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

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

data_AX0621
_database_code_depnum_ccdc_archive 'CCDC 1405811'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H41 N3 P2'
_chemical_formula_weight         469.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.1928(5)
_cell_length_b                   18.7757(6)
_cell_length_c                   11.8910(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.0964(9)
_cell_angle_gamma                90
_cell_volume                     2645.17(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.85

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.429
_exptl_crystal_size_min          0.225
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            60871
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.719
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6395
_reflns_number_gt                5451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+2.4653P] 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         6395
_refine_ls_number_parameters     292
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.23911(18) 0.65850(11) 1.05199(17) 0.0355(4) Uani 1 1 d . . . . .
H1A H 0.2935 0.6969 1.0654 0.053 Uiso 1 1 calc R U . . .
H1B H 0.2796 0.6136 1.0833 0.053 Uiso 1 1 calc R U . . .
H1C H 0.1941 0.6694 1.0969 0.053 Uiso 1 1 calc R U . . .
C2 C 0.09413(14) 0.71447(9) 0.85702(16) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.0415 0.6995 0.7699 0.028 Uiso 1 1 calc R U . . .
C3 C 0.16005(14) 0.77853(9) 0.84441(17) 0.0259(3) Uani 1 1 d . . . . .
H3A H 0.2132 0.7956 0.9287 0.031 Uiso 1 1 calc R U . . .
H3B H 0.2046 0.7640 0.7996 0.031 Uiso 1 1 calc R U . . .
C4 C 0.07959(16) 0.83869(10) 0.77274(18) 0.0309(4) Uani 1 1 d . . . . .
H4A H 0.1240 0.8805 0.7696 0.037 Uiso 1 1 calc R U . . .
H4B H 0.0321 0.8231 0.6856 0.037 Uiso 1 1 calc R U . . .
C5 C 0.00385(16) 0.86019(10) 0.83382(19) 0.0326(4) Uani 1 1 d . . . . .
H5A H 0.0505 0.8806 0.9177 0.039 Uiso 1 1 calc R U . . .
H5B H -0.0501 0.8972 0.7823 0.039 Uiso 1 1 calc R U . . .
C6 C -0.06069(16) 0.79600(11) 0.8464(2) 0.0354(4) Uani 1 1 d . . . . .
H6A H -0.1124 0.7782 0.7621 0.042 Uiso 1 1 calc R U . . .
H6B H -0.1068 0.8103 0.8896 0.042 Uiso 1 1 calc R U . . .
C7 C 0.02022(16) 0.73683(10) 0.9203(2) 0.0314(4) Uani 1 1 d . . . . .
H7A H -0.0234 0.6953 0.9261 0.038 Uiso 1 1 calc R U . . .
H7B H 0.0687 0.7536 1.0063 0.038 Uiso 1 1 calc R U . . .
C8 C 0.20450(13) 0.51143(9) 0.90358(15) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.13611(16) 0.49581(10) 0.96268(18) 0.0303(4) Uani 1 1 d . . . . .
H9 H 0.0889 0.5319 0.9702 0.036 Uiso 1 1 calc R U . . .
C10 C 0.13610(18) 0.42839(11) 1.01063(19) 0.0350(4) Uani 1 1 d . . . . .
H10 H 0.0890 0.4188 1.0505 0.042 Uiso 1 1 calc R U . . .
C11 C 0.20420(17) 0.37514(10) 1.00081(19) 0.0336(4) Uani 1 1 d . . . . .
H11 H 0.2044 0.3292 1.0343 0.040 Uiso 1 1 calc R U . . .
C12 C 0.27201(15) 0.38927(10) 0.94191(19) 0.0308(4) Uani 1 1 d . . . . .
H12 H 0.3189 0.3529 0.9347 0.037 Uiso 1 1 calc R U . . .
C13 C 0.27166(14) 0.45675(9) 0.89311(17) 0.0257(3) Uani 1 1 d . . . . .
H13 H 0.3179 0.4658 0.8520 0.031 Uiso 1 1 calc R U . . .
C14 C 0.42483(14) 0.60085(11) 0.95505(16) 0.0289(4) Uani 1 1 d . . . . .
H14A H 0.4358 0.6441 1.0053 0.043 Uiso 1 1 calc R U . . .
H14B H 0.4907 0.5934 0.9387 0.043 Uiso 1 1 calc R U . . .
H14C H 0.4157 0.5598 1.0008 0.043 Uiso 1 1 calc R U . . .
C15 C 0.44733(14) 0.68519(9) 0.74292(16) 0.0251(3) Uani 1 1 d . . . . .
C16 C 0.51689(16) 0.68242(11) 0.68204(19) 0.0329(4) Uani 1 1 d . . . . .
H16 H 0.5070 0.6453 0.6239 0.039 Uiso 1 1 calc R U . . .
C17 C 0.60035(19) 0.73334(12) 0.7055(2) 0.0428(5) Uani 1 1 d . . . . .
H17 H 0.6477 0.7304 0.6642 0.051 Uiso 1 1 calc R U . . .
C18 C 0.61462(19) 0.78804(12) 0.7882(2) 0.0450(5) Uani 1 1 d . . . . .
H18 H 0.6715 0.8229 0.8039 0.054 Uiso 1 1 calc R U . . .
C19 C 0.54581(18) 0.79209(11) 0.8484(2) 0.0409(5) Uani 1 1 d . . . . .
H19 H 0.5554 0.8299 0.9054 0.049 Uiso 1 1 calc R U . . .
C20 C 0.46265(16) 0.74116(10) 0.82602(18) 0.0315(4) Uani 1 1 d . . . . .
H20 H 0.4158 0.7445 0.8677 0.038 Uiso 1 1 calc R U . . .
C21 C 0.46938(18) 0.51398(11) 0.7266(2) 0.0354(4) Uani 1 1 d . . . . .
H21A H 0.4465 0.4766 0.7682 0.053 Uiso 1 1 calc R U . . .
H21B H 0.5244 0.5454 0.7898 0.053 Uiso 1 1 calc R U . . .
H21C H 0.5035 0.4922 0.6765 0.053 Uiso 1 1 calc R U . . .
N1 N 0.16446(12) 0.65186(8) 0.91782(13) 0.0241(3) Uani 1 1 d . . . . .
N2 N 0.32286(11) 0.60874(8) 0.83510(13) 0.0224(3) Uani 1 1 d . . . . .
N3 N 0.37074(13) 0.55526(9) 0.64515(16) 0.0328(4) Uani 1 1 d . . . . .
P1 P 0.18860(3) 0.59628(2) 0.82091(4) 0.01977(11) Uani 1 1 d . . . . .
P2 P 0.32447(4) 0.62649(3) 0.69419(4) 0.02371(12) Uani 1 1 d . . . . .
C22 C 0.28364(16) 0.52208(11) 0.52980(18) 0.0350(4) Uani 1 1 d D . . . .
H22 H 0.2326 0.5617 0.4809 0.042 Uiso 1 1 calc R U . . .
C23 C 0.20903(17) 0.46870(11) 0.55433(18) 0.0341(4) Uani 1 1 d . . . . .
H23A H 0.2568 0.4307 0.6102 0.041 Uiso 1 1 calc R U . . .
H23B H 0.1695 0.4930 0.5976 0.041 Uiso 1 1 calc R U . . .
C24 C 0.12238(19) 0.43548(13) 0.4338(2) 0.0468(6) Uani 1 1 d D . . . .
H24A H 0.0828 0.3968 0.4550 0.056 Uiso 1 1 calc R U . . .
H24B H 0.0656 0.4720 0.3859 0.056 Uiso 1 1 calc R U . . .
C25 C 0.1728(2) 0.40549(14) 0.3517(2) 0.0578(7) Uani 1 1 d D . . . .
H25A H 0.1114 0.3902 0.2707 0.069 Uiso 1 1 calc R U . . .
H25B H 0.2190 0.3631 0.3927 0.069 Uiso 1 1 calc R U . . .
C26 C 0.2463(2) 0.46051(14) 0.3279(2) 0.0456(5) Uani 1 1 d . . . . .
H26A H 0.2844 0.4377 0.2818 0.055 Uiso 1 1 calc R U . . .
H26B H 0.1976 0.4991 0.2746 0.055 Uiso 1 1 calc R U . . .
C27 C 0.33415(19) 0.49233(15) 0.4477(2) 0.0480(6) Uani 1 1 d D . . . .
H27A H 0.3743 0.5309 0.4270 0.058 Uiso 1 1 calc R U . . .
H27B H 0.3902 0.4552 0.4948 0.058 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
C1 N1 1.466(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.475(2) . ?
C2 C7 1.529(2) . ?
C2 C3 1.530(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.527(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.397(2) . ?
C8 C13 1.397(2) . ?
C8 P1 1.8349(17) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.476(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.395(3) . ?
C15 C16 1.398(2) . ?
C15 P2 1.8307(17) . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N3 1.457(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 P1 1.6856(14) . ?
N2 P2 1.7176(14) . ?
N2 P1 1.7198(14) . ?
N3 C22 1.484(2) . ?
N3 P2 1.6778(17) . ?
C22 C27 1.5100(17) . ?
C22 C23 1.520(3) . ?
C22 H22 1.0000 . ?
C23 C24 1.519(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5117(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.526(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.509(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C7 112.18(14) . . ?
N1 C2 C3 114.36(14) . . ?
C7 C2 C3 110.20(14) . . ?
N1 C2 H2 106.5 . . ?
C7 C2 H2 106.5 . . ?
C3 C2 H2 106.5 . . ?
C4 C3 C2 110.53(14) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.72(15) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 110.46(15) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 110.74(15) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C2 110.71(16) . . ?
C6 C7 H7A 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C13 117.77(16) . . ?
C9 C8 P1 120.32(13) . . ?
C13 C8 P1 121.19(13) . . ?
C10 C9 C8 120.98(17) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.46(18) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.54(18) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.08(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 121.16(16) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.13(17) . . ?
C20 C15 P2 120.66(14) . . ?
C16 C15 P2 120.35(14) . . ?
C17 C16 C15 120.87(19) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.75(19) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.67(18) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C2 116.25(14) . . ?
C1 N1 P1 123.93(12) . . ?
C2 N1 P1 115.19(11) . . ?
C14 N2 P2 124.41(11) . . ?
C14 N2 P1 122.87(12) . . ?
P2 N2 P1 112.63(8) . . ?
C21 N3 C22 119.53(16) . . ?
C21 N3 P2 123.24(13) . . ?
C22 N3 P2 113.81(13) . . ?
N1 P1 N2 110.17(7) . . ?
N1 P1 C8 100.53(7) . . ?
N2 P1 C8 101.27(7) . . ?
N3 P2 N2 110.30(8) . . ?
N3 P2 C15 100.55(8) . . ?
N2 P2 C15 101.38(7) . . ?
N3 C22 C27 111.72(16) . . ?
N3 C22 C23 113.76(16) . . ?
C27 C22 C23 112.78(18) . . ?
N3 C22 H22 105.9 . . ?
C27 C22 H22 105.9 . . ?
C23 C22 H22 105.9 . . ?
C24 C23 C22 111.81(16) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 113.57(19) . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 C26 111.32(19) . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
C26 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C27 C26 C25 112.3(2) . . ?
C27 C26 H26A 109.1 . . ?
C25 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C25 C26 H26B 109.1 . . ?
H26A C26 H26B 107.9 . . ?
C26 C27 C22 112.49(17) . . ?
C26 C27 H27A 109.1 . . ?
C22 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
C22 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 176.17(14) . . . . ?
C7 C2 C3 C4 -56.37(19) . . . . ?
C2 C3 C4 C5 55.9(2) . . . . ?
C3 C4 C5 C6 -55.8(2) . . . . ?
C4 C5 C6 C7 56.6(2) . . . . ?
C5 C6 C7 C2 -58.1(2) . . . . ?
N1 C2 C7 C6 -173.52(15) . . . . ?
C3 C2 C7 C6 57.8(2) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
P1 C8 C9 C10 171.08(15) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C9 C8 C13 C12 -1.1(3) . . . . ?
P1 C8 C13 C12 -171.36(14) . . . . ?
C20 C15 C16 C17 1.1(3) . . . . ?
P2 C15 C16 C17 170.60(17) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C16 C15 C20 C19 -0.8(3) . . . . ?
P2 C15 C20 C19 -170.19(16) . . . . ?
C7 C2 N1 C1 -56.6(2) . . . . ?
C3 C2 N1 C1 69.8(2) . . . . ?
C7 C2 N1 P1 146.50(13) . . . . ?
C3 C2 N1 P1 -87.06(16) . . . . ?
C1 N1 P1 N2 -51.88(17) . . . . ?
C2 N1 P1 N2 103.03(12) . . . . ?
C1 N1 P1 C8 54.39(16) . . . . ?
C2 N1 P1 C8 -150.70(12) . . . . ?
C14 N2 P1 N1 57.84(16) . . . . ?
P2 N2 P1 N1 -125.34(9) . . . . ?
C14 N2 P1 C8 -47.93(15) . . . . ?
P2 N2 P1 C8 128.89(9) . . . . ?
C9 C8 P1 N1 38.49(16) . . . . ?
C13 C8 P1 N1 -151.51(14) . . . . ?
C9 C8 P1 N2 151.74(14) . . . . ?
C13 C8 P1 N2 -38.27(15) . . . . ?
C21 N3 P2 N2 -45.38(17) . . . . ?
C22 N3 P2 N2 113.57(14) . . . . ?
C21 N3 P2 C15 61.04(17) . . . . ?
C22 N3 P2 C15 -140.00(14) . . . . ?
C14 N2 P2 N3 70.64(16) . . . . ?
P1 N2 P2 N3 -106.13(9) . . . . ?
C14 N2 P2 C15 -35.23(16) . . . . ?
P1 N2 P2 C15 148.00(9) . . . . ?
C20 C15 P2 N3 -159.46(15) . . . . ?
C16 C15 P2 N3 31.36(17) . . . . ?
C20 C15 P2 N2 -46.05(16) . . . . ?
C16 C15 P2 N2 144.77(15) . . . . ?
C21 N3 C22 C27 -54.6(3) . . . . ?
P2 N3 C22 C27 145.63(17) . . . . ?
C21 N3 C22 C23 74.5(2) . . . . ?
P2 N3 C22 C23 -85.3(2) . . . . ?
N3 C22 C23 C24 -179.23(18) . . . . ?
C27 C22 C23 C24 -50.7(3) . . . . ?
C22 C23 C24 C25 51.2(3) . . . . ?
C23 C24 C25 C26 -52.1(3) . . . . ?
C24 C25 C26 C27 52.7(3) . . . . ?
C25 C26 C27 C22 -53.2(3) . . . . ?
N3 C22 C27 C26 -178.1(2) . . . . ?
C23 C22 C27 C26 52.3(3) . . . . ?

_refine_diff_density_max         1.339
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.058

_shelxl_version_number           2014-3


_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_AX0636
_database_code_depnum_ccdc_archive 'CCDC 1405812'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H41 Cr N3 O4 P2'
_chemical_formula_weight         633.61

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 '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                   10.8808(3)
_cell_length_b                   16.6923(4)
_cell_length_c                   17.5806(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.4501(7)
_cell_angle_gamma                90
_cell_volume                     3158.42(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.89

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            65359
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7631
_reflns_number_gt                6335
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+2.0803P] 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         7631
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.26408(15) 0.84766(10) 0.02094(9) 0.0222(3) Uani 1 1 d . . . . .
H1 H 0.2323 0.8078 0.0559 0.027 Uiso 1 1 calc R U . . .
C2 C 0.37458(17) 0.80941(13) -0.00869(12) 0.0387(5) Uani 1 1 d . . . . .
H2A H 0.4412 0.7988 0.0349 0.046 Uiso 1 1 calc R U . . .
H2B H 0.4077 0.8466 -0.0446 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3358(2) 0.73085(13) -0.05012(13) 0.0466(5) Uani 1 1 d . . . . .
H3A H 0.4077 0.7080 -0.0711 0.056 Uiso 1 1 calc R U . . .
H3B H 0.3103 0.6920 -0.0128 0.056 Uiso 1 1 calc R U . . .
C4 C 0.22914(18) 0.74320(12) -0.11509(11) 0.0347(4) Uani 1 1 d . . . . .
H4A H 0.2027 0.6908 -0.1383 0.042 Uiso 1 1 calc R U . . .
H4B H 0.2574 0.7770 -0.1555 0.042 Uiso 1 1 calc R U . . .
C5 C 0.11989(17) 0.78319(12) -0.08578(11) 0.0332(4) Uani 1 1 d . . . . .
H5A H 0.0864 0.7471 -0.0491 0.040 Uiso 1 1 calc R U . . .
H5B H 0.0532 0.7934 -0.1294 0.040 Uiso 1 1 calc R U . . .
C6 C 0.15985(15) 0.86217(11) -0.04589(9) 0.0267(4) Uani 1 1 d . . . . .
H6A H 0.0880 0.8871 -0.0264 0.032 Uiso 1 1 calc R U . . .
H6B H 0.1890 0.8995 -0.0832 0.032 Uiso 1 1 calc R U . . .
C7 C 0.32366(19) 0.99191(11) 0.02381(10) 0.0331(4) Uani 1 1 d . . . . .
H7A H 0.3857 0.9792 -0.0095 0.050 Uiso 1 1 calc R U . . .
H7B H 0.3556 1.0344 0.0598 0.050 Uiso 1 1 calc R U . . .
H7C H 0.2469 1.0101 -0.0077 0.050 Uiso 1 1 calc R U . . .
C8 C 0.44240(13) 0.98378(9) 0.18905(9) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.44246(15) 1.05097(10) 0.23532(10) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.3672 1.0685 0.2513 0.029 Uiso 1 1 calc R U . . .
C10 C 0.55197(16) 1.09304(10) 0.25855(11) 0.0290(4) Uani 1 1 d . . . . .
H10 H 0.5510 1.1395 0.2896 0.035 Uiso 1 1 calc R U . . .
C11 C 0.66207(15) 1.06718(10) 0.23643(10) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.7369 1.0958 0.2525 0.032 Uiso 1 1 calc R U . . .
C12 C 0.66350(15) 0.99986(10) 0.19108(10) 0.0255(3) Uani 1 1 d . . . . .
H12 H 0.7393 0.9820 0.1761 0.031 Uiso 1 1 calc R U . . .
C13 C 0.55440(14) 0.95824(10) 0.16743(9) 0.0233(3) Uani 1 1 d . . . . .
H13 H 0.5559 0.9119 0.1362 0.028 Uiso 1 1 calc R U . . .
C14 C 0.12660(16) 1.04431(10) 0.16349(12) 0.0321(4) Uani 1 1 d . . . . .
H14A H 0.0373 1.0361 0.1476 0.048 Uiso 1 1 calc R U . . .
H14B H 0.1642 1.0638 0.1196 0.048 Uiso 1 1 calc R U . . .
H14C H 0.1395 1.0838 0.2051 0.048 Uiso 1 1 calc R U . . .
C15 C -0.02054(13) 0.86762(9) 0.19125(9) 0.0181(3) Uani 1 1 d . . . . .
C16 C -0.03989(15) 0.87482(10) 0.11169(9) 0.0245(3) Uani 1 1 d . . . . .
H16 H 0.0182 0.9036 0.0869 0.029 Uiso 1 1 calc R U . . .
C17 C -0.14306(17) 0.84048(11) 0.06797(10) 0.0304(4) Uani 1 1 d . . . . .
H17 H -0.1545 0.8451 0.0135 0.036 Uiso 1 1 calc R U . . .
C18 C -0.22893(16) 0.79960(10) 0.10351(11) 0.0323(4) Uani 1 1 d . . . . .
H18 H -0.3000 0.7766 0.0737 0.039 Uiso 1 1 calc R U . . .
C19 C -0.21137(16) 0.79225(11) 0.18256(11) 0.0302(4) Uani 1 1 d . . . . .
H19 H -0.2708 0.7644 0.2071 0.036 Uiso 1 1 calc R U . . .
C20 C -0.10706(15) 0.82538(10) 0.22630(10) 0.0238(3) Uani 1 1 d . . . . .
H20 H -0.0947 0.8191 0.2806 0.029 Uiso 1 1 calc R U . . .
C21 C -0.02349(16) 0.98939(12) 0.32153(11) 0.0327(4) Uani 1 1 d . . . . .
H21A H -0.0659 0.9793 0.3661 0.049 Uiso 1 1 calc R U . . .
H21B H -0.0808 0.9790 0.2741 0.049 Uiso 1 1 calc R U . . .
H21C H 0.0040 1.0453 0.3222 0.049 Uiso 1 1 calc R U . . .
C22 C 0.17783(14) 0.94310(10) 0.39484(9) 0.0219(3) Uani 1 1 d . . . . .
H22 H 0.2494 0.9082 0.3866 0.026 Uiso 1 1 calc R U . . .
C23 C 0.12994(17) 0.91152(11) 0.46615(10) 0.0308(4) Uani 1 1 d . . . . .
H23A H 0.1010 0.8556 0.4571 0.037 Uiso 1 1 calc R U . . .
H23B H 0.0584 0.9443 0.4765 0.037 Uiso 1 1 calc R U . . .
C24 C 0.2318(2) 0.91430(12) 0.53573(11) 0.0381(5) Uani 1 1 d . . . . .
H24A H 0.1970 0.8973 0.5821 0.046 Uiso 1 1 calc R U . . .
H24B H 0.2986 0.8762 0.5279 0.046 Uiso 1 1 calc R U . . .
C25 C 0.28669(19) 0.99806(12) 0.54857(10) 0.0355(4) Uani 1 1 d . . . . .
H25A H 0.2227 1.0348 0.5632 0.043 Uiso 1 1 calc R U . . .
H25B H 0.3567 0.9967 0.5914 0.043 Uiso 1 1 calc R U . . .
C26 C 0.33240(17) 1.02927(12) 0.47674(10) 0.0337(4) Uani 1 1 d . . . . .
H26A H 0.4027 0.9959 0.4654 0.040 Uiso 1 1 calc R U . . .
H26B H 0.3628 1.0849 0.4857 0.040 Uiso 1 1 calc R U . . .
C27 C 0.22924(17) 1.02776(11) 0.40811(10) 0.0308(4) Uani 1 1 d . . . . .
H27A H 0.2621 1.0465 0.3616 0.037 Uiso 1 1 calc R U . . .
H27B H 0.1617 1.0645 0.4176 0.037 Uiso 1 1 calc R U . . .
C28 C 0.18387(14) 0.74237(9) 0.17311(9) 0.0204(3) Uani 1 1 d . . . . .
C29 C 0.41995(15) 0.74518(10) 0.21491(10) 0.0235(3) Uani 1 1 d . . . . .
C30 C 0.25158(15) 0.74653(9) 0.32294(9) 0.0236(3) Uani 1 1 d . . . . .
C31 C 0.40923(14) 0.85919(9) 0.31370(9) 0.0214(3) Uani 1 1 d . . . . .
Cr1 Cr 0.29101(2) 0.80707(2) 0.24139(2) 0.01560(6) Uani 1 1 d . . . . .
N1 N 0.29794(13) 0.92045(8) 0.06678(8) 0.0236(3) Uani 1 1 d . . . . .
N2 N 0.18465(12) 0.96819(8) 0.19050(8) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.08487(12) 0.93621(8) 0.32481(8) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.12183(12) 0.69900(7) 0.13399(7) 0.0310(3) Uani 1 1 d . . . . .
O2 O 0.49906(12) 0.70620(8) 0.19778(9) 0.0393(3) Uani 1 1 d . . . . .
O3 O 0.22576(14) 0.71259(8) 0.37560(8) 0.0380(3) Uani 1 1 d . . . . .
O4 O 0.48416(11) 0.88694(8) 0.35850(7) 0.0325(3) Uani 1 1 d . . . . .
P1 P 0.30779(3) 0.91949(2) 0.16213(2) 0.01667(9) Uani 1 1 d . . . . .
P2 P 0.12796(3) 0.89760(2) 0.24583(2) 0.01647(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.475(2) . ?
C1 C2 1.519(2) . ?
C1 C6 1.528(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.529(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.518(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.526(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.461(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.385(2) . ?
C8 C13 1.395(2) . ?
C8 P1 1.8213(15) . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.467(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.389(2) . ?
C15 C20 1.391(2) . ?
C15 P2 1.8238(15) . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N3 1.470(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N3 1.4785(19) . ?
C22 C23 1.521(2) . ?
C22 C27 1.525(2) . ?
C22 H22 1.0000 . ?
C23 C24 1.526(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.524(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.516(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.523(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 O1 1.1474(19) . ?
C28 Cr1 1.8854(16) . ?
C29 O2 1.154(2) . ?
C29 Cr1 1.8558(16) . ?
C30 O3 1.155(2) . ?
C30 Cr1 1.8552(17) . ?
C31 O4 1.1451(19) . ?
C31 Cr1 1.8833(16) . ?
Cr1 P2 2.3406(4) . ?
Cr1 P1 2.3603(4) . ?
N1 P1 1.6639(14) . ?
N2 P2 1.7004(13) . ?
N2 P1 1.7033(13) . ?
N3 P2 1.6597(14) . ?
P1 P2 2.6409(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 112.76(14) . . ?
N1 C1 C6 112.79(13) . . ?
C2 C1 C6 109.77(14) . . ?
N1 C1 H1 107.1 . . ?
C2 C1 H1 107.1 . . ?
C6 C1 H1 107.1 . . ?
C1 C2 C3 110.28(16) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 111.65(17) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 110.76(16) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 110.57(15) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C1 110.22(14) . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.83(14) . . ?
C9 C8 P1 124.09(12) . . ?
C13 C8 P1 116.76(12) . . ?
C8 C9 C10 120.48(15) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.00(16) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.07(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.00(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.60(15) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.54(14) . . ?
C16 C15 P2 119.85(12) . . ?
C20 C15 P2 120.74(12) . . ?
C17 C16 C15 120.84(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.03(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.84(16) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.21(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.52(16) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 112.58(13) . . ?
N3 C22 C27 112.96(14) . . ?
C23 C22 C27 110.95(14) . . ?
N3 C22 H22 106.6 . . ?
C23 C22 H22 106.6 . . ?
C27 C22 H22 106.6 . . ?
C22 C23 C24 110.71(15) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C25 C24 C23 111.67(16) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
C26 C25 C24 111.18(16) . . ?
C26 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 111.13(15) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 C22 110.35(15) . . ?
C26 C27 H27A 109.6 . . ?
C22 C27 H27A 109.6 . . ?
C26 C27 H27B 109.6 . . ?
C22 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
O1 C28 Cr1 175.81(14) . . ?
O2 C29 Cr1 179.14(16) . . ?
O3 C30 Cr1 176.37(14) . . ?
O4 C31 Cr1 176.29(14) . . ?
C30 Cr1 C29 99.20(7) . . ?
C30 Cr1 C31 86.70(7) . . ?
C29 Cr1 C31 87.71(7) . . ?
C30 Cr1 C28 89.34(7) . . ?
C29 Cr1 C28 86.61(7) . . ?
C31 Cr1 C28 172.48(7) . . ?
C30 Cr1 P2 93.63(5) . . ?
C29 Cr1 P2 166.53(5) . . ?
C31 Cr1 P2 97.19(5) . . ?
C28 Cr1 P2 89.44(5) . . ?
C30 Cr1 P1 159.40(5) . . ?
C29 Cr1 P1 99.65(5) . . ?
C31 Cr1 P1 85.81(5) . . ?
C28 Cr1 P1 100.01(5) . . ?
P2 Cr1 P1 68.357(15) . . ?
C7 N1 C1 116.21(13) . . ?
C7 N1 P1 122.68(11) . . ?
C1 N1 P1 121.10(11) . . ?
C14 N2 P2 127.62(11) . . ?
C14 N2 P1 129.68(12) . . ?
P2 N2 P1 101.77(7) . . ?
C21 N3 C22 115.61(13) . . ?
C21 N3 P2 121.68(11) . . ?
C22 N3 P2 118.95(10) . . ?
N1 P1 N2 110.70(7) . . ?
N1 P1 C8 100.74(7) . . ?
N2 P1 C8 106.25(7) . . ?
N1 P1 Cr1 127.10(5) . . ?
N2 P1 Cr1 94.25(5) . . ?
C8 P1 Cr1 116.36(5) . . ?
N1 P1 P2 128.27(5) . . ?
N2 P1 P2 39.08(4) . . ?
C8 P1 P2 124.76(5) . . ?
Cr1 P1 P2 55.467(13) . . ?
N3 P2 N2 112.35(7) . . ?
N3 P2 C15 102.09(7) . . ?
N2 P2 C15 104.89(7) . . ?
N3 P2 Cr1 125.97(5) . . ?
N2 P2 Cr1 95.04(5) . . ?
C15 P2 Cr1 115.00(5) . . ?
N3 P2 P1 137.39(5) . . ?
N2 P2 P1 39.15(4) . . ?
C15 P2 P1 114.61(5) . . ?
Cr1 P2 P1 56.177(13) . . ?

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 C1 C2 C3 175.47(15) . . . . ?
C6 C1 C2 C3 -57.9(2) . . . . ?
C1 C2 C3 C4 56.4(2) . . . . ?
C2 C3 C4 C5 -55.3(2) . . . . ?
C3 C4 C5 C6 56.2(2) . . . . ?
C4 C5 C6 C1 -58.4(2) . . . . ?
N1 C1 C6 C5 -174.07(14) . . . . ?
C2 C1 C6 C5 59.28(19) . . . . ?
C13 C8 C9 C10 1.2(2) . . . . ?
P1 C8 C9 C10 174.52(13) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 -0.7(2) . . . . ?
P1 C8 C13 C12 -174.54(13) . . . . ?
C20 C15 C16 C17 -0.2(2) . . . . ?
P2 C15 C16 C17 169.23(13) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C15 1.3(3) . . . . ?
C16 C15 C20 C19 -1.0(2) . . . . ?
P2 C15 C20 C19 -170.26(13) . . . . ?
N3 C22 C23 C24 175.95(14) . . . . ?
C27 C22 C23 C24 -56.3(2) . . . . ?
C22 C23 C24 C25 54.8(2) . . . . ?
C23 C24 C25 C26 -54.6(2) . . . . ?
C24 C25 C26 C27 55.7(2) . . . . ?
C25 C26 C27 C22 -57.2(2) . . . . ?
N3 C22 C27 C26 -174.94(14) . . . . ?
C23 C22 C27 C26 57.55(19) . . . . ?
C2 C1 N1 C7 74.12(19) . . . . ?
C6 C1 N1 C7 -50.9(2) . . . . ?
C2 C1 N1 P1 -105.01(16) . . . . ?
C6 C1 N1 P1 129.95(13) . . . . ?
C23 C22 N3 C21 69.30(19) . . . . ?
C27 C22 N3 C21 -57.3(2) . . . . ?
C23 C22 N3 P2 -132.15(13) . . . . ?
C27 C22 N3 P2 101.21(15) . . . . ?
C7 N1 P1 N2 74.50(15) . . . . ?
C1 N1 P1 N2 -106.43(13) . . . . ?
C7 N1 P1 C8 -37.60(15) . . . . ?
C1 N1 P1 C8 141.47(12) . . . . ?
C7 N1 P1 Cr1 -172.85(12) . . . . ?
C1 N1 P1 Cr1 6.22(15) . . . . ?
C7 N1 P1 P2 115.13(13) . . . . ?
C1 N1 P1 P2 -65.81(14) . . . . ?
C14 N2 P1 N1 -43.62(16) . . . . ?
P2 N2 P1 N1 125.81(7) . . . . ?
C14 N2 P1 C8 64.90(16) . . . . ?
P2 N2 P1 C8 -125.67(7) . . . . ?
C14 N2 P1 Cr1 -176.06(14) . . . . ?
P2 N2 P1 Cr1 -6.63(6) . . . . ?
C14 N2 P1 P2 -169.43(19) . . . . ?
C9 C8 P1 N1 125.59(14) . . . . ?
C13 C8 P1 N1 -60.96(13) . . . . ?
C9 C8 P1 N2 10.12(15) . . . . ?
C13 C8 P1 N2 -176.43(12) . . . . ?
C9 C8 P1 Cr1 -93.21(14) . . . . ?
C13 C8 P1 Cr1 80.24(13) . . . . ?
C9 C8 P1 P2 -28.44(16) . . . . ?
C13 C8 P1 P2 145.01(10) . . . . ?
C21 N3 P2 N2 68.83(15) . . . . ?
C22 N3 P2 N2 -88.37(13) . . . . ?
C21 N3 P2 C15 -43.03(15) . . . . ?
C22 N3 P2 C15 159.77(12) . . . . ?
C21 N3 P2 Cr1 -176.61(11) . . . . ?
C22 N3 P2 Cr1 26.19(15) . . . . ?
C21 N3 P2 P1 106.51(13) . . . . ?
C22 N3 P2 P1 -50.69(15) . . . . ?
C14 N2 P2 N3 -51.22(16) . . . . ?
P1 N2 P2 N3 139.05(7) . . . . ?
C14 N2 P2 C15 58.88(16) . . . . ?
P1 N2 P2 C15 -110.85(7) . . . . ?
C14 N2 P2 Cr1 176.43(14) . . . . ?
P1 N2 P2 Cr1 6.69(6) . . . . ?
C14 N2 P2 P1 169.74(19) . . . . ?
C16 C15 P2 N3 143.89(13) . . . . ?
C20 C15 P2 N3 -46.95(14) . . . . ?
C16 C15 P2 N2 26.53(14) . . . . ?
C20 C15 P2 N2 -164.30(13) . . . . ?
C16 C15 P2 Cr1 -76.42(13) . . . . ?
C20 C15 P2 Cr1 92.74(13) . . . . ?
C16 C15 P2 P1 -13.93(14) . . . . ?
C20 C15 P2 P1 155.23(11) . . . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3


_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_AX0648
_database_code_depnum_ccdc_archive 'CCDC 1405813'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H37 N3 P2'
_chemical_formula_weight         429.50

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

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

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

_cell_length_a                   28.2829(8)
_cell_length_b                   9.4907(3)
_cell_length_c                   18.7206(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.0550(6)
_cell_angle_gamma                90
_cell_volume                     4804.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9741
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.91

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.309
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            41117
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.274
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5809
_reflns_number_gt                5145
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+3.8517P] 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         5809
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.80179(5) 0.83363(15) 0.09887(8) 0.0314(3) Uani 1 1 d . . . . .
H1A H 0.7842 0.8115 0.0467 0.047 Uiso 1 1 calc R U . . .
H1B H 0.8039 0.9361 0.1055 0.047 Uiso 1 1 calc R U . . .
H1C H 0.7839 0.7931 0.1315 0.047 Uiso 1 1 calc R U . . .
C2 C 0.85211(5) 0.62105(13) 0.10845(7) 0.0279(3) Uani 1 1 d . . . . .
H2A H 0.8277 0.5778 0.1304 0.033 Uiso 1 1 calc R U . . .
H2B H 0.8852 0.5844 0.1359 0.033 Uiso 1 1 calc R U . . .
C3 C 0.83998(5) 0.57794(15) 0.02674(7) 0.0340(3) Uani 1 1 d . . . . .
H3A H 0.8083 0.6196 -0.0014 0.051 Uiso 1 1 calc R U . . .
H3B H 0.8378 0.4750 0.0228 0.051 Uiso 1 1 calc R U . . .
H3C H 0.8661 0.6114 0.0062 0.051 Uiso 1 1 calc R U . . .
C4 C 0.90353(4) 1.02193(12) 0.14167(6) 0.0199(2) Uani 1 1 d . . . . .
C5 C 0.93441(5) 1.12266(13) 0.18666(7) 0.0252(2) Uani 1 1 d . . . . .
H5 H 0.9491 1.1035 0.2382 0.030 Uiso 1 1 calc R U . . .
C6 C 0.94392(5) 1.25001(14) 0.15726(8) 0.0312(3) Uani 1 1 d . . . . .
H6 H 0.9654 1.3166 0.1886 0.037 Uiso 1 1 calc R U . . .
C7 C 0.92227(5) 1.28048(15) 0.08247(8) 0.0332(3) Uani 1 1 d . . . . .
H7 H 0.9287 1.3678 0.0624 0.040 Uiso 1 1 calc R U . . .
C8 C 0.89115(6) 1.18292(15) 0.03715(7) 0.0328(3) Uani 1 1 d . . . . .
H8 H 0.8757 1.2042 -0.0140 0.039 Uiso 1 1 calc R U . . .
C9 C 0.88241(5) 1.05400(14) 0.06609(7) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.8618 0.9867 0.0341 0.032 Uiso 1 1 calc R U . . .
C10 C 0.92212(4) 0.81109(12) 0.33080(6) 0.0182(2) Uani 1 1 d . . . . .
H10 H 0.9066 0.8250 0.3719 0.022 Uiso 1 1 calc R U . . .
C11 C 0.92680(5) 0.65193(13) 0.32095(7) 0.0254(2) Uani 1 1 d . . . . .
H11A H 0.9432 0.6339 0.2819 0.030 Uiso 1 1 calc R U . . .
H11B H 0.8935 0.6090 0.3046 0.030 Uiso 1 1 calc R U . . .
C12 C 0.95697(5) 0.58449(14) 0.39464(7) 0.0305(3) Uani 1 1 d . . . . .
H12A H 0.9392 0.5964 0.4326 0.037 Uiso 1 1 calc R U . . .
H12B H 0.9605 0.4823 0.3870 0.037 Uiso 1 1 calc R U . . .
C13 C 1.00802(5) 0.65114(16) 0.42295(8) 0.0348(3) Uani 1 1 d . . . . .
H13A H 1.0273 0.6290 0.3879 0.042 Uiso 1 1 calc R U . . .
H13B H 1.0257 0.6105 0.4722 0.042 Uiso 1 1 calc R U . . .
C14 C 1.00455(5) 0.81048(15) 0.43020(7) 0.0304(3) Uani 1 1 d . . . . .
H14A H 1.0382 0.8515 0.4446 0.036 Uiso 1 1 calc R U . . .
H14B H 0.9893 0.8327 0.4702 0.036 Uiso 1 1 calc R U . . .
C15 C 0.97370(4) 0.87664(13) 0.35671(6) 0.0226(2) Uani 1 1 d . . . . .
H15A H 0.9707 0.9793 0.3637 0.027 Uiso 1 1 calc R U . . .
H15B H 0.9906 0.8623 0.3179 0.027 Uiso 1 1 calc R U . . .
C16 C 0.81398(4) 0.90833(12) 0.32583(6) 0.0203(2) Uani 1 1 d . . . . .
C17 C 0.80313(4) 0.76517(13) 0.31534(7) 0.0248(2) Uani 1 1 d . . . . .
H17 H 0.8163 0.7129 0.2823 0.030 Uiso 1 1 calc R U . . .
C18 C 0.77351(5) 0.69714(15) 0.35216(8) 0.0308(3) Uani 1 1 d . . . . .
H18 H 0.7664 0.5996 0.3439 0.037 Uiso 1 1 calc R U . . .
C19 C 0.75436(5) 0.77197(16) 0.40090(8) 0.0337(3) Uani 1 1 d . . . . .
H19 H 0.7341 0.7260 0.4263 0.040 Uiso 1 1 calc R U . . .
C20 C 0.76486(5) 0.91381(16) 0.41231(8) 0.0328(3) Uani 1 1 d . . . . .
H20 H 0.7521 0.9650 0.4462 0.039 Uiso 1 1 calc R U . . .
C21 C 0.79393(5) 0.98227(14) 0.37472(7) 0.0267(3) Uani 1 1 d . . . . .
H21 H 0.8002 1.0803 0.3823 0.032 Uiso 1 1 calc R U . . .
C22 C 0.89865(5) 1.14729(14) 0.39343(7) 0.0318(3) Uani 1 1 d . . . . .
H22A H 0.9318 1.1806 0.3953 0.048 Uiso 1 1 calc R U . . .
H22B H 0.9010 1.0526 0.4151 0.048 Uiso 1 1 calc R U . . .
H22C H 0.8839 1.2116 0.4219 0.048 Uiso 1 1 calc R U . . .
C23 C 0.86090(5) 1.27912(13) 0.27737(8) 0.0289(3) Uani 1 1 d . . . . .
H23A H 0.8483 1.2627 0.2228 0.035 Uiso 1 1 calc R U . . .
H23B H 0.8933 1.3268 0.2876 0.035 Uiso 1 1 calc R U . . .
C24 C 0.82530(6) 1.37515(14) 0.30094(9) 0.0355(3) Uani 1 1 d . . . . .
H24A H 0.7944 1.3246 0.2965 0.053 Uiso 1 1 calc R U . . .
H24B H 0.8185 1.4585 0.2686 0.053 Uiso 1 1 calc R U . . .
H24C H 0.8401 1.4044 0.3529 0.053 Uiso 1 1 calc R U . . .
N1 N 0.85159(4) 0.77446(11) 0.11811(6) 0.0234(2) Uani 1 1 d . . . . .
N2 N 0.88958(3) 0.88135(10) 0.26284(5) 0.01760(19) Uani 1 1 d . . . . .
N3 N 0.86778(4) 1.14294(10) 0.31600(6) 0.0245(2) Uani 1 1 d . . . . .
P1 P 0.90189(2) 0.84521(3) 0.17980(2) 0.01776(8) Uani 1 1 d . . . . .
P2 P 0.84425(2) 1.00069(3) 0.26486(2) 0.01785(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4598(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.4677(16) . ?
C2 C3 1.5221(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.3981(17) . ?
C4 C9 1.3984(16) . ?
C4 P1 1.8287(12) . ?
C5 C6 1.3867(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3841(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3893(18) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 N2 1.4911(13) . ?
C10 C15 1.5282(15) . ?
C10 C11 1.5322(16) . ?
C10 H10 1.0000 . ?
C11 C12 1.5331(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.524(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5310(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.3941(17) . ?
C16 C21 1.3986(16) . ?
C16 P2 1.8378(12) . ?
C17 C18 1.3900(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3904(19) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N3 1.4570(16) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N3 1.4658(16) . ?
C23 C24 1.5164(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 P1 1.6867(10) . ?
N2 P2 1.7194(10) . ?
N2 P1 1.7241(10) . ?
N3 P2 1.6758(10) . ?

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 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 112.52(11) . . ?
N1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 117.83(11) . . ?
C5 C4 P1 118.35(9) . . ?
C9 C4 P1 122.84(9) . . ?
C6 C5 C4 121.09(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 120.26(12) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 119.58(12) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.28(12) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 120.94(12) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
N2 C10 C15 112.43(9) . . ?
N2 C10 C11 113.06(9) . . ?
C15 C10 C11 109.35(9) . . ?
N2 C10 H10 107.2 . . ?
C15 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C10 C11 C12 110.38(10) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.14(11) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 111.35(11) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.19(11) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C10 C15 C14 110.96(10) . . ?
C10 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C10 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C21 117.81(11) . . ?
C17 C16 P2 120.05(9) . . ?
C21 C16 P2 121.28(9) . . ?
C18 C17 C16 121.51(12) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 119.82(13) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.56(12) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.62(12) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.68(12) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C24 112.94(11) . . ?
N3 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N3 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C2 113.26(10) . . ?
C1 N1 P1 125.09(8) . . ?
C2 N1 P1 116.26(8) . . ?
C10 N2 P2 123.59(7) . . ?
C10 N2 P1 116.30(7) . . ?
P2 N2 P1 119.99(5) . . ?
C22 N3 C23 114.83(10) . . ?
C22 N3 P2 127.80(9) . . ?
C23 N3 P2 117.09(8) . . ?
N1 P1 N2 110.11(5) . . ?
N1 P1 C4 102.17(5) . . ?
N2 P1 C4 101.80(5) . . ?
N3 P2 N2 111.69(5) . . ?
N3 P2 C16 102.04(5) . . ?
N2 P2 C16 100.70(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
C9 C4 C5 C6 -0.21(19) . . . . ?
P1 C4 C5 C6 168.77(10) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C7 C8 C9 C4 2.0(2) . . . . ?
C5 C4 C9 C8 -1.20(19) . . . . ?
P1 C4 C9 C8 -169.65(10) . . . . ?
N2 C10 C11 C12 -175.14(10) . . . . ?
C15 C10 C11 C12 58.77(13) . . . . ?
C10 C11 C12 C13 -57.45(15) . . . . ?
C11 C12 C13 C14 54.96(15) . . . . ?
C12 C13 C14 C15 -54.32(15) . . . . ?
N2 C10 C15 C14 175.12(10) . . . . ?
C11 C10 C15 C14 -58.44(13) . . . . ?
C13 C14 C15 C10 56.46(14) . . . . ?
C21 C16 C17 C18 -0.16(18) . . . . ?
P2 C16 C17 C18 -169.69(10) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C21 0.8(2) . . . . ?
C19 C20 C21 C16 -1.4(2) . . . . ?
C17 C16 C21 C20 1.04(18) . . . . ?
P2 C16 C21 C20 170.43(10) . . . . ?
C3 C2 N1 C1 75.49(14) . . . . ?
C3 C2 N1 P1 -129.05(10) . . . . ?
C15 C10 N2 P2 -102.17(10) . . . . ?
C11 C10 N2 P2 133.41(9) . . . . ?
C15 C10 N2 P1 74.01(11) . . . . ?
C11 C10 N2 P1 -50.41(12) . . . . ?
C24 C23 N3 C22 -75.11(15) . . . . ?
C24 C23 N3 P2 110.47(11) . . . . ?
C1 N1 P1 N2 50.68(12) . . . . ?
C2 N1 P1 N2 -101.53(9) . . . . ?
C1 N1 P1 C4 -56.87(12) . . . . ?
C2 N1 P1 C4 150.91(9) . . . . ?
C10 N2 P1 N1 121.46(8) . . . . ?
P2 N2 P1 N1 -62.21(7) . . . . ?
C10 N2 P1 C4 -130.74(8) . . . . ?
P2 N2 P1 C4 45.59(7) . . . . ?
C5 C4 P1 N1 166.66(9) . . . . ?
C9 C4 P1 N1 -24.95(11) . . . . ?
C5 C4 P1 N2 52.81(10) . . . . ?
C9 C4 P1 N2 -138.80(10) . . . . ?
C22 N3 P2 N2 -55.19(13) . . . . ?
C23 N3 P2 N2 118.41(9) . . . . ?
C22 N3 P2 C16 51.63(12) . . . . ?
C23 N3 P2 C16 -134.78(10) . . . . ?
C10 N2 P2 N3 61.11(10) . . . . ?
P1 N2 P2 N3 -114.94(7) . . . . ?
C10 N2 P2 C16 -46.57(10) . . . . ?
P1 N2 P2 C16 137.38(6) . . . . ?
C17 C16 P2 N3 -159.96(9) . . . . ?
C21 C16 P2 N3 30.89(11) . . . . ?
C17 C16 P2 N2 -44.81(10) . . . . ?
C21 C16 P2 N2 146.03(10) . . . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3


_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_ax0433
_database_code_depnum_ccdc_archive 'CCDC 1405814'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H33 N3 P2'
_chemical_formula_weight         389.44

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   19.6420(4)
_cell_length_b                   12.6315(2)
_cell_length_c                   18.2652(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4531.74(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            65452
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5207
_reflns_number_gt                4462
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0343P)²+3.2802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5207
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.82109(10) 0.71687(15) 0.42381(10) 0.0312(4) Uani 1 1 d . . .
C2 C 0.86060(13) 0.8194(2) 0.43160(14) 0.0554(6) Uani 1 1 d . . .
H2A H 0.8819 0.8373 0.3847 0.083 Uiso 1 1 calc R . .
H2B H 0.8959 0.8108 0.4690 0.083 Uiso 1 1 calc R . .
H2C H 0.8295 0.8763 0.4461 0.083 Uiso 1 1 calc R . .
C3 C 0.86876(11) 0.62742(19) 0.40185(13) 0.0474(5) Uani 1 1 d . . .
H3A H 0.8424 0.5624 0.3946 0.071 Uiso 1 1 calc R . .
H3B H 0.9025 0.6162 0.4406 0.071 Uiso 1 1 calc R . .
H3C H 0.8921 0.6461 0.3562 0.071 Uiso 1 1 calc R . .
C4 C 0.78721(13) 0.6892(2) 0.49670(11) 0.0532(6) Uani 1 1 d . . .
H4A H 0.7552 0.7454 0.5103 0.080 Uiso 1 1 calc R . .
H4B H 0.8221 0.6823 0.5348 0.080 Uiso 1 1 calc R . .
H4C H 0.7626 0.6220 0.4918 0.080 Uiso 1 1 calc R . .
C5 C 0.63140(9) 0.76106(14) 0.37735(9) 0.0246(3) Uani 1 1 d . . .
C6 C 0.62400(10) 0.65449(15) 0.39503(10) 0.0318(4) Uani 1 1 d . . .
H6 H 0.6631 0.6103 0.3969 0.038 Uiso 1 1 calc R . .
C7 C 0.56040(10) 0.61199(15) 0.40988(11) 0.0398(5) Uani 1 1 d D . .
H7 H 0.5561 0.5389 0.4213 0.048 Uiso 1 1 calc R . .
C8 C 0.50340(10) 0.67540(16) 0.40809(12) 0.0426(5) Uani 1 1 d D . .
H8 H 0.4598 0.6459 0.4177 0.051 Uiso 1 1 calc R . .
C9 C 0.50965(11) 0.78148(18) 0.39233(13) 0.0432(5) Uani 1 1 d . . .
H9 H 0.4705 0.8256 0.3918 0.052 Uiso 1 1 calc R . .
C10 C 0.57333(10) 0.82391(16) 0.37719(11) 0.0343(4) Uani 1 1 d . . .
H10 H 0.5773 0.8973 0.3665 0.041 Uiso 1 1 calc R . .
C11 C 0.68235(10) 0.76550(13) 0.21902(9) 0.0294(4) Uani 1 1 d . . .
H11A H 0.7196 0.7145 0.2135 0.044 Uiso 1 1 calc R . .
H11B H 0.6708 0.7953 0.1711 0.044 Uiso 1 1 calc R . .
H11C H 0.6424 0.7297 0.2395 0.044 Uiso 1 1 calc R . .
C12 C 0.67316(9) 1.00787(13) 0.17236(9) 0.0238(3) Uani 1 1 d . . .
C13 C 0.60547(9) 1.00406(15) 0.19532(11) 0.0316(4) Uani 1 1 d . . .
H13 H 0.5947 0.9738 0.2415 0.038 Uiso 1 1 calc R . .
C14 C 0.55364(10) 1.04400(16) 0.15146(13) 0.0405(5) Uani 1 1 d . . .
H14 H 0.5078 1.0411 0.1679 0.049 Uiso 1 1 calc R . .
C15 C 0.56834(11) 1.08764(16) 0.08441(12) 0.0412(5) Uani 1 1 d . . .
H15 H 0.5327 1.1140 0.0543 0.049 Uiso 1 1 calc R . .
C16 C 0.63498(11) 1.09311(16) 0.06095(11) 0.0389(5) Uani 1 1 d . . .
H16 H 0.6452 1.1234 0.0146 0.047 Uiso 1 1 calc R . .
C17 C 0.68714(10) 1.05449(14) 0.10479(10) 0.0304(4) Uani 1 1 d . . .
H17 H 0.7330 1.0599 0.0885 0.036 Uiso 1 1 calc R . .
C18 C 0.86944(9) 0.90563(15) 0.17768(10) 0.0310(4) Uani 1 1 d . . .
C19 C 0.90105(11) 0.90385(18) 0.10106(12) 0.0442(5) Uani 1 1 d . . .
H19A H 0.8794 0.8482 0.0718 0.066 Uiso 1 1 calc R . .
H19B H 0.9500 0.8896 0.1050 0.066 Uiso 1 1 calc R . .
H19C H 0.8940 0.9726 0.0774 0.066 Uiso 1 1 calc R . .
C20 C 0.90019(11) 0.9941(2) 0.22252(16) 0.0577(7) Uani 1 1 d . . .
H20A H 0.8892 1.0624 0.1998 0.086 Uiso 1 1 calc R . .
H20B H 0.9497 0.9854 0.2245 0.086 Uiso 1 1 calc R . .
H20C H 0.8816 0.9921 0.2723 0.086 Uiso 1 1 calc R . .
C21 C 0.88052(11) 0.79875(18) 0.21422(13) 0.0448(5) Uani 1 1 d . . .
H21A H 0.8585 0.7985 0.2623 0.067 Uiso 1 1 calc R . .
H21B H 0.9294 0.7861 0.2202 0.067 Uiso 1 1 calc R . .
H21C H 0.8608 0.7428 0.1837 0.067 Uiso 1 1 calc R . .
N1 N 0.77002(8) 0.72649(12) 0.36491(8) 0.0252(3) Uani 1 1 d . . .
N2 N 0.70366(7) 0.85093(10) 0.26849(7) 0.0220(3) Uani 1 1 d . . .
N3 N 0.79629(8) 0.92761(12) 0.16760(8) 0.0268(3) Uani 1 1 d . . .
P1 P 0.71359(2) 0.82658(3) 0.35999(2) 0.02099(11) Uani 1 1 d . . .
P2 P 0.74116(2) 0.96285(3) 0.23389(2) 0.02086(11) Uani 1 1 d . . .
H1 H 0.7580(12) 0.6696(19) 0.3480(12) 0.039(6) Uiso 1 1 d . . .
H3 H 0.7813(11) 0.8908(18) 0.1327(13) 0.040(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.476(2) . ?
C1 C2 1.516(3) . ?
C1 C3 1.521(3) . ?
C1 C4 1.529(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.390(3) . ?
C5 C6 1.392(2) . ?
C5 P1 1.8418(17) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.3769(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N2 1.468(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.395(2) . ?
C12 C13 1.395(2) . ?
C12 P2 1.8358(17) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 N3 1.475(2) . ?
C18 C20 1.512(3) . ?
C18 C21 1.522(3) . ?
C18 C19 1.531(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 P1 1.6838(15) . ?
N1 H1 0.82(2) . ?
N2 P1 1.7105(14) . ?
N2 P2 1.7148(14) . ?
N3 P2 1.6842(15) . ?
N3 H3 0.84(2) . ?

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 C1 C2 110.24(15) . . ?
N1 C1 C3 106.70(16) . . ?
C2 C1 C3 110.12(19) . . ?
N1 C1 C4 110.96(16) . . ?
C2 C1 C4 109.66(19) . . ?
C3 C1 C4 109.11(17) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 117.86(17) . . ?
C10 C5 P1 117.55(13) . . ?
C6 C5 P1 124.47(14) . . ?
C7 C6 C5 120.93(18) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.18(18) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.93(19) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 121.23(19) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 117.92(16) . . ?
C17 C12 P2 121.95(14) . . ?
C13 C12 P2 119.91(13) . . ?
C14 C13 C12 120.80(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.78(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.23(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.88(18) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N3 C18 C20 108.52(16) . . ?
N3 C18 C21 111.17(16) . . ?
C20 C18 C21 111.18(19) . . ?
N3 C18 C19 106.49(16) . . ?
C20 C18 C19 110.12(18) . . ?
C21 C18 C19 109.26(16) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 P1 123.24(12) . . ?
C1 N1 H1 113.6(16) . . ?
P1 N1 H1 116.7(17) . . ?
C11 N2 P1 120.11(11) . . ?
C11 N2 P2 120.10(11) . . ?
P1 N2 P2 117.34(8) . . ?
C18 N3 P2 125.91(12) . . ?
C18 N3 H3 109.4(15) . . ?
P2 N3 H3 117.7(15) . . ?
N1 P1 N2 105.21(7) . . ?
N1 P1 C5 103.32(8) . . ?
N2 P1 C5 98.57(7) . . ?
N3 P2 N2 108.86(7) . . ?
N3 P2 C12 96.29(8) . . ?
N2 P2 C12 99.70(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C6 C7 1.8(3) . . . . ?
P1 C5 C6 C7 177.66(14) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 C5 0.2(3) . . . . ?
C6 C5 C10 C9 -1.6(3) . . . . ?
P1 C5 C10 C9 -177.71(16) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
P2 C12 C13 C14 175.86(15) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C12 1.2(3) . . . . ?
C13 C12 C17 C16 -1.8(3) . . . . ?
P2 C12 C17 C16 -176.48(15) . . . . ?
C2 C1 N1 P1 -51.5(2) . . . . ?
C3 C1 N1 P1 -171.02(14) . . . . ?
C4 C1 N1 P1 70.2(2) . . . . ?
C20 C18 N3 P2 -48.0(2) . . . . ?
C21 C18 N3 P2 74.6(2) . . . . ?
C19 C18 N3 P2 -166.49(14) . . . . ?
C1 N1 P1 N2 144.95(14) . . . . ?
C1 N1 P1 C5 -112.16(15) . . . . ?
C11 N2 P1 N1 56.32(15) . . . . ?
P2 N2 P1 N1 -105.95(9) . . . . ?
C11 N2 P1 C5 -50.09(14) . . . . ?
P2 N2 P1 C5 147.65(9) . . . . ?
C10 C5 P1 N1 179.80(14) . . . . ?
C6 C5 P1 N1 3.96(17) . . . . ?
C10 C5 P1 N2 -72.25(15) . . . . ?
C6 C5 P1 N2 111.92(15) . . . . ?
C18 N3 P2 N2 -92.07(16) . . . . ?
C18 N3 P2 C12 165.41(15) . . . . ?
C11 N2 P2 N3 -41.27(15) . . . . ?
P1 N2 P2 N3 121.00(9) . . . . ?
C11 N2 P2 C12 58.87(14) . . . . ?
P1 N2 P2 C12 -138.86(9) . . . . ?
C17 C12 P2 N3 -32.77(15) . . . . ?
C13 C12 P2 N3 152.64(15) . . . . ?
C17 C12 P2 N2 -143.19(14) . . . . ?
C13 C12 P2 N2 42.22(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_AX0659
_database_code_depnum_ccdc_archive 'CCDC 1405815'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H33 N3 O2 P2'
_chemical_formula_weight         517.52

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   9.8140(3)
_cell_length_b                   6.7216(2)
_cell_length_c                   20.3460(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.8118(10)
_cell_angle_gamma                90
_cell_volume                     1322.51(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.91

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            32668
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.032
_diffrn_reflns_theta_max         28.948
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6987
_reflns_number_gt                6581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.1945P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.111(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6987
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.3890(2) 0.2759(3) 0.32279(13) 0.0308(5) Uani 1 1 d . . . . .
H1A H 0.3634 0.1592 0.3469 0.046 Uiso 1 1 calc R U . . .
H1B H 0.4853 0.3119 0.3400 0.046 Uiso 1 1 calc R U . . .
H1C H 0.3791 0.2448 0.2751 0.046 Uiso 1 1 calc R U . . .
C2 C 0.15677(19) 0.3949(3) 0.32945(10) 0.0233(4) Uani 1 1 d . . . . .
C3 C 0.0957(2) 0.2354(3) 0.29145(12) 0.0324(5) Uani 1 1 d . . . . .
H3 H 0.1490 0.1595 0.2657 0.039 Uiso 1 1 calc R U . . .
C4 C -0.0422(2) 0.1861(4) 0.29077(13) 0.0408(5) Uani 1 1 d . . . . .
H4 H -0.0817 0.0755 0.2654 0.049 Uiso 1 1 calc R U . . .
C5 C -0.1211(2) 0.2967(4) 0.32667(14) 0.0423(6) Uani 1 1 d . . . . .
H5 H -0.2160 0.2650 0.3249 0.051 Uiso 1 1 calc R U . . .
C6 C -0.0629(2) 0.4550(4) 0.36558(12) 0.0349(5) Uani 1 1 d . . . . .
H6 H -0.1179 0.5313 0.3904 0.042 Uiso 1 1 calc R U . . .
C7 C 0.0761(2) 0.5015(3) 0.36809(10) 0.0261(4) Uani 1 1 d . . . . .
C8 C 0.0668(3) 0.7672(5) 0.44454(19) 0.0602(9) Uani 1 1 d . . . . .
H8A H 0.0020 0.8453 0.4126 0.090 Uiso 1 1 calc R U . . .
H8B H 0.1290 0.8573 0.4733 0.090 Uiso 1 1 calc R U . . .
H8C H 0.0150 0.6865 0.4719 0.090 Uiso 1 1 calc R U . . .
C9 C 0.50103(19) 0.6963(3) 0.38807(9) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.5173(2) 0.5732(3) 0.44389(10) 0.0283(4) Uani 1 1 d . . . . .
H10 H 0.4515 0.4713 0.4469 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6295(2) 0.5980(4) 0.49555(11) 0.0338(5) Uani 1 1 d . . . . .
H11 H 0.6405 0.5113 0.5329 0.041 Uiso 1 1 calc R U . . .
C12 C 0.7239(2) 0.7474(4) 0.49258(11) 0.0323(5) Uani 1 1 d . . . . .
H12 H 0.8003 0.7635 0.5277 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7075(2) 0.8741(3) 0.43828(11) 0.0307(5) Uani 1 1 d . . . . .
H13 H 0.7715 0.9792 0.4367 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5980(2) 0.8484(3) 0.38617(10) 0.0259(4) Uani 1 1 d . . . . .
H14 H 0.5885 0.9349 0.3487 0.031 Uiso 1 1 calc R U . . .
C15 C 0.54311(19) 0.5940(3) 0.24282(10) 0.0240(4) Uani 1 1 d . . . . .
H15A H 0.5160 0.4592 0.2276 0.036 Uiso 1 1 calc R U . . .
H15B H 0.6088 0.5869 0.2848 0.036 Uiso 1 1 calc R U . . .
H15C H 0.5867 0.6614 0.2090 0.036 Uiso 1 1 calc R U . . .
C16 C 0.44607(18) 0.9462(3) 0.14724(9) 0.0185(3) Uani 1 1 d . . . . .
C17 C 0.56123(19) 1.0451(3) 0.18215(10) 0.0222(4) Uani 1 1 d . . . . .
H17 H 0.5807 1.0364 0.2294 0.027 Uiso 1 1 calc R U . . .
C18 C 0.64774(19) 1.1559(3) 0.14894(10) 0.0259(4) Uani 1 1 d . . . . .
H18 H 0.7249 1.2239 0.1735 0.031 Uiso 1 1 calc R U . . .
C19 C 0.6213(2) 1.1672(3) 0.08009(10) 0.0279(4) Uani 1 1 d . . . . .
H19 H 0.6809 1.2413 0.0571 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5077(2) 1.0700(4) 0.04476(11) 0.0297(4) Uani 1 1 d . . . . .
H20 H 0.4893 1.0779 -0.0025 0.036 Uiso 1 1 calc R U . . .
C21 C 0.4201(2) 0.9608(3) 0.07809(10) 0.0235(4) Uani 1 1 d . . . . .
H21 H 0.3419 0.8957 0.0534 0.028 Uiso 1 1 calc R U . . .
C22 C 0.3090(2) 0.5088(3) 0.10814(11) 0.0270(4) Uani 1 1 d . . . . .
H22A H 0.3024 0.3915 0.1360 0.040 Uiso 1 1 calc R U . . .
H22B H 0.4064 0.5434 0.1096 0.040 Uiso 1 1 calc R U . . .
H22C H 0.2662 0.4796 0.0620 0.040 Uiso 1 1 calc R U . . .
C23 C 0.08954(18) 0.6647(3) 0.12504(10) 0.0220(4) Uani 1 1 d . . . . .
C24 C 0.0222(2) 0.6633(4) 0.17959(11) 0.0299(4) Uani 1 1 d . . . . .
H24 H 0.0754 0.6606 0.2232 0.036 Uiso 1 1 calc R U . . .
C25 C -0.1215(2) 0.6658(4) 0.17220(12) 0.0352(5) Uani 1 1 d . . . . .
H25 H -0.1655 0.6669 0.2103 0.042 Uiso 1 1 calc R U . . .
C26 C -0.1989(2) 0.6664(4) 0.10907(12) 0.0347(5) Uani 1 1 d . . . . .
H26 H -0.2970 0.6693 0.1036 0.042 Uiso 1 1 calc R U . . .
C27 C -0.1348(2) 0.6629(3) 0.05357(11) 0.0292(4) Uani 1 1 d . . . . .
H27 H -0.1892 0.6607 0.0102 0.035 Uiso 1 1 calc R U . . .
C28 C 0.00892(19) 0.6626(3) 0.06073(10) 0.0233(4) Uani 1 1 d . . . . .
C29 C 0.0014(2) 0.6552(4) -0.05739(11) 0.0322(5) Uani 1 1 d . . . . .
H29A H -0.0626 0.5424 -0.0605 0.048 Uiso 1 1 calc R U . . .
H29B H 0.0641 0.6376 -0.0896 0.048 Uiso 1 1 calc R U . . .
H29C H -0.0511 0.7787 -0.0673 0.048 Uiso 1 1 calc R U . . .
N1 N 0.29829(16) 0.4431(2) 0.33232(8) 0.0224(3) Uani 1 1 d . . . . .
N2 N 0.41923(15) 0.7065(3) 0.25335(7) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.23687(14) 0.6763(3) 0.13324(8) 0.0212(3) Uani 1 1 d . . . . .
O1 O 0.14470(14) 0.6419(3) 0.40974(8) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.08006(14) 0.6652(3) 0.00861(7) 0.0291(3) Uani 1 1 d . . . . .
P1 P 0.34575(4) 0.68654(7) 0.32400(2) 0.01896(10) Uani 1 1 d . . . . .
P2 P 0.31609(4) 0.83782(7) 0.19162(2) 0.01771(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.467(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.396(3) . ?
C2 C7 1.404(3) . ?
C2 N1 1.418(2) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 O1 1.366(3) . ?
C8 O1 1.408(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.392(3) . ?
C9 C14 1.402(3) . ?
C9 P1 1.8300(19) . ?
C10 C11 1.396(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.478(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.390(3) . ?
C16 C17 1.397(3) . ?
C16 P2 1.8346(18) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N3 1.467(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.385(3) . ?
C23 C28 1.409(3) . ?
C23 N3 1.429(2) . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.393(3) . ?
C27 H27 0.9500 . ?
C28 O2 1.366(2) . ?
C29 O2 1.432(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N1 P1 1.7178(17) . ?
N2 P2 1.7169(16) . ?
N2 P1 1.7198(15) . ?
N3 P2 1.6968(16) . ?

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 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.18(18) . . ?
C3 C2 N1 121.56(19) . . ?
C7 C2 N1 120.18(18) . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
O1 C7 C6 123.7(2) . . ?
O1 C7 C2 115.73(17) . . ?
C6 C7 C2 120.5(2) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 118.17(18) . . ?
C10 C9 P1 121.71(16) . . ?
C14 C9 P1 119.55(16) . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.30(17) . . ?
C21 C16 P2 120.22(14) . . ?
C17 C16 P2 120.60(14) . . ?
C18 C17 C16 121.13(18) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 119.83(18) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.77(18) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.39(19) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.58(18) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 118.35(17) . . ?
C24 C23 N3 121.21(17) . . ?
C28 C23 N3 120.39(17) . . ?
C23 C24 C25 121.74(19) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C26 C25 C24 119.3(2) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 120.39(18) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C28 120.52(19) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
O2 C28 C27 124.14(18) . . ?
O2 C28 C23 116.13(16) . . ?
C27 C28 C23 119.71(19) . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C2 N1 C1 115.62(17) . . ?
C2 N1 P1 119.57(13) . . ?
C1 N1 P1 122.40(13) . . ?
C15 N2 P2 123.64(12) . . ?
C15 N2 P1 123.63(13) . . ?
P2 N2 P1 111.87(8) . . ?
C23 N3 C22 117.13(16) . . ?
C23 N3 P2 116.77(13) . . ?
C22 N3 P2 122.96(12) . . ?
C7 O1 C8 118.20(18) . . ?
C28 O2 C29 117.54(16) . . ?
N1 P1 N2 108.42(8) . . ?
N1 P1 C9 99.83(9) . . ?
N2 P1 C9 100.12(8) . . ?
N3 P2 N2 109.02(8) . . ?
N3 P2 C16 100.58(8) . . ?
N2 P2 C16 101.04(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 1.4(3) . . . . ?
N1 C2 C3 C4 178.0(2) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 -2.0(4) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 O1 -173.5(2) . . . . ?
C5 C6 C7 C2 2.6(3) . . . . ?
C3 C2 C7 O1 173.18(19) . . . . ?
N1 C2 C7 O1 -3.5(3) . . . . ?
C3 C2 C7 C6 -3.3(3) . . . . ?
N1 C2 C7 C6 -179.94(19) . . . . ?
C14 C9 C10 C11 -1.7(3) . . . . ?
P1 C9 C10 C11 -173.00(17) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C9 1.0(3) . . . . ?
C10 C9 C14 C13 0.5(3) . . . . ?
P1 C9 C14 C13 172.01(16) . . . . ?
C21 C16 C17 C18 0.2(3) . . . . ?
P2 C16 C17 C18 -169.09(15) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C17 C16 C21 C20 0.5(3) . . . . ?
P2 C16 C21 C20 169.87(16) . . . . ?
C19 C20 C21 C16 -0.6(3) . . . . ?
C28 C23 C24 C25 -1.9(4) . . . . ?
N3 C23 C24 C25 175.6(2) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C24 C25 C26 C27 0.6(4) . . . . ?
C25 C26 C27 C28 -1.3(4) . . . . ?
C26 C27 C28 O2 -178.0(2) . . . . ?
C26 C27 C28 C23 0.3(3) . . . . ?
C24 C23 C28 O2 179.7(2) . . . . ?
N3 C23 C28 O2 2.1(3) . . . . ?
C24 C23 C28 C27 1.2(3) . . . . ?
N3 C23 C28 C27 -176.28(19) . . . . ?
C3 C2 N1 C1 -28.6(3) . . . . ?
C7 C2 N1 C1 147.9(2) . . . . ?
C3 C2 N1 P1 134.24(18) . . . . ?
C7 C2 N1 P1 -49.2(2) . . . . ?
C24 C23 N3 C22 118.4(2) . . . . ?
C28 C23 N3 C22 -64.2(2) . . . . ?
C24 C23 N3 P2 -42.2(3) . . . . ?
C28 C23 N3 P2 135.23(17) . . . . ?
C6 C7 O1 C8 -10.1(3) . . . . ?
C2 C7 O1 C8 173.6(2) . . . . ?
C27 C28 O2 C29 -4.0(3) . . . . ?
C23 C28 O2 C29 177.61(18) . . . . ?
C2 N1 P1 N2 -117.02(15) . . . . ?
C1 N1 P1 N2 44.59(19) . . . . ?
C2 N1 P1 C9 138.76(15) . . . . ?
C1 N1 P1 C9 -59.63(18) . . . . ?
C15 N2 P1 N1 -59.20(17) . . . . ?
P2 N2 P1 N1 110.49(10) . . . . ?
C15 N2 P1 C9 44.82(17) . . . . ?
P2 N2 P1 C9 -145.49(10) . . . . ?
C10 C9 P1 N1 -27.85(18) . . . . ?
C14 C9 P1 N1 160.96(16) . . . . ?
C10 C9 P1 N2 -138.75(17) . . . . ?
C14 C9 P1 N2 50.07(17) . . . . ?
C23 N3 P2 N2 115.95(14) . . . . ?
C22 N3 P2 N2 -43.39(17) . . . . ?
C23 N3 P2 C16 -138.37(15) . . . . ?
C22 N3 P2 C16 62.29(17) . . . . ?
C15 N2 P2 N3 66.08(17) . . . . ?
P1 N2 P2 N3 -103.61(10) . . . . ?
C15 N2 P2 C16 -39.28(17) . . . . ?
P1 N2 P2 C16 151.02(10) . . . . ?
C21 C16 P2 N3 29.56(17) . . . . ?
C17 C16 P2 N3 -161.37(15) . . . . ?
C21 C16 P2 N2 141.53(15) . . . . ?
C17 C16 P2 N2 -49.40(17) . . . . ?

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3


_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_AX0650
_database_code_depnum_ccdc_archive 'CCDC 1405816'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H29 N3 O2 P2'
_chemical_formula_weight         489.47

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.6955(6)
_cell_length_b                   11.8223(5)
_cell_length_c                   14.3639(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.7107(7)
_cell_angle_gamma                90
_cell_volume                     2487.08(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            41193
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.390
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6010
_reflns_number_gt                4510
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.9236P] 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         6010
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.14812(11) -0.00880(13) 0.07817(11) 0.0255(3) Uani 1 1 d . . . . .
C2 C 0.16722(11) -0.09589(14) 0.14329(11) 0.0262(3) Uani 1 1 d . . . . .
C3 C 0.15901(12) -0.20761(14) 0.11689(13) 0.0327(4) Uani 1 1 d . . . . .
H3B H 0.1729 -0.2658 0.1614 0.039 Uiso 1 1 calc R U . . .
C4 C 0.13044(13) -0.23523(15) 0.02528(14) 0.0373(4) Uani 1 1 d . . . . .
H4 H 0.1244 -0.3123 0.0071 0.045 Uiso 1 1 calc R U . . .
C5 C 0.11084(14) -0.15095(16) -0.03908(13) 0.0386(4) Uani 1 1 d . . . . .
H5 H 0.0909 -0.1699 -0.1017 0.046 Uiso 1 1 calc R U . . .
C6 C 0.12013(13) -0.03814(15) -0.01290(12) 0.0338(4) Uani 1 1 d . . . . .
H6 H 0.1071 0.0195 -0.0581 0.041 Uiso 1 1 calc R U . . .
C7 C 0.19891(14) -0.13963(17) 0.30500(14) 0.0436(5) Uani 1 1 d . . . . .
H7A H 0.1404 -0.1796 0.3042 0.065 Uiso 1 1 calc R U . . .
H7B H 0.2113 -0.1013 0.3652 0.065 Uiso 1 1 calc R U . . .
H7C H 0.2477 -0.1941 0.2961 0.065 Uiso 1 1 calc R U . . .
C8 C 0.10015(10) 0.31712(13) 0.12906(11) 0.0245(3) Uani 1 1 d . . . . .
C9 C 0.08057(12) 0.42756(14) 0.09814(12) 0.0315(4) Uani 1 1 d . . . . .
H9 H 0.0924 0.4488 0.0365 0.038 Uiso 1 1 calc R U . . .
C10 C 0.04414(12) 0.50647(15) 0.15630(13) 0.0348(4) Uani 1 1 d . . . . .
H10 H 0.0314 0.5811 0.1344 0.042 Uiso 1 1 calc R U . . .
C11 C 0.02645(12) 0.47650(15) 0.24615(13) 0.0336(4) Uani 1 1 d . . . . .
H11 H 0.0018 0.5305 0.2861 0.040 Uiso 1 1 calc R U . . .
C12 C 0.04488(11) 0.36759(15) 0.27760(12) 0.0308(4) Uani 1 1 d . . . . .
H12 H 0.0329 0.3469 0.3393 0.037 Uiso 1 1 calc R U . . .
C13 C 0.08072(11) 0.28862(14) 0.21943(11) 0.0265(3) Uani 1 1 d . . . . .
H13 H 0.0922 0.2138 0.2415 0.032 Uiso 1 1 calc R U . . .
C14 C 0.31677(11) 0.27082(15) 0.11759(12) 0.0309(4) Uani 1 1 d . . . . .
H14A H 0.3292 0.1927 0.1376 0.046 Uiso 1 1 calc R U . . .
H14B H 0.2917 0.3129 0.1684 0.046 Uiso 1 1 calc R U . . .
H14C H 0.3736 0.3066 0.1018 0.046 Uiso 1 1 calc R U . . .
C15 C 0.33945(11) 0.43634(14) -0.05733(11) 0.0249(3) Uani 1 1 d . . . . .
C16 C 0.39994(12) 0.47067(15) -0.12163(12) 0.0312(4) Uani 1 1 d . . . . .
H16 H 0.4152 0.4198 -0.1691 0.037 Uiso 1 1 calc R U . . .
C17 C 0.43821(12) 0.57787(16) -0.11734(13) 0.0359(4) Uani 1 1 d . . . . .
H17 H 0.4791 0.6001 -0.1618 0.043 Uiso 1 1 calc R U . . .
C18 C 0.41679(12) 0.65256(15) -0.04824(13) 0.0343(4) Uani 1 1 d . . . . .
H18 H 0.4425 0.7263 -0.0455 0.041 Uiso 1 1 calc R U . . .
C19 C 0.35786(12) 0.61955(15) 0.01678(13) 0.0336(4) Uani 1 1 d . . . . .
H19 H 0.3441 0.6703 0.0649 0.040 Uiso 1 1 calc R U . . .
C20 C 0.31865(12) 0.51260(14) 0.01220(12) 0.0298(4) Uani 1 1 d . . . . .
H20 H 0.2774 0.4911 0.0566 0.036 Uiso 1 1 calc R U . . .
C21 C 0.37412(11) 0.11470(13) -0.13065(10) 0.0240(3) Uani 1 1 d . . . . .
C22 C 0.45767(11) 0.05698(14) -0.13130(11) 0.0261(3) Uani 1 1 d . . . . .
C23 C 0.46135(12) -0.04926(15) -0.17082(12) 0.0316(4) Uani 1 1 d . . . . .
H23 H 0.5181 -0.0877 -0.1709 0.038 Uiso 1 1 calc R U . . .
C24 C 0.38201(14) -0.09995(15) -0.21044(13) 0.0381(4) Uani 1 1 d . . . . .
H24 H 0.3846 -0.1726 -0.2384 0.046 Uiso 1 1 calc R U . . .
C25 C 0.29979(13) -0.04484(15) -0.20911(13) 0.0381(4) Uani 1 1 d . . . . .
H25 H 0.2456 -0.0798 -0.2358 0.046 Uiso 1 1 calc R U . . .
C26 C 0.29546(12) 0.06181(14) -0.16893(12) 0.0301(4) Uani 1 1 d . . . . .
H26 H 0.2382 0.0988 -0.1677 0.036 Uiso 1 1 calc R U . . .
C27 C 0.61760(12) 0.05946(17) -0.08224(14) 0.0382(4) Uani 1 1 d . . . . .
H27A H 0.6123 -0.0137 -0.0510 0.057 Uiso 1 1 calc R U . . .
H27B H 0.6623 0.1067 -0.0458 0.057 Uiso 1 1 calc R U . . .
H27C H 0.6377 0.0474 -0.1449 0.057 Uiso 1 1 calc R U . . .
N1 N 0.15605(10) 0.10324(12) 0.10992(10) 0.0303(3) Uani 1 1 d . . . . .
N2 N 0.25049(9) 0.27109(11) 0.03516(9) 0.0245(3) Uani 1 1 d . . . . .
N3 N 0.37432(10) 0.22267(12) -0.09083(11) 0.0293(3) Uani 1 1 d . . . . .
O1 O 0.19490(8) -0.05812(10) 0.23149(8) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.53086(8) 0.11476(10) -0.08948(9) 0.0366(3) Uani 1 1 d . . . . .
P1 P 0.14213(3) 0.22020(3) 0.04245(3) 0.02368(10) Uani 1 1 d . . . . .
P2 P 0.27976(3) 0.30102(3) -0.07441(3) 0.02350(10) Uani 1 1 d . . . . .
H1 H 0.1779(13) 0.1055(17) 0.1698(14) 0.038(5) Uiso 1 1 d . . . . .
H3A H 0.4237(14) 0.2436(18) -0.0670(14) 0.041(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.383(2) . ?
C1 N1 1.403(2) . ?
C1 C2 1.404(2) . ?
C2 O1 1.373(2) . ?
C2 C3 1.377(2) . ?
C3 C4 1.387(3) . ?
C3 H3B 0.9500 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.427(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.393(2) . ?
C8 C9 1.401(2) . ?
C8 P1 1.8350(16) . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.470(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.394(2) . ?
C15 C20 1.398(2) . ?
C15 P2 1.8313(17) . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.387(2) . ?
C21 N3 1.399(2) . ?
C21 C22 1.405(2) . ?
C22 O2 1.370(2) . ?
C22 C23 1.381(2) . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O2 1.429(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N1 P1 1.6913(15) . ?
N1 H1 0.89(2) . ?
N2 P2 1.7024(13) . ?
N2 P1 1.7135(13) . ?
N3 P2 1.7025(14) . ?
N3 H3A 0.81(2) . ?

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
C6 C1 N1 123.69(15) . . ?
C6 C1 C2 118.30(15) . . ?
N1 C1 C2 117.99(15) . . ?
O1 C2 C3 125.36(15) . . ?
O1 C2 C1 113.84(14) . . ?
C3 C2 C1 120.79(16) . . ?
C2 C3 C4 120.00(16) . . ?
C2 C3 H3B 120.0 . . ?
C4 C3 H3B 120.0 . . ?
C5 C4 C3 119.87(17) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.25(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.78(17) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 117.92(15) . . ?
C13 C8 P1 125.92(13) . . ?
C9 C8 P1 116.02(12) . . ?
C10 C9 C8 120.96(16) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.03(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.74(16) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.26(16) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 121.07(15) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.32(15) . . ?
C16 C15 P2 119.35(12) . . ?
C20 C15 P2 121.92(12) . . ?
C17 C16 C15 121.03(16) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.00(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.79(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.40(16) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.45(16) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C26 C21 N3 123.17(15) . . ?
C26 C21 C22 118.58(15) . . ?
N3 C21 C22 118.25(15) . . ?
O2 C22 C23 125.28(15) . . ?
O2 C22 C21 114.19(14) . . ?
C23 C22 C21 120.52(15) . . ?
C22 C23 C24 120.03(16) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.91(17) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.40(17) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.55(16) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C1 N1 P1 125.65(12) . . ?
C1 N1 H1 110.8(13) . . ?
P1 N1 H1 123.0(13) . . ?
C14 N2 P2 122.96(11) . . ?
C14 N2 P1 120.50(11) . . ?
P2 N2 P1 115.85(8) . . ?
C21 N3 P2 125.37(12) . . ?
C21 N3 H3A 114.9(15) . . ?
P2 N3 H3A 119.1(15) . . ?
C2 O1 C7 117.01(14) . . ?
C22 O2 C27 117.86(14) . . ?
N1 P1 N2 104.64(7) . . ?
N1 P1 C8 98.84(7) . . ?
N2 P1 C8 100.84(7) . . ?
N2 P2 N3 106.62(7) . . ?
N2 P2 C15 102.26(7) . . ?
N3 P2 C15 96.11(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 179.67(15) . . . . ?
N1 C1 C2 O1 -2.1(2) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
N1 C1 C2 C3 178.76(15) . . . . ?
O1 C2 C3 C4 -179.86(16) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
N1 C1 C6 C5 -177.86(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C13 C8 C9 C10 0.9(2) . . . . ?
P1 C8 C9 C10 176.79(14) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C8 0.9(2) . . . . ?
C9 C8 C13 C12 -1.3(2) . . . . ?
P1 C8 C13 C12 -176.73(13) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
P2 C15 C16 C17 172.40(14) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C18 C19 C20 C15 1.0(3) . . . . ?
C16 C15 C20 C19 -0.2(2) . . . . ?
P2 C15 C20 C19 -172.85(13) . . . . ?
C26 C21 C22 O2 -178.16(14) . . . . ?
N3 C21 C22 O2 1.5(2) . . . . ?
C26 C21 C22 C23 1.2(2) . . . . ?
N3 C21 C22 C23 -179.19(15) . . . . ?
O2 C22 C23 C24 179.30(16) . . . . ?
C21 C22 C23 C24 0.0(2) . . . . ?
C22 C23 C24 C25 -0.9(3) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
N3 C21 C26 C25 178.80(16) . . . . ?
C22 C21 C26 C25 -1.6(2) . . . . ?
C24 C25 C26 C21 0.8(3) . . . . ?
C6 C1 N1 P1 -5.5(2) . . . . ?
C2 C1 N1 P1 176.33(12) . . . . ?
C26 C21 N3 P2 5.5(2) . . . . ?
C22 C21 N3 P2 -174.16(12) . . . . ?
C3 C2 O1 C7 -12.4(2) . . . . ?
C1 C2 O1 C7 168.48(15) . . . . ?
C23 C22 O2 C27 -2.9(2) . . . . ?
C21 C22 O2 C27 176.44(15) . . . . ?
C1 N1 P1 N2 -106.04(15) . . . . ?
C1 N1 P1 C8 150.23(14) . . . . ?
C14 N2 P1 N1 -40.64(14) . . . . ?
P2 N2 P1 N1 130.16(9) . . . . ?
C14 N2 P1 C8 61.58(14) . . . . ?
P2 N2 P1 C8 -127.62(9) . . . . ?
C13 C8 P1 N1 -4.83(16) . . . . ?
C9 C8 P1 N1 179.65(13) . . . . ?
C13 C8 P1 N2 -111.70(14) . . . . ?
C9 C8 P1 N2 72.77(14) . . . . ?
C14 N2 P2 N3 47.85(15) . . . . ?
P1 N2 P2 N3 -122.71(9) . . . . ?
C14 N2 P2 C15 -52.44(14) . . . . ?
P1 N2 P2 C15 137.01(8) . . . . ?
C21 N3 P2 N2 92.24(15) . . . . ?
C21 N3 P2 C15 -163.00(14) . . . . ?
C16 C15 P2 N2 158.46(13) . . . . ?
C20 C15 P2 N2 -29.01(15) . . . . ?
C16 C15 P2 N3 49.94(15) . . . . ?
C20 C15 P2 N3 -137.53(14) . . . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3


_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_ax0464
_database_code_depnum_ccdc_archive 'CCDC 1405817'
_audit_update_record             
;
2015-06-09 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H41 N3 P2'
_chemical_formula_weight         457.56

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.5529(2)
_cell_length_b                   14.8073(3)
_cell_length_c                   17.6501(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.706(1)
_cell_angle_gamma                90.00
_cell_volume                     2641.59(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.73

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.45
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45478
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         28.00
_reflns_number_total             6374
_reflns_number_gt                5481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.8713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6374
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66019(13) 0.94704(9) 0.99180(8) 0.0300(3) Uani 1 1 d . . .
H1A H 0.6923 0.9976 1.0280 0.045 Uiso 1 1 calc R . .
H1B H 0.5632 0.9470 0.9750 0.045 Uiso 1 1 calc R . .
H1C H 0.6928 0.9534 0.9454 0.045 Uiso 1 1 calc R . .
C2 C 0.85266(13) 0.85334(11) 1.06363(9) 0.0359(3) Uani 1 1 d . . .
H2 H 0.8719 0.7916 1.0872 0.043 Uiso 1 1 calc R . .
C3 C 0.90709(16) 0.92198(14) 1.12938(10) 0.0493(4) Uani 1 1 d . . .
H3A H 0.9013 0.9827 1.1066 0.074 Uiso 1 1 calc R . .
H3B H 0.9997 0.9078 1.1565 0.074 Uiso 1 1 calc R . .
H3C H 0.8552 0.9196 1.1673 0.074 Uiso 1 1 calc R . .
C4 C 0.92280(16) 0.86247(15) 0.99961(12) 0.0544(5) Uani 1 1 d . . .
H4A H 0.8866 0.8182 0.9577 0.082 Uiso 1 1 calc R . .
H4B H 1.0177 0.8516 1.0227 0.082 Uiso 1 1 calc R . .
H4C H 0.9091 0.9235 0.9773 0.082 Uiso 1 1 calc R . .
C5 C 0.48402(12) 0.80945(8) 1.06876(7) 0.0222(2) Uani 1 1 d . . .
C6 C 0.37414(13) 0.75403(9) 1.06146(7) 0.0272(3) Uani 1 1 d . . .
H6 H 0.3610 0.7030 1.0275 0.033 Uiso 1 1 calc R . .
C7 C 0.28377(14) 0.77244(10) 1.10317(8) 0.0357(3) Uani 1 1 d D . .
H7 H 0.2088 0.7346 1.0970 0.043 Uiso 1 1 calc R . .
C8 C 0.30308(14) 0.84573(9) 1.15354(8) 0.0393(4) Uani 1 1 d D . .
H8 H 0.2416 0.8581 1.1824 0.047 Uiso 1 1 calc R . .
C9 C 0.41140(15) 0.90094(10) 1.16207(8) 0.0365(3) Uani 1 1 d D . .
H9 H 0.4245 0.9513 1.1968 0.044 Uiso 1 1 calc R . .
C10 C 0.50177(14) 0.88319(9) 1.11993(7) 0.0284(3) Uani 1 1 d . . .
H10 H 0.5761 0.9216 1.1261 0.034 Uiso 1 1 calc R . .
C11 C 0.55200(12) 0.66840(8) 0.89159(7) 0.0220(2) Uani 1 1 d . . .
H11 H 0.5105 0.6752 0.8333 0.026 Uiso 1 1 calc R . .
C12 C 0.69930(13) 0.65074(9) 0.90389(9) 0.0306(3) Uani 1 1 d . . .
H12A H 0.7443 0.6428 0.9610 0.037 Uiso 1 1 calc R . .
H12B H 0.7396 0.7033 0.8849 0.037 Uiso 1 1 calc R . .
C13 C 0.71859(16) 0.56595(10) 0.85883(10) 0.0381(3) Uani 1 1 d . . .
H13A H 0.6797 0.5760 0.8014 0.046 Uiso 1 1 calc R . .
H13B H 0.8144 0.5544 0.8688 0.046 Uiso 1 1 calc R . .
C14 C 0.65394(16) 0.48403(9) 0.88407(10) 0.0385(3) Uani 1 1 d . . .
H14A H 0.6986 0.4703 0.9403 0.046 Uiso 1 1 calc R . .
H14B H 0.6641 0.4311 0.8521 0.046 Uiso 1 1 calc R . .
C15 C 0.50779(15) 0.50121(9) 0.87326(8) 0.0313(3) Uani 1 1 d . . .
H15A H 0.4689 0.4487 0.8931 0.038 Uiso 1 1 calc R . .
H15B H 0.4614 0.5084 0.8163 0.038 Uiso 1 1 calc R . .
C16 C 0.48810(13) 0.58622(8) 0.91779(7) 0.0256(2) Uani 1 1 d . . .
H16A H 0.3923 0.5974 0.9080 0.031 Uiso 1 1 calc R . .
H16B H 0.5275 0.5768 0.9753 0.031 Uiso 1 1 calc R . .
C17 C 0.44141(12) 0.85171(8) 0.79177(7) 0.0242(2) Uani 1 1 d . . .
C18 C 0.57154(14) 0.84976(9) 0.78833(8) 0.0293(3) Uani 1 1 d . . .
H18 H 0.6396 0.8289 0.8327 0.035 Uiso 1 1 calc R . .
C19 C 0.60327(16) 0.87791(10) 0.72097(9) 0.0390(3) Uani 1 1 d . . .
H19 H 0.6924 0.8753 0.7193 0.047 Uiso 1 1 calc R . .
C20 C 0.50592(18) 0.90964(11) 0.65645(9) 0.0456(4) Uani 1 1 d . . .
H20 H 0.5276 0.9281 0.6102 0.055 Uiso 1 1 calc R . .
C21 C 0.37700(18) 0.91442(12) 0.65937(9) 0.0466(4) Uani 1 1 d . . .
H21 H 0.3099 0.9372 0.6153 0.056 Uiso 1 1 calc R . .
C22 C 0.34500(15) 0.88604(11) 0.72644(8) 0.0366(3) Uani 1 1 d . . .
H22 H 0.2559 0.8900 0.7280 0.044 Uiso 1 1 calc R . .
C23 C 0.23991(14) 0.69866(10) 0.77355(8) 0.0329(3) Uani 1 1 d . . .
H23A H 0.2338 0.6365 0.7912 0.049 Uiso 1 1 calc R . .
H23B H 0.3151 0.7038 0.7517 0.049 Uiso 1 1 calc R . .
H23C H 0.1582 0.7145 0.7327 0.049 Uiso 1 1 calc R . .
C24 C 0.14257(12) 0.77290(9) 0.86971(8) 0.0276(3) Uani 1 1 d . . .
H24 H 0.1711 0.8107 0.9187 0.033 Uiso 1 1 calc R . .
C25 C 0.09129(15) 0.68330(11) 0.89235(10) 0.0393(3) Uani 1 1 d . . .
H25A H 0.0538 0.6473 0.8446 0.059 Uiso 1 1 calc R . .
H25B H 0.0228 0.6951 0.9186 0.059 Uiso 1 1 calc R . .
H25C H 0.1644 0.6501 0.9284 0.059 Uiso 1 1 calc R . .
C26 C 0.03237(14) 0.82387(11) 0.80994(9) 0.0401(3) Uani 1 1 d . . .
H26A H 0.0662 0.8820 0.7977 0.060 Uiso 1 1 calc R . .
H26B H -0.0413 0.8342 0.8324 0.060 Uiso 1 1 calc R . .
H26C H 0.0014 0.7881 0.7614 0.060 Uiso 1 1 calc R . .
N1 N 0.70805(10) 0.86242(7) 1.03198(6) 0.0263(2) Uani 1 1 d . . .
N2 N 0.52336(10) 0.75301(7) 0.92938(6) 0.0202(2) Uani 1 1 d . . .
N3 N 0.25879(10) 0.75995(7) 0.84054(6) 0.0248(2) Uani 1 1 d . . .
P1 P 0.61357(3) 0.77022(2) 1.026606(17) 0.02028(8) Uani 1 1 d . . .
P2 P 0.39449(3) 0.82235(2) 0.881172(17) 0.01901(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4567(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.4727(16) . ?
C2 C4 1.524(2) . ?
C2 C3 1.525(2) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.3948(17) . ?
C5 C6 1.3960(18) . ?
C5 P1 1.8288(12) . ?
C6 C7 1.3891(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3804(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3780(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3927(19) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N2 1.4907(14) . ?
C11 C16 1.5260(17) . ?
C11 C12 1.5290(17) . ?
C11 H11 1.0000 . ?
C12 C13 1.5308(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5295(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.3921(18) . ?
C17 C22 1.3960(18) . ?
C17 P2 1.8367(12) . ?
C18 C19 1.3886(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 N3 1.4582(16) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 N3 1.4728(16) . ?
C24 C26 1.5264(19) . ?
C24 C25 1.529(2) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 P1 1.6770(11) . ?
N2 P2 1.7211(10) . ?
N2 P1 1.7253(10) . ?
N3 P2 1.6817(10) . ?

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 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C4 112.44(13) . . ?
N1 C2 C3 110.51(13) . . ?
C4 C2 C3 110.37(13) . . ?
N1 C2 H2 107.8 . . ?
C4 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 118.25(12) . . ?
C10 C5 P1 122.35(10) . . ?
C6 C5 P1 118.29(9) . . ?
C7 C6 C5 120.95(13) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 119.93(13) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.07(13) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.23(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.56(13) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
N2 C11 C16 111.75(9) . . ?
N2 C11 C12 114.14(10) . . ?
C16 C11 C12 109.90(10) . . ?
N2 C11 H11 106.9 . . ?
C16 C11 H11 106.9 . . ?
C12 C11 H11 106.9 . . ?
C11 C12 C13 110.37(11) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.36(12) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.76(12) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 110.86(12) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C15 111.31(10) . . ?
C11 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C11 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C22 117.74(12) . . ?
C18 C17 P2 123.05(10) . . ?
C22 C17 P2 118.90(10) . . ?
C19 C18 C17 120.98(13) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.25(14) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.73(13) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.12(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.13(14) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C26 111.61(11) . . ?
N3 C24 C25 111.80(11) . . ?
C26 C24 C25 110.68(12) . . ?
N3 C24 H24 107.5 . . ?
C26 C24 H24 107.5 . . ?
C25 C24 H24 107.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 C2 116.08(11) . . ?
C1 N1 P1 123.74(8) . . ?
C2 N1 P1 118.79(9) . . ?
C11 N2 P2 120.87(8) . . ?
C11 N2 P1 116.38(8) . . ?
P2 N2 P1 122.36(6) . . ?
C23 N3 C24 115.54(10) . . ?
C23 N3 P2 126.07(9) . . ?
C24 N3 P2 118.17(8) . . ?
N1 P1 N2 109.00(5) . . ?
N1 P1 C5 102.72(6) . . ?
N2 P1 C5 100.85(5) . . ?
N3 P2 N2 109.76(5) . . ?
N3 P2 C17 99.82(5) . . ?
N2 P2 C17 101.31(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
C10 C5 C6 C7 0.87(18) . . . . ?
P1 C5 C6 C7 169.12(10) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C5 -0.09(19) . . . . ?
C6 C5 C10 C9 -0.38(18) . . . . ?
P1 C5 C10 C9 -168.12(10) . . . . ?
N2 C11 C12 C13 -176.46(11) . . . . ?
C16 C11 C12 C13 57.11(14) . . . . ?
C11 C12 C13 C14 -57.24(17) . . . . ?
C12 C13 C14 C15 56.33(17) . . . . ?
C13 C14 C15 C16 -55.61(16) . . . . ?
N2 C11 C16 C15 175.00(10) . . . . ?
C12 C11 C16 C15 -57.23(14) . . . . ?
C14 C15 C16 C11 56.65(15) . . . . ?
C22 C17 C18 C19 -2.4(2) . . . . ?
P2 C17 C18 C19 -175.96(11) . . . . ?
C17 C18 C19 C20 0.9(2) . . . . ?
C18 C19 C20 C21 0.8(2) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C18 C17 C22 C21 2.1(2) . . . . ?
P2 C17 C22 C21 175.99(13) . . . . ?
C4 C2 N1 C1 -58.75(17) . . . . ?
C3 C2 N1 C1 65.06(16) . . . . ?
C4 C2 N1 P1 108.27(14) . . . . ?
C3 C2 N1 P1 -127.92(12) . . . . ?
C16 C11 N2 P2 -95.78(11) . . . . ?
C12 C11 N2 P2 138.76(10) . . . . ?
C16 C11 N2 P1 77.31(11) . . . . ?
C12 C11 N2 P1 -48.15(13) . . . . ?
C26 C24 N3 C23 -68.25(15) . . . . ?
C25 C24 N3 C23 56.33(15) . . . . ?
C26 C24 N3 P2 106.70(12) . . . . ?
C25 C24 N3 P2 -128.72(11) . . . . ?
C1 N1 P1 N2 45.32(12) . . . . ?
C2 N1 P1 N2 -120.64(10) . . . . ?
C1 N1 P1 C5 -61.06(11) . . . . ?
C2 N1 P1 C5 132.98(10) . . . . ?
C11 N2 P1 N1 115.98(9) . . . . ?
P2 N2 P1 N1 -71.04(8) . . . . ?
C11 N2 P1 C5 -136.37(8) . . . . ?
P2 N2 P1 C5 36.61(8) . . . . ?
C10 C5 P1 N1 -22.98(11) . . . . ?
C6 C5 P1 N1 169.28(9) . . . . ?
C10 C5 P1 N2 -135.51(10) . . . . ?
C6 C5 P1 N2 56.75(10) . . . . ?
C23 N3 P2 N2 -69.60(12) . . . . ?
C24 N3 P2 N2 116.04(10) . . . . ?
C23 N3 P2 C17 36.28(12) . . . . ?
C24 N3 P2 C17 -138.08(10) . . . . ?
C11 N2 P2 N3 45.25(10) . . . . ?
P1 N2 P2 N3 -127.42(7) . . . . ?
C11 N2 P2 C17 -59.62(10) . . . . ?
P1 N2 P2 C17 127.71(7) . . . . ?
C18 C17 P2 N3 -137.28(11) . . . . ?
C22 C17 P2 N3 49.19(12) . . . . ?
C18 C17 P2 N2 -24.67(12) . . . . ?
C22 C17 P2 N2 161.81(11) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
