4105(14) . ?
N1 C10 1.4357(14) . ?
C20 C25 1.3972(16) . ?
C20 C21 1.4015(16) . ?
C21 C22 1.3870(16) . ?
C21 H21 0.9600 . ?
C25 C24 1.3867(16) . ?
C25 H25 0.9600 . ?
C22 C23 1.3857(18) . ?
C22 H22 0.9600 . ?
C23 C24 1.3846(18) . ?
C23 H23 0.9600 . ?
C24 H24 0.9600 . ?
C10 C15 1.3905(16) . ?
C10 C11 1.3922(16) . ?
C15 C14 1.3888(17) . ?
C15 H15 0.9600 . ?
C11 C12 1.3929(17) . ?
C11 H11 0.9600 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9600 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9600 . ?
C14 H14 0.9600 . ?
C32 H32A 0.9599 . ?
C32 H32B 0.9599 . ?
C32 H32C 0.9599 . ?
C31 H31A 0.9599 . ?
C31 H31B 0.9599 . ?
C31 H31C 0.9599 . ?
C33 H33A 0.9599 . ?
C33 H33B 0.9599 . ?
C33 H33C 0.9599 . ?

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
N1 P1 C1 101.31(5) . . ?
N1 P1 C4 99.77(5) . . ?
C1 P1 C4 107.86(5) . . ?
C5 C4 C9 119.14(10) . . ?
C5 C4 P1 128.64(9) . . ?
C9 C4 P1 112.16(8) . . ?
C7 C6 C5 122.72(11) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C8 C9 C4 119.84(11) . . ?
C8 C9 C91 117.83(11) . . ?
C4 C9 C91 122.31(11) . . ?
C6 C5 C4 118.69(10) . . ?
C6 C5 C51 116.87(10) . . ?
C4 C5 C51 124.42(10) . . ?
C7 C8 C9 121.64(11) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C6 C7 C8 117.93(11) . . ?
C6 C7 C71 121.32(12) . . ?
C8 C7 C71 120.75(12) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 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 . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C2 C1 P1 167.12(11) . . ?
C1 C2 C3 174.69(13) . . ?
C2 C3 C33 108.98(12) . . ?
C2 C3 C32 110.23(11) . . ?
C33 C3 C32 110.94(15) . . ?
C2 C3 C31 108.01(11) . . ?
C33 C3 C31 110.35(17) . . ?
C32 C3 C31 108.28(12) . . ?
C20 N1 C10 118.38(9) . . ?
C20 N1 P1 121.20(8) . . ?
C10 N1 P1 119.14(7) . . ?
C25 C20 C21 118.01(10) . . ?
C25 C20 N1 121.64(10) . . ?
C21 C20 N1 120.35(10) . . ?
C22 C21 C20 120.57(11) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C24 C25 C20 120.74(11) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C23 C22 C21 121.02(11) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 118.66(11) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 121.00(12) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C15 C10 C11 119.89(11) . . ?
C15 C10 N1 120.26(10) . . ?
C11 C10 N1 119.84(10) . . ?
C14 C15 C10 120.28(11) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C10 C11 C12 119.52(11) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.46(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.95(11) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 119.88(12) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 . . ?
C3 C33 H33A 109.5 . . ?
C3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
N1 P1 C4 C5 92.22(11) . . . . ?
C1 P1 C4 C5 -13.13(12) . . . . ?
N1 P1 C4 C9 -84.76(9) . . . . ?
C1 P1 C4 C9 169.89(8) . . . . ?
C5 C4 C9 C8 -1.91(17) . . . . ?
P1 C4 C9 C8 175.39(9) . . . . ?
C5 C4 C9 C91 179.84(12) . . . . ?
P1 C4 C9 C91 -2.86(15) . . . . ?
C7 C6 C5 C4 1.02(18) . . . . ?
C7 C6 C5 C51 -177.30(11) . . . . ?
C9 C4 C5 C6 1.05(16) . . . . ?
P1 C4 C5 C6 -175.75(9) . . . . ?
C9 C4 C5 C51 179.23(11) . . . . ?
P1 C4 C5 C51 2.43(18) . . . . ?
C4 C9 C8 C7 0.76(19) . . . . ?
C91 C9 C8 C7 179.09(12) . . . . ?
C5 C6 C7 C8 -2.16(18) . . . . ?
C5 C6 C7 C71 176.73(12) . . . . ?
C9 C8 C7 C6 1.24(18) . . . . ?
C9 C8 C7 C71 -177.65(12) . . . . ?
N1 P1 C1 C2 83.8(5) . . . . ?
C4 P1 C1 C2 -172.0(5) . . . . ?
C1 P1 N1 C20 -108.53(9) . . . . ?
C4 P1 N1 C20 140.87(9) . . . . ?
C1 P1 N1 C10 58.38(10) . . . . ?
C4 P1 N1 C10 -52.22(9) . . . . ?
C10 N1 C20 C25 -171.51(11) . . . . ?
P1 N1 C20 C25 -4.50(15) . . . . ?
C10 N1 C20 C21 9.09(16) . . . . ?
P1 N1 C20 C21 176.09(8) . . . . ?
C25 C20 C21 C22 0.08(17) . . . . ?
N1 C20 C21 C22 179.51(11) . . . . ?
C21 C20 C25 C24 0.09(18) . . . . ?
N1 C20 C25 C24 -179.33(11) . . . . ?
C20 C21 C22 C23 -0.08(19) . . . . ?
C21 C22 C23 C24 -0.10(19) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C20 C25 C24 C23 -0.3(2) . . . . ?
C20 N1 C10 C15 77.13(14) . . . . ?
P1 N1 C10 C15 -90.15(12) . . . . ?
C20 N1 C10 C11 -103.95(12) . . . . ?
P1 N1 C10 C11 88.78(12) . . . . ?
C11 C10 C15 C14 -0.96(18) . . . . ?
N1 C10 C15 C14 177.96(11) . . . . ?
C15 C10 C11 C12 1.44(17) . . . . ?
N1 C10 C11 C12 -177.49(10) . . . . ?
C10 C11 C12 C13 -0.70(18) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C10 C15 C14 C13 -0.26(19) . . . . ?

_refine_diff_density_max         0.598
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    'Air-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1414319'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-14 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 H49 Al N P'
_chemical_formula_weight         445.62

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.8218(5)
_cell_length_b                   11.4057(5)
_cell_length_c                   12.6079(6)
_cell_angle_alpha                74.3410(10)
_cell_angle_beta                 70.4020(10)
_cell_angle_gamma                84.6710(10)
_cell_volume                     1411.63(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.567
_cell_measurement_theta_max      30.248

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.048
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6587
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19636
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.567
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             6903
_reflns_number_gt                6138
_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 SMART'
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0633P)²+0.3434P] 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         6903
_refine_ls_number_parameters     343
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.050
_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 0.27999(3) 0.23882(3) 0.16180(2) 0.02563(9) Uani 1 1 d . . . . .
C4 C 0.13141(11) 0.20287(10) 0.13600(10) 0.0282(2) Uani 1 1 d . . . . .
C5 C 0.01995(12) 0.13901(12) 0.21908(12) 0.0337(3) Uani 1 1 d . . . . .
C51 C -0.00387(14) 0.10071(15) 0.34842(13) 0.0455(3) Uani 1 1 d . . . . .
H51A H 0.0021 0.0137 0.3732 0.055 Uiso 1 1 calc R U . . .
H51B H -0.0897 0.1269 0.3884 0.055 Uiso 1 1 calc R U . . .
H51C H 0.0609 0.1372 0.3660 0.055 Uiso 1 1 calc R U . . .
C6 C -0.07777(14) 0.10891(13) 0.18146(14) 0.0420(3) Uani 1 1 d . . . . .
H6 H -0.1534 0.0652 0.2383 0.050 Uiso 1 1 calc R U . . .
C7 C -0.06953(15) 0.13977(13) 0.06513(15) 0.0448(3) Uani 1 1 d . . . . .
C71 C -0.17712(18) 0.10550(19) 0.0279(2) 0.0649(5) Uani 1 1 d . . . . .
H71A H -0.2040 0.0232 0.0690 0.078 Uiso 1 1 calc R U . . .
H71B H -0.1452 0.1123 -0.0543 0.078 Uiso 1 1 calc R U . . .
H71C H -0.2506 0.1592 0.0455 0.078 Uiso 1 1 calc R U . . .
C8 C 0.03961(15) 0.20340(13) -0.01523(13) 0.0411(3) Uani 1 1 d . . . . .
H8 H 0.0464 0.2260 -0.0960 0.049 Uiso 1 1 calc R U . . .
C9 C 0.13983(13) 0.23582(11) 0.01681(11) 0.0333(3) Uani 1 1 d . . . . .
C91 C 0.25183(16) 0.30843(16) -0.07822(12) 0.0478(4) Uani 1 1 d . . . . .
H91A H 0.2454 0.3099 -0.1527 0.057 Uiso 1 1 calc R U . . .
H91B H 0.3335 0.2716 -0.0723 0.057 Uiso 1 1 calc R U . . .
H91C H 0.2480 0.3902 -0.0703 0.057 Uiso 1 1 calc R U . . .
C1 C 0.2970(7) 0.1521(5) 0.2997(5) 0.0249(16) Uani 0.672(4) 1 d D . P A -1
C2 C 0.3309(9) 0.0344(4) 0.3371(6) 0.0241(9) Uani 0.672(4) 1 d D . P A -1
H2 H 0.3405 0.0145 0.4130 0.029 Uiso 0.672(4) 1 calc R U P A -1
C3 C 0.3564(6) -0.0712(6) 0.2810(5) 0.0338(11) Uani 0.672(4) 1 d D . P A -1
C31 C 0.3072(3) -0.0531(2) 0.1773(3) 0.0520(8) Uani 0.672(4) 1 d D U P A -1
H31A H 0.2136 -0.0432 0.2024 0.062 Uiso 0.672(4) 1 calc R U P A -1
H31B H 0.3300 -0.1229 0.1457 0.062 Uiso 0.672(4) 1 calc R U P A -1
H31C H 0.3470 0.0182 0.1185 0.062 Uiso 0.672(4) 1 calc R U P A -1
C32 C 0.2909(3) -0.1861(2) 0.3735(2) 0.0582(8) Uani 0.672(4) 1 d D U P A -1
H32A H 0.3216 -0.1997 0.4390 0.070 Uiso 0.672(4) 1 calc R U P A -1
H32B H 0.3128 -0.2550 0.3407 0.070 Uiso 0.672(4) 1 calc R U P A -1
H32C H 0.1975 -0.1751 0.3985 0.070 Uiso 0.672(4) 1 calc R U P A -1
C33 C 0.5036(3) -0.0905(4) 0.2407(4) 0.0648(9) Uani 0.672(4) 1 d D U P A -1
H33A H 0.5445 -0.0227 0.1777 0.078 Uiso 0.672(4) 1 calc R U P A -1
H33B H 0.5232 -0.1639 0.2147 0.078 Uiso 0.672(4) 1 calc R U P A -1
H33C H 0.5362 -0.0972 0.3041 0.078 Uiso 0.672(4) 1 calc R U P A -1
C1A C 0.2973(15) 0.1528(10) 0.2939(12) 0.032(4) Uani 0.328(4) 1 d D U P A -2
C2A C 0.3362(19) 0.0367(12) 0.3154(13) 0.032(2) Uani 0.328(4) 1 d D U P A -2
H2A H 0.3619 0.0125 0.3840 0.038 Uiso 0.328(4) 1 calc R U P A -2
C3A C 0.3492(10) -0.0656(10) 0.2571(10) 0.0281(19) Uani 0.328(4) 1 d D U P A -2
C31A C 0.2213(5) -0.1314(4) 0.3009(5) 0.0544(15) Uani 0.328(4) 1 d D U P A -2
H31D H 0.2331 -0.2037 0.2733 0.065 Uiso 0.328(4) 1 calc R U P A -2
H31E H 0.1578 -0.0794 0.2731 0.065 Uiso 0.328(4) 1 calc R U P A -2
H31F H 0.1910 -0.1534 0.3845 0.065 Uiso 0.328(4) 1 calc R U P A -2
C32A C 0.3937(6) -0.0167(4) 0.1253(4) 0.0414(11) Uani 0.328(4) 1 d D U P A -2
H32D H 0.4170 -0.0834 0.0894 0.050 Uiso 0.328(4) 1 calc R U P A -2
H32E H 0.4686 0.0350 0.1009 0.050 Uiso 0.328(4) 1 calc R U P A -2
H32F H 0.3238 0.0292 0.1025 0.050 Uiso 0.328(4) 1 calc R U P A -2
C33A C 0.4566(7) -0.1521(6) 0.2888(6) 0.0565(16) Uani 0.328(4) 1 d D U P A -2
H33D H 0.4301 -0.1852 0.3716 0.068 Uiso 0.328(4) 1 calc R U P A -2
H33E H 0.5370 -0.1079 0.2635 0.068 Uiso 0.328(4) 1 calc R U P A -2
H33F H 0.4697 -0.2171 0.2511 0.068 Uiso 0.328(4) 1 calc R U P A -2
Al1 Al 0.31985(3) 0.29732(3) 0.34992(3) 0.02531(10) Uani 1 1 d . . . . .
C10 C 0.20692(13) 0.32175(13) 0.50606(11) 0.0346(3) Uani 1 1 d D . . . .
C101 C 0.20147(16) 0.45453(15) 0.51236(15) 0.0510(4) Uani 1 1 d D . . . .
H10A H 0.1562 0.5028 0.4617 0.061 Uiso 1 1 calc R U . . .
H10B H 0.2890 0.4848 0.4885 0.061 Uiso 1 1 calc R U . . .
H10C H 0.1558 0.4591 0.5909 0.061 Uiso 1 1 calc R U . . .
C102 C 0.27237(16) 0.24608(18) 0.59365(12) 0.0536(4) Uani 1 1 d D . . . .
H10D H 0.2190 0.2486 0.6711 0.064 Uiso 1 1 calc R U . . .
H10E H 0.3573 0.2791 0.5766 0.064 Uiso 1 1 calc R U . . .
H10F H 0.2816 0.1633 0.5880 0.064 Uiso 1 1 calc R U . . .
C103 C 0.06594(14) 0.27462(15) 0.54887(12) 0.0427(3) Uani 1 1 d D . . . .
H10G H 0.0246 0.2773 0.6285 0.051 Uiso 1 1 calc R U . . .
H10H H 0.0672 0.1922 0.5432 0.051 Uiso 1 1 calc R U . . .
H10I H 0.0178 0.3248 0.5017 0.051 Uiso 1 1 calc R U . . .
C11 C 0.51476(13) 0.32533(13) 0.31046(12) 0.0360(3) Uani 1 1 d . . . . .
C111 C 0.56787(14) 0.20262(15) 0.36697(14) 0.0460(3) Uani 1 1 d . . . . .
H11A H 0.5583 0.1414 0.3308 0.055 Uiso 1 1 calc R U . . .
H11B H 0.5194 0.1791 0.4486 0.055 Uiso 1 1 calc R U . . .
H11C H 0.6589 0.2110 0.3566 0.055 Uiso 1 1 calc R U . . .
C112 C 0.55180(16) 0.42343(17) 0.35733(16) 0.0527(4) Uani 1 1 d . . . . .
H11D H 0.6452 0.4238 0.3400 0.063 Uiso 1 1 calc R U . . .
H11E H 0.5097 0.4061 0.4401 0.063 Uiso 1 1 calc R U . . .
H11F H 0.5236 0.5017 0.3211 0.063 Uiso 1 1 calc R U . . .
C113 C 0.59225(15) 0.35280(17) 0.18014(13) 0.0504(4) Uani 1 1 d . . . . .
H11G H 0.6844 0.3438 0.1696 0.060 Uiso 1 1 calc R U . . .
H11H H 0.5744 0.4347 0.1429 0.060 Uiso 1 1 calc R U . . .
H11I H 0.5666 0.2971 0.1463 0.060 Uiso 1 1 calc R U . . .
N1 N 0.24278(10) 0.37830(9) 0.21285(8) 0.0280(2) Uani 1 1 d . . . . .
C20 C 0.10071(13) 0.40972(12) 0.26201(11) 0.0343(3) Uani 1 1 d . . . . .
H20A H 0.0941 0.4620 0.3119 0.041 Uiso 1 1 calc R U . . .
H20B H 0.0545 0.3361 0.3098 0.041 Uiso 1 1 calc R U . . .
C21 C 0.03070(17) 0.47174(15) 0.17450(14) 0.0485(4) Uani 1 1 d . . . . .
H21A H 0.0671 0.5513 0.1338 0.058 Uiso 1 1 calc R U . . .
H21B H -0.0611 0.4790 0.2149 0.058 Uiso 1 1 calc R U . . .
H21C H 0.0421 0.4239 0.1198 0.058 Uiso 1 1 calc R U . . .
C22 C 0.31570(15) 0.48325(12) 0.12038(11) 0.0392(3) Uani 1 1 d . . . . .
H22A H 0.2731 0.5088 0.0622 0.047 Uiso 1 1 calc R U . . .
H22B H 0.4030 0.4575 0.0837 0.047 Uiso 1 1 calc R U . . .
C23 C 0.3233(2) 0.59066(13) 0.16765(15) 0.0539(4) Uani 1 1 d . . . . .
H23A H 0.2371 0.6239 0.1949 0.065 Uiso 1 1 calc R U . . .
H23B H 0.3794 0.6520 0.1070 0.065 Uiso 1 1 calc R U . . .
H23C H 0.3582 0.5639 0.2309 0.065 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 C1A 1.751(12) . ?
P1 C1 1.813(5) . ?
P1 N1 1.8351(10) . ?
P1 C4 1.8451(12) . ?
P1 Al1 2.8019(4) . ?
C4 C5 1.4093(18) . ?
C4 C9 1.4204(16) . ?
C5 C6 1.3975(18) . ?
C5 C51 1.5069(19) . ?
C51 H51A 0.9599 . ?
C51 H51B 0.9599 . ?
C51 H51C 0.9599 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9600 . ?
C7 C8 1.381(2) . ?
C7 C71 1.509(2) . ?
C71 H71A 0.9599 . ?
C71 H71B 0.9599 . ?
C71 H71C 0.9599 . ?
C8 C9 1.3876(18) . ?
C8 H8 0.9600 . ?
C9 C91 1.506(2) . ?
C91 H91A 0.9599 . ?
C91 H91B 0.9599 . ?
C91 H91C 0.9599 . ?
C1 C2 1.357(5) . ?
C1 Al1 1.988(6) . ?
C2 C3 1.515(6) . ?
C2 H2 0.9600 . ?
C3 C33 1.515(6) . ?
C3 C31 1.529(5) . ?
C3 C32 1.541(7) . ?
C31 H31A 0.9599 . ?
C31 H31B 0.9599 . ?
C31 H31C 0.9599 . ?
C32 H32A 0.9599 . ?
C32 H32B 0.9599 . ?
C32 H32C 0.9599 . ?
C33 H33A 0.9599 . ?
C33 H33B 0.9599 . ?
C33 H33C 0.9599 . ?
C1A C2A 1.335(12) . ?
C1A Al1 2.023(12) . ?
C2A C3A 1.512(11) . ?
C2A H2A 0.9600 . ?
C3A C31A 1.497(12) . ?
C3A C32A 1.522(12) . ?
C3A C33A 1.539(10) . ?
C31A H31D 0.9599 . ?
C31A H31E 0.9599 . ?
C31A H31F 0.9599 . ?
C32A H32D 0.9599 . ?
C32A H32E 0.9599 . ?
C32A H32F 0.9599 . ?
C33A H33D 0.9599 . ?
C33A H33E 0.9599 . ?
C33A H33F 0.9599 . ?
Al1 C10 2.0163(12) . ?
Al1 C11 2.0332(13) . ?
Al1 N1 2.1207(10) . ?
C10 C101 1.533(2) . ?
C10 C103 1.5334(19) . ?
C10 C102 1.5371(19) . ?
C101 H10A 0.9599 . ?
C101 H10B 0.9599 . ?
C101 H10C 0.9599 . ?
C102 H10D 0.9599 . ?
C102 H10E 0.9599 . ?
C102 H10F 0.9599 . ?
C103 H10G 0.9599 . ?
C103 H10H 0.9599 . ?
C103 H10I 0.9599 . ?
C11 C113 1.5322(19) . ?
C11 C112 1.5365(19) . ?
C11 C111 1.544(2) . ?
C111 H11A 0.9599 . ?
C111 H11B 0.9599 . ?
C111 H11C 0.9599 . ?
C112 H11D 0.9599 . ?
C112 H11E 0.9599 . ?
C112 H11F 0.9599 . ?
C113 H11G 0.9599 . ?
C113 H11H 0.9599 . ?
C113 H11I 0.9599 . ?
N1 C22 1.4899(16) . ?
N1 C20 1.5015(16) . ?
C20 C21 1.5270(18) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C21 H21A 0.9599 . ?
C21 H21B 0.9599 . ?
C21 H21C 0.9599 . ?
C22 C23 1.5193(19) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C23 H23A 0.9599 . ?
C23 H23B 0.9599 . ?
C23 H23C 0.9599 . ?

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
C1A P1 N1 92.5(4) . . ?
C1 P1 N1 91.5(2) . . ?
C1A P1 C4 114.1(5) . . ?
C1 P1 C4 114.3(2) . . ?
N1 P1 C4 106.30(5) . . ?
C1A P1 Al1 45.9(4) . . ?
C1 P1 Al1 45.0(2) . . ?
N1 P1 Al1 49.19(3) . . ?
C4 P1 Al1 132.64(4) . . ?
C5 C4 C9 118.79(11) . . ?
C5 C4 P1 127.05(9) . . ?
C9 C4 P1 113.91(9) . . ?
C6 C5 C4 119.02(13) . . ?
C6 C5 C51 116.27(13) . . ?
C4 C5 C51 124.70(11) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C7 C6 C5 122.46(14) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C8 C7 C6 117.92(12) . . ?
C8 C7 C71 121.21(16) . . ?
C6 C7 C71 120.87(16) . . ?
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 . . ?
C7 C8 C9 122.26(13) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C4 119.54(13) . . ?
C8 C9 C91 117.38(12) . . ?
C4 C9 C91 123.06(12) . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C2 C1 P1 132.0(5) . . ?
C2 C1 Al1 129.3(5) . . ?
P1 C1 Al1 94.9(2) . . ?
C1 C2 C3 131.7(6) . . ?
C1 C2 H2 114.1 . . ?
C3 C2 H2 114.1 . . ?
C33 C3 C2 106.8(5) . . ?
C33 C3 C31 108.8(4) . . ?
C2 C3 C31 115.2(5) . . ?
C33 C3 C32 108.9(4) . . ?
C2 C3 C32 108.7(5) . . ?
C31 C3 C32 108.2(4) . . ?
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 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C3 C33 H33A 109.5 . . ?
C3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C2A C1A P1 125.3(11) . . ?
C2A C1A Al1 133.6(11) . . ?
P1 C1A Al1 95.6(5) . . ?
C1A C2A C3A 135.1(13) . . ?
C1A C2A H2A 112.5 . . ?
C3A C2A H2A 112.5 . . ?
C31A C3A C2A 109.5(10) . . ?
C31A C3A C32A 111.3(7) . . ?
C2A C3A C32A 110.6(9) . . ?
C31A C3A C33A 110.3(8) . . ?
C2A C3A C33A 107.1(9) . . ?
C32A C3A C33A 107.9(7) . . ?
C3A C31A H31D 109.5 . . ?
C3A C31A H31E 109.5 . . ?
H31D C31A H31E 109.5 . . ?
C3A C31A H31F 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?
C3A C32A H32D 109.5 . . ?
C3A C32A H32E 109.5 . . ?
H32D C32A H32E 109.5 . . ?
C3A C32A H32F 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
C3A C33A H33D 109.5 . . ?
C3A C33A H33E 109.5 . . ?
H33D C33A H33E 109.5 . . ?
C3A C33A H33F 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?
C1 Al1 C10 120.8(2) . . ?
C10 Al1 C1A 122.2(4) . . ?
C1 Al1 C11 108.9(2) . . ?
C10 Al1 C11 114.82(5) . . ?
C1A Al1 C11 108.7(4) . . ?
C1 Al1 N1 78.88(13) . . ?
C10 Al1 N1 113.91(5) . . ?
C1A Al1 N1 77.3(3) . . ?
C11 Al1 N1 114.74(5) . . ?
C1 Al1 P1 40.15(13) . . ?
C10 Al1 P1 136.66(4) . . ?
C1A Al1 P1 38.4(3) . . ?
C11 Al1 P1 108.50(4) . . ?
N1 Al1 P1 40.91(3) . . ?
C101 C10 C103 108.23(11) . . ?
C101 C10 C102 107.97(12) . . ?
C103 C10 C102 106.17(12) . . ?
C101 C10 Al1 113.18(10) . . ?
C103 C10 Al1 115.38(9) . . ?
C102 C10 Al1 105.41(9) . . ?
C10 C101 H10A 109.5 . . ?
C10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C10 C102 H10D 109.5 . . ?
C10 C102 H10E 109.5 . . ?
H10D C102 H10E 109.5 . . ?
C10 C102 H10F 109.5 . . ?
H10D C102 H10F 109.5 . . ?
H10E C102 H10F 109.5 . . ?
C10 C103 H10G 109.5 . . ?
C10 C103 H10H 109.5 . . ?
H10G C103 H10H 109.5 . . ?
C10 C103 H10I 109.5 . . ?
H10G C103 H10I 109.5 . . ?
H10H C103 H10I 109.5 . . ?
C113 C11 C112 106.95(12) . . ?
C113 C11 C111 106.07(12) . . ?
C112 C11 C111 107.30(12) . . ?
C113 C11 Al1 114.39(9) . . ?
C112 C11 Al1 116.46(10) . . ?
C111 C11 Al1 104.97(9) . . ?
C11 C111 H11A 109.5 . . ?
C11 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
C11 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C11 C112 H11D 109.5 . . ?
C11 C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?
C11 C112 H11F 109.5 . . ?
H11D C112 H11F 109.5 . . ?
H11E C112 H11F 109.5 . . ?
C11 C113 H11G 109.5 . . ?
C11 C113 H11H 109.5 . . ?
H11G C113 H11H 109.5 . . ?
C11 C113 H11I 109.5 . . ?
H11G C113 H11I 109.5 . . ?
H11H C113 H11I 109.5 . . ?
C22 N1 C20 110.92(10) . . ?
C22 N1 P1 110.18(8) . . ?
C20 N1 P1 117.22(8) . . ?
C22 N1 Al1 117.46(8) . . ?
C20 N1 Al1 109.97(7) . . ?
P1 N1 Al1 89.90(4) . . ?
N1 C20 C21 116.73(11) . . ?
N1 C20 H20A 108.1 . . ?
C21 C20 H20A 108.1 . . ?
N1 C20 H20B 108.1 . . ?
C21 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 C23 112.55(11) . . ?
N1 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
N1 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C1A P1 C4 C5 16.4(5) . . . . ?
C1 P1 C4 C5 15.3(3) . . . . ?
N1 P1 C4 C5 -83.95(11) . . . . ?
Al1 P1 C4 C5 -34.97(13) . . . . ?
C1A P1 C4 C9 -157.8(5) . . . . ?
C1 P1 C4 C9 -158.9(2) . . . . ?
N1 P1 C4 C9 101.79(9) . . . . ?
Al1 P1 C4 C9 150.77(7) . . . . ?
C9 C4 C5 C6 0.77(17) . . . . ?
P1 C4 C5 C6 -173.24(9) . . . . ?
C9 C4 C5 C51 -178.53(12) . . . . ?
P1 C4 C5 C51 7.46(19) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C51 C5 C6 C7 179.21(13) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C5 C6 C7 C71 179.95(13) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C71 C7 C8 C9 -179.94(13) . . . . ?
C7 C8 C9 C4 0.13(19) . . . . ?
C7 C8 C9 C91 -178.18(13) . . . . ?
C5 C4 C9 C8 -0.77(17) . . . . ?
P1 C4 C9 C8 174.01(9) . . . . ?
C5 C4 C9 C91 177.45(12) . . . . ?
P1 C4 C9 C91 -7.78(16) . . . . ?
C1A P1 C1 C2 -3(40) . . . . ?
N1 P1 C1 C2 -176.9(8) . . . . ?
C4 P1 C1 C2 74.5(9) . . . . ?
Al1 P1 C1 C2 -158.7(10) . . . . ?
C1A P1 C1 Al1 156(41) . . . . ?
N1 P1 C1 Al1 -18.2(3) . . . . ?
C4 P1 C1 Al1 -126.8(2) . . . . ?
P1 C1 C2 C3 -5.8(15) . . . . ?
Al1 C1 C2 C3 -157.9(7) . . . . ?
C1 C2 C3 C33 105.2(10) . . . . ?
C1 C2 C3 C31 -15.7(12) . . . . ?
C1 C2 C3 C32 -137.4(9) . . . . ?
C1 P1 C1A C2A 179(100) . . . . ?
N1 P1 C1A C2A -174.7(15) . . . . ?
C4 P1 C1A C2A 76.2(16) . . . . ?
Al1 P1 C1A C2A -156.9(19) . . . . ?
C1 P1 C1A Al1 -24(40) . . . . ?
N1 P1 C1A Al1 -17.8(5) . . . . ?
C4 P1 C1A Al1 -126.9(4) . . . . ?
P1 C1A C2A C3A -16(3) . . . . ?
Al1 C1A C2A C3A -163.0(14) . . . . ?
C1A C2A C3A C31A -87(2) . . . . ?
C1A C2A C3A C32A 36(3) . . . . ?
C1A C2A C3A C33A 153(2) . . . . ?
C1A P1 N1 C22 136.2(5) . . . . ?
C1 P1 N1 C22 136.3(3) . . . . ?
C4 P1 N1 C22 -107.78(9) . . . . ?
Al1 P1 N1 C22 119.38(10) . . . . ?
C1A P1 N1 C20 -95.7(5) . . . . ?
C1 P1 N1 C20 -95.6(3) . . . . ?
C4 P1 N1 C20 20.30(9) . . . . ?
Al1 P1 N1 C20 -112.53(9) . . . . ?
C1A P1 N1 Al1 16.8(5) . . . . ?
C1 P1 N1 Al1 16.9(2) . . . . ?
C4 P1 N1 Al1 132.84(5) . . . . ?
C22 N1 C20 C21 47.04(15) . . . . ?
P1 N1 C20 C21 -80.69(13) . . . . ?
Al1 N1 C20 C21 178.66(10) . . . . ?
C20 N1 C22 C23 66.19(15) . . . . ?
P1 N1 C22 C23 -162.34(11) . . . . ?
Al1 N1 C22 C23 -61.46(15) . . . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    'Air-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_sadp21n
_database_code_depnum_ccdc_archive 'CCDC 1414320'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H61 Al P2'
_chemical_formula_weight         606.78

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'
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'

_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                   8.7959(4)
_cell_length_b                   19.1209(8)
_cell_length_c                   21.9957(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.433(2)
_cell_angle_gamma                90
_cell_volume                     3688.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.438
_cell_measurement_theta_max      29.654

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52283
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.130
_diffrn_reflns_theta_max         30.124
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10795
_reflns_number_gt                7493
_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 SMART'
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0653P)²+2.1281P] 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         10795
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.52077(6) 0.77945(2) 0.09784(2) 0.01739(12) Uani 1 1 d . . . . .
P2 P 0.36584(6) 0.68027(2) 0.18340(2) 0.01463(11) Uani 1 1 d . . . . .
H2 H 0.258(3) 0.7147(11) 0.1961(10) 0.020(6) Uiso 1 1 d . . . . .
Al1 Al 0.35730(7) 0.69968(3) 0.03850(2) 0.01512(13) Uani 1 1 d . . . . .
C11 C 0.5195(2) 0.74232(9) 0.17383(8) 0.0169(4) Uani 1 1 d . . . . .
C12 C 0.6119(2) 0.75412(10) 0.22462(8) 0.0188(4) Uani 1 1 d . . . . .
H12 H 0.5858 0.7272 0.2592 0.023 Uiso 1 1 calc R U . . .
C13 C 0.7476(2) 0.80105(10) 0.23797(9) 0.0204(4) Uani 1 1 d . . . . .
C131 C 0.8328(3) 0.82213(13) 0.18285(10) 0.0310(5) Uani 1 1 d . . . . .
H13A H 0.8556 0.7811 0.1601 0.037 Uiso 1 1 calc R U . . .
H13B H 0.9260 0.8454 0.1965 0.037 Uiso 1 1 calc R U . . .
H13C H 0.7703 0.8532 0.1573 0.037 Uiso 1 1 calc R U . . .
C132 C 0.6964(3) 0.86668(11) 0.27094(10) 0.0296(5) Uani 1 1 d . . . . .
H13D H 0.6330 0.8948 0.2431 0.036 Uiso 1 1 calc R U . . .
H13E H 0.7843 0.8932 0.2857 0.036 Uiso 1 1 calc R U . . .
H13F H 0.6399 0.8531 0.3047 0.036 Uiso 1 1 calc R U . . .
C133 C 0.8581(3) 0.76071(12) 0.28186(11) 0.0329(5) Uani 1 1 d . . . . .
H13G H 0.8074 0.7475 0.3172 0.039 Uiso 1 1 calc R U . . .
H13H H 0.9442 0.7898 0.2940 0.039 Uiso 1 1 calc R U . . .
H13I H 0.8922 0.7195 0.2620 0.039 Uiso 1 1 calc R U . . .
C21 C 0.3117(2) 0.64004(9) 0.11207(8) 0.0156(4) Uani 1 1 d . . . . .
C22 C 0.2139(2) 0.58689(10) 0.10013(8) 0.0183(4) Uani 1 1 d . . . . .
H22 H 0.2063 0.5739 0.0578 0.022 Uiso 1 1 calc R U . . .
C23 C 0.1116(2) 0.54212(10) 0.13785(9) 0.0204(4) Uani 1 1 d . . . . .
C231 C 0.0445(3) 0.58431(12) 0.18820(10) 0.0274(5) Uani 1 1 d . . . . .
H23A H 0.1248 0.5986 0.2176 0.033 Uiso 1 1 calc R U . . .
H23B H -0.0274 0.5560 0.2078 0.033 Uiso 1 1 calc R U . . .
H23C H -0.0062 0.6249 0.1709 0.033 Uiso 1 1 calc R U . . .
C232 C 0.2005(3) 0.47873(11) 0.16495(10) 0.0290(5) Uani 1 1 d . . . . .
H23D H 0.2776 0.4944 0.1951 0.035 Uiso 1 1 calc R U . . .
H23E H 0.2475 0.4545 0.1331 0.035 Uiso 1 1 calc R U . . .
H23F H 0.1317 0.4478 0.1835 0.035 Uiso 1 1 calc R U . . .
C233 C -0.0194(3) 0.51506(13) 0.09445(10) 0.0335(5) Uani 1 1 d . . . . .
H23G H -0.0868 0.4872 0.1168 0.040 Uiso 1 1 calc R U . . .
H23H H 0.0208 0.4870 0.0632 0.040 Uiso 1 1 calc R U . . .
H23I H -0.0746 0.5539 0.0760 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4929(2) 0.87438(10) 0.10566(8) 0.0179(4) Uani 1 1 d . . . . .
C15 C 0.5781(2) 0.91740(10) 0.06835(9) 0.0202(4) Uani 1 1 d . . . . .
C151 C 0.6640(3) 0.88710(11) 0.01764(9) 0.0274(5) Uani 1 1 d . . . . .
H15A H 0.7104 0.9243 -0.0037 0.033 Uiso 1 1 calc R U . . .
H15B H 0.5946 0.8619 -0.0102 0.033 Uiso 1 1 calc R U . . .
H15C H 0.7416 0.8559 0.0346 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5870(3) 0.98896(10) 0.07909(9) 0.0235(4) Uani 1 1 d . . . . .
H16 H 0.6446 1.0176 0.0533 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5147(2) 1.02021(10) 0.12627(9) 0.0218(4) Uani 1 1 d . . . . .
C171 C 0.5398(3) 1.09658(10) 0.14166(10) 0.0301(5) Uani 1 1 d . . . . .
H17A H 0.5042 1.1248 0.1074 0.036 Uiso 1 1 calc R U . . .
H17B H 0.6466 1.1049 0.1512 0.036 Uiso 1 1 calc R U . . .
H17C H 0.4847 1.1085 0.1762 0.036 Uiso 1 1 calc R U . . .
C18 C 0.4208(2) 0.97883(10) 0.15898(9) 0.0207(4) Uani 1 1 d . . . . .
H18 H 0.3640 1.0003 0.1896 0.025 Uiso 1 1 calc R U . . .
C19 C 0.4057(2) 0.90688(10) 0.14902(9) 0.0181(4) Uani 1 1 d . . . . .
C191 C 0.2958(2) 0.86795(10) 0.18582(9) 0.0231(4) Uani 1 1 d . . . . .
H19A H 0.3504 0.8470 0.2206 0.028 Uiso 1 1 calc R U . . .
H19B H 0.2458 0.8321 0.1611 0.028 Uiso 1 1 calc R U . . .
H19C H 0.2212 0.8999 0.1992 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4139(2) 0.62740(9) 0.25035(8) 0.0139(4) Uani 1 1 d . . . . .
C25 C 0.3550(2) 0.64514(10) 0.30646(8) 0.0161(4) Uani 1 1 d . . . . .
C251 C 0.2649(3) 0.71127(10) 0.31551(9) 0.0232(4) Uani 1 1 d . . . . .
H25A H 0.2461 0.7158 0.3577 0.028 Uiso 1 1 calc R U . . .
H25B H 0.1695 0.7090 0.2913 0.028 Uiso 1 1 calc R U . . .
H25C H 0.3219 0.7510 0.3033 0.028 Uiso 1 1 calc R U . . .
C26 C 0.3864(2) 0.60104(10) 0.35596(8) 0.0190(4) Uani 1 1 d . . . . .
H26 H 0.3452 0.6122 0.3940 0.023 Uiso 1 1 calc R U . . .
C27 C 0.4755(2) 0.54132(10) 0.35247(8) 0.0208(4) Uani 1 1 d . . . . .
C271 C 0.4981(3) 0.49298(12) 0.40657(10) 0.0302(5) Uani 1 1 d . . . . .
H27A H 0.5295 0.5196 0.4423 0.036 Uiso 1 1 calc R U . . .
H27B H 0.5751 0.4591 0.3993 0.036 Uiso 1 1 calc R U . . .
H27C H 0.4040 0.4694 0.4125 0.036 Uiso 1 1 calc R U . . .
C28 C 0.5421(2) 0.52819(10) 0.29842(9) 0.0202(4) Uani 1 1 d . . . . .
H28 H 0.6094 0.4889 0.2963 0.024 Uiso 1 1 calc R U . . .
C29 C 0.5140(2) 0.57043(10) 0.24705(8) 0.0161(4) Uani 1 1 d . . . . .
C291 C 0.5925(2) 0.55447(11) 0.19002(9) 0.0223(4) Uani 1 1 d . . . . .
H29A H 0.6769 0.5236 0.1998 0.027 Uiso 1 1 calc R U . . .
H29B H 0.6289 0.5972 0.1733 0.027 Uiso 1 1 calc R U . . .
H29C H 0.5216 0.5325 0.1606 0.027 Uiso 1 1 calc R U . . .
C31 C 0.4967(2) 0.64941(10) -0.01557(8) 0.0186(4) Uani 1 1 d . . . . .
C311 C 0.6303(3) 0.61626(12) 0.02277(10) 0.0317(5) Uani 1 1 d . . . . .
H31A H 0.6972 0.5938 -0.0036 0.038 Uiso 1 1 calc R U . . .
H31B H 0.5922 0.5823 0.0499 0.038 Uiso 1 1 calc R U . . .
H31C H 0.6852 0.6519 0.0460 0.038 Uiso 1 1 calc R U . . .
C312 C 0.5649(3) 0.70022(12) -0.05986(10) 0.0312(5) Uani 1 1 d . . . . .
H31D H 0.6274 0.6748 -0.0862 0.037 Uiso 1 1 calc R U . . .
H31E H 0.6259 0.7344 -0.0372 0.037 Uiso 1 1 calc R U . . .
H31F H 0.4842 0.7233 -0.0840 0.037 Uiso 1 1 calc R U . . .
C313 C 0.4159(3) 0.59083(13) -0.05279(12) 0.0382(6) Uani 1 1 d . . . . .
H31G H 0.3352 0.6103 -0.0794 0.046 Uiso 1 1 calc R U . . .
H31H H 0.3743 0.5578 -0.0257 0.046 Uiso 1 1 calc R U . . .
H31I H 0.4877 0.5676 -0.0766 0.046 Uiso 1 1 calc R U . . .
C32 C 0.1645(2) 0.74410(11) 0.00078(9) 0.0233(4) Uani 1 1 d . . . . .
C321 C 0.0546(3) 0.75946(19) 0.04846(13) 0.0583(9) Uani 1 1 d . . . . .
H32A H -0.0384 0.7780 0.0291 0.070 Uiso 1 1 calc R U . . .
H32B H 0.0991 0.7930 0.0770 0.070 Uiso 1 1 calc R U . . .
H32C H 0.0331 0.7171 0.0696 0.070 Uiso 1 1 calc R U . . .
C322 C 0.0807(4) 0.69921(18) -0.04756(15) 0.0618(10) Uani 1 1 d . . . . .
H32D H 0.0520 0.6558 -0.0298 0.074 Uiso 1 1 calc R U . . .
H32E H 0.1460 0.6901 -0.0797 0.074 Uiso 1 1 calc R U . . .
H32F H -0.0091 0.7233 -0.0639 0.074 Uiso 1 1 calc R U . . .
C323 C 0.2045(4) 0.81272(17) -0.02918(18) 0.0739(12) Uani 1 1 d . . . . .
H32G H 0.1127 0.8354 -0.0454 0.089 Uiso 1 1 calc R U . . .
H32H H 0.2687 0.8036 -0.0616 0.089 Uiso 1 1 calc R U . . .
H32I H 0.2572 0.8426 0.0005 0.089 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 C11 1.8167(19) . ?
P1 C14 1.8415(19) . ?
P1 Al1 2.4100(7) . ?
P2 C21 1.7790(18) . ?
P2 C24 1.8091(18) . ?
P2 C11 1.823(2) . ?
P2 H2 1.20(2) . ?
Al1 C31 2.016(2) . ?
Al1 C32 2.017(2) . ?
Al1 C21 2.0447(18) . ?
C11 C12 1.349(3) . ?
C12 C13 1.504(3) . ?
C12 H12 0.9600 . ?
C13 C133 1.525(3) . ?
C13 C131 1.528(3) . ?
C13 C132 1.534(3) . ?
C131 H13A 0.9599 . ?
C131 H13B 0.9599 . ?
C131 H13C 0.9599 . ?
C132 H13D 0.9599 . ?
C132 H13E 0.9599 . ?
C132 H13F 0.9599 . ?
C133 H13G 0.9599 . ?
C133 H13H 0.9599 . ?
C133 H13I 0.9599 . ?
C21 C22 1.344(3) . ?
C22 C23 1.531(3) . ?
C22 H22 0.9600 . ?
C23 C231 1.526(3) . ?
C23 C233 1.529(3) . ?
C23 C232 1.537(3) . ?
C231 H23A 0.9599 . ?
C231 H23B 0.9599 . ?
C231 H23C 0.9599 . ?
C232 H23D 0.9599 . ?
C232 H23E 0.9599 . ?
C232 H23F 0.9599 . ?
C233 H23G 0.9599 . ?
C233 H23H 0.9599 . ?
C233 H23I 0.9599 . ?
C14 C19 1.413(3) . ?
C14 C15 1.416(3) . ?
C15 C16 1.390(3) . ?
C15 C151 1.510(3) . ?
C151 H15A 0.9599 . ?
C151 H15B 0.9599 . ?
C151 H15C 0.9599 . ?
C16 C17 1.393(3) . ?
C16 H16 0.9600 . ?
C17 C18 1.385(3) . ?
C17 C171 1.511(3) . ?
C171 H17A 0.9599 . ?
C171 H17B 0.9599 . ?
C171 H17C 0.9599 . ?
C18 C19 1.398(3) . ?
C18 H18 0.9600 . ?
C19 C191 1.505(3) . ?
C191 H19A 0.9599 . ?
C191 H19B 0.9599 . ?
C191 H19C 0.9599 . ?
C24 C29 1.406(3) . ?
C24 C25 1.416(2) . ?
C25 C26 1.388(2) . ?
C25 C251 1.513(3) . ?
C251 H25A 0.9599 . ?
C251 H25B 0.9599 . ?
C251 H25C 0.9599 . ?
C26 C27 1.390(3) . ?
C26 H26 0.9600 . ?
C27 C28 1.388(3) . ?
C27 C271 1.508(3) . ?
C271 H27A 0.9599 . ?
C271 H27B 0.9599 . ?
C271 H27C 0.9599 . ?
C28 C29 1.395(3) . ?
C28 H28 0.9600 . ?
C29 C291 1.509(3) . ?
C291 H29A 0.9599 . ?
C291 H29B 0.9599 . ?
C291 H29C 0.9599 . ?
C31 C313 1.529(3) . ?
C31 C311 1.530(3) . ?
C31 C312 1.531(3) . ?
C311 H31A 0.9599 . ?
C311 H31B 0.9599 . ?
C311 H31C 0.9599 . ?
C312 H31D 0.9599 . ?
C312 H31E 0.9599 . ?
C312 H31F 0.9599 . ?
C313 H31G 0.9599 . ?
C313 H31H 0.9599 . ?
C313 H31I 0.9599 . ?
C32 C321 1.509(3) . ?
C32 C322 1.513(3) . ?
C32 C323 1.522(3) . ?
C321 H32A 0.9599 . ?
C321 H32B 0.9599 . ?
C321 H32C 0.9599 . ?
C322 H32D 0.9599 . ?
C322 H32E 0.9599 . ?
C322 H32F 0.9599 . ?
C323 H32G 0.9599 . ?
C323 H32H 0.9599 . ?
C323 H32I 0.9599 . ?

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
C11 P1 C14 106.80(8) . . ?
C11 P1 Al1 101.84(6) . . ?
C14 P1 Al1 126.60(7) . . ?
C21 P2 C24 120.40(8) . . ?
C21 P2 C11 109.27(9) . . ?
C24 P2 C11 109.22(9) . . ?
C21 P2 H2 106.3(10) . . ?
C24 P2 H2 104.7(10) . . ?
C11 P2 H2 105.9(10) . . ?
C31 Al1 C32 119.23(8) . . ?
C31 Al1 C21 111.49(8) . . ?
C32 Al1 C21 110.50(9) . . ?
C31 Al1 P1 104.87(6) . . ?
C32 Al1 P1 113.81(7) . . ?
C21 Al1 P1 93.99(6) . . ?
C12 C11 P1 130.57(15) . . ?
C12 C11 P2 114.70(14) . . ?
P1 C11 P2 114.71(10) . . ?
C11 C12 C13 132.83(18) . . ?
C11 C12 H12 113.6 . . ?
C13 C12 H12 113.6 . . ?
C12 C13 C133 106.20(16) . . ?
C12 C13 C131 115.66(16) . . ?
C133 C13 C131 107.96(19) . . ?
C12 C13 C132 108.80(17) . . ?
C133 C13 C132 108.09(17) . . ?
C131 C13 C132 109.84(18) . . ?
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 . . ?
C13 C132 H13D 109.5 . . ?
C13 C132 H13E 109.5 . . ?
H13D C132 H13E 109.5 . . ?
C13 C132 H13F 109.5 . . ?
H13D C132 H13F 109.5 . . ?
H13E C132 H13F 109.5 . . ?
C13 C133 H13G 109.5 . . ?
C13 C133 H13H 109.5 . . ?
H13G C133 H13H 109.5 . . ?
C13 C133 H13I 109.5 . . ?
H13G C133 H13I 109.5 . . ?
H13H C133 H13I 109.5 . . ?
C22 C21 P2 128.54(15) . . ?
C22 C21 Al1 115.39(13) . . ?
P2 C21 Al1 113.66(9) . . ?
C21 C22 C23 135.27(17) . . ?
C21 C22 H22 112.4 . . ?
C23 C22 H22 112.4 . . ?
C231 C23 C233 108.46(18) . . ?
C231 C23 C22 111.98(16) . . ?
C233 C23 C22 107.27(16) . . ?
C231 C23 C232 110.44(17) . . ?
C233 C23 C232 108.14(17) . . ?
C22 C23 C232 110.41(17) . . ?
C23 C231 H23A 109.5 . . ?
C23 C231 H23B 109.5 . . ?
H23A C231 H23B 109.5 . . ?
C23 C231 H23C 109.5 . . ?
H23A C231 H23C 109.5 . . ?
H23B C231 H23C 109.5 . . ?
C23 C232 H23D 109.5 . . ?
C23 C232 H23E 109.5 . . ?
H23D C232 H23E 109.5 . . ?
C23 C232 H23F 109.5 . . ?
H23D C232 H23F 109.5 . . ?
H23E C232 H23F 109.5 . . ?
C23 C233 H23G 109.5 . . ?
C23 C233 H23H 109.5 . . ?
H23G C233 H23H 109.5 . . ?
C23 C233 H23I 109.5 . . ?
H23G C233 H23I 109.5 . . ?
H23H C233 H23I 109.5 . . ?
C19 C14 C15 118.33(17) . . ?
C19 C14 P1 125.43(15) . . ?
C15 C14 P1 115.98(15) . . ?
C16 C15 C14 119.93(19) . . ?
C16 C15 C151 118.56(18) . . ?
C14 C15 C151 121.50(17) . . ?
C15 C151 H15A 109.5 . . ?
C15 C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
C15 C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
C15 C16 C17 121.71(19) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 117.85(18) . . ?
C18 C17 C171 121.23(19) . . ?
C16 C17 C171 120.92(19) . . ?
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 . . ?
C17 C18 C19 122.27(19) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C14 119.28(18) . . ?
C18 C19 C191 117.35(18) . . ?
C14 C19 C191 123.37(17) . . ?
C19 C191 H19A 109.5 . . ?
C19 C191 H19B 109.5 . . ?
H19A C191 H19B 109.5 . . ?
C19 C191 H19C 109.5 . . ?
H19A C191 H19C 109.5 . . ?
H19B C191 H19C 109.5 . . ?
C29 C24 C25 120.22(16) . . ?
C29 C24 P2 119.92(13) . . ?
C25 C24 P2 119.82(14) . . ?
C26 C25 C24 118.29(17) . . ?
C26 C25 C251 118.62(16) . . ?
C24 C25 C251 123.05(16) . . ?
C25 C251 H25A 109.5 . . ?
C25 C251 H25B 109.5 . . ?
H25A C251 H25B 109.5 . . ?
C25 C251 H25C 109.5 . . ?
H25A C251 H25C 109.5 . . ?
H25B C251 H25C 109.5 . . ?
C25 C26 C27 122.33(17) . . ?
C25 C26 H26 118.8 . . ?
C27 C26 H26 118.8 . . ?
C28 C27 C26 118.21(17) . . ?
C28 C27 C271 121.75(19) . . ?
C26 C27 C271 120.04(18) . . ?
C27 C271 H27A 109.5 . . ?
C27 C271 H27B 109.5 . . ?
H27A C271 H27B 109.5 . . ?
C27 C271 H27C 109.5 . . ?
H27A C271 H27C 109.5 . . ?
H27B C271 H27C 109.5 . . ?
C27 C28 C29 121.92(18) . . ?
C27 C28 H28 119.0 . . ?
C29 C28 H28 119.0 . . ?
C28 C29 C24 118.63(17) . . ?
C28 C29 C291 119.50(17) . . ?
C24 C29 C291 121.88(16) . . ?
C29 C291 H29A 109.5 . . ?
C29 C291 H29B 109.5 . . ?
H29A C291 H29B 109.5 . . ?
C29 C291 H29C 109.5 . . ?
H29A C291 H29C 109.5 . . ?
H29B C291 H29C 109.5 . . ?
C313 C31 C311 107.26(18) . . ?
C313 C31 C312 108.22(17) . . ?
C311 C31 C312 106.94(18) . . ?
C313 C31 Al1 112.74(15) . . ?
C311 C31 Al1 110.40(13) . . ?
C312 C31 Al1 111.03(13) . . ?
C31 C311 H31A 109.5 . . ?
C31 C311 H31B 109.5 . . ?
H31A C311 H31B 109.5 . . ?
C31 C311 H31C 109.5 . . ?
H31A C311 H31C 109.5 . . ?
H31B C311 H31C 109.5 . . ?
C31 C312 H31D 109.5 . . ?
C31 C312 H31E 109.5 . . ?
H31D C312 H31E 109.5 . . ?
C31 C312 H31F 109.5 . . ?
H31D C312 H31F 109.5 . . ?
H31E C312 H31F 109.5 . . ?
C31 C313 H31G 109.5 . . ?
C31 C313 H31H 109.5 . . ?
H31G C313 H31H 109.5 . . ?
C31 C313 H31I 109.5 . . ?
H31G C313 H31I 109.5 . . ?
H31H C313 H31I 109.5 . . ?
C321 C32 C322 107.2(2) . . ?
C321 C32 C323 108.4(2) . . ?
C322 C32 C323 107.5(2) . . ?
C321 C32 Al1 111.08(15) . . ?
C322 C32 Al1 113.49(17) . . ?
C323 C32 Al1 109.04(16) . . ?
C32 C321 H32A 109.5 . . ?
C32 C321 H32B 109.5 . . ?
H32A C321 H32B 109.5 . . ?
C32 C321 H32C 109.5 . . ?
H32A C321 H32C 109.5 . . ?
H32B C321 H32C 109.5 . . ?
C32 C322 H32D 109.5 . . ?
C32 C322 H32E 109.5 . . ?
H32D C322 H32E 109.5 . . ?
C32 C322 H32F 109.5 . . ?
H32D C322 H32F 109.5 . . ?
H32E C322 H32F 109.5 . . ?
C32 C323 H32G 109.5 . . ?
C32 C323 H32H 109.5 . . ?
H32G C323 H32H 109.5 . . ?
C32 C323 H32I 109.5 . . ?
H32G C323 H32I 109.5 . . ?
H32H C323 H32I 109.5 . . ?

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
C14 P1 C11 C12 -60.9(2) . . . . ?
Al1 P1 C11 C12 164.74(18) . . . . ?
C14 P1 C11 P2 117.73(11) . . . . ?
Al1 P1 C11 P2 -16.66(11) . . . . ?
C21 P2 C11 C12 -153.59(15) . . . . ?
C24 P2 C11 C12 -19.99(18) . . . . ?
C21 P2 C11 P1 27.59(13) . . . . ?
C24 P2 C11 P1 161.18(10) . . . . ?
P1 C11 C12 C13 0.1(3) . . . . ?
P2 C11 C12 C13 -178.54(18) . . . . ?
C11 C12 C13 C133 -143.2(2) . . . . ?
C11 C12 C13 C131 -23.4(3) . . . . ?
C11 C12 C13 C132 100.7(3) . . . . ?
C24 P2 C21 C22 45.5(2) . . . . ?
C11 P2 C21 C22 173.03(18) . . . . ?
C24 P2 C21 Al1 -153.19(9) . . . . ?
C11 P2 C21 Al1 -25.64(13) . . . . ?
P2 C21 C22 C23 1.6(4) . . . . ?
Al1 C21 C22 C23 -159.46(19) . . . . ?
C21 C22 C23 C231 35.7(3) . . . . ?
C21 C22 C23 C233 154.6(2) . . . . ?
C21 C22 C23 C232 -87.8(3) . . . . ?
C11 P1 C14 C19 -32.36(19) . . . . ?
Al1 P1 C14 C19 87.05(17) . . . . ?
C11 P1 C14 C15 141.61(15) . . . . ?
Al1 P1 C14 C15 -98.98(15) . . . . ?
C19 C14 C15 C16 6.6(3) . . . . ?
P1 C14 C15 C16 -167.83(16) . . . . ?
C19 C14 C15 C151 -175.11(19) . . . . ?
P1 C14 C15 C151 10.5(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C151 C15 C16 C17 -177.98(19) . . . . ?
C15 C16 C17 C18 -6.0(3) . . . . ?
C15 C16 C17 C171 173.2(2) . . . . ?
C16 C17 C18 C19 4.7(3) . . . . ?
C171 C17 C18 C19 -174.5(2) . . . . ?
C17 C18 C19 C14 2.2(3) . . . . ?
C17 C18 C19 C191 -177.81(19) . . . . ?
C15 C14 C19 C18 -7.8(3) . . . . ?
P1 C14 C19 C18 166.01(15) . . . . ?
C15 C14 C19 C191 172.22(18) . . . . ?
P1 C14 C19 C191 -13.9(3) . . . . ?
C21 P2 C24 C29 47.34(19) . . . . ?
C11 P2 C24 C29 -80.23(16) . . . . ?
C21 P2 C24 C25 -135.03(15) . . . . ?
C11 P2 C24 C25 97.39(16) . . . . ?
C29 C24 C25 C26 -6.3(3) . . . . ?
P2 C24 C25 C26 176.10(14) . . . . ?
C29 C24 C25 C251 171.23(18) . . . . ?
P2 C24 C25 C251 -6.4(3) . . . . ?
C24 C25 C26 C27 1.2(3) . . . . ?
C251 C25 C26 C27 -176.38(19) . . . . ?
C25 C26 C27 C28 3.9(3) . . . . ?
C25 C26 C27 C271 -176.30(19) . . . . ?
C26 C27 C28 C29 -4.2(3) . . . . ?
C271 C27 C28 C29 176.02(19) . . . . ?
C27 C28 C29 C24 -0.7(3) . . . . ?
C27 C28 C29 C291 178.64(19) . . . . ?
C25 C24 C29 C28 6.0(3) . . . . ?
P2 C24 C29 C28 -176.36(14) . . . . ?
C25 C24 C29 C291 -173.31(18) . . . . ?
P2 C24 C29 C291 4.3(3) . . . . ?

_refine_diff_density_max         0.694
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    'Air-sensitive, Hygroscopic'
####################################################################### 
# 
# 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_sad1
_database_code_depnum_ccdc_archive 'CCDC 1414321'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H76 Al2 P2'
_chemical_formula_weight         793.00

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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.6742(4)
_cell_length_b                   10.5505(4)
_cell_length_c                   12.2107(5)
_cell_angle_alpha                92.1847(10)
_cell_angle_beta                 106.3506(10)
_cell_angle_gamma                92.2788(10)
_cell_volume                     1193.38(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.385
_cell_measurement_theta_max      27.956

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16216
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         27.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5648
_reflns_number_gt                5015
_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 SMART'
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0547P)²+0.5233P] 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         5648
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.032
_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 0.05978(3) 0.59350(3) 0.64670(3) 0.01923(9) Uani 1 1 d . . . . .
H1 H 0.0793(18) 0.4763(16) 0.6800(14) 0.032(4) Uiso 1 1 d . . . . .
C1 C 0.17945(13) 0.59803(12) 0.55623(10) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.25283(14) 0.69727(12) 0.52933(11) 0.0222(3) Uani 1 1 d . . . . .
H2 H 0.3047 0.6727 0.4762 0.027 Uiso 1 1 calc R U . . .
C3 C 0.27422(15) 0.83881(12) 0.56206(12) 0.0247(3) Uani 1 1 d . . . . .
C31 C 0.14774(19) 0.89447(14) 0.59384(16) 0.0382(4) Uani 1 1 d . . . . .
H31A H 0.1409 0.8614 0.6644 0.046 Uiso 1 1 calc R U . . .
H31B H 0.0603 0.8720 0.5346 0.046 Uiso 1 1 calc R U . . .
H31C H 0.1620 0.9853 0.6027 0.046 Uiso 1 1 calc R U . . .
C32 C 0.2917(2) 0.90743(15) 0.45800(17) 0.0469(5) Uani 1 1 d . . . . .
H32A H 0.3080 0.9970 0.4769 0.056 Uiso 1 1 calc R U . . .
H32B H 0.2057 0.8925 0.3956 0.056 Uiso 1 1 calc R U . . .
H32C H 0.3724 0.8758 0.4363 0.056 Uiso 1 1 calc R U . . .
C33 C 0.4107(2) 0.86077(17) 0.6609(2) 0.0576(6) Uani 1 1 d . . . . .
H33A H 0.4304 0.9503 0.6783 0.069 Uiso 1 1 calc R U . . .
H33B H 0.4902 0.8253 0.6400 0.069 Uiso 1 1 calc R U . . .
H33C H 0.3978 0.8205 0.7268 0.069 Uiso 1 1 calc R U . . .
C4 C 0.12779(14) 0.67504(12) 0.78864(11) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.04979(15) 0.76889(12) 0.82658(11) 0.0235(3) Uani 1 1 d . . . . .
C51 C -0.09010(15) 0.81619(14) 0.75503(12) 0.0285(3) Uani 1 1 d . . . . .
H51A H -0.1050 0.7885 0.6766 0.034 Uiso 1 1 calc R U . . .
H51B H -0.0863 0.9073 0.7615 0.034 Uiso 1 1 calc R U . . .
H51C H -0.1682 0.7830 0.7814 0.034 Uiso 1 1 calc R U . . .
C6 C 0.10500(16) 0.82379(13) 0.93702(12) 0.0283(3) Uani 1 1 d . . . . .
H6 H 0.0518 0.8877 0.9629 0.034 Uiso 1 1 calc R U . . .
C7 C 0.23337(17) 0.78958(14) 1.01043(12) 0.0310(3) Uani 1 1 d . . . . .
C71 C 0.2910(2) 0.85319(18) 1.12824(13) 0.0441(4) Uani 1 1 d . . . . .
H71A H 0.3179 0.7897 1.1835 0.053 Uiso 1 1 calc R U . . .
H71B H 0.2179 0.9027 1.1453 0.053 Uiso 1 1 calc R U . . .
H71C H 0.3739 0.9076 1.1309 0.053 Uiso 1 1 calc R U . . .
C8 C 0.30862(16) 0.69645(14) 0.97177(12) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.3976 0.6713 1.0220 0.036 Uiso 1 1 calc R U . . .
C9 C 0.25910(15) 0.63856(13) 0.86264(12) 0.0251(3) Uani 1 1 d . . . . .
C91 C 0.34899(16) 0.54008(15) 0.82759(13) 0.0311(3) Uani 1 1 d . . . . .
H91A H 0.4366 0.5335 0.8878 0.037 Uiso 1 1 calc R U . . .
H91B H 0.3718 0.5645 0.7595 0.037 Uiso 1 1 calc R U . . .
H91C H 0.2959 0.4594 0.8131 0.037 Uiso 1 1 calc R U . . .
Al1 Al 0.19813(4) 0.43127(3) 0.47548(3) 0.01949(10) Uani 1 1 d . . . . .
C10 C 0.31675(15) 0.45437(13) 0.36817(12) 0.0258(3) Uani 1 1 d . . . . .
H10A H 0.4054 0.4998 0.4090 0.031 Uiso 1 1 calc R U . . .
H10B H 0.3409 0.3720 0.3454 0.031 Uiso 1 1 calc R U . . .
C11 C 0.24938(18) 0.52426(16) 0.26004(13) 0.0361(3) Uani 1 1 d . . . . .
H11A H 0.1638 0.4773 0.2153 0.043 Uiso 1 1 calc R U . . .
H11B H 0.3172 0.5321 0.2161 0.043 Uiso 1 1 calc R U . . .
H11C H 0.2249 0.6073 0.2809 0.043 Uiso 1 1 calc R U . . .
C12 C 0.22985(15) 0.28152(12) 0.57002(12) 0.0258(3) Uani 1 1 d . . . . .
H12A H 0.1734 0.2875 0.6232 0.031 Uiso 1 1 calc R U . . .
H12B H 0.1950 0.2067 0.5212 0.031 Uiso 1 1 calc R U . . .
C13 C 0.38668(17) 0.26562(15) 0.63680(16) 0.0395(4) Uani 1 1 d . . . . .
H13A H 0.4447 0.2610 0.5848 0.047 Uiso 1 1 calc R U . . .
H13B H 0.3933 0.1890 0.6775 0.047 Uiso 1 1 calc R U . . .
H13C H 0.4207 0.3369 0.6902 0.047 Uiso 1 1 calc R U . . .
C21 C 0.0905(3) 1.2644(3) 0.8654(2) 0.0695(7) Uani 1 1 d . . . . .
H21 H 0.0037 1.2980 0.8191 0.083 Uiso 1 1 calc R U . . .
C22 C 0.1430(3) 1.1558(2) 0.83075(18) 0.0590(6) Uani 1 1 d . . . . .
H22 H 0.0929 1.1121 0.7594 0.071 Uiso 1 1 calc R U . . .
C23 C 0.2651(3) 1.1108(2) 0.8973(2) 0.0671(6) Uani 1 1 d . . . . .
H23 H 0.3016 1.0347 0.8730 0.080 Uiso 1 1 calc R U . . .
C24 C 0.3363(3) 1.1711(3) 0.9972(3) 0.0776(8) Uani 1 1 d . . . . .
H24 H 0.4234 1.1373 1.0428 0.093 Uiso 1 1 calc R U . . .
C25 C 0.2900(3) 1.2747(3) 1.0341(2) 0.0785(9) Uani 1 1 d . . . . .
H25 H 0.3430 1.3151 1.1064 0.094 Uiso 1 1 calc R U . . .
C26 C 0.1680(4) 1.3258(2) 0.9717(3) 0.0798(9) Uani 1 1 d . . . . .
H26 H 0.1347 1.4021 0.9989 0.096 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 C1 1.8118(13) . ?
P1 C4 1.8375(13) . ?
P1 Al1 2.5183(5) 2_566 ?
P1 H1 1.320(17) . ?
C1 C2 1.3441(18) . ?
C1 Al1 2.0233(13) . ?
C2 C3 1.5218(17) . ?
C2 H2 0.9600 . ?
C3 C31 1.516(2) . ?
C3 C33 1.520(2) . ?
C3 C32 1.533(2) . ?
C31 H31A 0.9599 . ?
C31 H31B 0.9599 . ?
C31 H31C 0.9599 . ?
C32 H32A 0.9599 . ?
C32 H32B 0.9599 . ?
C32 H32C 0.9599 . ?
C33 H33A 0.9599 . ?
C33 H33B 0.9599 . ?
C33 H33C 0.9599 . ?
C4 C5 1.4091(18) . ?
C4 C9 1.4133(18) . ?
C5 C6 1.3963(19) . ?
C5 C51 1.5049(19) . ?
C51 H51A 0.9599 . ?
C51 H51B 0.9599 . ?
C51 H51C 0.9599 . ?
C6 C7 1.382(2) . ?
C6 H6 0.9600 . ?
C7 C8 1.390(2) . ?
C7 C71 1.509(2) . ?
C71 H71A 0.9599 . ?
C71 H71B 0.9599 . ?
C71 H71C 0.9599 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9600 . ?
C9 C91 1.505(2) . ?
C91 H91A 0.9599 . ?
C91 H91B 0.9599 . ?
C91 H91C 0.9599 . ?
Al1 C12 1.9752(14) . ?
Al1 C10 1.9853(14) . ?
Al1 P1 2.5184(5) 2_566 ?
C10 C11 1.530(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C11 H11A 0.9599 . ?
C11 H11B 0.9599 . ?
C11 H11C 0.9599 . ?
C12 C13 1.526(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C13 H13A 0.9599 . ?
C13 H13B 0.9599 . ?
C13 H13C 0.9599 . ?
C21 C22 1.371(4) . ?
C21 C26 1.421(4) . ?
C21 H21 0.9600 . ?
C22 C23 1.347(4) . ?
C22 H22 0.9600 . ?
C23 C24 1.341(4) . ?
C23 H23 0.9600 . ?
C24 C25 1.310(4) . ?
C24 H24 0.9600 . ?
C25 C26 1.356(4) . ?
C25 H25 0.9600 . ?
C26 H26 0.9600 . ?

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 C4 116.39(6) . . ?
C1 P1 Al1 109.65(4) . 2_566 ?
C4 P1 Al1 127.24(4) . 2_566 ?
C1 P1 H1 98.7(7) . . ?
C4 P1 H1 97.3(7) . . ?
Al1 P1 H1 100.0(7) 2_566 . ?
C2 C1 P1 129.77(10) . . ?
C2 C1 Al1 114.25(9) . . ?
P1 C1 Al1 115.88(7) . . ?
C1 C2 C3 135.96(12) . . ?
C1 C2 H2 112.0 . . ?
C3 C2 H2 112.0 . . ?
C31 C3 C33 110.03(15) . . ?
C31 C3 C2 113.78(12) . . ?
C33 C3 C2 108.40(12) . . ?
C31 C3 C32 107.07(13) . . ?
C33 C3 C32 109.80(15) . . ?
C2 C3 C32 107.68(12) . . ?
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 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C3 C33 H33A 109.5 . . ?
C3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C5 C4 C9 119.60(12) . . ?
C5 C4 P1 121.68(10) . . ?
C9 C4 P1 118.67(10) . . ?
C6 C5 C4 118.77(13) . . ?
C6 C5 C51 116.96(12) . . ?
C4 C5 C51 124.26(12) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C7 C6 C5 122.43(13) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 C7 C8 118.03(13) . . ?
C6 C7 C71 120.82(15) . . ?
C8 C7 C71 121.15(15) . . ?
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 . . ?
C7 C8 C9 122.12(13) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C4 119.04(13) . . ?
C8 C9 C91 118.39(13) . . ?
C4 C9 C91 122.56(12) . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C12 Al1 C10 117.75(6) . . ?
C12 Al1 C1 116.36(6) . . ?
C10 Al1 C1 111.24(6) . . ?
C12 Al1 P1 105.95(4) . 2_566 ?
C10 Al1 P1 105.95(4) . 2_566 ?
C1 Al1 P1 96.54(4) . 2_566 ?
C11 C10 Al1 116.81(10) . . ?
C11 C10 H10A 108.1 . . ?
Al1 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
Al1 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 Al1 114.76(10) . . ?
C13 C12 H12A 108.6 . . ?
Al1 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
Al1 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C22 C21 C26 118.2(2) . . ?
C22 C21 H21 120.9 . . ?
C26 C21 H21 120.9 . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 121.7(3) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 120.9(2) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 118.7(2) . . ?
C25 C26 H26 120.6 . . ?
C21 C26 H26 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 P1 C1 C2 -49.47(14) . . . . ?
Al1 P1 C1 C2 103.97(12) 2_566 . . . ?
C4 P1 C1 Al1 134.48(7) . . . . ?
Al1 P1 C1 Al1 -72.08(7) 2_566 . . . ?
P1 C1 C2 C3 2.9(2) . . . . ?
Al1 C1 C2 C3 178.99(13) . . . . ?
C1 C2 C3 C31 -28.8(2) . . . . ?
C1 C2 C3 C33 94.0(2) . . . . ?
C1 C2 C3 C32 -147.27(17) . . . . ?
C1 P1 C4 C5 125.53(11) . . . . ?
Al1 P1 C4 C5 -22.54(13) 2_566 . . . ?
C1 P1 C4 C9 -56.93(12) . . . . ?
Al1 P1 C4 C9 155.00(9) 2_566 . . . ?
C9 C4 C5 C6 0.11(19) . . . . ?
P1 C4 C5 C6 177.63(10) . . . . ?
C9 C4 C5 C51 179.32(13) . . . . ?
P1 C4 C5 C51 -3.16(19) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C51 C5 C6 C7 -179.19(14) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C5 C6 C7 C71 178.66(14) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C71 C7 C8 C9 -178.56(15) . . . . ?
C7 C8 C9 C4 -0.3(2) . . . . ?
C7 C8 C9 C91 179.07(14) . . . . ?
C5 C4 C9 C8 0.0(2) . . . . ?
P1 C4 C9 C8 -177.62(11) . . . . ?
C5 C4 C9 C91 -179.32(13) . . . . ?
P1 C4 C9 C91 3.08(18) . . . . ?
C26 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C24 C25 C26 C21 0.4(4) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    'Air-sensitive, Hygroscopic'
