# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1560634'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2017-07-05T22:28:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H29 N P2'
_chemical_formula_sum            'C24 H29 N P2'
_chemical_formula_weight         393.42

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_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                   37.194(2)
_cell_length_b                   8.2421(4)
_cell_length_c                   15.7504(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.193(4)
_cell_angle_gamma                90
_cell_volume                     4438.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4358
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      90.00
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.955

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_unetI/netI     0.077
_diffrn_reflns_number            4590
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.814
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.949
_reflns_Friedel_coverage         0
_reflns_number_total             4590
_reflns_number_gt                3442
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        'STOE X-Area'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1257P)²+10.4999P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4590
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.077
_refine_ls_wR_factor_ref         0.2517
_refine_ls_wR_factor_gt          0.2279
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.111

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.08479(3) 0.83522(13) 0.03291(8) 0.0262(3) Uani 1 1 d . . . . .
P2 P 0.14613(3) 0.74386(13) 0.08713(8) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.16989(11) 0.9224(4) 0.1161(3) 0.0276(8) Uani 1 1 d . . . . .
C1 C 0.07911(12) 0.8508(5) 0.1437(3) 0.0265(9) Uani 1 1 d . . . . .
C2 C 0.05967(15) 0.9871(6) 0.1566(4) 0.0343(10) Uani 1 1 d . . . . .
H2 H 0.0507 1.0683 0.1101 0.041 Uiso 1 1 calc R U . . .
C3 C 0.05334(15) 1.0045(6) 0.2371(4) 0.0367(11) Uani 1 1 d . . . . .
H3 H 0.0401 1.0979 0.2454 0.044 Uiso 1 1 calc R U . . .
C4 C 0.06590(15) 0.8890(7) 0.3049(3) 0.0367(11) Uani 1 1 d . . . . .
H4 H 0.0616 0.9024 0.36 0.044 Uiso 1 1 calc R U . . .
C5 C 0.08489(15) 0.7530(6) 0.2925(3) 0.0359(11) Uani 1 1 d . . . . .
H5 H 0.0934 0.672 0.3391 0.043 Uiso 1 1 calc R U . . .
C6 C 0.09160(15) 0.7337(6) 0.2129(3) 0.0336(10) Uani 1 1 d . . . . .
H6 H 0.1048 0.6398 0.2052 0.04 Uiso 1 1 calc R U . . .
C7 C 0.05722(13) 0.6505(6) -0.0180(3) 0.0287(9) Uani 1 1 d . . . . .
C8 C 0.02219(15) 0.6731(7) -0.0948(4) 0.0400(11) Uani 1 1 d . . . . .
H8 H 0.0142 0.7795 -0.1176 0.048 Uiso 1 1 calc R U . . .
C9 C -0.00077(17) 0.5419(7) -0.1377(4) 0.0482(14) Uani 1 1 d . . . . .
H9 H -0.0247 0.5589 -0.1893 0.058 Uiso 1 1 calc R U . . .
C10 C 0.01053(16) 0.3877(7) -0.1067(4) 0.0432(12) Uani 1 1 d . . . . .
H10 H -0.0055 0.2977 -0.1361 0.052 Uiso 1 1 calc R U . . .
C11 C 0.04576(17) 0.3639(7) -0.0316(4) 0.0413(12) Uani 1 1 d . . . . .
H11 H 0.0542 0.2569 -0.0108 0.05 Uiso 1 1 calc R U . . .
C12 C 0.06838(16) 0.4938(6) 0.0126(3) 0.0349(10) Uani 1 1 d . . . . .
H12 H 0.092 0.4761 0.0649 0.042 Uiso 1 1 calc R U . . .
C13 C 0.15089(13) 0.6833(5) -0.0207(3) 0.0276(9) Uani 1 1 d . . . . .
C14 C 0.12555(15) 0.7276(6) -0.1097(3) 0.0325(10) Uani 1 1 d . . . . .
H14 H 0.1032 0.7923 -0.1184 0.039 Uiso 1 1 calc R U . . .
C15 C 0.13287(17) 0.6775(6) -0.1861(4) 0.0381(11) Uani 1 1 d . . . . .
H15 H 0.1155 0.7081 -0.2465 0.046 Uiso 1 1 calc R U . . .
C16 C 0.16512(18) 0.5838(6) -0.1745(4) 0.0420(12) Uani 1 1 d . . . . .
H16 H 0.1701 0.5509 -0.2266 0.05 Uiso 1 1 calc R U . . .
C17 C 0.19026(17) 0.5379(6) -0.0867(4) 0.0429(12) Uani 1 1 d . . . . .
H17 H 0.2123 0.4719 -0.0788 0.051 Uiso 1 1 calc R U . . .
C18 C 0.18355(16) 0.5874(6) -0.0101(4) 0.0381(11) Uani 1 1 d . . . . .
H18 H 0.2012 0.5563 0.0499 0.046 Uiso 1 1 calc R U . . .
C20 C 0.16310(14) 1.0563(5) 0.0498(3) 0.0294(9) Uani 1 1 d . . . . .
H20 H 0.1412 1.0222 -0.0087 0.035 Uiso 1 1 calc R U . . .
C21 C 0.19849(16) 1.0892(7) 0.0260(4) 0.0397(11) Uani 1 1 d . . . . .
H21A H 0.2062 0.9888 0.0043 0.06 Uiso 1 1 calc R U . . .
H21B H 0.2203 1.1284 0.0811 0.06 Uiso 1 1 calc R U . . .
H21C H 0.1917 1.1716 -0.0227 0.06 Uiso 1 1 calc R U . . .
C22 C 0.14982(16) 1.2097(6) 0.0829(4) 0.0361(10) Uani 1 1 d . . . . .
H22A H 0.1273 1.1847 0.0982 0.054 Uiso 1 1 calc R U . . .
H22B H 0.1423 1.2918 0.0339 0.054 Uiso 1 1 calc R U . . .
H22C H 0.1713 1.2515 0.1379 0.054 Uiso 1 1 calc R U . . .
C23 C 0.20236(14) 0.9409(6) 0.2076(3) 0.0351(10) Uani 1 1 d . . . . .
H23 H 0.2124 1.0542 0.2109 0.042 Uiso 1 1 calc R U . . .
C24 C 0.23620(17) 0.8276(8) 0.2188(5) 0.0542(15) Uani 1 1 d . . . . .
H24A H 0.244 0.8422 0.1668 0.081 Uiso 1 1 calc R U . . .
H24B H 0.228 0.715 0.2203 0.081 Uiso 1 1 calc R U . . .
H24C H 0.2584 0.8527 0.2767 0.081 Uiso 1 1 calc R U . . .
C25 C 0.1889(2) 0.9220(8) 0.2857(4) 0.0509(14) Uani 1 1 d . . . . .
H25A H 0.1673 0.9971 0.2767 0.076 Uiso 1 1 calc R U . . .
H25B H 0.2107 0.9462 0.3444 0.076 Uiso 1 1 calc R U . . .
H25C H 0.1801 0.8103 0.2868 0.076 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C7 1.835(5) . ?
P1 C1 1.843(5) . ?
P1 P2 2.2285(15) . ?
P2 N1 1.685(4) . ?
P2 C13 1.845(5) . ?
N1 C20 1.472(5) . ?
N1 C23 1.479(6) . ?
C1 C6 1.391(6) . ?
C1 C2 1.393(6) . ?
C2 C3 1.385(7) . ?
C2 H2 0.95 . ?
C3 C4 1.368(8) . ?
C3 H3 0.95 . ?
C4 C5 1.379(8) . ?
C4 H4 0.95 . ?
C5 C6 1.381(6) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.383(7) . ?
C7 C8 1.398(7) . ?
C8 C9 1.378(8) . ?
C8 H8 0.95 . ?
C9 C10 1.368(9) . ?
C9 H9 0.95 . ?
C10 C11 1.390(8) . ?
C10 H10 0.95 . ?
C11 C12 1.370(7) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C14 1.395(7) . ?
C13 C18 1.403(7) . ?
C14 C15 1.396(7) . ?
C14 H14 0.95 . ?
C15 C16 1.377(8) . ?
C15 H15 0.95 . ?
C16 C17 1.383(8) . ?
C16 H16 0.95 . ?
C17 C18 1.385(7) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C20 C22 1.523(7) . ?
C20 C21 1.528(6) . ?
C20 H20 1 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 C25 1.506(8) . ?
C23 C24 1.520(8) . ?
C23 H23 1 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?

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
C7 P1 C1 102.67(19) . . ?
C7 P1 P2 101.46(15) . . ?
C1 P1 P2 98.19(15) . . ?
N1 P2 C13 104.81(19) . . ?
N1 P2 P1 99.06(14) . . ?
C13 P2 P1 101.16(15) . . ?
C20 N1 C23 117.4(4) . . ?
C20 N1 P2 122.5(3) . . ?
C23 N1 P2 119.6(3) . . ?
C6 C1 C2 118.5(4) . . ?
C6 C1 P1 124.4(3) . . ?
C2 C1 P1 117.0(4) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.5(5) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 118.4(5) . . ?
C12 C7 P1 125.7(4) . . ?
C8 C7 P1 116.0(4) . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.3(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 120.8(5) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 118.5(4) . . ?
C14 C13 P2 125.6(3) . . ?
C18 C13 P2 115.8(4) . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.5(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.5(5) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
N1 C20 C22 111.6(4) . . ?
N1 C20 C21 112.6(4) . . ?
C22 C20 C21 111.3(4) . . ?
N1 C20 H20 107 . . ?
C22 C20 H20 107 . . ?
C21 C20 H20 107 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C25 112.3(4) . . ?
N1 C23 C24 111.8(4) . . ?
C25 C23 C24 111.5(5) . . ?
N1 C23 H23 107 . . ?
C25 C23 H23 107 . . ?
C24 C23 H23 107 . . ?
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 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 P2 N1 C20 48.9(4) . . . . ?
P1 P2 N1 C20 -55.3(4) . . . . ?
C13 P2 N1 C23 -123.3(4) . . . . ?
P1 P2 N1 C23 132.5(3) . . . . ?
C7 P1 C1 C6 60.1(4) . . . . ?
P2 P1 C1 C6 -43.6(4) . . . . ?
C7 P1 C1 C2 -117.4(4) . . . . ?
P2 P1 C1 C2 138.8(3) . . . . ?
C6 C1 C2 C3 0.4(7) . . . . ?
P1 C1 C2 C3 178.1(4) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C2 C1 C6 C5 -0.2(7) . . . . ?
P1 C1 C6 C5 -177.7(4) . . . . ?
C1 P1 C7 C12 -70.7(4) . . . . ?
P2 P1 C7 C12 30.5(4) . . . . ?
C1 P1 C7 C8 109.9(4) . . . . ?
P2 P1 C7 C8 -148.9(3) . . . . ?
C12 C7 C8 C9 1.0(8) . . . . ?
P1 C7 C8 C9 -179.6(4) . . . . ?
C7 C8 C9 C10 -0.8(9) . . . . ?
C8 C9 C10 C11 -0.6(9) . . . . ?
C9 C10 C11 C12 1.9(8) . . . . ?
C10 C11 C12 C7 -1.8(8) . . . . ?
C8 C7 C12 C11 0.3(7) . . . . ?
P1 C7 C12 C11 -179.0(4) . . . . ?
N1 P2 C13 C14 -87.8(4) . . . . ?
P1 P2 C13 C14 14.8(4) . . . . ?
N1 P2 C13 C18 90.7(4) . . . . ?
P1 P2 C13 C18 -166.7(3) . . . . ?
C18 C13 C14 C15 -0.2(7) . . . . ?
P2 C13 C14 C15 178.3(4) . . . . ?
C13 C14 C15 C16 0.0(8) . . . . ?
C14 C15 C16 C17 0.6(8) . . . . ?
C15 C16 C17 C18 -1.0(8) . . . . ?
C16 C17 C18 C13 0.8(8) . . . . ?
C14 C13 C18 C17 -0.2(7) . . . . ?
P2 C13 C18 C17 -178.8(4) . . . . ?
C23 N1 C20 C22 -65.8(5) . . . . ?
P2 N1 C20 C22 121.9(4) . . . . ?
C23 N1 C20 C21 60.2(5) . . . . ?
P2 N1 C20 C21 -112.1(4) . . . . ?
C20 N1 C23 C25 124.3(5) . . . . ?
P2 N1 C23 C25 -63.1(5) . . . . ?
C20 N1 C23 C24 -109.5(5) . . . . ?
P2 N1 C23 C24 63.1(5) . . . . ?


# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1560635'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-30T16:00:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22 H42 N2 P2'
_chemical_formula_sum            'C22 H42 N2 P2'
_chemical_formula_weight         396.52

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   12.3408(8)
_cell_length_b                   14.1744(8)
_cell_length_c                   14.1341(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.363(5)
_cell_angle_gamma                90
_cell_volume                     2359.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9284
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      29.43
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.968

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 140 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_unetI/netI     0.1167
_diffrn_reflns_number            15157
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.613
_diffrn_reflns_theta_max         29.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             6343
_reflns_number_gt                3756
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+2.7867P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6343
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.092

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 -0.1842(2) 0.7210(2) 0.3189(2) 0.0175(6) Uani 1 1 d . . . . .
C2 C -0.2475(2) 0.7165(2) 0.2195(3) 0.0200(6) Uani 1 1 d . . . . .
H2 H -0.210056 0.722763 0.170059 0.024 Uiso 1 1 calc R U . . .
C3 C -0.3646(3) 0.7031(2) 0.1908(3) 0.0274(7) Uani 1 1 d . . . . .
H3 H -0.406244 0.700036 0.122482 0.033 Uiso 1 1 calc R U . . .
C4 C -0.4201(3) 0.6943(3) 0.2623(3) 0.0334(9) Uani 1 1 d . . . . .
H4 H -0.499986 0.68528 0.243248 0.04 Uiso 1 1 calc R U . . .
C5 C -0.3587(3) 0.6987(3) 0.3616(3) 0.0333(9) Uani 1 1 d . . . . .
H5 H -0.396808 0.69253 0.41056 0.04 Uiso 1 1 calc R U . . .
C6 C -0.2421(3) 0.7120(2) 0.3903(3) 0.0236(7) Uani 1 1 d . . . . .
H6 H -0.201051 0.715064 0.458757 0.028 Uiso 1 1 calc R U . . .
C7 C -0.0233(2) 0.8706(2) 0.3377(2) 0.0194(6) Uani 1 1 d . . . . .
C8 C -0.0999(3) 0.9191(2) 0.3912(3) 0.0260(7) Uani 1 1 d . . . . .
H8A H -0.075221 0.901361 0.461448 0.039 Uiso 1 1 calc R U . . .
H8B H -0.094414 0.987711 0.385277 0.039 Uiso 1 1 calc R U . . .
H8C H -0.178696 0.899182 0.361141 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0983(3) 0.9041(2) 0.3867(3) 0.0263(7) Uani 1 1 d . . . . .
H9A H 0.122134 0.885585 0.456708 0.039 Uiso 1 1 calc R U . . .
H9B H 0.149003 0.875207 0.353209 0.039 Uiso 1 1 calc R U . . .
H9C H 0.10166 0.972907 0.381659 0.039 Uiso 1 1 calc R U . . .
C10 C -0.0623(3) 0.8986(2) 0.2287(3) 0.0222(7) Uani 1 1 d . . . . .
H10A H -0.140233 0.87671 0.19823 0.033 Uiso 1 1 calc R U . . .
H10B H -0.059456 0.967416 0.223032 0.033 Uiso 1 1 calc R U . . .
H10C H -0.012112 0.869716 0.194582 0.033 Uiso 1 1 calc R U . . .
C11 C -0.0592(2) 0.4904(2) 0.1745(2) 0.0181(6) Uani 1 1 d . . . . .
H11 H -0.097945 0.436446 0.196432 0.022 Uiso 1 1 calc R U . . .
C12 C -0.1477(3) 0.5359(2) 0.0878(2) 0.0208(6) Uani 1 1 d . . . . .
H12A H -0.171004 0.490841 0.032781 0.031 Uiso 1 1 calc R U . . .
H12B H -0.213929 0.553948 0.108401 0.031 Uiso 1 1 calc R U . . .
H12C H -0.115359 0.592099 0.066197 0.031 Uiso 1 1 calc R U . . .
C13 C 0.0362(3) 0.4476(2) 0.1404(3) 0.0246(7) Uani 1 1 d . . . . .
H13A H 0.003723 0.406754 0.083027 0.037 Uiso 1 1 calc R U . . .
H13B H 0.080112 0.498174 0.121962 0.037 Uiso 1 1 calc R U . . .
H13C H 0.086044 0.410344 0.194481 0.037 Uiso 1 1 calc R U . . .
C14 C -0.0228(2) 0.5108(2) 0.3558(2) 0.0159(6) Uani 1 1 d . . . . .
H14 H 0.00219 0.560047 0.40851 0.019 Uiso 1 1 calc R U . . .
C15 C -0.1436(3) 0.4812(2) 0.3523(2) 0.0206(6) Uani 1 1 d . . . . .
H15A H -0.142429 0.453056 0.415906 0.031 Uiso 1 1 calc R U . . .
H15B H -0.193131 0.53677 0.339556 0.031 Uiso 1 1 calc R U . . .
H15C H -0.172317 0.434981 0.299165 0.031 Uiso 1 1 calc R U . . .
C16 C 0.0568(3) 0.4269(2) 0.3879(2) 0.0213(6) Uani 1 1 d . . . . .
H16A H 0.050028 0.401671 0.450467 0.032 Uiso 1 1 calc R U . . .
H16B H 0.036324 0.377858 0.336809 0.032 Uiso 1 1 calc R U . . .
H16C H 0.135147 0.447242 0.397147 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2356(2) 0.6413(2) 0.3893(2) 0.0202(6) Uani 1 1 d . . . . .
H17 H 0.180921 0.616262 0.423034 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3055(3) 0.7172(3) 0.4566(3) 0.0302(8) Uani 1 1 d . . . . .
H18A H 0.348934 0.688846 0.519821 0.045 Uiso 1 1 calc R U . . .
H18B H 0.357875 0.745836 0.424693 0.045 Uiso 1 1 calc R U . . .
H18C H 0.254746 0.765803 0.468766 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3123(3) 0.5591(3) 0.3805(3) 0.0315(8) Uani 1 1 d . . . . .
H19A H 0.355418 0.537387 0.446861 0.047 Uiso 1 1 calc R U . . .
H19B H 0.265589 0.507229 0.344073 0.047 Uiso 1 1 calc R U . . .
H19C H 0.36497 0.580016 0.344808 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2321(2) 0.7076(2) 0.2237(2) 0.0203(6) Uani 1 1 d . . . . .
H20 H 0.312415 0.717632 0.265335 0.024 Uiso 1 1 calc R U . . .
C21 C 0.1913(3) 0.8005(2) 0.1716(3) 0.0270(7) Uani 1 1 d . . . . .
H21A H 0.236911 0.81621 0.127667 0.04 Uiso 1 1 calc R U . . .
H21B H 0.111356 0.79479 0.132518 0.04 Uiso 1 1 calc R U . . .
H21C H 0.199377 0.85057 0.221107 0.04 Uiso 1 1 calc R U . . .
C22 C 0.2353(3) 0.6341(3) 0.1456(3) 0.0309(8) Uani 1 1 d . . . . .
H22A H 0.279479 0.658619 0.103761 0.046 Uiso 1 1 calc R U . . .
H22B H 0.270835 0.576154 0.178507 0.046 Uiso 1 1 calc R U . . .
H22C H 0.157765 0.620292 0.104523 0.046 Uiso 1 1 calc R U . . .
N1 N -0.0187(2) 0.55397(17) 0.26170(18) 0.0142(5) Uani 1 1 d . . . . .
N2 N 0.16730(19) 0.67840(18) 0.29209(19) 0.0160(5) Uani 1 1 d . . . . .
P1 P -0.02994(6) 0.73947(5) 0.36431(6) 0.01571(17) Uani 1 1 d . . . . .
P2 P 0.02375(6) 0.66518(5) 0.24479(6) 0.01346(16) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.391(5) . ?
C1 C6 1.406(4) . ?
C1 P1 1.837(3) . ?
C2 C3 1.392(4) . ?
C2 H2 0.95 . ?
C3 C4 1.386(5) . ?
C3 H3 0.95 . ?
C4 C5 1.382(6) . ?
C4 H4 0.95 . ?
C5 C6 1.387(5) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C10 1.523(5) . ?
C7 C9 1.529(4) . ?
C7 C8 1.538(4) . ?
C7 P1 1.903(3) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 N1 1.488(4) . ?
C11 C12 1.520(4) . ?
C11 C13 1.524(4) . ?
C11 H11 1 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 N1 1.479(4) . ?
C14 C16 1.522(4) . ?
C14 C15 1.535(4) . ?
C14 H14 1 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 N2 1.478(4) . ?
C17 C18 1.522(5) . ?
C17 C19 1.530(4) . ?
C17 H17 1 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 N2 1.486(4) . ?
C20 C21 1.520(5) . ?
C20 C22 1.526(5) . ?
C20 H20 1 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
N1 P2 1.700(2) . ?
N2 P2 1.707(2) . ?
P1 P2 2.2516(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.9(3) . . ?
C2 C1 P1 124.8(2) . . ?
C6 C1 P1 117.3(3) . . ?
C1 C2 C3 121.5(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C10 C7 C9 110.4(3) . . ?
C10 C7 C8 109.1(3) . . ?
C9 C7 C8 107.6(3) . . ?
C10 C7 P1 115.8(2) . . ?
C9 C7 P1 107.9(2) . . ?
C8 C7 P1 105.7(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.2(2) . . ?
N1 C11 C13 113.8(2) . . ?
C12 C11 C13 110.6(3) . . ?
N1 C11 H11 106.2 . . ?
C12 C11 H11 106.2 . . ?
C13 C11 H11 106.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C16 113.5(2) . . ?
N1 C14 C15 112.2(2) . . ?
C16 C14 C15 109.3(2) . . ?
N1 C14 H14 107.2 . . ?
C16 C14 H14 107.2 . . ?
C15 C14 H14 107.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 112.9(3) . . ?
N2 C17 C19 112.9(3) . . ?
C18 C17 C19 109.9(3) . . ?
N2 C17 H17 106.9 . . ?
C18 C17 H17 106.9 . . ?
C19 C17 H17 106.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 113.0(2) . . ?
N2 C20 C22 114.6(3) . . ?
C21 C20 C22 108.5(3) . . ?
N2 C20 H20 106.7 . . ?
C21 C20 H20 106.7 . . ?
C22 C20 H20 106.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 N1 C11 113.7(2) . . ?
C14 N1 P2 127.2(2) . . ?
C11 N1 P2 119.07(19) . . ?
C17 N2 C20 115.8(2) . . ?
C17 N2 P2 124.22(19) . . ?
C20 N2 P2 118.2(2) . . ?
C1 P1 C7 99.88(13) . . ?
C1 P1 P2 100.22(10) . . ?
C7 P1 P2 105.58(10) . . ?
N1 P2 N2 111.97(12) . . ?
N1 P2 P1 98.98(9) . . ?
N2 P2 P1 99.10(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(4) . . . . ?
P1 C1 C2 C3 -179.4(2) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
P1 C1 C6 C5 179.5(3) . . . . ?
C16 C14 N1 C11 64.7(3) . . . . ?
C15 C14 N1 C11 -59.8(3) . . . . ?
C16 C14 N1 P2 -116.5(3) . . . . ?
C15 C14 N1 P2 119.0(3) . . . . ?
C12 C11 N1 C14 129.3(3) . . . . ?
C13 C11 N1 C14 -103.4(3) . . . . ?
C12 C11 N1 P2 -49.6(3) . . . . ?
C13 C11 N1 P2 77.7(3) . . . . ?
C18 C17 N2 C20 70.7(3) . . . . ?
C19 C17 N2 C20 -54.8(3) . . . . ?
C18 C17 N2 P2 -124.5(3) . . . . ?
C19 C17 N2 P2 110.0(3) . . . . ?
C21 C20 N2 C17 -136.7(3) . . . . ?
C22 C20 N2 C17 98.3(3) . . . . ?
C21 C20 N2 P2 57.6(3) . . . . ?
C22 C20 N2 P2 -67.5(3) . . . . ?
C2 C1 P1 C7 75.0(3) . . . . ?
C6 C1 P1 C7 -104.1(3) . . . . ?
C2 C1 P1 P2 -33.0(3) . . . . ?
C6 C1 P1 P2 148.0(2) . . . . ?
C14 N1 P2 N2 72.4(3) . . . . ?
C11 N1 P2 N2 -108.8(2) . . . . ?
C14 N1 P2 P1 -31.3(2) . . . . ?
C11 N1 P2 P1 147.48(19) . . . . ?
C17 N2 P2 N1 -43.5(3) . . . . ?
C20 N2 P2 N1 121.0(2) . . . . ?
C17 N2 P2 P1 60.1(2) . . . . ?
C20 N2 P2 P1 -135.4(2) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1560637'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-30T19:31:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H38 N2 P2'
_chemical_formula_sum            'C24 H38 N2 P2'
_chemical_formula_weight         416.5

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3641(18)
_cell_length_b                   10.299(2)
_cell_length_c                   12.778(3)
_cell_angle_alpha                91.018(17)
_cell_angle_beta                 95.368(16)
_cell_angle_gamma                105.102(16)
_cell_volume                     1183.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5992
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.00
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.967

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 217 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.04
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_number            12798
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         29.215
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.976
_reflns_Friedel_coverage         0
_reflns_number_total             6272
_reflns_number_gt                5435
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.5724P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6272
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 -0.07427(13) 0.25141(12) 0.75135(10) 0.0167(2) Uani 1 1 d . . . . .
C2 C -0.09811(15) 0.35437(13) 0.68793(11) 0.0229(3) Uani 1 1 d . . . . .
H2 H -0.094961 0.34615 0.61406 0.027 Uiso 1 1 calc R U . . .
C3 C -0.12651(16) 0.46923(14) 0.73164(14) 0.0288(3) Uani 1 1 d . . . . .
H3 H -0.141676 0.538825 0.687627 0.035 Uiso 1 1 calc R U . . .
C4 C -0.13255(16) 0.48169(14) 0.83884(14) 0.0288(3) Uani 1 1 d . . . . .
H4 H -0.14911 0.560911 0.868825 0.035 Uiso 1 1 calc R U . . .
C5 C -0.11441(16) 0.37844(14) 0.90269(13) 0.0262(3) Uani 1 1 d . . . . .
H5 H -0.121602 0.385686 0.976126 0.031 Uiso 1 1 calc R U . . .
C6 C -0.08571(15) 0.26434(13) 0.85911(11) 0.0204(2) Uani 1 1 d . . . . .
H6 H -0.073665 0.19396 0.903318 0.024 Uiso 1 1 calc R U . . .
C7 C -0.13784(13) -0.03509(11) 0.74853(9) 0.0147(2) Uani 1 1 d . . . . .
C8 C -0.25839(14) -0.11848(13) 0.68496(10) 0.0195(2) Uani 1 1 d . . . . .
H8 H -0.275779 -0.099013 0.613219 0.023 Uiso 1 1 calc R U . . .
C9 C -0.35267(15) -0.22921(13) 0.72568(11) 0.0228(3) Uani 1 1 d . . . . .
H9 H -0.433515 -0.285244 0.681762 0.027 Uiso 1 1 calc R U . . .
C10 C -0.32859(15) -0.25768(13) 0.83024(11) 0.0220(3) Uani 1 1 d . . . . .
H10 H -0.394052 -0.332363 0.858421 0.026 Uiso 1 1 calc R U . . .
C11 C -0.20876(15) -0.17721(13) 0.89415(10) 0.0198(2) Uani 1 1 d . . . . .
H11 H -0.191945 -0.197353 0.96579 0.024 Uiso 1 1 calc R U . . .
C12 C -0.11388(14) -0.06765(12) 0.85339(9) 0.0162(2) Uani 1 1 d . . . . .
H12 H -0.031396 -0.013887 0.897251 0.019 Uiso 1 1 calc R U . . .
C13 C 0.32208(15) 0.28515(13) 0.61466(10) 0.0200(2) Uani 1 1 d . . . . .
H13 H 0.261824 0.198991 0.578013 0.024 Uiso 1 1 calc R U . . .
C14 C 0.48487(16) 0.29712(16) 0.59847(12) 0.0285(3) Uani 1 1 d . . . . .
H14A H 0.497531 0.303194 0.523289 0.043 Uiso 1 1 calc R U . . .
H14B H 0.548264 0.378163 0.63667 0.043 Uiso 1 1 calc R U . . .
H14C H 0.513036 0.217668 0.62509 0.043 Uiso 1 1 calc R U . . .
C15 C 0.26917(18) 0.39870(15) 0.56257(12) 0.0290(3) Uani 1 1 d . . . . .
H15A H 0.288559 0.400634 0.488484 0.043 Uiso 1 1 calc R U . . .
H15B H 0.162238 0.383629 0.567151 0.043 Uiso 1 1 calc R U . . .
H15C H 0.322683 0.484824 0.598578 0.043 Uiso 1 1 calc R U . . .
C16 C 0.37777(14) 0.39443(12) 0.79622(10) 0.0176(2) Uani 1 1 d . . . . .
H16 H 0.440535 0.4594 0.750964 0.021 Uiso 1 1 calc R U . . .
C17 C 0.48345(15) 0.36130(14) 0.88326(11) 0.0224(3) Uani 1 1 d . . . . .
H17A H 0.533346 0.443109 0.926245 0.034 Uiso 1 1 calc R U . . .
H17B H 0.427169 0.293793 0.927555 0.034 Uiso 1 1 calc R U . . .
H17C H 0.557901 0.325647 0.852012 0.034 Uiso 1 1 calc R U . . .
C18 C 0.27394(16) 0.46774(15) 0.84220(13) 0.0286(3) Uani 1 1 d . . . . .
H18A H 0.332823 0.544744 0.887209 0.043 Uiso 1 1 calc R U . . .
H18B H 0.216455 0.499572 0.784881 0.043 Uiso 1 1 calc R U . . .
H18C H 0.205952 0.405919 0.883991 0.043 Uiso 1 1 calc R U . . .
C19 C 0.19606(14) -0.07215(12) 0.62845(9) 0.0173(2) Uani 1 1 d . . . . .
H19 H 0.137452 -0.018405 0.5872 0.021 Uiso 1 1 calc R U . . .
C20 C 0.09477(16) -0.21449(13) 0.63275(11) 0.0242(3) Uani 1 1 d . . . . .
H20A H 0.068053 -0.255211 0.561328 0.036 Uiso 1 1 calc R U . . .
H20B H 0.14702 -0.269123 0.675632 0.036 Uiso 1 1 calc R U . . .
H20C H 0.004352 -0.210329 0.664055 0.036 Uiso 1 1 calc R U . . .
C21 C 0.32907(16) -0.07519(15) 0.56835(10) 0.0233(3) Uani 1 1 d . . . . .
H21A H 0.293473 -0.120537 0.499133 0.035 Uiso 1 1 calc R U . . .
H21B H 0.387384 0.017128 0.559379 0.035 Uiso 1 1 calc R U . . .
H21C H 0.391549 -0.124113 0.608023 0.035 Uiso 1 1 calc R U . . .
C22 C 0.32850(15) -0.07246(13) 0.80742(10) 0.0183(2) Uani 1 1 d . . . . .
H22 H 0.343966 -0.150539 0.766568 0.022 Uiso 1 1 calc R U . . .
C23 C 0.24614(17) -0.13009(15) 0.90057(11) 0.0270(3) Uani 1 1 d . . . . .
H23A H 0.308644 -0.173399 0.946023 0.04 Uiso 1 1 calc R U . . .
H23B H 0.223428 -0.0573 0.940728 0.04 Uiso 1 1 calc R U . . .
H23C H 0.153388 -0.196639 0.874873 0.04 Uiso 1 1 calc R U . . .
C24 C 0.48261(16) 0.01723(15) 0.84501(12) 0.0261(3) Uani 1 1 d . . . . .
H24A H 0.53545 -0.032225 0.892628 0.039 Uiso 1 1 calc R U . . .
H24B H 0.538619 0.043589 0.784286 0.039 Uiso 1 1 calc R U . . .
H24C H 0.472767 0.097941 0.882285 0.039 Uiso 1 1 calc R U . . .
N1 N 0.29667(12) 0.27567(10) 0.72662(8) 0.0162(2) Uani 1 1 d . . . . .
N2 N 0.24059(12) -0.00486(10) 0.73456(8) 0.01523(19) Uani 1 1 d . . . . .
P1 P -0.02347(3) 0.11073(3) 0.68719(2) 0.01431(8) Uani 1 1 d . . . . .
P2 P 0.19818(3) 0.13487(3) 0.78004(2) 0.01235(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.3969(18) . ?
C1 C6 1.3977(18) . ?
C1 P1 1.8405(13) . ?
C2 C3 1.397(2) . ?
C2 H2 0.95 . ?
C3 C4 1.381(2) . ?
C3 H3 0.95 . ?
C4 C5 1.387(2) . ?
C4 H4 0.95 . ?
C5 C6 1.3902(18) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.3989(17) . ?
C7 C8 1.4037(17) . ?
C7 P1 1.8379(13) . ?
C8 C9 1.3904(18) . ?
C8 H8 0.95 . ?
C9 C10 1.383(2) . ?
C9 H9 0.95 . ?
C10 C11 1.3903(19) . ?
C10 H10 0.95 . ?
C11 C12 1.3852(17) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 N1 1.4728(16) . ?
C13 C15 1.525(2) . ?
C13 C14 1.531(2) . ?
C13 H13 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 N1 1.4883(15) . ?
C16 C17 1.5218(18) . ?
C16 C18 1.5277(19) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 N2 1.4842(15) . ?
C19 C21 1.5298(18) . ?
C19 C20 1.5297(18) . ?
C19 H19 1 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 N2 1.4858(16) . ?
C22 C23 1.5238(19) . ?
C22 C24 1.5253(19) . ?
C22 H22 1 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
N1 P2 1.6957(11) . ?
N2 P2 1.6964(11) . ?
P1 P2 2.2444(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
C2 C1 C6 118.01(12) . . ?
C2 C1 P1 117.33(10) . . ?
C6 C1 P1 124.63(10) . . ?
C3 C2 C1 120.89(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.02(13) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
C3 C4 C5 119.95(13) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C4 C5 C6 119.93(14) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C5 C6 C1 121.13(13) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C12 C7 C8 118.20(11) . . ?
C12 C7 P1 124.77(9) . . ?
C8 C7 P1 117.03(9) . . ?
C9 C8 C7 120.81(12) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.92(12) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C10 C11 120.12(12) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.00(12) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
C11 C12 C7 120.92(11) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
N1 C13 C15 112.74(11) . . ?
N1 C13 C14 111.78(11) . . ?
C15 C13 C14 110.86(12) . . ?
N1 C13 H13 107 . . ?
C15 C13 H13 107 . . ?
C14 C13 H13 107 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 113.28(10) . . ?
N1 C16 C18 112.84(10) . . ?
C17 C16 C18 110.45(11) . . ?
N1 C16 H16 106.6 . . ?
C17 C16 H16 106.6 . . ?
C18 C16 H16 106.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C21 112.89(11) . . ?
N2 C19 C20 112.09(11) . . ?
C21 C19 C20 110.10(11) . . ?
N2 C19 H19 107.1 . . ?
C21 C19 H19 107.1 . . ?
C20 C19 H19 107.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 112.71(11) . . ?
N2 C22 C24 112.95(11) . . ?
C23 C22 C24 110.69(11) . . ?
N2 C22 H22 106.7 . . ?
C23 C22 H22 106.7 . . ?
C24 C22 H22 106.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C13 N1 C16 115.86(10) . . ?
C13 N1 P2 124.12(8) . . ?
C16 N1 P2 119.69(8) . . ?
C19 N2 C22 114.50(10) . . ?
C19 N2 P2 127.17(8) . . ?
C22 N2 P2 118.31(8) . . ?
C7 P1 C1 101.72(6) . . ?
C7 P1 P2 101.04(4) . . ?
C1 P1 P2 97.62(4) . . ?
N1 P2 N2 111.52(5) . . ?
N1 P2 P1 99.43(4) . . ?
N2 P2 P1 99.54(4) . . ?

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 C3 2.56(19) . . . . ?
P1 C1 C2 C3 -175.37(10) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C5 -2.37(19) . . . . ?
P1 C1 C6 C5 175.39(10) . . . . ?
C12 C7 C8 C9 0.97(18) . . . . ?
P1 C7 C8 C9 -178.52(10) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 C7 0.91(19) . . . . ?
C8 C7 C12 C11 -1.63(18) . . . . ?
P1 C7 C12 C11 177.82(9) . . . . ?
C15 C13 N1 C16 -62.98(14) . . . . ?
C14 C13 N1 C16 62.70(15) . . . . ?
C15 C13 N1 P2 123.73(11) . . . . ?
C14 C13 N1 P2 -110.60(12) . . . . ?
C17 C16 N1 C13 -119.39(12) . . . . ?
C18 C16 N1 C13 114.18(13) . . . . ?
C17 C16 N1 P2 54.22(13) . . . . ?
C18 C16 N1 P2 -72.21(14) . . . . ?
C21 C19 N2 C22 -62.73(14) . . . . ?
C20 C19 N2 C22 62.29(14) . . . . ?
C21 C19 N2 P2 118.97(11) . . . . ?
C20 C19 N2 P2 -116.01(11) . . . . ?
C23 C22 N2 C19 -114.05(12) . . . . ?
C24 C22 N2 C19 119.58(12) . . . . ?
C23 C22 N2 P2 64.41(13) . . . . ?
C24 C22 N2 P2 -61.96(13) . . . . ?
C12 C7 P1 C1 -70.52(11) . . . . ?
C8 C7 P1 C1 108.94(10) . . . . ?
C12 C7 P1 P2 29.76(11) . . . . ?
C8 C7 P1 P2 -150.78(9) . . . . ?
C2 C1 P1 C7 -137.34(10) . . . . ?
C6 C1 P1 C7 44.88(12) . . . . ?
C2 C1 P1 P2 119.66(10) . . . . ?
C6 C1 P1 P2 -58.12(11) . . . . ?
C13 N1 P2 N2 42.92(12) . . . . ?
C16 N1 P2 N2 -130.13(9) . . . . ?
C13 N1 P2 P1 -61.33(11) . . . . ?
C16 N1 P2 P1 125.62(9) . . . . ?
C19 N2 P2 N1 -73.35(11) . . . . ?
C22 N2 P2 N1 108.41(10) . . . . ?
C19 N2 P2 P1 30.83(11) . . . . ?
C22 N2 P2 P1 -147.42(9) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1560636'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-30T19:09:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H46 N2 P2'
_chemical_formula_sum            'C20 H46 N2 P2'
_chemical_formula_weight         376.55
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   15.252(3)
_cell_length_b                   10.681(2)
_cell_length_c                   43.197(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7037(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    18057
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.75
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2520

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.965

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 191 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_av_unetI/netI     0.1841
_diffrn_reflns_number            30874
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.512
_diffrn_reflns_theta_max         29.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.823
_reflns_Friedel_fraction_full    0.708
_reflns_Friedel_fraction_max     0.663
_reflns_Friedel_coverage         0.66
_reflns_number_total             15769
_reflns_number_gt                8572
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         15769
_refine_ls_number_parameters     677
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 
;
 Flack x determined using 2265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(8)
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.09

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C14 C 0.1490(8) 0.9292(6) 0.8956(2) 0.064(3) Uani 1 1 d . . . . .
H14A H 0.201444 0.905274 0.907358 0.097 Uiso 1 1 calc R U . . .
H14B H 0.107388 0.971136 0.909461 0.097 Uiso 1 1 calc R U . . .
H14C H 0.1656 0.986202 0.878864 0.097 Uiso 1 1 calc R U . . .
C21 C 0.5381(4) 0.5959(4) 0.76462(17) 0.0210(15) Uani 1 1 d . . . . .
C22 C 0.6080(4) 0.5324(5) 0.74430(17) 0.0215(14) Uani 1 1 d . . . . .
H22A H 0.586329 0.525694 0.723011 0.032 Uiso 1 1 calc R U . . .
H22B H 0.661833 0.582582 0.744551 0.032 Uiso 1 1 calc R U . . .
H22C H 0.620479 0.448586 0.752399 0.032 Uiso 1 1 calc R U . . .
C23 C 0.5268(5) 0.7285(5) 0.75058(19) 0.0325(18) Uani 1 1 d . . . . .
H23A H 0.505266 0.721287 0.729279 0.049 Uiso 1 1 calc R U . . .
H23B H 0.484539 0.776058 0.762978 0.049 Uiso 1 1 calc R U . . .
H23C H 0.583404 0.771825 0.750614 0.049 Uiso 1 1 calc R U . . .
C24 C 0.5710(5) 0.6064(6) 0.79719(18) 0.0320(17) Uani 1 1 d . . . . .
H24A H 0.526293 0.646872 0.810064 0.048 Uiso 1 1 calc R U . . .
H24B H 0.583387 0.522633 0.805326 0.048 Uiso 1 1 calc R U . . .
H24C H 0.62474 0.656629 0.797478 0.048 Uiso 1 1 calc R U . . .
C25 C 0.3466(5) 0.5593(5) 0.78670(16) 0.0210(15) Uani 1 1 d . . . . .
C26 C 0.3318(5) 0.7020(5) 0.78378(18) 0.0279(17) Uani 1 1 d . . . . .
H26A H 0.322147 0.723713 0.762002 0.042 Uiso 1 1 calc R U . . .
H26B H 0.28031 0.726222 0.795971 0.042 Uiso 1 1 calc R U . . .
H26C H 0.383497 0.746557 0.791521 0.042 Uiso 1 1 calc R U . . .
C27 C 0.2608(4) 0.4978(5) 0.77558(17) 0.0244(15) Uani 1 1 d . . . . .
H27A H 0.251223 0.518092 0.75371 0.037 Uiso 1 1 calc R U . . .
H27B H 0.26499 0.406835 0.778043 0.037 Uiso 1 1 calc R U . . .
H27C H 0.211643 0.529536 0.787904 0.037 Uiso 1 1 calc R U . . .
C28 C 0.3614(5) 0.5277(5) 0.82074(17) 0.0257(16) Uani 1 1 d . . . . .
H28A H 0.415973 0.566718 0.82784 0.039 Uiso 1 1 calc R U . . .
H28B H 0.312222 0.559357 0.833058 0.039 Uiso 1 1 calc R U . . .
H28C H 0.36557 0.436655 0.823197 0.039 Uiso 1 1 calc R U . . .
C29 C 0.4740(4) 0.1820(5) 0.82375(16) 0.0215(14) Uani 1 1 d . . . . .
H29 H 0.431372 0.13197 0.836285 0.026 Uiso 1 1 calc R U . . .
C30 C 0.5078(5) 0.2838(5) 0.84526(17) 0.0307(17) Uani 1 1 d . . . . .
H30A H 0.540523 0.245398 0.862328 0.046 Uiso 1 1 calc R U . . .
H30B H 0.546528 0.340188 0.833715 0.046 Uiso 1 1 calc R U . . .
H30C H 0.458216 0.331362 0.853601 0.046 Uiso 1 1 calc R U . . .
C31 C 0.5470(5) 0.0929(5) 0.81546(19) 0.0278(16) Uani 1 1 d . . . . .
H31A H 0.576703 0.065331 0.834386 0.042 Uiso 1 1 calc R U . . .
H31B H 0.522603 0.020081 0.80468 0.042 Uiso 1 1 calc R U . . .
H31C H 0.589098 0.135452 0.80194 0.042 Uiso 1 1 calc R U . . .
C32 C 0.3357(4) 0.1741(4) 0.79186(16) 0.0192(14) Uani 1 1 d . . . . .
H32 H 0.311004 0.210764 0.772432 0.023 Uiso 1 1 calc R U . . .
C33 C 0.2704(5) 0.2017(5) 0.81760(18) 0.0276(16) Uani 1 1 d . . . . .
H33A H 0.214513 0.160609 0.812966 0.041 Uiso 1 1 calc R U . . .
H33B H 0.293386 0.169991 0.837288 0.041 Uiso 1 1 calc R U . . .
H33C H 0.261359 0.292335 0.819136 0.041 Uiso 1 1 calc R U . . .
C34 C 0.3412(5) 0.0310(5) 0.78689(18) 0.0281(17) Uani 1 1 d . . . . .
H34A H 0.282049 -0.002764 0.783858 0.042 Uiso 1 1 calc R U . . .
H34B H 0.376947 0.013307 0.768561 0.042 Uiso 1 1 calc R U . . .
H34C H 0.367953 -0.00817 0.805088 0.042 Uiso 1 1 calc R U . . .
C35 C 0.5298(4) 0.1655(4) 0.71829(16) 0.0194(13) Uani 1 1 d . . . . .
H35 H 0.513284 0.161292 0.695908 0.023 Uiso 1 1 calc R U . . .
C36 C 0.6213(5) 0.2191(5) 0.71943(18) 0.0278(17) Uani 1 1 d . . . . .
H36A H 0.661996 0.161705 0.709086 0.042 Uiso 1 1 calc R U . . .
H36B H 0.622198 0.300337 0.708887 0.042 Uiso 1 1 calc R U . . .
H36C H 0.639165 0.230058 0.741053 0.042 Uiso 1 1 calc R U . . .
C37 C 0.5303(5) 0.0317(5) 0.73001(18) 0.0275(17) Uani 1 1 d . . . . .
H37A H 0.575446 -0.016124 0.719025 0.041 Uiso 1 1 calc R U . . .
H37B H 0.542948 0.031232 0.752247 0.041 Uiso 1 1 calc R U . . .
H37C H 0.472799 -0.006438 0.726319 0.041 Uiso 1 1 calc R U . . .
C38 C 0.3851(4) 0.2719(4) 0.71437(16) 0.0171(13) Uani 1 1 d . . . . .
H38 H 0.344106 0.322539 0.727389 0.02 Uiso 1 1 calc R U . . .
C39 C 0.4062(5) 0.3502(5) 0.68592(16) 0.0251(15) Uani 1 1 d . . . . .
H39A H 0.352526 0.364466 0.673985 0.038 Uiso 1 1 calc R U . . .
H39B H 0.430849 0.430764 0.692397 0.038 Uiso 1 1 calc R U . . .
H39C H 0.448998 0.305674 0.673037 0.038 Uiso 1 1 calc R U . . .
C40 C 0.3354(5) 0.1531(5) 0.70485(18) 0.0291(17) Uani 1 1 d . . . . .
H40A H 0.284443 0.176101 0.692265 0.044 Uiso 1 1 calc R U . . .
H40B H 0.374313 0.098798 0.692772 0.044 Uiso 1 1 calc R U . . .
H40C H 0.315779 0.108527 0.723425 0.044 Uiso 1 1 calc R U . . .
C41 C 0.8663(4) 0.6024(4) 0.11024(17) 0.0213(14) Uani 1 1 d . . . . .
C42 C 0.9380(4) 0.5448(5) 0.13061(17) 0.0243(15) Uani 1 1 d . . . . .
H42A H 0.989104 0.600407 0.130996 0.037 Uiso 1 1 calc R U . . .
H42B H 0.955122 0.463225 0.122165 0.037 Uiso 1 1 calc R U . . .
H42C H 0.915633 0.533887 0.151709 0.037 Uiso 1 1 calc R U . . .
C43 C 0.8966(6) 0.6039(6) 0.07679(19) 0.0357(19) Uani 1 1 d . . . . .
H43A H 0.956665 0.636066 0.07571 0.054 Uiso 1 1 calc R U . . .
H43B H 0.857726 0.657908 0.064621 0.054 Uiso 1 1 calc R U . . .
H43C H 0.894853 0.518623 0.068437 0.054 Uiso 1 1 calc R U . . .
C44 C 0.8532(5) 0.7367(5) 0.1227(2) 0.0351(19) Uani 1 1 d . . . . .
H44A H 0.811793 0.781656 0.109384 0.053 Uiso 1 1 calc R U . . .
H44B H 0.909563 0.780762 0.122829 0.053 Uiso 1 1 calc R U . . .
H44C H 0.82988 0.732944 0.143832 0.053 Uiso 1 1 calc R U . . .
C45 C 0.6732(4) 0.5542(4) 0.09163(16) 0.0195(14) Uani 1 1 d . . . . .
C46 C 0.6831(5) 0.5136(5) 0.05796(16) 0.0237(14) Uani 1 1 d . . . . .
H46A H 0.731586 0.559766 0.048403 0.036 Uiso 1 1 calc R U . . .
H46B H 0.62867 0.531379 0.046727 0.036 Uiso 1 1 calc R U . . .
H46C H 0.695375 0.423629 0.057118 0.036 Uiso 1 1 calc R U . . .
C47 C 0.6594(5) 0.6960(5) 0.09256(18) 0.0286(17) Uani 1 1 d . . . . .
H47A H 0.602793 0.716705 0.083151 0.043 Uiso 1 1 calc R U . . .
H47B H 0.706529 0.737468 0.081019 0.043 Uiso 1 1 calc R U . . .
H47C H 0.66017 0.724754 0.114105 0.043 Uiso 1 1 calc R U . . .
C48 C 0.5898(4) 0.4954(5) 0.10566(18) 0.0242(15) Uani 1 1 d . . . . .
H48A H 0.598829 0.405228 0.10848 0.036 Uiso 1 1 calc R U . . .
H48B H 0.54015 0.509193 0.091674 0.036 Uiso 1 1 calc R U . . .
H48C H 0.577447 0.534232 0.125744 0.036 Uiso 1 1 calc R U . . .
C49 C 0.6677(4) 0.1695(5) 0.09246(16) 0.0179(13) Uani 1 1 d . . . . .
H49 H 0.647904 0.210788 0.112021 0.021 Uiso 1 1 calc R U . . .
C50 C 0.5954(5) 0.1890(5) 0.06886(17) 0.0248(15) Uani 1 1 d . . . . .
H50A H 0.608598 0.140924 0.050117 0.037 Uiso 1 1 calc R U . . .
H50B H 0.591296 0.278161 0.063672 0.037 Uiso 1 1 calc R U . . .
H50C H 0.539455 0.160615 0.077555 0.037 Uiso 1 1 calc R U . . .
C51 C 0.6746(5) 0.0290(5) 0.09938(17) 0.0253(15) Uani 1 1 d . . . . .
H51A H 0.722714 0.014249 0.113963 0.038 Uiso 1 1 calc R U . . .
H51B H 0.685958 -0.016674 0.080116 0.038 Uiso 1 1 calc R U . . .
H51C H 0.619451 -0.000412 0.108487 0.038 Uiso 1 1 calc R U . . .
C52 C 0.7943(5) 0.1720(5) 0.05632(16) 0.0228(14) Uani 1 1 d . . . . .
H52 H 0.748149 0.123084 0.04521 0.027 Uiso 1 1 calc R U . . .
C53 C 0.8291(6) 0.2697(6) 0.03360(18) 0.0331(18) Uani 1 1 d . . . . .
H53A H 0.875818 0.318245 0.043497 0.05 Uiso 1 1 calc R U . . .
H53B H 0.781312 0.32593 0.027515 0.05 Uiso 1 1 calc R U . . .
H53C H 0.852344 0.22755 0.015196 0.05 Uiso 1 1 calc R U . . .
C54 C 0.8686(5) 0.0810(6) 0.06393(18) 0.0303(17) Uani 1 1 d . . . . .
H54A H 0.844359 0.006616 0.0741 0.045 Uiso 1 1 calc R U . . .
H54B H 0.910612 0.121833 0.077798 0.045 Uiso 1 1 calc R U . . .
H54C H 0.898288 0.056196 0.04478 0.045 Uiso 1 1 calc R U . . .
C55 C 0.7302(4) 0.2827(5) 0.16648(15) 0.0152(12) Uani 1 1 d . . . . .
H55 H 0.68608 0.329908 0.153933 0.018 Uiso 1 1 calc R U . . .
C56 C 0.7545(4) 0.3659(5) 0.19363(15) 0.0199(14) Uani 1 1 d . . . . .
H56A H 0.78472 0.440794 0.186007 0.03 Uiso 1 1 calc R U . . .
H56B H 0.793279 0.319954 0.207702 0.03 Uiso 1 1 calc R U . . .
H56C H 0.701204 0.390779 0.204717 0.03 Uiso 1 1 calc R U . . .
C57 C 0.6835(4) 0.1641(5) 0.17856(16) 0.0206(13) Uani 1 1 d . . . . .
H57A H 0.722577 0.119113 0.192742 0.031 Uiso 1 1 calc R U . . .
H57B H 0.668534 0.109664 0.161073 0.031 Uiso 1 1 calc R U . . .
H57C H 0.629871 0.188078 0.189538 0.031 Uiso 1 1 calc R U . . .
C58 C 0.8751(4) 0.1803(4) 0.16040(15) 0.0174(13) Uani 1 1 d . . . . .
H58 H 0.86274 0.179897 0.183133 0.021 Uiso 1 1 calc R U . . .
C59 C 0.9657(4) 0.2336(5) 0.15667(17) 0.0225(15) Uani 1 1 d . . . . .
H59A H 0.966994 0.319185 0.164837 0.034 Uiso 1 1 calc R U . . .
H59B H 0.981438 0.234627 0.134681 0.034 Uiso 1 1 calc R U . . .
H59C H 1.007697 0.181711 0.168078 0.034 Uiso 1 1 calc R U . . .
C60 C 0.8742(4) 0.0425(5) 0.15003(17) 0.0238(15) Uani 1 1 d . . . . .
H60A H 0.886351 0.037713 0.127792 0.036 Uiso 1 1 calc R U . . .
H60B H 0.816411 0.006092 0.154278 0.036 Uiso 1 1 calc R U . . .
H60C H 0.919113 -0.004098 0.161434 0.036 Uiso 1 1 calc R U . . .
N4 N 0.4634(4) 0.2466(4) 0.73349(13) 0.0171(11) Uani 1 1 d . . . . .
N5 N 0.7525(3) 0.2268(4) 0.08420(13) 0.0164(11) Uani 1 1 d . . . . .
N6 N 0.8040(3) 0.2555(4) 0.14587(12) 0.0136(11) Uani 1 1 d . . . . .
P5 P 0.76347(10) 0.50804(11) 0.11948(4) 0.0152(3) Uani 1 1 d . . . . .
P6 P 0.81706(10) 0.31097(11) 0.10907(4) 0.0138(3) Uani 1 1 d . . . . .
N3 N 0.4225(3) 0.2319(4) 0.79660(13) 0.0157(11) Uani 1 1 d . . . . .
P3 P 0.43137(10) 0.50535(11) 0.75790(4) 0.0143(3) Uani 1 1 d . . . . .
P4 P 0.48298(10) 0.30869(11) 0.76942(4) 0.0140(3) Uani 1 1 d . . . . .
C1 C 0.2033(4) 0.3842(4) 0.92287(18) 0.0234(14) Uani 1 1 d . . . . .
C2 C 0.1990(5) 0.2430(5) 0.9210(2) 0.0371(19) Uani 1 1 d . . . . .
H2A H 0.188215 0.208576 0.941703 0.056 Uiso 1 1 calc R U . . .
H2B H 0.254786 0.21059 0.913071 0.056 Uiso 1 1 calc R U . . .
H2C H 0.151373 0.218251 0.907097 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2662(5) 0.4223(6) 0.9480(2) 0.038(2) Uani 1 1 d . . . . .
H3A H 0.324321 0.38735 0.943553 0.057 Uiso 1 1 calc R U . . .
H3B H 0.245355 0.390462 0.967936 0.057 Uiso 1 1 calc R U . . .
H3C H 0.270045 0.513811 0.948797 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2427(6) 0.4276(5) 0.89207(19) 0.0372(19) Uani 1 1 d . . . . .
H4A H 0.20614 0.397624 0.874953 0.056 Uiso 1 1 calc R U . . .
H4B H 0.302093 0.393681 0.889911 0.056 Uiso 1 1 calc R U . . .
H4C H 0.245097 0.519285 0.891638 0.056 Uiso 1 1 calc R U . . .
C5 C 0.0223(5) 0.3824(5) 0.95525(17) 0.0272(15) Uani 1 1 d . . . . .
C6 C -0.0033(5) 0.2505(5) 0.9446(2) 0.039(2) Uani 1 1 d . . . . .
H6A H -0.030288 0.255156 0.923999 0.059 Uiso 1 1 calc R U . . .
H6B H -0.04524 0.214339 0.959252 0.059 Uiso 1 1 calc R U . . .
H6C H 0.049139 0.197687 0.943598 0.059 Uiso 1 1 calc R U . . .
C7 C 0.0679(6) 0.3740(6) 0.98678(19) 0.041(2) Uani 1 1 d . . . . .
H7A H 0.025961 0.344851 1.002377 0.062 Uiso 1 1 calc R U . . .
H7B H 0.089965 0.456876 0.992653 0.062 Uiso 1 1 calc R U . . .
H7C H 0.116972 0.315029 0.98548 0.062 Uiso 1 1 calc R U . . .
C8 C -0.0619(5) 0.4570(6) 0.9586(2) 0.0335(17) Uani 1 1 d . . . . .
H8A H -0.047847 0.543018 0.964802 0.05 Uiso 1 1 calc R U . . .
H8B H -0.098992 0.418175 0.974472 0.05 Uiso 1 1 calc R U . . .
H8C H -0.093154 0.458038 0.938819 0.05 Uiso 1 1 calc R U . . .
C9 C -0.0274(5) 0.7071(5) 0.90126(17) 0.0279(15) Uani 1 1 d . . . . .
H9 H -0.046304 0.649832 0.918313 0.034 Uiso 1 1 calc R U . . .
C10 C -0.0840(5) 0.8236(6) 0.90346(18) 0.0333(18) Uani 1 1 d . . . . .
H10A H -0.074152 0.876277 0.885209 0.05 Uiso 1 1 calc R U . . .
H10B H -0.068428 0.87051 0.922174 0.05 Uiso 1 1 calc R U . . .
H10C H -0.145862 0.799309 0.904425 0.05 Uiso 1 1 calc R U . . .
C11 C -0.0478(5) 0.6400(6) 0.87062(18) 0.0321(17) Uani 1 1 d . . . . .
H11A H -0.011775 0.564263 0.868985 0.048 Uiso 1 1 calc R U . . .
H11B H -0.034655 0.695924 0.853254 0.048 Uiso 1 1 calc R U . . .
H11C H -0.10996 0.616901 0.870099 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1066(5) 0.8127(5) 0.88207(16) 0.0281(15) Uani 1 1 d . . . . .
H12 H 0.058027 0.841185 0.868207 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1733(6) 0.7424(6) 0.86180(18) 0.0371(18) Uani 1 1 d . . . . .
H13A H 0.147181 0.663966 0.854457 0.056 Uiso 1 1 calc R U . . .
H13B H 0.225833 0.723858 0.874002 0.056 Uiso 1 1 calc R U . . .
H13C H 0.189222 0.794578 0.844007 0.056 Uiso 1 1 calc R U . . .
C15 C 0.0239(5) 0.7709(5) 0.97735(16) 0.0239(14) Uani 1 1 d . . . . .
H15 H -0.020639 0.738122 0.962424 0.029 Uiso 1 1 calc R U . . .
C16 C 0.0201(5) 0.9133(5) 0.97563(19) 0.0352(18) Uani 1 1 d . . . . .
H16A H 0.036668 0.940749 0.954777 0.053 Uiso 1 1 calc R U . . .
H16B H 0.060867 0.949176 0.990766 0.053 Uiso 1 1 calc R U . . .
H16C H -0.039583 0.941653 0.980225 0.053 Uiso 1 1 calc R U . . .
C17 C -0.0045(6) 0.7288(6) 1.00964(18) 0.0333(16) Uani 1 1 d . . . . .
H17A H 0.037954 0.758842 1.02497 0.05 Uiso 1 1 calc R U . . .
H17B H -0.007083 0.637162 1.010326 0.05 Uiso 1 1 calc R U . . .
H17C H -0.062495 0.763364 1.014323 0.05 Uiso 1 1 calc R U . . .
C18 C 0.1838(5) 0.7566(5) 0.98840(17) 0.0259(15) Uani 1 1 d . . . . .
H18 H 0.159172 0.8209 1.002816 0.031 Uiso 1 1 calc R U . . .
C19 C 0.2177(5) 0.6527(6) 1.00880(19) 0.0366(18) Uani 1 1 d . . . . .
H19A H 0.241875 0.585657 0.995857 0.055 Uiso 1 1 calc R U . . .
H19B H 0.169558 0.619408 1.021369 0.055 Uiso 1 1 calc R U . . .
H19C H 0.263718 0.685381 1.022409 0.055 Uiso 1 1 calc R U . . .
C20 C 0.2591(5) 0.8209(8) 0.9716(2) 0.043(2) Uani 1 1 d . . . . .
H20A H 0.235902 0.887515 0.958337 0.064 Uiso 1 1 calc R U . . .
H20B H 0.29043 0.759525 0.958878 0.064 Uiso 1 1 calc R U . . .
H20C H 0.299544 0.857075 0.986813 0.064 Uiso 1 1 calc R U . . .
N1 N 0.0673(4) 0.7325(4) 0.90603(13) 0.0215(12) Uani 1 1 d . . . . .
N2 N 0.1098(4) 0.7189(4) 0.96794(13) 0.0211(12) Uani 1 1 d . . . . .
P1 P 0.08975(11) 0.45750(12) 0.92317(4) 0.0190(3) Uani 1 1 d . . . . .
P2 P 0.13223(11) 0.65952(12) 0.93214(4) 0.0195(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C14 C12 1.520(10) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C21 C24 1.498(10) . ?
C21 C22 1.539(9) . ?
C21 C23 1.550(7) . ?
C21 P3 1.915(6) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 C28 1.526(10) . ?
C25 C27 1.540(9) . ?
C25 C26 1.546(7) . ?
C25 P3 1.885(7) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C29 N3 1.509(8) . ?
C29 C31 1.508(9) . ?
C29 C30 1.521(9) . ?
C29 H29 1 . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C32 N3 1.475(8) . ?
C32 C33 1.521(9) . ?
C32 C34 1.545(7) . ?
C32 H32 1 . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
C35 N4 1.486(8) . ?
C35 C36 1.509(9) . ?
C35 C37 1.516(7) . ?
C35 H35 1 . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?
C37 H37A 0.98 . ?
C37 H37B 0.98 . ?
C37 H37C 0.98 . ?
C38 N4 1.477(8) . ?
C38 C39 1.521(9) . ?
C38 C40 1.534(8) . ?
C38 H38 1 . ?
C39 H39A 0.98 . ?
C39 H39B 0.98 . ?
C39 H39C 0.98 . ?
C40 H40A 0.98 . ?
C40 H40B 0.98 . ?
C40 H40C 0.98 . ?
C41 C43 1.517(10) . ?
C41 C42 1.532(9) . ?
C41 C44 1.545(8) . ?
C41 P5 1.907(6) . ?
C42 H42A 0.98 . ?
C42 H42B 0.98 . ?
C42 H42C 0.98 . ?
C43 H43A 0.98 . ?
C43 H43B 0.98 . ?
C43 H43C 0.98 . ?
C44 H44A 0.98 . ?
C44 H44B 0.98 . ?
C44 H44C 0.98 . ?
C45 C46 1.525(9) . ?
C45 C47 1.529(7) . ?
C45 C48 1.543(9) . ?
C45 P5 1.894(7) . ?
C46 H46A 0.98 . ?
C46 H46B 0.98 . ?
C46 H46C 0.98 . ?
C47 H47A 0.98 . ?
C47 H47B 0.98 . ?
C47 H47C 0.98 . ?
C48 H48A 0.98 . ?
C48 H48B 0.98 . ?
C48 H48C 0.98 . ?
C49 N5 1.474(8) . ?
C49 C50 1.517(9) . ?
C49 C51 1.534(7) . ?
C49 H49 1 . ?
C50 H50A 0.98 . ?
C50 H50B 0.98 . ?
C50 H50C 0.98 . ?
C51 H51A 0.98 . ?
C51 H51B 0.98 . ?
C51 H51C 0.98 . ?
C52 N5 1.483(8) . ?
C52 C54 1.528(9) . ?
C52 C53 1.527(9) . ?
C52 H52 1 . ?
C53 H53A 0.98 . ?
C53 H53B 0.98 . ?
C53 H53C 0.98 . ?
C54 H54A 0.98 . ?
C54 H54B 0.98 . ?
C54 H54C 0.98 . ?
C55 N6 1.465(8) . ?
C55 C56 1.518(8) . ?
C55 C57 1.544(7) . ?
C55 H55 1 . ?
C56 H56A 0.98 . ?
C56 H56B 0.98 . ?
C56 H56C 0.98 . ?
C57 H57A 0.98 . ?
C57 H57B 0.98 . ?
C57 H57C 0.98 . ?
C58 N6 1.488(7) . ?
C58 C59 1.503(9) . ?
C58 C60 1.539(7) . ?
C58 H58 1 . ?
C59 H59A 0.98 . ?
C59 H59B 0.98 . ?
C59 H59C 0.98 . ?
C60 H60A 0.98 . ?
C60 H60B 0.98 . ?
C60 H60C 0.98 . ?
N4 P4 1.714(5) . ?
N5 P6 1.712(5) . ?
N6 P6 1.708(5) . ?
P5 P6 2.3024(18) . ?
N3 P4 1.704(5) . ?
P3 P4 2.2977(18) . ?
C1 C3 1.504(10) . ?
C1 C2 1.512(7) . ?
C1 C4 1.531(10) . ?
C1 P1 1.901(6) . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C8 1.518(10) . ?
C5 C7 1.532(11) . ?
C5 C6 1.533(8) . ?
C5 P1 1.903(7) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 N1 1.484(9) . ?
C9 C10 1.518(8) . ?
C9 C11 1.537(10) . ?
C9 H9 1 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 N1 1.471(8) . ?
C12 C13 1.538(10) . ?
C12 H12 1 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C15 N2 1.479(8) . ?
C15 C16 1.524(8) . ?
C15 C17 1.528(10) . ?
C15 H15 1 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 N2 1.490(9) . ?
C18 C19 1.509(10) . ?
C18 C20 1.522(10) . ?
C18 H18 1 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
N1 P2 1.691(6) . ?
N2 P2 1.706(6) . ?
P1 P2 2.2860(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C24 C21 C22 109.7(6) . . ?
C24 C21 C23 109.7(5) . . ?
C22 C21 C23 104.9(5) . . ?
C24 C21 P3 117.7(5) . . ?
C22 C21 P3 106.3(4) . . ?
C23 C21 P3 107.9(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C28 C25 C27 109.4(5) . . ?
C28 C25 C26 108.6(5) . . ?
C27 C25 C26 105.7(5) . . ?
C28 C25 P3 117.8(5) . . ?
C27 C25 P3 104.3(4) . . ?
C26 C25 P3 110.3(5) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C31 115.0(6) . . ?
N3 C29 C30 113.5(5) . . ?
C31 C29 C30 110.2(6) . . ?
N3 C29 H29 105.8 . . ?
C31 C29 H29 105.8 . . ?
C30 C29 H29 105.8 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N3 C32 C33 113.9(5) . . ?
N3 C32 C34 112.7(5) . . ?
C33 C32 C34 109.2(5) . . ?
N3 C32 H32 106.9 . . ?
C33 C32 H32 106.9 . . ?
C34 C32 H32 106.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C35 C36 113.3(5) . . ?
N4 C35 C37 113.9(5) . . ?
C36 C35 C37 110.0(5) . . ?
N4 C35 H35 106.4 . . ?
C36 C35 H35 106.4 . . ?
C37 C35 H35 106.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N4 C38 C39 112.4(5) . . ?
N4 C38 C40 113.5(4) . . ?
C39 C38 C40 110.0(6) . . ?
N4 C38 H38 106.8 . . ?
C39 C38 H38 106.8 . . ?
C40 C38 H38 106.8 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C43 C41 C42 109.5(6) . . ?
C43 C41 C44 111.2(5) . . ?
C42 C41 C44 105.4(6) . . ?
C43 C41 P5 117.0(5) . . ?
C42 C41 P5 104.7(4) . . ?
C44 C41 P5 108.1(5) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C46 C45 C47 108.7(5) . . ?
C46 C45 C48 109.9(5) . . ?
C47 C45 C48 106.3(5) . . ?
C46 C45 P5 117.4(4) . . ?
C47 C45 P5 110.0(4) . . ?
C48 C45 P5 104.1(4) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N5 C49 C50 114.7(5) . . ?
N5 C49 C51 113.2(5) . . ?
C50 C49 C51 108.4(5) . . ?
N5 C49 H49 106.7 . . ?
C50 C49 H49 106.7 . . ?
C51 C49 H49 106.7 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C49 C51 H51A 109.5 . . ?
C49 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C49 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N5 C52 C54 113.3(6) . . ?
N5 C52 C53 113.7(5) . . ?
C54 C52 C53 108.4(6) . . ?
N5 C52 H52 107 . . ?
C54 C52 H52 107 . . ?
C53 C52 H52 107 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
N6 C55 C56 113.4(5) . . ?
N6 C55 C57 113.4(4) . . ?
C56 C55 C57 109.4(5) . . ?
N6 C55 H55 106.7 . . ?
C56 C55 H55 106.7 . . ?
C57 C55 H55 106.7 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C55 C57 H57A 109.5 . . ?
C55 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C55 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
N6 C58 C59 114.9(5) . . ?
N6 C58 C60 112.8(5) . . ?
C59 C58 C60 109.8(5) . . ?
N6 C58 H58 106.2 . . ?
C59 C58 H58 106.2 . . ?
C60 C58 H58 106.2 . . ?
C58 C59 H59A 109.5 . . ?
C58 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C58 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C58 C60 H60A 109.5 . . ?
C58 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C58 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C38 N4 C35 114.2(5) . . ?
C38 N4 P4 125.2(4) . . ?
C35 N4 P4 120.4(4) . . ?
C49 N5 C52 114.2(5) . . ?
C49 N5 P6 124.8(4) . . ?
C52 N5 P6 118.0(4) . . ?
C55 N6 C58 114.3(5) . . ?
C55 N6 P6 125.9(4) . . ?
C58 N6 P6 119.7(4) . . ?
C45 P5 C41 109.1(3) . . ?
C45 P5 P6 111.86(18) . . ?
C41 P5 P6 98.65(18) . . ?
N6 P6 N5 109.6(2) . . ?
N6 P6 P5 95.39(16) . . ?
N5 P6 P5 113.48(18) . . ?
C32 N3 C29 115.3(4) . . ?
C32 N3 P4 126.3(4) . . ?
C29 N3 P4 115.1(4) . . ?
C25 P3 C21 109.2(3) . . ?
C25 P3 P4 111.81(19) . . ?
C21 P3 P4 97.92(18) . . ?
N3 P4 N4 110.1(3) . . ?
N3 P4 P3 113.81(17) . . ?
N4 P4 P3 95.60(16) . . ?
C3 C1 C2 109.6(5) . . ?
C3 C1 C4 107.1(6) . . ?
C2 C1 C4 105.8(6) . . ?
C3 C1 P1 117.7(5) . . ?
C2 C1 P1 111.8(4) . . ?
C4 C1 P1 103.8(5) . . ?
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 . . ?
C8 C5 C7 109.2(7) . . ?
C8 C5 C6 107.2(6) . . ?
C7 C5 C6 109.3(5) . . ?
C8 C5 P1 107.8(4) . . ?
C7 C5 P1 115.3(5) . . ?
C6 C5 P1 107.8(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 113.3(5) . . ?
N1 C9 C11 113.7(6) . . ?
C10 C9 C11 108.7(6) . . ?
N1 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
C11 C9 H9 106.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C14 112.3(6) . . ?
N1 C12 C13 112.7(5) . . ?
C14 C12 C13 109.7(7) . . ?
N1 C12 H12 107.3 . . ?
C14 C12 H12 107.3 . . ?
C13 C12 H12 107.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C15 C16 113.3(6) . . ?
N2 C15 C17 113.0(6) . . ?
C16 C15 C17 109.1(6) . . ?
N2 C15 H15 107 . . ?
C16 C15 H15 107 . . ?
C17 C15 H15 107 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 114.0(5) . . ?
N2 C18 C20 114.3(6) . . ?
C19 C18 C20 110.6(7) . . ?
N2 C18 H18 105.7 . . ?
C19 C18 H18 105.7 . . ?
C20 C18 H18 105.7 . . ?
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 . . ?
C12 N1 C9 113.9(5) . . ?
C12 N1 P2 120.0(5) . . ?
C9 N1 P2 125.3(4) . . ?
C15 N2 C18 114.0(5) . . ?
C15 N2 P2 124.5(4) . . ?
C18 N2 P2 119.1(4) . . ?
C1 P1 C5 108.9(3) . . ?
C1 P1 P2 97.55(18) . . ?
C5 P1 P2 115.3(2) . . ?
N1 P2 N2 108.4(3) . . ?
N1 P2 P1 98.98(18) . . ?
N2 P2 P1 116.59(18) . . ?

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
C39 C38 N4 C35 -66.4(6) . . . . ?
C40 C38 N4 C35 59.3(7) . . . . ?
C39 C38 N4 P4 110.3(5) . . . . ?
C40 C38 N4 P4 -124.0(5) . . . . ?
C36 C35 N4 C38 129.6(6) . . . . ?
C37 C35 N4 C38 -103.6(6) . . . . ?
C36 C35 N4 P4 -47.2(7) . . . . ?
C37 C35 N4 P4 79.5(6) . . . . ?
C50 C49 N5 C52 -65.0(6) . . . . ?
C51 C49 N5 C52 60.0(7) . . . . ?
C50 C49 N5 P6 135.2(5) . . . . ?
C51 C49 N5 P6 -99.7(5) . . . . ?
C54 C52 N5 C49 -101.8(6) . . . . ?
C53 C52 N5 C49 133.8(6) . . . . ?
C54 C52 N5 P6 59.4(6) . . . . ?
C53 C52 N5 P6 -64.9(7) . . . . ?
C56 C55 N6 C58 65.2(6) . . . . ?
C57 C55 N6 C58 -60.4(6) . . . . ?
C56 C55 N6 P6 -110.0(5) . . . . ?
C57 C55 N6 P6 124.4(5) . . . . ?
C59 C58 N6 C55 -129.3(6) . . . . ?
C60 C58 N6 C55 103.8(6) . . . . ?
C59 C58 N6 P6 46.2(6) . . . . ?
C60 C58 N6 P6 -80.7(6) . . . . ?
C46 C45 P5 C41 70.4(5) . . . . ?
C47 C45 P5 C41 -54.4(5) . . . . ?
C48 C45 P5 C41 -167.9(4) . . . . ?
C46 C45 P5 P6 -37.7(5) . . . . ?
C47 C45 P5 P6 -162.5(4) . . . . ?
C48 C45 P5 P6 84.0(4) . . . . ?
C55 N6 P6 N5 -78.4(5) . . . . ?
C58 N6 P6 N5 106.6(4) . . . . ?
C55 N6 P6 P5 38.9(4) . . . . ?
C58 N6 P6 P5 -136.1(4) . . . . ?
C49 N5 P6 N6 31.1(5) . . . . ?
C52 N5 P6 N6 -128.0(4) . . . . ?
C49 N5 P6 P5 -74.1(4) . . . . ?
C52 N5 P6 P5 126.8(4) . . . . ?
C33 C32 N3 C29 66.4(6) . . . . ?
C34 C32 N3 C29 -58.7(7) . . . . ?
C33 C32 N3 P4 -135.5(5) . . . . ?
C34 C32 N3 P4 99.5(6) . . . . ?
C31 C29 N3 C32 103.1(6) . . . . ?
C30 C29 N3 C32 -128.7(6) . . . . ?
C31 C29 N3 P4 -57.6(6) . . . . ?
C30 C29 N3 P4 70.6(6) . . . . ?
C28 C25 P3 C21 -67.9(5) . . . . ?
C27 C25 P3 C21 170.6(4) . . . . ?
C26 C25 P3 C21 57.5(6) . . . . ?
C28 C25 P3 P4 39.3(5) . . . . ?
C27 C25 P3 P4 -82.2(4) . . . . ?
C26 C25 P3 P4 164.7(4) . . . . ?
C32 N3 P4 N4 -31.2(5) . . . . ?
C29 N3 P4 N4 127.0(4) . . . . ?
C32 N3 P4 P3 74.8(4) . . . . ?
C29 N3 P4 P3 -127.0(4) . . . . ?
C38 N4 P4 N3 77.8(5) . . . . ?
C35 N4 P4 N3 -105.7(4) . . . . ?
C38 N4 P4 P3 -40.1(4) . . . . ?
C35 N4 P4 P3 136.4(4) . . . . ?
C14 C12 N1 C9 123.3(7) . . . . ?
C13 C12 N1 C9 -112.2(6) . . . . ?
C14 C12 N1 P2 -66.6(7) . . . . ?
C13 C12 N1 P2 57.9(7) . . . . ?
C10 C9 N1 C12 -64.5(8) . . . . ?
C11 C9 N1 C12 60.3(6) . . . . ?
C10 C9 N1 P2 126.0(6) . . . . ?
C11 C9 N1 P2 -109.2(6) . . . . ?
C16 C15 N2 C18 63.6(7) . . . . ?
C17 C15 N2 C18 -61.1(7) . . . . ?
C16 C15 N2 P2 -98.4(6) . . . . ?
C17 C15 N2 P2 136.8(5) . . . . ?
C19 C18 N2 C15 107.7(6) . . . . ?
C20 C18 N2 C15 -123.7(6) . . . . ?
C19 C18 N2 P2 -89.2(6) . . . . ?
C20 C18 N2 P2 39.4(7) . . . . ?
C12 N1 P2 N2 114.8(5) . . . . ?
C9 N1 P2 N2 -76.2(5) . . . . ?
C12 N1 P2 P1 -123.2(4) . . . . ?
C9 N1 P2 P1 45.8(5) . . . . ?
C15 N2 P2 N1 28.6(5) . . . . ?
C18 N2 P2 N1 -132.6(4) . . . . ?
C15 N2 P2 P1 -81.9(4) . . . . ?
C18 N2 P2 P1 116.9(4) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1560639'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-29T23:14:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H37 N P2'
_chemical_formula_sum            'C20 H37 N P2'
_chemical_formula_weight         353.44

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1194(5)
_cell_length_b                   10.2329(6)
_cell_length_c                   13.1351(7)
_cell_angle_alpha                78.296(4)
_cell_angle_beta                 89.626(4)
_cell_angle_gamma                63.969(4)
_cell_volume                     1073.75(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2756
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.42
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.978

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 227 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_number            11230
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.272
_diffrn_reflns_theta_max         29.176
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             5699
_reflns_number_gt                4580
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0890P)²+0.1179P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5699
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.20386(15) 0.72023(14) 0.38034(10) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.20778(16) 0.59775(15) 0.45333(10) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.298379 0.502397 0.459488 0.027 Uiso 1 1 calc R U . . .
C3 C 0.08193(18) 0.61346(16) 0.51652(11) 0.0265(3) Uani 1 1 d . . . . .
H3 H 0.086386 0.528979 0.565159 0.032 Uiso 1 1 calc R U . . .
C4 C -0.05055(19) 0.75169(18) 0.50925(13) 0.0331(3) Uani 1 1 d . . . . .
H4 H -0.138105 0.762091 0.551631 0.04 Uiso 1 1 calc R U . . .
C5 C -0.0542(2) 0.87393(18) 0.44003(14) 0.0379(4) Uani 1 1 d . . . . .
H5 H -0.143724 0.969411 0.435787 0.045 Uiso 1 1 calc R U . . .
C6 C 0.07211(18) 0.85882(16) 0.37619(12) 0.0301(3) Uani 1 1 d . . . . .
H6 H 0.068215 0.944361 0.329182 0.036 Uiso 1 1 calc R U . . .
C7 C 0.45994(17) 0.92623(16) 0.25919(12) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.420943 1.026397 0.210783 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4555(2) 0.9509(2) 0.37020(14) 0.0413(4) Uani 1 1 d . . . . .
H8A H 0.532947 0.990297 0.381733 0.062 Uiso 1 1 calc R U . . .
H8B H 0.344581 1.022423 0.379839 0.062 Uiso 1 1 calc R U . . .
H8C H 0.486007 0.855939 0.420263 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6353(2) 0.8319(2) 0.23680(16) 0.0416(4) Uani 1 1 d . . . . .
H9A H 0.704871 0.877546 0.251948 0.062 Uiso 1 1 calc R U . . .
H9B H 0.67667 0.731139 0.280937 0.062 Uiso 1 1 calc R U . . .
H9C H 0.636805 0.826445 0.163146 0.062 Uiso 1 1 calc R U . . .
C10 C 0.22440(18) 0.95018(15) 0.14624(11) 0.0267(3) Uani 1 1 d . . . . .
H10 H 0.149883 0.901954 0.146124 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3036(3) 0.94327(19) 0.04335(13) 0.0438(4) Uani 1 1 d . . . . .
H11A H 0.218465 1.000381 -0.015082 0.066 Uiso 1 1 calc R U . . .
H11B H 0.381302 0.985856 0.041794 0.066 Uiso 1 1 calc R U . . .
H11C H 0.361663 0.839151 0.037321 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1166(2) 1.11374(17) 0.14976(14) 0.0361(3) Uani 1 1 d . . . . .
H12A H 0.039541 1.16378 0.08678 0.054 Uiso 1 1 calc R U . . .
H12B H 0.055422 1.118016 0.211617 0.054 Uiso 1 1 calc R U . . .
H12C H 0.186045 1.163847 0.153144 0.054 Uiso 1 1 calc R U . . .
C13 C 0.21104(16) 0.52617(15) 0.17188(10) 0.0237(3) Uani 1 1 d . . . . .
C14 C 0.2237(2) 0.4751(2) 0.06818(12) 0.0343(3) Uani 1 1 d . . . . .
H14A H 0.235959 0.548223 0.012309 0.052 Uiso 1 1 calc R U . . .
H14B H 0.31903 0.377806 0.07516 0.052 Uiso 1 1 calc R U . . .
H14C H 0.124016 0.466909 0.051122 0.052 Uiso 1 1 calc R U . . .
C15 C 0.05588(18) 0.67477(18) 0.15694(15) 0.0377(4) Uani 1 1 d . . . . .
H15A H 0.067067 0.74888 0.101385 0.057 Uiso 1 1 calc R U . . .
H15B H -0.039119 0.660876 0.137671 0.057 Uiso 1 1 calc R U . . .
H15C H 0.040435 0.70962 0.222211 0.057 Uiso 1 1 calc R U . . .
C16 C 0.19194(18) 0.41203(18) 0.25846(12) 0.0296(3) Uani 1 1 d . . . . .
H16A H 0.290716 0.316526 0.268569 0.044 Uiso 1 1 calc R U . . .
H16B H 0.176183 0.447476 0.323498 0.044 Uiso 1 1 calc R U . . .
H16C H 0.096629 0.398732 0.238958 0.044 Uiso 1 1 calc R U . . .
C17 C 0.58186(16) 0.38377(15) 0.24733(11) 0.0253(3) Uani 1 1 d . . . . .
C18 C 0.57985(18) 0.31560(16) 0.36230(12) 0.0307(3) Uani 1 1 d . . . . .
H18A H 0.489002 0.288642 0.369537 0.046 Uiso 1 1 calc R U . . .
H18B H 0.683683 0.226129 0.386397 0.046 Uiso 1 1 calc R U . . .
H18C H 0.565587 0.388438 0.404447 0.046 Uiso 1 1 calc R U . . .
C19 C 0.72562(17) 0.42482(18) 0.23861(14) 0.0337(3) Uani 1 1 d . . . . .
H19A H 0.729049 0.468677 0.165556 0.051 Uiso 1 1 calc R U . . .
H19B H 0.710618 0.497103 0.281389 0.051 Uiso 1 1 calc R U . . .
H19C H 0.828715 0.334795 0.263339 0.051 Uiso 1 1 calc R U . . .
C20 C 0.61203(19) 0.26748(18) 0.18148(14) 0.0361(3) Uani 1 1 d . . . . .
H20A H 0.613237 0.311415 0.108072 0.054 Uiso 1 1 calc R U . . .
H20B H 0.717754 0.180602 0.206321 0.054 Uiso 1 1 calc R U . . .
H20C H 0.524329 0.236331 0.188118 0.054 Uiso 1 1 calc R U . . .
N1 N 0.34432(13) 0.86671(12) 0.23875(9) 0.0215(2) Uani 1 1 d . . . . .
P1 P 0.38373(4) 0.69438(3) 0.30787(2) 0.01801(9) Uani 1 1 d . . . . .
P2 P 0.39522(4) 0.56490(4) 0.18656(2) 0.01900(10) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3899(18) . ?
C1 C2 1.4018(18) . ?
C1 P1 1.8352(13) . ?
C2 C3 1.3826(19) . ?
C2 H2 0.95 . ?
C3 C4 1.384(2) . ?
C3 H3 0.95 . ?
C4 C5 1.376(2) . ?
C4 H4 0.95 . ?
C5 C6 1.392(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.4793(17) . ?
C7 C8 1.527(2) . ?
C7 C9 1.526(2) . ?
C7 H7 1 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 N1 1.4759(17) . ?
C10 C11 1.528(2) . ?
C10 C12 1.535(2) . ?
C10 H10 1 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C16 1.5248(19) . ?
C13 C15 1.532(2) . ?
C13 C14 1.541(2) . ?
C13 P2 1.9065(13) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 C18 1.533(2) . ?
C17 C19 1.5396(19) . ?
C17 C20 1.539(2) . ?
C17 P2 1.9021(14) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
N1 P1 1.6916(11) . ?
P1 P2 2.2446(5) . ?

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 C2 117.76(12) . . ?
C6 C1 P1 123.23(10) . . ?
C2 C1 P1 118.52(10) . . ?
C3 C2 C1 121.07(12) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.32(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.38(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.56(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.86(13) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N1 C7 C8 111.08(12) . . ?
N1 C7 C9 113.81(12) . . ?
C8 C7 C9 110.83(14) . . ?
N1 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C9 C7 H7 106.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 113.09(13) . . ?
N1 C10 C12 112.84(12) . . ?
C11 C10 C12 109.44(12) . . ?
N1 C10 H10 107 . . ?
C11 C10 H10 107 . . ?
C12 C10 H10 107 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C13 C15 108.90(13) . . ?
C16 C13 C14 109.22(12) . . ?
C15 C13 C14 106.63(12) . . ?
C16 C13 P2 118.10(9) . . ?
C15 C13 P2 107.89(9) . . ?
C14 C13 P2 105.52(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C19 108.19(12) . . ?
C18 C17 C20 109.69(12) . . ?
C19 C17 C20 107.89(12) . . ?
C18 C17 P2 116.41(9) . . ?
C19 C17 P2 104.35(10) . . ?
C20 C17 P2 109.88(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 N1 C7 116.38(11) . . ?
C10 N1 P1 125.19(9) . . ?
C7 N1 P1 117.31(9) . . ?
N1 P1 C1 105.32(6) . . ?
N1 P1 P2 104.65(4) . . ?
C1 P1 P2 109.82(4) . . ?
C17 P2 C13 109.50(6) . . ?
C17 P2 P1 98.82(4) . . ?
C13 P2 P1 115.05(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
C6 C1 C2 C3 2.2(2) . . . . ?
P1 C1 C2 C3 174.43(10) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C2 C1 C6 C5 -2.2(2) . . . . ?
P1 C1 C6 C5 -174.02(13) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C11 C10 N1 C7 66.92(16) . . . . ?
C12 C10 N1 C7 -57.98(16) . . . . ?
C11 C10 N1 P1 -100.59(14) . . . . ?
C12 C10 N1 P1 134.51(11) . . . . ?
C8 C7 N1 C10 126.01(14) . . . . ?
C9 C7 N1 C10 -108.07(15) . . . . ?
C8 C7 N1 P1 -65.46(14) . . . . ?
C9 C7 N1 P1 60.46(16) . . . . ?
C10 N1 P1 C1 -72.57(12) . . . . ?
C7 N1 P1 C1 120.03(10) . . . . ?
C10 N1 P1 P2 43.22(11) . . . . ?
C7 N1 P1 P2 -124.19(9) . . . . ?
C6 C1 P1 N1 -2.02(14) . . . . ?
C2 C1 P1 N1 -173.79(10) . . . . ?
C6 C1 P1 P2 -114.19(12) . . . . ?
C2 C1 P1 P2 74.04(11) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1576833'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-09-10T13:26:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H46 N2 P2'
_chemical_formula_sum            'C20 H46 N2 P2'
_chemical_formula_weight         376.53
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3368(3)
_cell_length_b                   13.5116(7)
_cell_length_c                   17.2599(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2410.63(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6567
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.40
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.976

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 114 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_number            11770
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_coverage         0.768
_reflns_number_total             5755
_reflns_number_gt                3970
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5755
_refine_ls_number_parameters     290
_refine_ls_number_restraints     9
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2943
_refine_ls_wR_factor_gt          0.2623
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1267 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.26(9)
_refine_diff_density_max         2.066
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.084

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.2890(2) 0.9870(2) 0.90427(16) 0.0223(6) Uani 0.568(4) 1 d D . P A 1
P2 P 0.4903(2) 0.94310(18) 0.85679(13) 0.0361(7) Uani 0.568(4) 1 d D . P A 1
N1 N 0.2422(12) 1.1057(10) 0.9075(7) 0.043(3) Uani 0.568(4) 1 d . . P A 1
N2 N 0.569(3) 0.904(2) 0.9343(13) 0.039(4) Uani 0.568(4) 1 d . . P A 1
C1 C 0.1665(14) 1.1256(11) 0.9930(8) 0.0555(16) Uani 0.568(4) 1 d D . P A 1
H1 H 0.12919 1.193634 0.988431 0.067 Uiso 0.568(4) 1 calc R U P A 1
C2 C 0.059(3) 1.0635(17) 1.016(2) 0.181(18) Uani 0.568(4) 1 d . . P A 1
H2A H -0.005733 1.062333 0.973878 0.271 Uiso 0.568(4) 1 calc R U P A 1
H2B H 0.08952 0.996044 1.025354 0.271 Uiso 0.568(4) 1 calc R U P A 1
H2C H 0.018982 1.089996 1.06281 0.271 Uiso 0.568(4) 1 calc R U P A 1
C3 C 0.2767(19) 1.136(2) 1.0517(13) 0.140(14) Uani 0.568(4) 1 d D . P A 1
H3A H 0.343914 1.179228 1.030365 0.21 Uiso 0.568(4) 1 calc R U P A 1
H3B H 0.243171 1.164439 1.09981 0.21 Uiso 0.568(4) 1 calc R U P A 1
H3C H 0.313709 1.070487 1.062354 0.21 Uiso 0.568(4) 1 calc R U P A 1
C4 C 0.2403(11) 1.1875(9) 0.8566(9) 0.0555(16) Uani 0.568(4) 1 d D . P A 1
H4 H 0.281435 1.164983 0.807168 0.067 Uiso 0.568(4) 1 calc R U P A 1
C5 C 0.3275(15) 1.2687(11) 0.8897(13) 0.106(5) Uani 0.568(4) 1 d D . P A 1
H5A H 0.327075 1.325928 0.854845 0.16 Uiso 0.568(4) 1 calc R U P A 1
H5B H 0.295332 1.288635 0.940771 0.16 Uiso 0.568(4) 1 calc R U P A 1
H5C H 0.416016 1.243437 0.894715 0.16 Uiso 0.568(4) 1 calc R U P A 1
C6 C 0.1086(13) 1.2310(15) 0.8349(14) 0.106(5) Uani 0.568(4) 1 d D . P A 1
H6A H 0.120912 1.286977 0.79949 0.16 Uiso 0.568(4) 1 calc R U P A 1
H6B H 0.056079 1.180166 0.809386 0.16 Uiso 0.568(4) 1 calc R U P A 1
H6C H 0.064398 1.253832 0.88182 0.16 Uiso 0.568(4) 1 calc R U P A 1
C7 C 0.1868(8) 0.9201(9) 0.8339(7) 0.038(3) Uani 0.568(4) 1 d . . P A 1
C8 C 0.1881(11) 0.9616(11) 0.7475(6) 0.057(3) Uani 0.568(4) 1 d D . P A 1
H8A H 0.276592 0.959696 0.727173 0.086 Uiso 0.568(4) 1 calc R U P A 1
H8B H 0.131901 0.920596 0.71488 0.086 Uiso 0.568(4) 1 calc R U P A 1
H8C H 0.156562 1.029989 0.747211 0.086 Uiso 0.568(4) 1 calc R U P A 1
C9 C 0.0471(9) 0.9262(11) 0.8594(9) 0.056(3) Uani 0.568(4) 1 d . . P A 1
H9A H 0.021157 0.995806 0.86324 0.084 Uiso 0.568(4) 1 calc R U P A 1
H9B H -0.00788 0.89246 0.821416 0.084 Uiso 0.568(4) 1 calc R U P A 1
H9C H 0.037367 0.89434 0.910075 0.084 Uiso 0.568(4) 1 calc R U P A 1
C10 C 0.2279(10) 0.8108(9) 0.8278(8) 0.049(3) Uani 0.568(4) 1 d . . P A 1
H10A H 0.318491 0.807027 0.811268 0.073 Uiso 0.568(4) 1 calc R U P A 1
H10B H 0.218352 0.778831 0.878448 0.073 Uiso 0.568(4) 1 calc R U P A 1
H10C H 0.173105 0.776951 0.789788 0.073 Uiso 0.568(4) 1 calc R U P A 1
C11 C 0.5736(12) 0.9564(10) 1.0115(7) 0.0555(16) Uani 0.568(4) 1 d . . P A 1
H11 H 0.538168 1.024184 1.002082 0.067 Uiso 0.568(4) 1 calc R U P A 1
C12 C 0.4885(15) 0.9112(11) 1.0762(6) 0.054(3) Uani 0.568(4) 1 d . . P A 1
H12A H 0.498435 0.950077 1.12374 0.081 Uiso 0.568(4) 1 calc R U P A 1
H12B H 0.397706 0.912007 1.059947 0.081 Uiso 0.568(4) 1 calc R U P A 1
H12C H 0.51561 0.842762 1.085879 0.081 Uiso 0.568(4) 1 calc R U P A 1
C13 C 0.7146(14) 0.9717(11) 1.0381(9) 0.058(3) Uani 0.568(4) 1 d . . P A 1
H13A H 0.715314 1.005574 1.08835 0.087 Uiso 0.568(4) 1 calc R U P A 1
H13B H 0.757364 0.907279 1.043165 0.087 Uiso 0.568(4) 1 calc R U P A 1
H13C H 0.760735 1.011971 0.999852 0.087 Uiso 0.568(4) 1 calc R U P A 1
C14 C 0.6091(12) 0.7981(9) 0.9408(8) 0.0555(16) Uani 0.568(4) 1 d . . P A 1
H14 H 0.65406 0.789629 0.991633 0.067 Uiso 0.568(4) 1 calc R U P A 1
C15 C 0.4946(15) 0.7271(8) 0.9392(8) 0.055(3) Uani 0.568(4) 1 d . . P A 1
H15A H 0.431741 0.74666 0.978921 0.082 Uiso 0.568(4) 1 calc R U P A 1
H15B H 0.453414 0.729405 0.888114 0.082 Uiso 0.568(4) 1 calc R U P A 1
H15C H 0.524871 0.65973 0.94968 0.082 Uiso 0.568(4) 1 calc R U P A 1
C16 C 0.690(2) 0.7654(15) 0.8843(15) 0.069(7) Uani 0.568(4) 1 d . . P A 1
H16A H 0.711186 0.695605 0.89336 0.103 Uiso 0.568(4) 1 calc R U P A 1
H16B H 0.648282 0.772415 0.833676 0.103 Uiso 0.568(4) 1 calc R U P A 1
H16C H 0.770059 0.804636 0.885074 0.103 Uiso 0.568(4) 1 calc R U P A 1
C17 C 0.5889(16) 1.0583(12) 0.8250(11) 0.052(4) Uani 0.568(4) 1 d . . P A 1
C18 C 0.7226(11) 1.0137(12) 0.8021(8) 0.064(4) Uani 0.568(4) 1 d . . P A 1
H18A H 0.709643 0.958449 0.766219 0.096 Uiso 0.568(4) 1 calc R U P A 1
H18B H 0.775344 1.064799 0.777058 0.096 Uiso 0.568(4) 1 calc R U P A 1
H18C H 0.76696 0.989954 0.848744 0.096 Uiso 0.568(4) 1 calc R U P A 1
C19 C 0.5232(12) 1.0884(11) 0.7462(7) 0.058(3) Uani 0.568(4) 1 d . . P A 1
H19A H 0.517982 1.030426 0.712225 0.088 Uiso 0.568(4) 1 calc R U P A 1
H19B H 0.435844 1.113577 0.756271 0.088 Uiso 0.568(4) 1 calc R U P A 1
H19C H 0.574737 1.140057 0.720944 0.088 Uiso 0.568(4) 1 calc R U P A 1
C20 C 0.5997(17) 1.1403(12) 0.8779(9) 0.083(5) Uani 0.568(4) 1 d . . P A 1
H20A H 0.513183 1.165318 0.890338 0.124 Uiso 0.568(4) 1 calc R U P A 1
H20B H 0.642466 1.118217 0.925588 0.124 Uiso 0.568(4) 1 calc R U P A 1
H20C H 0.65085 1.193062 0.853902 0.124 Uiso 0.568(4) 1 calc R U P A 1
P1A P 0.2776(4) 0.9886(8) 0.9052(7) 0.098(5) Uiso 0.432(4) 1 d D . P A 2
P2A P 0.4971(3) 1.0210(2) 0.90282(17) 0.0346(9) Uiso 0.432(4) 1 d D . P A 2
N1A N 0.2098(14) 1.1053(14) 0.9182(9) 0.031(4) Uiso 0.432(4) 1 d . . P A 2
N2A N 0.561(3) 0.915(3) 0.9440(18) 0.032(6) Uiso 0.432(4) 1 d . . P A 2
C1A C 0.2166(17) 1.1469(13) 0.9868(9) 0.050(4) Uiso 0.432(4) 1 d . . P A 2
H1A H 0.181368 1.214954 0.978168 0.06 Uiso 0.432(4) 1 calc R U P A 2
C2A C 0.1036(19) 1.0908(16) 1.0273(13) 0.057(4) Uiso 0.432(4) 1 d . . P A 2
H2A1 H 0.095375 1.113958 1.080857 0.086 Uiso 0.432(4) 1 calc R U P A 2
H2A2 H 0.022741 1.103534 0.999383 0.086 Uiso 0.432(4) 1 calc R U P A 2
H2A3 H 0.121679 1.019589 1.027087 0.086 Uiso 0.432(4) 1 calc R U P A 2
C3A C 0.321(2) 1.162(2) 1.0369(13) 0.050(4) Uiso 0.432(4) 1 d . . P A 2
H3A1 H 0.291532 1.195673 1.083856 0.075 Uiso 0.432(4) 1 calc R U P A 2
H3A2 H 0.3592 1.097762 1.050996 0.075 Uiso 0.432(4) 1 calc R U P A 2
H3A3 H 0.387004 1.202516 1.011061 0.075 Uiso 0.432(4) 1 calc R U P A 2
C4A C 0.2000(15) 1.1806(9) 0.8461(17) 0.089(8) Uiso 0.432(4) 1 d D . P A 2
H4A H 0.23821 1.142292 0.802096 0.107 Uiso 0.432(4) 1 calc R U P A 2
C5A C 0.2849(16) 1.2734(11) 0.8505(11) 0.067(4) Uiso 0.432(4) 1 d D . P A 2
H5A1 H 0.374564 1.254174 0.861002 0.1 Uiso 0.432(4) 1 calc R U P A 2
H5A2 H 0.280707 1.308993 0.801038 0.1 Uiso 0.432(4) 1 calc R U P A 2
H5A3 H 0.253599 1.316483 0.892137 0.1 Uiso 0.432(4) 1 calc R U P A 2
C6A C 0.0542(14) 1.1758(15) 0.8308(16) 0.091(7) Uiso 0.432(4) 1 d D . P A 2
H6A1 H 0.025853 1.106566 0.831221 0.137 Uiso 0.432(4) 1 calc R U P A 2
H6A2 H 0.008158 1.212586 0.871176 0.137 Uiso 0.432(4) 1 calc R U P A 2
H6A3 H 0.035266 1.205096 0.780077 0.137 Uiso 0.432(4) 1 calc R U P A 2
C7A C 0.1973(18) 0.9383(15) 0.8091(12) 0.048(5) Uiso 0.432(4) 1 d . . P A 2
C8A C 0.229(3) 1.006(2) 0.7390(9) 0.104(9) Uiso 0.432(4) 1 d D . P A 2
H8A1 H 0.192681 1.072166 0.748195 0.157 Uiso 0.432(4) 1 calc R U P A 2
H8A2 H 0.322554 1.010824 0.732662 0.157 Uiso 0.432(4) 1 calc R U P A 2
H8A3 H 0.190204 0.977968 0.692008 0.157 Uiso 0.432(4) 1 calc R U P A 2
C9A C 0.060(3) 0.942(2) 0.8246(16) 0.081(8) Uiso 0.432(4) 1 d . . P A 2
H9A1 H 0.034858 1.010378 0.836645 0.122 Uiso 0.432(4) 1 calc R U P A 2
H9A2 H 0.012351 0.919316 0.778908 0.122 Uiso 0.432(4) 1 calc R U P A 2
H9A3 H 0.039715 0.89936 0.868821 0.122 Uiso 0.432(4) 1 calc R U P A 2
C10A C 0.250(2) 0.8493(19) 0.7912(15) 0.089(7) Uiso 0.432(4) 1 d . . P A 2
H10D H 0.343375 0.857422 0.782163 0.133 Uiso 0.432(4) 1 calc R U P A 2
H10E H 0.236733 0.803112 0.834224 0.133 Uiso 0.432(4) 1 calc R U P A 2
H10F H 0.209369 0.823068 0.744311 0.133 Uiso 0.432(4) 1 calc R U P A 2
C11A C 0.6143(15) 0.9141(14) 1.0190(9) 0.053(4) Uiso 0.432(4) 1 d . . P A 2
H11A H 0.639754 0.844468 1.031489 0.063 Uiso 0.432(4) 1 calc R U P A 2
C12A C 0.524(2) 0.9471(18) 1.0777(13) 0.066(6) Uiso 0.432(4) 1 d . . P A 2
H12D H 0.566475 0.945194 1.12854 0.099 Uiso 0.432(4) 1 calc R U P A 2
H12E H 0.496976 1.015007 1.066269 0.099 Uiso 0.432(4) 1 calc R U P A 2
H12F H 0.448537 0.903532 1.078099 0.099 Uiso 0.432(4) 1 calc R U P A 2
C13A C 0.752(2) 0.983(2) 1.0125(14) 0.074(8) Uiso 0.432(4) 1 d . . P A 2
H13D H 0.794877 0.985705 1.063202 0.111 Uiso 0.432(4) 1 calc R U P A 2
H13E H 0.811138 0.953056 0.974608 0.111 Uiso 0.432(4) 1 calc R U P A 2
H13F H 0.730591 1.050511 0.995815 0.111 Uiso 0.432(4) 1 calc R U P A 2
C14A C 0.5494(13) 0.8165(11) 0.9080(9) 0.046(3) Uiso 0.432(4) 1 d . . P A 2
H14A H 0.503252 0.825593 0.857626 0.055 Uiso 0.432(4) 1 calc R U P A 2
C15A C 0.461(3) 0.755(2) 0.9599(16) 0.085(8) Uiso 0.432(4) 1 d . . P A 2
H15D H 0.451207 0.688725 0.93781 0.128 Uiso 0.432(4) 1 calc R U P A 2
H15E H 0.499341 0.75008 1.011696 0.128 Uiso 0.432(4) 1 calc R U P A 2
H15F H 0.376306 0.787077 0.963439 0.128 Uiso 0.432(4) 1 calc R U P A 2
C16A C 0.704(5) 0.772(4) 0.887(3) 0.118(19) Uiso 0.432(4) 1 d . . P A 2
H16D H 0.696858 0.706552 0.862536 0.176 Uiso 0.432(4) 1 calc R U P A 2
H16E H 0.746723 0.817632 0.850555 0.176 Uiso 0.432(4) 1 calc R U P A 2
H16F H 0.75454 0.767174 0.934309 0.176 Uiso 0.432(4) 1 calc R U P A 2
C17A C 0.585(2) 1.0375(17) 0.8076(12) 0.043(5) Uiso 0.432(4) 1 d . . P A 2
C18A C 0.728(2) 1.0499(16) 0.8323(13) 0.065(5) Uiso 0.432(4) 1 d . . P A 2
H18D H 0.735223 1.103044 0.870722 0.098 Uiso 0.432(4) 1 calc R U P A 2
H18E H 0.759826 0.987855 0.854956 0.098 Uiso 0.432(4) 1 calc R U P A 2
H18F H 0.780889 1.066593 0.786849 0.098 Uiso 0.432(4) 1 calc R U P A 2
C19A C 0.541(2) 1.1410(17) 0.7781(13) 0.076(5) Uiso 0.432(4) 1 d . . P A 2
H19D H 0.449989 1.137447 0.76158 0.115 Uiso 0.432(4) 1 calc R U P A 2
H19E H 0.549166 1.189654 0.819879 0.115 Uiso 0.432(4) 1 calc R U P A 2
H19F H 0.594579 1.161115 0.734099 0.115 Uiso 0.432(4) 1 calc R U P A 2
C20A C 0.575(2) 0.9530(17) 0.7466(13) 0.084(6) Uiso 0.432(4) 1 d . . P A 2
H20D H 0.484536 0.944955 0.730912 0.125 Uiso 0.432(4) 1 calc R U P A 2
H20E H 0.627586 0.969775 0.70125 0.125 Uiso 0.432(4) 1 calc R U P A 2
H20F H 0.606523 0.891037 0.769357 0.125 Uiso 0.432(4) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.676(14) . ?
P1 C7 1.847(11) . ?
P1 P2 2.314(3) . ?
P2 N2 1.65(3) . ?
P2 C17 1.939(15) . ?
N1 C4 1.412(18) . ?
N1 C1 1.691(18) . ?
N2 C14 1.50(3) . ?
N2 C11 1.51(2) . ?
C1 C2 1.45(3) . ?
C1 C3 1.530(3) . ?
C1 H1 1 . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 C6 1.530(3) . ?
C4 C5 1.530(3) . ?
C4 H4 1 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 C9 1.512(14) . ?
C7 C10 1.540(16) . ?
C7 C8 1.594(15) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C13 1.543(18) . ?
C11 C12 1.547(18) . ?
C11 H11 1 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 C16 1.36(3) . ?
C14 C15 1.523(18) . ?
C14 H14 1 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 C20 1.44(2) . ?
C17 C18 1.56(2) . ?
C17 C19 1.57(2) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
P1A N1A 1.74(2) . ?
P1A C7A 1.98(2) . ?
P1A P2A 2.311(4) . ?
P2A N2A 1.73(4) . ?
P2A C17A 1.89(2) . ?
N1A C1A 1.31(2) . ?
N1A C4A 1.61(3) . ?
N2A C11A 1.41(4) . ?
N2A C14A 1.47(3) . ?
C1A C3A 1.40(3) . ?
C1A C2A 1.56(2) . ?
C1A H1A 1 . ?
C2A H2A1 0.98 . ?
C2A H2A2 0.98 . ?
C2A H2A3 0.98 . ?
C3A H3A1 0.98 . ?
C3A H3A2 0.98 . ?
C3A H3A3 0.98 . ?
C4A C6A 1.532(3) . ?
C4A C5A 1.532(3) . ?
C4A H4A 1 . ?
C5A H5A1 0.98 . ?
C5A H5A2 0.98 . ?
C5A H5A3 0.98 . ?
C6A H6A1 0.98 . ?
C6A H6A2 0.98 . ?
C6A H6A3 0.98 . ?
C7A C10A 1.36(3) . ?
C7A C9A 1.44(3) . ?
C7A C8A 1.55(3) . ?
C8A H8A1 0.98 . ?
C8A H8A2 0.98 . ?
C8A H8A3 0.98 . ?
C9A H9A1 0.98 . ?
C9A H9A2 0.98 . ?
C9A H9A3 0.98 . ?
C10A H10D 0.98 . ?
C10A H10E 0.98 . ?
C10A H10F 0.98 . ?
C11A C12A 1.45(3) . ?
C11A C13A 1.71(3) . ?
C11A H11A 1 . ?
C12A H12D 0.98 . ?
C12A H12E 0.98 . ?
C12A H12F 0.98 . ?
C13A H13D 0.98 . ?
C13A H13E 0.98 . ?
C13A H13F 0.98 . ?
C14A C15A 1.52(3) . ?
C14A C16A 1.75(5) . ?
C14A H14A 1 . ?
C15A H15D 0.98 . ?
C15A H15E 0.98 . ?
C15A H15F 0.98 . ?
C16A H16D 0.98 . ?
C16A H16E 0.98 . ?
C16A H16F 0.98 . ?
C17A C18A 1.55(3) . ?
C17A C20A 1.56(3) . ?
C17A C19A 1.56(3) . ?
C18A H18D 0.98 . ?
C18A H18E 0.98 . ?
C18A H18F 0.98 . ?
C19A H19D 0.98 . ?
C19A H19E 0.98 . ?
C19A H19F 0.98 . ?
C20A H20D 0.98 . ?
C20A H20E 0.98 . ?
C20A H20F 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C7 109.0(5) . . ?
N1 P1 P2 121.2(5) . . ?
C7 P1 P2 99.0(3) . . ?
N2 P2 C17 103.1(11) . . ?
N2 P2 P1 103.7(9) . . ?
C17 P2 P1 111.5(5) . . ?
C4 N1 P1 137.1(10) . . ?
C4 N1 C1 114.3(11) . . ?
P1 N1 C1 108.3(8) . . ?
C14 N2 C11 111.8(18) . . ?
C14 N2 P2 120.1(15) . . ?
C11 N2 P2 125.8(18) . . ?
C2 C1 C3 117(2) . . ?
C2 C1 N1 119.9(14) . . ?
C3 C1 N1 104.3(13) . . ?
C2 C1 H1 104.8 . . ?
C3 C1 H1 104.8 . . ?
N1 C1 H1 104.8 . . ?
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 . . ?
N1 C4 C6 117.7(13) . . ?
N1 C4 C5 108.7(13) . . ?
C6 C4 C5 109.9(13) . . ?
N1 C4 H4 106.7 . . ?
C6 C4 H4 106.7 . . ?
C5 C4 H4 106.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C7 C10 109.6(10) . . ?
C9 C7 C8 105.1(10) . . ?
C10 C7 C8 105.7(10) . . ?
C9 C7 P1 109.2(8) . . ?
C10 C7 P1 110.9(7) . . ?
C8 C7 P1 116.0(8) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C13 111.0(14) . . ?
N2 C11 C12 115.8(15) . . ?
C13 C11 C12 112.0(11) . . ?
N2 C11 H11 105.7 . . ?
C13 C11 H11 105.7 . . ?
C12 C11 H11 105.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 N2 115.4(17) . . ?
C16 C14 C15 105.2(14) . . ?
N2 C14 C15 112.6(14) . . ?
C16 C14 H14 107.7 . . ?
N2 C14 H14 107.7 . . ?
C15 C14 H14 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C17 C18 112.9(14) . . ?
C20 C17 C19 112.5(14) . . ?
C18 C17 C19 105.3(13) . . ?
C20 C17 P2 118.6(12) . . ?
C18 C17 P2 103.2(10) . . ?
C19 C17 P2 103.0(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1A P1A C7A 104.5(9) . . ?
N1A P1A P2A 103.1(7) . . ?
C7A P1A P2A 117.6(7) . . ?
N2A P2A C17A 105.7(13) . . ?
N2A P2A P1A 102.0(12) . . ?
C17A P2A P1A 120.7(8) . . ?
C1A N1A C4A 115.5(17) . . ?
C1A N1A P1A 118.9(14) . . ?
C4A N1A P1A 119.8(13) . . ?
C11A N2A C14A 114(3) . . ?
C11A N2A P2A 122(2) . . ?
C14A N2A P2A 123(2) . . ?
N1A C1A C3A 131.3(18) . . ?
N1A C1A C2A 99.0(15) . . ?
C3A C1A C2A 111.8(15) . . ?
N1A C1A H1A 103.9 . . ?
C3A C1A H1A 103.9 . . ?
C2A C1A H1A 103.9 . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
C1A C3A H3A1 109.5 . . ?
C1A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C1A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C6A C4A C5A 127.3(4) . . ?
C6A C4A N1A 99.7(16) . . ?
C5A C4A N1A 116.3(17) . . ?
C6A C4A H4A 103.6 . . ?
C5A C4A H4A 103.6 . . ?
N1A C4A H4A 103.6 . . ?
C4A C5A H5A1 109.5 . . ?
C4A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C4A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C4A C6A H6A1 109.5 . . ?
C4A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C4A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
C10A C7A C9A 118(2) . . ?
C10A C7A C8A 105(2) . . ?
C9A C7A C8A 109(2) . . ?
C10A C7A P1A 109.0(16) . . ?
C9A C7A P1A 104.2(16) . . ?
C8A C7A P1A 111.4(15) . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7A C9A H9A1 109.5 . . ?
C7A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C7A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C7A C10A H10D 109.5 . . ?
C7A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C7A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
N2A C11A C12A 113(2) . . ?
N2A C11A C13A 105.4(19) . . ?
C12A C11A C13A 114.5(16) . . ?
N2A C11A H11A 107.9 . . ?
C12A C11A H11A 107.9 . . ?
C13A C11A H11A 107.9 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C11A C13A H13D 109.5 . . ?
C11A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C11A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
N2A C14A C15A 106.9(19) . . ?
N2A C14A C16A 109(2) . . ?
C15A C14A C16A 119(2) . . ?
N2A C14A H14A 107 . . ?
C15A C14A H14A 107 . . ?
C16A C14A H14A 107 . . ?
C14A C15A H15D 109.5 . . ?
C14A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C14A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C14A C16A H16D 109.5 . . ?
C14A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C14A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C18A C17A C20A 109.3(18) . . ?
C18A C17A C19A 106.0(18) . . ?
C20A C17A C19A 114.6(18) . . ?
C18A C17A P2A 103.5(14) . . ?
C20A C17A P2A 117.9(16) . . ?
C19A C17A P2A 104.3(15) . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C17A C19A H19D 109.5 . . ?
C17A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C17A C20A H20D 109.5 . . ?
C17A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C17A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 P1 N1 C4 -65.1(16) . . . . ?
P2 P1 N1 C4 48.5(16) . . . . ?
C7 P1 N1 C1 108.5(8) . . . . ?
P2 P1 N1 C1 -137.9(7) . . . . ?
C17 P2 N2 C14 -129.0(18) . . . . ?
P1 P2 N2 C14 114.7(17) . . . . ?
C17 P2 N2 C11 70(2) . . . . ?
P1 P2 N2 C11 -47(2) . . . . ?
C4 N1 C1 C2 121(2) . . . . ?
P1 N1 C1 C2 -54(2) . . . . ?
C4 N1 C1 C3 -106.4(17) . . . . ?
P1 N1 C1 C3 78.4(17) . . . . ?
P1 N1 C4 C6 117.3(17) . . . . ?
C1 N1 C4 C6 -56.0(18) . . . . ?
P1 N1 C4 C5 -117.0(15) . . . . ?
C1 N1 C4 C5 69.7(14) . . . . ?
N1 P1 C7 C9 -60.1(11) . . . . ?
P2 P1 C7 C9 172.4(9) . . . . ?
N1 P1 C7 C10 179.0(8) . . . . ?
P2 P1 C7 C10 51.5(8) . . . . ?
N1 P1 C7 C8 58.4(9) . . . . ?
P2 P1 C7 C8 -69.1(8) . . . . ?
C14 N2 C11 C13 70(2) . . . . ?
P2 N2 C11 C13 -126.8(19) . . . . ?
C14 N2 C11 C12 -59(2) . . . . ?
P2 N2 C11 C12 104(2) . . . . ?
C11 N2 C14 C16 -136.2(17) . . . . ?
P2 N2 C14 C16 60(2) . . . . ?
C11 N2 C14 C15 102.9(18) . . . . ?
P2 N2 C14 C15 -61(2) . . . . ?
C7A P1A N1A C1A 162.0(14) . . . . ?
P2A P1A N1A C1A -74.6(14) . . . . ?
C7A P1A N1A C4A -46.0(14) . . . . ?
P2A P1A N1A C4A 77.4(13) . . . . ?
C17A P2A N2A C11A 125(2) . . . . ?
P1A P2A N2A C11A -108(2) . . . . ?
C17A P2A N2A C14A -63(3) . . . . ?
P1A P2A N2A C14A 64(3) . . . . ?
C4A N1A C1A C3A -103(2) . . . . ?
P1A N1A C1A C3A 50(3) . . . . ?
C4A N1A C1A C2A 127.3(14) . . . . ?
P1A N1A C1A C2A -79.6(15) . . . . ?
C1A N1A C4A C6A -100.0(18) . . . . ?
P1A N1A C4A C6A 107.1(15) . . . . ?
C1A N1A C4A C5A 40(2) . . . . ?
P1A N1A C4A C5A -112.5(17) . . . . ?
C14A N2A C11A C12A -116(3) . . . . ?
P2A N2A C11A C12A 58(3) . . . . ?
C14A N2A C11A C13A 119(2) . . . . ?
P2A N2A C11A C13A -68(3) . . . . ?
C11A N2A C14A C15A 61(3) . . . . ?
P2A N2A C14A C15A -112(2) . . . . ?
C11A N2A C14A C16A -69(3) . . . . ?
P2A N2A C14A C16A 117(3) . . . . ?
N2A P2A C17A C18A -61.3(19) . . . . ?
P1A P2A C17A C18A -176.1(11) . . . . ?
N2A P2A C17A C20A 59(2) . . . . ?
P1A P2A C17A C20A -55(2) . . . . ?
N2A P2A C17A C19A -172.1(17) . . . . ?
P1A P2A C17A C19A 73.2(15) . . . . ?


# start Validation Reply Form
_vrf_PLAT097_I                   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.07 eA-3  
RESPONSE: The whole molecule is disorder and was calculated in two position.
The P1a atom was fixed in the q1 position at the beginning (Residual Density - 2.07 eA-3 ).
During the refinement the P1a atom appraoched to the P1 atom (P1 - P2 = 0.121 A),
whereas in the distance 1.289 A from P1 a new high maximum appeared again.
Additionally, the fixing P1a in the distance of 1.289 A from the P1 atom, 
resulted the destabilization of the structure.
;

# end Validation Reply Form 
# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1560638'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-30T12:40:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22 H24 P2'
_chemical_formula_sum            'C22 H24 P2'
_chemical_formula_weight         350.35

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3090(3)
_cell_length_b                   20.0750(4)
_cell_length_c                   16.5350(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.950(2)
_cell_angle_gamma                90
_cell_volume                     3840.66(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    17386
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      29.59
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.954

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 138 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_number            17651
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             8263
_reflns_number_gt                6692
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+3.5683P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8263
_refine_ls_number_parameters     572
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.11638(6) 0.71672(3) 0.90831(4) 0.02567(16) Uani 0.8045(13) 1 d . . P A 1
P2 P 0.13448(6) 0.69800(3) 0.78107(4) 0.02382(16) Uani 0.8045(13) 1 d . . P A 1
P3 P 0.27464(6) 0.30315(4) 0.12342(4) 0.02912(17) Uani 0.8045(13) 1 d . . P A 1
P4 P 0.46667(6) 0.30927(3) 0.17943(4) 0.02655(17) Uani 0.8045(13) 1 d . . P A 1
C1 C 0.2061(3) 0.79175(14) 0.94006(17) 0.0266(6) Uani 0.8045(13) 1 d . . P A 1
C2 C 0.1617(3) 0.84354(16) 0.97670(18) 0.0335(6) Uani 0.8045(13) 1 d . . P A 1
H2 H 0.088841 0.838334 0.983868 0.04 Uiso 0.8045(13) 1 calc R U P A 1
C3 C 0.2236(4) 0.90252(16) 1.0026(2) 0.0395(7) Uani 0.8045(13) 1 d . . P A 1
H3 H 0.193723 0.937018 1.028343 0.047 Uiso 0.8045(13) 1 calc R U P A 1
C4 C 0.3282(3) 0.91050(16) 0.9908(2) 0.0380(7) Uani 0.8045(13) 1 d . . P A 1
H4 H 0.3699 0.95093 1.007627 0.046 Uiso 0.8045(13) 1 calc R U P A 1
C5 C 0.3730(3) 0.86011(18) 0.9546(2) 0.0404(8) Uani 0.8045(13) 1 d . . P A 1
H5 H 0.445422 0.865939 0.946795 0.048 Uiso 0.8045(13) 1 calc R U P A 1
C6 C 0.3122(3) 0.80098(17) 0.9295(2) 0.0354(7) Uani 0.8045(13) 1 d . . P A 1
H6 H 0.343629 0.766463 0.904933 0.043 Uiso 0.8045(13) 1 calc R U P A 1
C7 C 0.2137(3) 0.65064(14) 0.97073(18) 0.0258(6) Uani 0.8045(13) 1 d . . P A 1
C8 C 0.3135(4) 0.62916(17) 0.95790(19) 0.0322(6) Uani 0.8045(13) 1 d . . P A 1
H8 H 0.335419 0.64838 0.91324 0.039 Uiso 0.8045(13) 1 calc R U P A 1
C9 C 0.3821(3) 0.57971(19) 1.0097(3) 0.0372(7) Uani 0.8045(13) 1 d . . P A 1
H9 H 0.450157 0.565221 1.000064 0.045 Uiso 0.8045(13) 1 calc R U P A 1
C10 C 0.3512(3) 0.55154(15) 1.0755(2) 0.0351(7) Uani 0.8045(13) 1 d . . P A 1
H10 H 0.397764 0.517748 1.110947 0.042 Uiso 0.8045(13) 1 calc R U P A 1
C11 C 0.2520(4) 0.57320(17) 1.0889(2) 0.0378(8) Uani 0.8045(13) 1 d . . P A 1
H11 H 0.231049 0.554592 1.13429 0.045 Uiso 0.8045(13) 1 calc R U P A 1
C12 C 0.1828(3) 0.62187(16) 1.0365(2) 0.0311(7) Uani 0.8045(13) 1 d . . P A 1
H12 H 0.113948 0.635653 1.045544 0.037 Uiso 0.8045(13) 1 calc R U P A 1
C13 C 0.0536(3) 0.61937(14) 0.75356(18) 0.0267(7) Uani 0.8045(13) 1 d . . P A 1
C14 C 0.0846(3) 0.57620(17) 0.6987(2) 0.0406(8) Uani 0.8045(13) 1 d . . P A 1
H14 H 0.146374 0.587503 0.679034 0.049 Uiso 0.8045(13) 1 calc R U P A 1
C15 C 0.0248(4) 0.51650(19) 0.6728(2) 0.0529(10) Uani 0.8045(13) 1 d . . P A 1
H15 H 0.045143 0.487765 0.634629 0.063 Uiso 0.8045(13) 1 calc R U P A 1
C16 C -0.0625(4) 0.49890(18) 0.7016(3) 0.0514(10) Uani 0.8045(13) 1 d . . P A 1
H16 H -0.102459 0.458096 0.683437 0.062 Uiso 0.8045(13) 1 calc R U P A 1
C17 C -0.0928(3) 0.5400(2) 0.7567(2) 0.0451(8) Uani 0.8045(13) 1 d . . P A 1
H17 H -0.152557 0.527065 0.777645 0.054 Uiso 0.8045(13) 1 calc R U P A 1
C18 C -0.0365(3) 0.60011(18) 0.78187(19) 0.0352(7) Uani 0.8045(13) 1 d . . P A
1
H18 H -0.059454 0.628708 0.818914 0.042 Uiso 0.8045(13) 1 calc R U P A 1
C19 C 0.0313(3) 0.75947(17) 0.7078(2) 0.0280(5) Uani 0.8045(13) 1 d . . P A 1
C20 C 0.0222(3) 0.74049(15) 0.61669(19) 0.0329(6) Uani 0.8045(13) 1 d . . P A 1
H20A H -0.013132 0.696308 0.60294 0.049 Uiso 0.8045(13) 1 calc R U P A 1
H20B H -0.02565 0.773279 0.576145 0.049 Uiso 0.8045(13) 1 calc R U P A 1
H20C H 0.099613 0.739663 0.61228 0.049 Uiso 0.8045(13) 1 calc R U P A 1
C21 C -0.0906(3) 0.7597(2) 0.7127(3) 0.0553(11) Uani 0.8045(13) 1 d . . P A 1
H21A H -0.124195 0.715018 0.699527 0.083 Uiso 0.8045(13) 1 calc R U P A 1
H21B H -0.086904 0.772541 0.770717 0.083 Uiso 0.8045(13) 1 calc R U P A 1
H21C H -0.138797 0.791577 0.67085 0.083 Uiso 0.8045(13) 1 calc R U P A 1
C22 C 0.0863(4) 0.82804(16) 0.7279(2) 0.0509(10) Uani 0.8045(13) 1 d . . P A 1
H22A H 0.092626 0.840877 0.786499 0.076 Uiso 0.8045(13) 1 calc R U P A 1
H22B H 0.163442 0.826918 0.723095 0.076 Uiso 0.8045(13) 1 calc R U P A 1
H22C H 0.038179 0.860534 0.68696 0.076 Uiso 0.8045(13) 1 calc R U P A 1
C23 C 0.2607(3) 0.22214(15) 0.06689(18) 0.0269(6) Uani 0.8045(13) 1 d . . P A 1
C24 C 0.3172(3) 0.20445(18) 0.0114(2) 0.0426(8) Uani 0.8045(13) 1 d . . P A 1
H24 H 0.368893 0.234999 -0.000338 0.051 Uiso 0.8045(13) 1 calc R U P A 1
C25 C 0.2993(3) 0.14230(19) -0.0278(2) 0.0449(8) Uani 0.8045(13) 1 d . . P A 1
H25 H 0.339169 0.13064 -0.065828 0.054 Uiso 0.8045(13) 1 calc R U P A 1
C26 C 0.2246(3) 0.09748(17) -0.0120(2) 0.0380(8) Uani 0.8045(13) 1 d . . P A 1
H26 H 0.212845 0.054993 -0.038946 0.046 Uiso 0.8045(13) 1 calc R U P A 1
C27 C 0.1674(4) 0.1145(2) 0.0425(3) 0.0499(9) Uani 0.8045(13) 1 d . . P A 1
H27 H 0.115314 0.083777 0.053346 0.06 Uiso 0.8045(13) 1 calc R U P A 1
C28 C 0.1849(3) 0.17644(19) 0.0822(3) 0.0418(8) Uani 0.8045(13) 1 d . . P A 1
H28 H 0.144748 0.187745 0.120198 0.05 Uiso 0.8045(13) 1 calc R U P A 1
C29 C 0.2487(3) 0.36311(16) 0.03484(19) 0.0302(7) Uani 0.8045(13) 1 d . . P A 1
C30 C 0.1465(3) 0.40028(19) 0.0156(2) 0.0359(7) Uani 0.8045(13) 1 d . . P A 1
H30 H 0.097991 0.39454 0.049091 0.043 Uiso 0.8045(13) 1 calc R U P A 1
C31 C 0.1157(3) 0.44536(18) -0.0521(3) 0.0410(8) Uani 0.8045(13) 1 d . . P A 1
H31 H 0.045764 0.469824 -0.06529 0.049 Uiso 0.8045(13) 1 calc R U P A 1
C32 C 0.1870(4) 0.45477(17) -0.1004(2) 0.0411(8) Uani 0.8045(13) 1 d . . P A 1
H32 H 0.166018 0.485607 -0.146796 0.049 Uiso 0.8045(13) 1 calc R U P A 1
C33 C 0.2894(3) 0.4188(2) -0.0807(2) 0.0417(9) Uani 0.8045(13) 1 d . . P A 1
H33 H 0.338441 0.425264 -0.113688 0.05 Uiso 0.8045(13) 1 calc R U P A 1
C34 C 0.3202(3) 0.37392(19) -0.0137(2) 0.0356(9) Uani 0.8045(13) 1 d . . P A 1
H34 H 0.390791 0.350071 -0.000398 0.043 Uiso 0.8045(13) 1 calc R U P A 1
C35 C 0.4790(3) 0.39064(15) 0.23236(19) 0.0281(7) Uani 0.8045(13) 1 d . . P A 1
C36 C 0.4008(3) 0.41760(17) 0.2673(2) 0.0344(8) Uani 0.8045(13) 1 d . . P A 1
H36 H 0.331942 0.393825 0.261873 0.041 Uiso 0.8045(13) 1 calc R U P A 1
C37 C 0.4209(3) 0.47860(17) 0.3101(2) 0.0391(8) Uani 0.8045(13) 1 d . . P A 1
H37 H 0.366687 0.496122 0.333946 0.047 Uiso 0.8045(13) 1 calc R U P A 1
C38 C 0.5214(4) 0.51336(16) 0.3175(2) 0.0393(8) Uani 0.8045(13) 1 d . . P A 1
H38 H 0.537001 0.554466 0.34772 0.047 Uiso 0.8045(13) 1 calc R U P A 1
C39 C 0.5992(3) 0.48855(19) 0.2810(2) 0.0398(8) Uani 0.8045(13) 1 d . . P A 1
H39 H 0.666718 0.513194 0.284852 0.048 Uiso 0.8045(13) 1 calc R U P A 1
C40 C 0.5783(3) 0.4277(2) 0.2389(2) 0.0362(7) Uani 0.8045(13) 1 d . . P A 1
H40 H 0.631921 0.410895 0.214085 0.043 Uiso 0.8045(13) 1 calc R U P A 1
C41 C 0.5029(3) 0.24971(16) 0.27372(19) 0.0280(5) Uani 0.8045(13) 1 d . . P A 1
C42 C 0.4245(3) 0.2526(2) 0.3265(3) 0.0560(10) Uani 0.8045(13) 1 d . . P A 1
H42A H 0.424631 0.297911 0.348703 0.084 Uiso 0.8045(13) 1 calc R U P A 1
H42B H 0.345698 0.240541 0.290377 0.084 Uiso 0.8045(13) 1 calc R U P A 1
H42C H 0.452069 0.221367 0.374711 0.084 Uiso 0.8045(13) 1 calc R U P A 1
C43 C 0.6265(3) 0.26688(19) 0.3312(2) 0.0398(8) Uani 0.8045(13) 1 d . . P A 1
H43A H 0.677781 0.265029 0.297089 0.06 Uiso 0.8045(13) 1 calc R U P A 1
H43B H 0.628021 0.311831 0.354636 0.06 Uiso 0.8045(13) 1 calc R U P A 1
H43C H 0.652673 0.23474 0.378497 0.06 Uiso 0.8045(13) 1 calc R U P A 1
C44 C 0.5047(4) 0.18008(17) 0.2382(2) 0.0569(11) Uani 0.8045(13) 1 d . . P A 1
H44A H 0.55613 0.179369 0.204153 0.085 Uiso 0.8045(13) 1 calc R U P A 1
H44B H 0.532771 0.148398 0.285891 0.085 Uiso 0.8045(13) 1 calc R U P A 1
H44C H 0.4264 0.167571 0.201557 0.085 Uiso 0.8045(13) 1 calc R U P A 1
P1A P 0.2283(3) 0.70232(16) 0.8698(2) 0.0333(8) Uani 0.1955(13) 1 d . . P A 2
P2A P 0.0379(2) 0.69563(15) 0.81513(18) 0.0288(7) Uani 0.1955(13) 1 d . . P A 2
P3A P 0.3808(3) 0.28503(14) 0.09052(18) 0.0275(7) Uani 0.1955(13) 1 d . . P A 2
P4A P 0.3669(2) 0.30459(14) 0.21805(17) 0.0251(7) Uani 0.1955(13) 1 d . . P A 2
C1A C 0.2447(11) 0.7840(4) 0.9270(6) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
C2A C 0.1760(8) 0.8047(5) 0.9738(7) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H2A H 0.11535 0.776869 0.977403 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C3A C 0.1959(8) 0.8660(6) 1.0152(6) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H3A H 0.148974 0.880143 1.0472 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C4A C 0.2847(10) 0.9067(4) 1.0099(7) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H4A H 0.2983 0.948628 1.038274 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C5A C 0.3534(8) 0.8860(6) 0.9632(8) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H5A H 0.414004 0.91384 0.959551 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C6A C 0.3334(10) 0.8247(6) 0.9217(7) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H6A H 0.380382 0.810566 0.889753 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C7A C 0.2552(13) 0.6423(5) 0.9587(6) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
C8A C 0.3573(11) 0.6062(7) 0.9785(8) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H8A H 0.406841 0.612584 0.945849 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C9A C 0.3870(8) 0.5607(6) 1.0459(9) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H9A H 0.456816 0.536027 1.059365 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C10A C 0.3146(12) 0.5514(5) 1.0936(6) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H10A H 0.3349 0.520277 1.13968 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C11A C 0.2125(10) 0.5875(7) 1.0739(8) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H11A H 0.163007 0.581083 1.10648 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C12A C 0.1828(8) 0.6330(6) 1.0064(9) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H12A H 0.11303 0.657641 0.992965 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C13A C 0.0257(12) 0.6119(5) 0.7655(7) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
C14A C 0.1017(9) 0.5870(6) 0.7272(8) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H14A H 0.167419 0.612354 0.728337 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C15A C 0.0816(9) 0.5251(6) 0.6871(7) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H15A H 0.133537 0.508163 0.660882 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C16A C -0.0146(10) 0.4881(4) 0.6854(7) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H16A H -0.028349 0.445798 0.657997 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C17A C -0.0906(7) 0.5129(7) 0.7237(8) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H17A H -0.156355 0.487624 0.722569 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C18A C -0.0705(10) 0.5748(7) 0.7638(7) 0.0355(10) Uani 0.1955(13) 1 d G . P A 2
H18A H -0.122475 0.591816 0.790025 0.043 Uiso 0.1955(13) 1 calc R U P A 2
C19A C -0.0027(13) 0.7552(8) 0.7174(9) 0.0280(5) Uani 0.1955(13) 1 d . . P A 2
C20A C 0.0644(17) 0.7430(10) 0.6587(13) 0.067(3) Uani 0.1955(13) 1 d . . P A 2
H20D H 0.146364 0.752086 0.689393 0.1 Uiso 0.1955(13) 1 calc R U P A 2
H20E H 0.054844 0.696414 0.639737 0.1 Uiso 0.1955(13) 1 calc R U P A 2
H20F H 0.035861 0.772335 0.608564 0.1 Uiso 0.1955(13) 1 calc R U P A 2
C21A C -0.1296(17) 0.7405(10) 0.6673(13) 0.067(3) Uani 0.1955(13) 1 d . . P A 2
H21D H -0.175623 0.748147 0.704461 0.1 Uiso 0.1955(13) 1 calc R U P A 2
H21E H -0.156761 0.769858 0.617066 0.1 Uiso 0.1955(13) 1 calc R U P A 2
H21F H -0.137777 0.693937 0.648239 0.1 Uiso 0.1955(13) 1 calc R U P A 2
C22A C 0.0163(17) 0.8262(9) 0.7529(12) 0.067(3) Uani 0.1955(13) 1 d . . P A 2
H22D H -0.028422 0.833078 0.791125 0.1 Uiso 0.1955(13) 1 calc R U P A 2
H22E H 0.098622 0.833006 0.785127 0.1 Uiso 0.1955(13) 1 calc R U P A 2
H22F H -0.009016 0.858013 0.705134 0.1 Uiso 0.1955(13) 1 calc R U P A 2
C23A C 0.2929(11) 0.2089(5) 0.0588(10) 0.0455(19) Uani 0.1955(13) 1 d G . P A 2
C24A C 0.3291(9) 0.1602(7) 0.0139(9) 0.0455(19) Uani 0.1955(13) 1 d G . P A 2
H24A H 0.396959 0.166935 -0.000218 0.055 Uiso 0.1955(13) 1 calc R U P A 2
C25A C 0.2660(11) 0.1017(6) -0.0105(8) 0.0455(19) Uani 0.1955(13) 1 d G . P A 2
H25A H 0.290782 0.068405 -0.041224 0.055 Uiso 0.1955(13) 1 calc R U P A 2
C26A C 0.1668(10) 0.0918(5) 0.0101(8) 0.0455(19) Uani 0.1955(13) 1 d G . P A 2
H26A H 0.123676 0.05182 -0.006541 0.055 Uiso 0.1955(13) 1 calc R U P A 2
C27A C 0.1306(9) 0.1405(6) 0.0551(8) 0.0455(19) Uani 0.1955(13) 1 d G . P A 2
H27A H 0.062747 0.133765 0.06915 0.055 Uiso 0.1955(13) 1 calc R U P A 2
C28A C 0.1937(12) 0.1990(5) 0.0794(9) 0.0455(19) Uani 0.1955(13) 1 d G . P A 2
H28A H 0.168922 0.232296 0.110157 0.055 Uiso 0.1955(13) 1 calc R U P A 2
C29A C 0.2867(11) 0.3515(5) 0.0271(6) 0.0306(17) Uani 0.1955(13) 1 d G . P A 2
C30A C 0.1871(11) 0.3728(5) 0.0410(5) 0.0306(17) Uani 0.1955(13) 1 d G . P A 2
H30A H 0.165849 0.353768 0.086011 0.037 Uiso 0.1955(13) 1 calc R U P A 2
C31A C 0.1186(8) 0.4221(6) -0.0110(8) 0.0306(17) Uani 0.1955(13) 1 d G . P A 2
H31A H 0.050574 0.436674 -0.001484 0.037 Uiso 0.1955(13) 1 calc R U P A 2
C32A C 0.1498(11) 0.4500(5) -0.0769(7) 0.0306(17) Uani 0.1955(13) 1 d G . P A 2
H32A H 0.10297 0.48364 -0.112399 0.037 Uiso 0.1955(13) 1 calc R U P A 2
C33A C 0.2494(12) 0.4286(7) -0.0908(6) 0.0306(17) Uani 0.1955(13) 1 d G . P A 2
H33A H 0.270643 0.4477 -0.13582 0.037 Uiso 0.1955(13) 1 calc R U P A 2
C34A C 0.3178(8) 0.3794(7) -0.0388(8) 0.0306(17) Uani 0.1955(13) 1 d G . P A 2
H34A H 0.38592 0.364794 -0.048326 0.037 Uiso 0.1955(13) 1 calc R U P A 2
C35A C 0.4431(11) 0.3867(5) 0.2444(8) 0.042(2) Uani 0.1955(13) 1 d G . P A 2
C36A C 0.4107(9) 0.4331(8) 0.2943(8) 0.042(2) Uani 0.1955(13) 1 d G . P A 2
H36A H 0.3467 0.424332 0.31247 0.05 Uiso 0.1955(13) 1 calc R U P A 2
C37A C 0.4719(12) 0.4923(7) 0.3177(7) 0.042(2) Uani 0.1955(13) 1 d G . P A 2
H37A H 0.449759 0.524038 0.351792 0.05 Uiso 0.1955(13) 1 calc R U P A 2
C38A C 0.5655(11) 0.5052(5) 0.2911(9) 0.042(2) Uani 0.1955(13) 1 d G . P A 2
H38A H 0.607365 0.545635 0.307107 0.05 Uiso 0.1955(13) 1 calc R U P A 2
C39A C 0.5979(8) 0.4588(7) 0.2412(8) 0.042(2) Uani 0.1955(13) 1 d G . P A 2
H39A H 0.661913 0.467526 0.223098 0.05 Uiso 0.1955(13) 1 calc R U P A 2
C40A C 0.5367(12) 0.3995(6) 0.2179(6) 0.042(2) Uani 0.1955(13) 1 d G . P A 2
H40A H 0.558855 0.36782 0.183775 0.05 Uiso 0.1955(13) 1 calc R U P A 2
C41A C 0.4727(13) 0.2455(7) 0.2924(9) 0.0280(5) Uani 0.1955(13) 1 d . . P A 2
C42A C 0.4769(15) 0.2617(8) 0.3837(10) 0.058(4) Uani 0.1955(13) 1 d . . P A 2
H42D H 0.39826 0.262106 0.385626 0.087 Uiso 0.1955(13) 1 calc R U P A 2
H42E H 0.522915 0.22795 0.423531 0.087 Uiso 0.1955(13) 1 calc R U P A 2
H42F H 0.512348 0.305634 0.400419 0.087 Uiso 0.1955(13) 1 calc R U P A 2
C43A C 0.5902(17) 0.2444(11) 0.2865(14) 0.065(5) Uani 0.1955(13) 1 d . . P A 2
H43D H 0.584746 0.233849 0.227359 0.097 Uiso 0.1955(13) 1 calc R U P A 2
H43E H 0.626431 0.288154 0.302518 0.097 Uiso 0.1955(13) 1 calc R U P A 2
H43F H 0.636998 0.21047 0.32563 0.097 Uiso 0.1955(13) 1 calc R U P A 2
C44A C 0.4155(14) 0.1737(6) 0.2721(9) 0.049(4) Uani 0.1955(13) 1 d . . P A 2
H44D H 0.338001 0.174965 0.276244 0.073 Uiso 0.1955(13) 1 calc R U P A 2
H44E H 0.410043 0.160304 0.213863 0.073 Uiso 0.1955(13) 1 calc R U P A 2
H44F H 0.46327 0.141496 0.313746 0.073 Uiso 0.1955(13) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.835(3) . ?
P1 C7 1.849(3) . ?
P1 P2 2.2219(9) . ?
P2 C13 1.839(3) . ?
P2 C19 1.885(3) . ?
P3 C29 1.838(3) . ?
P3 C23 1.854(3) . ?
P3 P4 2.2284(10) . ?
P4 C35 1.835(3) . ?
P4 C41 1.893(3) . ?
C1 C6 1.388(5) . ?
C1 C2 1.404(4) . ?
C2 C3 1.394(5) . ?
C2 H2 0.95 . ?
C3 C4 1.376(5) . ?
C3 H3 0.95 . ?
C4 C5 1.383(5) . ?
C4 H4 0.95 . ?
C5 C6 1.389(4) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.385(4) . ?
C7 C12 1.395(4) . ?
C8 C9 1.392(4) . ?
C8 H8 0.95 . ?
C9 C10 1.389(5) . ?
C9 H9 0.95 . ?
C10 C11 1.383(5) . ?
C10 H10 0.95 . ?
C11 C12 1.388(4) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C18 1.398(4) . ?
C13 C14 1.399(4) . ?
C14 C15 1.395(5) . ?
C14 H14 0.95 . ?
C15 C16 1.361(7) . ?
C15 H15 0.95 . ?
C16 C17 1.372(6) . ?
C16 H16 0.95 . ?
C17 C18 1.383(4) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C19 C22 1.520(5) . ?
C19 C20 1.521(4) . ?
C19 C21 1.530(5) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 C24 1.374(4) . ?
C23 C28 1.392(4) . ?
C24 C25 1.388(5) . ?
C24 H24 0.95 . ?
C25 C26 1.373(5) . ?
C25 H25 0.95 . ?
C26 C27 1.363(6) . ?
C26 H26 0.95 . ?
C27 C28 1.389(5) . ?
C27 H27 0.95 . ?
C28 H28 0.95 . ?
C29 C34 1.395(5) . ?
C29 C30 1.403(5) . ?
C30 C31 1.387(5) . ?
C30 H30 0.95 . ?
C31 C32 1.387(6) . ?
C31 H31 0.95 . ?
C32 C33 1.391(5) . ?
C32 H32 0.95 . ?
C33 C34 1.377(5) . ?
C33 H33 0.95 . ?
C34 H34 0.95 . ?
C35 C36 1.391(5) . ?
C35 C40 1.403(5) . ?
C36 C37 1.394(4) . ?
C36 H36 0.95 . ?
C37 C38 1.390(5) . ?
C37 H37 0.95 . ?
C38 C39 1.387(5) . ?
C38 H38 0.95 . ?
C39 C40 1.385(5) . ?
C39 H39 0.95 . ?
C40 H40 0.95 . ?
C41 C42 1.507(4) . ?
C41 C44 1.519(4) . ?
C41 C43 1.533(4) . ?
C42 H42A 0.98 . ?
C42 H42B 0.98 . ?
C42 H42C 0.98 . ?
C43 H43A 0.98 . ?
C43 H43B 0.98 . ?
C43 H43C 0.98 . ?
C44 H44A 0.98 . ?
C44 H44B 0.98 . ?
C44 H44C 0.98 . ?
P1A C7A 1.842(10) . ?
P1A C1A 1.870(8) . ?
P1A P2A 2.210(4) . ?
P2A C13A 1.854(9) . ?
P2A C19A 1.934(15) . ?
P3A C29A 1.842(9) . ?
P3A C23A 1.843(9) . ?
P3A P4A 2.209(4) . ?
P4A C35A 1.873(9) . ?
P4A C41A 1.878(14) . ?
C1A C2A 1.39 . ?
C1A C6A 1.39 . ?
C2A C3A 1.39 . ?
C2A H2A 0.95 . ?
C3A C4A 1.39 . ?
C3A H3A 0.95 . ?
C4A C5A 1.39 . ?
C4A H4A 0.95 . ?
C5A C6A 1.39 . ?
C5A H5A 0.95 . ?
C6A H6A 0.95 . ?
C7A C8A 1.39 . ?
C7A C12A 1.39 . ?
C8A C9A 1.39 . ?
C8A H8A 0.95 . ?
C9A C10A 1.39 . ?
C9A H9A 0.95 . ?
C10A C11A 1.39 . ?
C10A H10A 0.95 . ?
C11A C12A 1.39 . ?
C11A H11A 0.95 . ?
C12A H12A 0.95 . ?
C13A C14A 1.39 . ?
C13A C18A 1.39 . ?
C14A C15A 1.39 . ?
C14A H14A 0.95 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A C17A 1.39 . ?
C16A H16A 0.95 . ?
C17A C18A 1.39 . ?
C17A H17A 0.95 . ?
C18A H18A 0.95 . ?
C19A C20A 1.49(2) . ?
C19A C21A 1.53(2) . ?
C19A C22A 1.53(2) . ?
C20A H20D 0.98 . ?
C20A H20E 0.98 . ?
C20A H20F 0.98 . ?
C21A H21D 0.98 . ?
C21A H21E 0.98 . ?
C21A H21F 0.98 . ?
C22A H22D 0.98 . ?
C22A H22E 0.98 . ?
C22A H22F 0.98 . ?
C23A C24A 1.39 . ?
C23A C28A 1.39 . ?
C24A C25A 1.39 . ?
C24A H24A 0.95 . ?
C25A C26A 1.39 . ?
C25A H25A 0.95 . ?
C26A C27A 1.39 . ?
C26A H26A 0.95 . ?
C27A C28A 1.39 . ?
C27A H27A 0.95 . ?
C28A H28A 0.95 . ?
C29A C30A 1.39 . ?
C29A C34A 1.39 . ?
C30A C31A 1.39 . ?
C30A H30A 0.95 . ?
C31A C32A 1.39 . ?
C31A H31A 0.95 . ?
C32A C33A 1.39 . ?
C32A H32A 0.95 . ?
C33A C34A 1.39 . ?
C33A H33A 0.95 . ?
C34A H34A 0.95 . ?
C35A C36A 1.39 . ?
C35A C40A 1.39 . ?
C36A C37A 1.39 . ?
C36A H36A 0.95 . ?
C37A C38A 1.39 . ?
C37A H37A 0.95 . ?
C38A C39A 1.39 . ?
C38A H38A 0.95 . ?
C39A C40A 1.39 . ?
C39A H39A 0.95 . ?
C40A H40A 0.95 . ?
C41A C43A 1.48(2) . ?
C41A C42A 1.53(2) . ?
C41A C44A 1.589(19) . ?
C42A H42D 0.98 . ?
C42A H42E 0.98 . ?
C42A H42F 0.98 . ?
C43A H43D 0.98 . ?
C43A H43E 0.98 . ?
C43A H43F 0.98 . ?
C44A H44D 0.98 . ?
C44A H44E 0.98 . ?
C44A H44F 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C7 102.53(13) . . ?
C1 P1 P2 99.48(10) . . ?
C7 P1 P2 98.74(11) . . ?
C13 P2 C19 102.35(14) . . ?
C13 P2 P1 99.13(10) . . ?
C19 P2 P1 103.55(10) . . ?
C29 P3 C23 102.22(14) . . ?
C29 P3 P4 99.57(12) . . ?
C23 P3 P4 99.22(10) . . ?
C35 P4 C41 102.21(14) . . ?
C35 P4 P3 98.68(11) . . ?
C41 P4 P3 103.04(11) . . ?
C6 C1 C2 118.5(3) . . ?
C6 C1 P1 125.0(3) . . ?
C2 C1 P1 116.5(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C12 118.9(3) . . ?
C8 C7 P1 125.3(3) . . ?
C12 C7 P1 115.8(3) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C18 C13 C14 118.0(3) . . ?
C18 C13 P2 125.4(3) . . ?
C14 C13 P2 116.6(3) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.2(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C22 C19 C20 108.6(3) . . ?
C22 C19 C21 111.0(3) . . ?
C20 C19 C21 108.1(3) . . ?
C22 C19 P2 107.5(2) . . ?
C20 C19 P2 106.1(2) . . ?
C21 C19 P2 115.2(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 118.3(3) . . ?
C24 C23 P3 125.7(3) . . ?
C28 C23 P3 116.0(3) . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 120.7(4) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C25 119.4(3) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 120.4(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 120.6(3) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
C34 C29 C30 118.6(3) . . ?
C34 C29 P3 126.0(3) . . ?
C30 C29 P3 115.3(3) . . ?
C31 C30 C29 120.5(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 120.1(4) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 119.7(4) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 120.4(4) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C29 120.7(3) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?
C36 C35 C40 118.0(3) . . ?
C36 C35 P4 126.0(3) . . ?
C40 C35 P4 115.9(3) . . ?
C35 C36 C37 121.7(3) . . ?
C35 C36 H36 119.2 . . ?
C37 C36 H36 119.2 . . ?
C38 C37 C36 118.9(4) . . ?
C38 C37 H37 120.5 . . ?
C36 C37 H37 120.5 . . ?
C39 C38 C37 120.6(4) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C38 119.8(4) . . ?
C40 C39 H39 120.1 . . ?
C38 C39 H39 120.1 . . ?
C39 C40 C35 120.9(3) . . ?
C39 C40 H40 119.5 . . ?
C35 C40 H40 119.5 . . ?
C42 C41 C44 110.9(3) . . ?
C42 C41 C43 109.2(3) . . ?
C44 C41 C43 107.7(3) . . ?
C42 C41 P4 115.8(2) . . ?
C44 C41 P4 107.0(2) . . ?
C43 C41 P4 105.9(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C7A P1A C1A 102.1(5) . . ?
C7A P1A P2A 99.4(5) . . ?
C1A P1A P2A 100.2(4) . . ?
C13A P2A C19A 103.4(6) . . ?
C13A P2A P1A 98.7(5) . . ?
C19A P2A P1A 103.8(5) . . ?
C29A P3A C23A 104.2(6) . . ?
C29A P3A P4A 100.2(4) . . ?
C23A P3A P4A 100.9(5) . . ?
C35A P4A C41A 102.9(6) . . ?
C35A P4A P3A 100.5(5) . . ?
C41A P4A P3A 104.5(5) . . ?
C2A C1A C6A 120 . . ?
C2A C1A P1A 124.2(8) . . ?
C6A C1A P1A 115.8(8) . . ?
C3A C2A C1A 120 . . ?
C3A C2A H2A 120 . . ?
C1A C2A H2A 120 . . ?
C2A C3A C4A 120 . . ?
C2A C3A H3A 120 . . ?
C4A C3A H3A 120 . . ?
C5A C4A C3A 120 . . ?
C5A C4A H4A 120 . . ?
C3A C4A H4A 120 . . ?
C6A C5A C4A 120 . . ?
C6A C5A H5A 120 . . ?
C4A C5A H5A 120 . . ?
C5A C6A C1A 120 . . ?
C5A C6A H6A 120 . . ?
C1A C6A H6A 120 . . ?
C8A C7A C12A 120 . . ?
C8A C7A P1A 115.5(11) . . ?
C12A C7A P1A 124.5(11) . . ?
C9A C8A C7A 120 . . ?
C9A C8A H8A 120 . . ?
C7A C8A H8A 120 . . ?
C8A C9A C10A 120 . . ?
C8A C9A H9A 120 . . ?
C10A C9A H9A 120 . . ?
C9A C10A C11A 120 . . ?
C9A C10A H10A 120 . . ?
C11A C10A H10A 120 . . ?
C12A C11A C10A 120 . . ?
C12A C11A H11A 120 . . ?
C10A C11A H11A 120 . . ?
C11A C12A C7A 120 . . ?
C11A C12A H12A 120 . . ?
C7A C12A H12A 120 . . ?
C14A C13A C18A 120 . . ?
C14A C13A P2A 124.2(9) . . ?
C18A C13A P2A 115.7(9) . . ?
C13A C14A C15A 120 . . ?
C13A C14A H14A 120 . . ?
C15A C14A H14A 120 . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A C17A 120 . . ?
C15A C16A H16A 120 . . ?
C17A C16A H16A 120 . . ?
C18A C17A C16A 120 . . ?
C18A C17A H17A 120 . . ?
C16A C17A H17A 120 . . ?
C17A C18A C13A 120 . . ?
C17A C18A H18A 120 . . ?
C13A C18A H18A 120 . . ?
C20A C19A C21A 107.8(15) . . ?
C20A C19A C22A 110.9(15) . . ?
C21A C19A C22A 112.5(14) . . ?
C20A C19A P2A 113.5(12) . . ?
C21A C19A P2A 104.9(11) . . ?
C22A C19A P2A 107.1(11) . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19A C21A H21D 109.5 . . ?
C19A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
C19A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C19A C22A H22D 109.5 . . ?
C19A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C19A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C24A C23A C28A 120 . . ?
C24A C23A P3A 118.1(8) . . ?
C28A C23A P3A 121.9(8) . . ?
C23A C24A C25A 120 . . ?
C23A C24A H24A 120 . . ?
C25A C24A H24A 120 . . ?
C26A C25A C24A 120 . . ?
C26A C25A H25A 120 . . ?
C24A C25A H25A 120 . . ?
C25A C26A C27A 120 . . ?
C25A C26A H26A 120 . . ?
C27A C26A H26A 120 . . ?
C26A C27A C28A 120 . . ?
C26A C27A H27A 120 . . ?
C28A C27A H27A 120 . . ?
C27A C28A C23A 120 . . ?
C27A C28A H28A 120 . . ?
C23A C28A H28A 120 . . ?
C30A C29A C34A 120 . . ?
C30A C29A P3A 123.2(9) . . ?
C34A C29A P3A 116.8(9) . . ?
C31A C30A C29A 120 . . ?
C31A C30A H30A 120 . . ?
C29A C30A H30A 120 . . ?
C30A C31A C32A 120 . . ?
C30A C31A H31A 120 . . ?
C32A C31A H31A 120 . . ?
C33A C32A C31A 120 . . ?
C33A C32A H32A 120 . . ?
C31A C32A H32A 120 . . ?
C32A C33A C34A 120 . . ?
C32A C33A H33A 120 . . ?
C34A C33A H33A 120 . . ?
C33A C34A C29A 120 . . ?
C33A C34A H34A 120 . . ?
C29A C34A H34A 120 . . ?
C36A C35A C40A 120 . . ?
C36A C35A P4A 120.4(10) . . ?
C40A C35A P4A 119.5(10) . . ?
C37A C36A C35A 120 . . ?
C37A C36A H36A 120 . . ?
C35A C36A H36A 120 . . ?
C38A C37A C36A 120 . . ?
C38A C37A H37A 120 . . ?
C36A C37A H37A 120 . . ?
C37A C38A C39A 120 . . ?
C37A C38A H38A 120 . . ?
C39A C38A H38A 120 . . ?
C38A C39A C40A 120 . . ?
C38A C39A H39A 120 . . ?
C40A C39A H39A 120 . . ?
C39A C40A C35A 120 . . ?
C39A C40A H40A 120 . . ?
C35A C40A H40A 120 . . ?
C43A C41A C42A 111.3(14) . . ?
C43A C41A C44A 110.2(15) . . ?
C42A C41A C44A 105.4(13) . . ?
C43A C41A P4A 116.1(11) . . ?
C42A C41A P4A 107.1(10) . . ?
C44A C41A P4A 106.0(9) . . ?
C41A C42A H42D 109.5 . . ?
C41A C42A H42E 109.5 . . ?
H42D C42A H42E 109.5 . . ?
C41A C42A H42F 109.5 . . ?
H42D C42A H42F 109.5 . . ?
H42E C42A H42F 109.5 . . ?
C41A C43A H43D 109.5 . . ?
C41A C43A H43E 109.5 . . ?
H43D C43A H43E 109.5 . . ?
C41A C43A H43F 109.5 . . ?
H43D C43A H43F 109.5 . . ?
H43E C43A H43F 109.5 . . ?
C41A C44A H44D 109.5 . . ?
C41A C44A H44E 109.5 . . ?
H44D C44A H44E 109.5 . . ?
C41A C44A H44F 109.5 . . ?
H44D C44A H44F 109.5 . . ?
H44E C44A H44F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 P1 C1 C6 58.5(3) . . . . ?
P2 P1 C1 C6 -42.7(3) . . . . ?
C7 P1 C1 C2 -122.3(2) . . . . ?
P2 P1 C1 C2 136.4(2) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
P1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
P1 C1 C6 C5 179.0(2) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C1 P1 C7 C8 -67.5(3) . . . . ?
P2 P1 C7 C8 34.3(2) . . . . ?
C1 P1 C7 C12 111.4(2) . . . . ?
P2 P1 C7 C12 -146.81(19) . . . . ?
C12 C7 C8 C9 -0.1(4) . . . . ?
P1 C7 C8 C9 178.8(2) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C7 -1.4(4) . . . . ?
C8 C7 C12 C11 0.9(4) . . . . ?
P1 C7 C12 C11 -178.1(2) . . . . ?
C19 P2 C13 C18 -78.0(3) . . . . ?
P1 P2 C13 C18 28.1(3) . . . . ?
C19 P2 C13 C14 101.0(2) . . . . ?
P1 P2 C13 C14 -152.9(2) . . . . ?
C18 C13 C14 C15 1.0(4) . . . . ?
P2 C13 C14 C15 -178.0(3) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 1.4(5) . . . . ?
C16 C17 C18 C13 -1.6(5) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
P2 C13 C18 C17 179.4(2) . . . . ?
C13 P2 C19 C22 177.1(2) . . . . ?
P1 P2 C19 C22 74.4(2) . . . . ?
C13 P2 C19 C20 -66.8(2) . . . . ?
P1 P2 C19 C20 -169.47(19) . . . . ?
C13 P2 C19 C21 52.8(3) . . . . ?
P1 P2 C19 C21 -49.9(3) . . . . ?
C29 P3 C23 C24 51.3(3) . . . . ?
P4 P3 C23 C24 -50.7(3) . . . . ?
C29 P3 C23 C28 -127.8(3) . . . . ?
P4 P3 C23 C28 130.2(2) . . . . ?
C28 C23 C24 C25 -0.5(5) . . . . ?
P3 C23 C24 C25 -179.6(3) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C24 C25 C26 C27 0.1(5) . . . . ?
C25 C26 C27 C28 -0.3(6) . . . . ?
C26 C27 C28 C23 0.1(6) . . . . ?
C24 C23 C28 C27 0.3(5) . . . . ?
P3 C23 C28 C27 179.4(3) . . . . ?
C23 P3 C29 C34 -66.9(3) . . . . ?
P4 P3 C29 C34 34.8(3) . . . . ?
C23 P3 C29 C30 112.6(2) . . . . ?
P4 P3 C29 C30 -145.7(2) . . . . ?
C34 C29 C30 C31 1.9(4) . . . . ?
P3 C29 C30 C31 -177.7(2) . . . . ?
C29 C30 C31 C32 -1.0(5) . . . . ?
C30 C31 C32 C33 0.0(5) . . . . ?
C31 C32 C33 C34 0.1(5) . . . . ?
C32 C33 C34 C29 0.8(5) . . . . ?
C30 C29 C34 C33 -1.8(4) . . . . ?
P3 C29 C34 C33 177.7(3) . . . . ?
C41 P4 C35 C36 -73.9(3) . . . . ?
P3 P4 C35 C36 31.6(3) . . . . ?
C41 P4 C35 C40 104.8(2) . . . . ?
P3 P4 C35 C40 -149.7(2) . . . . ?
C40 C35 C36 C37 -2.0(4) . . . . ?
P4 C35 C36 C37 176.7(3) . . . . ?
C35 C36 C37 C38 0.4(5) . . . . ?
C36 C37 C38 C39 1.5(5) . . . . ?
C37 C38 C39 C40 -1.8(5) . . . . ?
C38 C39 C40 C35 0.1(5) . . . . ?
C36 C35 C40 C39 1.7(4) . . . . ?
P4 C35 C40 C39 -177.1(2) . . . . ?
C35 P4 C41 C42 60.2(3) . . . . ?
P3 P4 C41 C42 -41.9(3) . . . . ?
C35 P4 C41 C44 -175.6(3) . . . . ?
P3 P4 C41 C44 82.4(3) . . . . ?
C35 P4 C41 C43 -60.9(3) . . . . ?
P3 P4 C41 C43 -163.0(2) . . . . ?
C7A P1A C1A C2A -61.2(8) . . . . ?
P2A P1A C1A C2A 40.8(6) . . . . ?
C7A P1A C1A C6A 117.9(7) . . . . ?
P2A P1A C1A C6A -140.1(5) . . . . ?
C6A C1A C2A C3A 0 . . . . ?
P1A C1A C2A C3A 179.1(8) . . . . ?
C1A C2A C3A C4A 0 . . . . ?
C2A C3A C4A C5A 0 . . . . ?
C3A C4A C5A C6A 0 . . . . ?
C4A C5A C6A C1A 0 . . . . ?
C2A C1A C6A C5A 0 . . . . ?
P1A C1A C6A C5A -179.1(7) . . . . ?
C1A P1A C7A C8A -110.9(6) . . . . ?
P2A P1A C7A C8A 146.4(5) . . . . ?
C1A P1A C7A C12A 67.5(7) . . . . ?
P2A P1A C7A C12A -35.1(6) . . . . ?
C12A C7A C8A C9A 0 . . . . ?
P1A C7A C8A C9A 178.5(7) . . . . ?
C7A C8A C9A C10A 0 . . . . ?
C8A C9A C10A C11A 0 . . . . ?
C9A C10A C11A C12A 0 . . . . ?
C10A C11A C12A C7A 0 . . . . ?
C8A C7A C12A C11A 0 . . . . ?
P1A C7A C12A C11A -178.4(8) . . . . ?
C19A P2A C13A C14A 70.6(8) . . . . ?
P1A P2A C13A C14A -36.0(7) . . . . ?
C19A P2A C13A C18A -105.8(7) . . . . ?
P1A P2A C13A C18A 147.7(5) . . . . ?
C18A C13A C14A C15A 0 . . . . ?
P2A C13A C14A C15A -176.2(9) . . . . ?
C13A C14A C15A C16A 0 . . . . ?
C14A C15A C16A C17A 0 . . . . ?
C15A C16A C17A C18A 0 . . . . ?
C16A C17A C18A C13A 0 . . . . ?
C14A C13A C18A C17A 0 . . . . ?
P2A C13A C18A C17A 176.5(8) . . . . ?
C29A P3A C23A C24A 113.7(8) . . . . ?
P4A P3A C23A C24A -142.8(7) . . . . ?
C29A P3A C23A C28A -67.0(8) . . . . ?
P4A P3A C23A C28A 36.5(7) . . . . ?
C28A C23A C24A C25A 0 . . . . ?
P3A C23A C24A C25A 179.3(10) . . . . ?
C23A C24A C25A C26A 0 . . . . ?
C24A C25A C26A C27A 0 . . . . ?
C25A C26A C27A C28A 0 . . . . ?
C26A C27A C28A C23A 0 . . . . ?
C24A C23A C28A C27A 0 . . . . ?
P3A C23A C28A C27A -179.3(10) . . . . ?
C23A P3A C29A C30A 68.5(8) . . . . ?
P4A P3A C29A C30A -35.6(7) . . . . ?
C23A P3A C29A C34A -109.8(7) . . . . ?
P4A P3A C29A C34A 146.1(5) . . . . ?
C34A C29A C30A C31A 0 . . . . ?
P3A C29A C30A C31A -178.3(8) . . . . ?
C29A C30A C31A C32A 0 . . . . ?
C30A C31A C32A C33A 0 . . . . ?
C31A C32A C33A C34A 0 . . . . ?
C32A C33A C34A C29A 0 . . . . ?
C30A C29A C34A C33A 0 . . . . ?
P3A C29A C34A C33A 178.4(8) . . . . ?
C41A P4A C35A C36A -103.6(7) . . . . ?
P3A P4A C35A C36A 148.7(5) . . . . ?
C41A P4A C35A C40A 72.8(8) . . . . ?
P3A P4A C35A C40A -34.9(6) . . . . ?
C40A C35A C36A C37A 0 . . . . ?
P4A C35A C36A C37A 176.3(8) . . . . ?
C35A C36A C37A C38A 0 . . . . ?
C36A C37A C38A C39A 0 . . . . ?
C37A C38A C39A C40A 0 . . . . ?
C38A C39A C40A C35A 0 . . . . ?
C36A C35A C40A C39A 0 . . . . ?
P4A C35A C40A C39A -176.4(8) . . . . ?
C35A P4A C41A C43A -55.8(16) . . . . ?
P3A P4A C41A C43A 48.9(15) . . . . ?
C35A P4A C41A C42A 69.3(12) . . . . ?
P3A P4A C41A C42A 174.0(10) . . . . ?
C35A P4A C41A C44A -178.5(10) . . . . ?
P3A P4A C41A C44A -73.8(10) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1560642'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2017-07-06T10:21:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20  H28  P2'
_chemical_formula_sum            'C20 H28 P2'
_chemical_formula_weight         330.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.4482(13)
_cell_length_b                   6.2244(3)
_cell_length_c                   17.8241(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.474(6)
_cell_angle_gamma                90
_cell_volume                     1914.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    11511
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      29.6
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.953

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.072
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_number            11432
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.471
_diffrn_reflns_theta_max         29.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_reflns_Friedel_coverage         0
_reflns_number_total             5109
_reflns_number_gt                3361
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.1703P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5109
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2643
_refine_ls_wR_factor_gt          0.225
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.622
_refine_diff_density_min         -1.135
_refine_diff_density_rms         0.101

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.30697(19) -0.0120(5) 0.10982(14) 0.0386(7) Uani 1 1 d . . . . .
C2 C 0.2941(2) -0.2078(6) 0.07288(15) 0.0420(7) Uani 1 1 d . . . . .
H2 H 0.2659 -0.3168 0.0942 0.05 Uiso 1 1 calc R U . . .
C3 C 0.3223(2) -0.2460(6) 0.00466(15) 0.0480(8) Uani 1 1 d . . . . .
H3 H 0.3126 -0.3798 -0.0206 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3642(2) -0.0890(6) -0.02587(14) 0.0471(8) Uani 1 1 d . . . . .
H4 H 0.3838 -0.115 -0.072 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3776(2) 0.1066(6) 0.01082(15) 0.0458(8) Uani 1 1 d . . . . .
H5 H 0.4068 0.2144 -0.01 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3486(2) 0.1452(6) 0.07789(15) 0.0433(7) Uani 1 1 d . . . . .
H6 H 0.3572 0.2806 0.1023 0.052 Uiso 1 1 calc R U . . .
C7 C 0.35814(18) 0.1201(5) 0.25972(13) 0.0373(6) Uani 1 1 d . . . . .
C8 C 0.3951(2) -0.0263(6) 0.31281(15) 0.0437(7) Uani 1 1 d . . . . .
H8 H 0.3737 -0.1656 0.3165 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4626(2) 0.0304(6) 0.36008(15) 0.0477(8) Uani 1 1 d . . . . .
H9 H 0.4872 -0.0706 0.3957 0.057 Uiso 1 1 calc R U . . .
C10 C 0.4940(2) 0.2312(7) 0.35568(15) 0.0486(8) Uani 1 1 d . . . . .
H10 H 0.5402 0.269 0.3882 0.058 Uiso 1 1 calc R U . . .
C11 C 0.4584(2) 0.3787(6) 0.30374(15) 0.0459(8) Uani 1 1 d . . . . .
H11 H 0.4804 0.5175 0.3005 0.055 Uiso 1 1 calc R U . . .
C12 C 0.39044(19) 0.3244(6) 0.25621(14) 0.0405(7) Uani 1 1 d . . . . .
H12 H 0.3659 0.4271 0.2212 0.049 Uiso 1 1 calc R U . . .
C13 C 0.11644(19) 0.2168(6) 0.10392(14) 0.0422(7) Uani 1 1 d . . . . .
C14 C 0.0453(2) 0.3583(7) 0.10316(17) 0.0512(8) Uani 1 1 d . . . . .
H14A H 0.0603 0.5096 0.1008 0.077 Uiso 1 1 calc R U . . .
H14B H 0.0224 0.3333 0.1494 0.077 Uiso 1 1 calc R U . . .
H14C H 0.0072 0.3233 0.0587 0.077 Uiso 1 1 calc R U . . .
C15 C 0.0941(2) -0.0179(6) 0.10767(17) 0.0508(9) Uani 1 1 d . . . . .
H15A H 0.1404 -0.1076 0.1085 0.076 Uiso 1 1 calc R U . . .
H15B H 0.0564 -0.0543 0.0631 0.076 Uiso 1 1 calc R U . . .
H15C H 0.0712 -0.0435 0.1538 0.076 Uiso 1 1 calc R U . . .
C16 C 0.1467(2) 0.2552(7) 0.02734(15) 0.0534(9) Uani 1 1 d . . . . .
H16A H 0.1612 0.4066 0.0235 0.08 Uiso 1 1 calc R U . . .
H16B H 0.106 0.219 -0.0147 0.08 Uiso 1 1 calc R U . . .
H16C H 0.1922 0.1644 0.0248 0.08 Uiso 1 1 calc R U . . .
C17 C 0.15866(19) 0.3363(6) 0.27363(14) 0.0410(7) Uani 1 1 d . . . . .
C18 C 0.2269(2) 0.3472(7) 0.33724(16) 0.0562(10) Uani 1 1 d . . . . .
H18A H 0.2627 0.4601 0.326 0.084 Uiso 1 1 calc R U . . .
H18B H 0.2539 0.2087 0.3415 0.084 Uiso 1 1 calc R U . . .
H18C H 0.2082 0.38 0.3851 0.084 Uiso 1 1 calc R U . . .
C19 C 0.1188(3) 0.5566(7) 0.27286(19) 0.0569(9) Uani 1 1 d . . . . .
H19A H 0.1546 0.6685 0.2611 0.085 Uiso 1 1 calc R U . . .
H19B H 0.1037 0.5847 0.3228 0.085 Uiso 1 1 calc R U . . .
H19C H 0.0725 0.557 0.2343 0.085 Uiso 1 1 calc R U . . .
C20 C 0.1036(2) 0.1632(7) 0.29175(18) 0.0547(9) Uani 1 1 d . . . . .
H20A H 0.1291 0.0229 0.2919 0.082 Uiso 1 1 calc R U . . .
H20B H 0.0572 0.1639 0.2533 0.082 Uiso 1 1 calc R U . . .
H20C H 0.0887 0.1905 0.3418 0.082 Uiso 1 1 calc R U . . .
P1 P 0.26997(5) 0.01744(13) 0.20137(3) 0.0377(3) Uani 1 1 d . . . . .
P2 P 0.19793(5) 0.31449(14) 0.17986(3) 0.0374(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.388(4) . ?
C1 C6 1.389(5) . ?
C1 P1 1.850(3) . ?
C2 C3 1.398(4) . ?
C2 H2 0.95 . ?
C3 C4 1.379(5) . ?
C3 H3 0.95 . ?
C4 C5 1.386(5) . ?
C4 H4 0.95 . ?
C5 C6 1.387(4) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.396(5) . ?
C7 C8 1.400(4) . ?
C7 P1 1.840(3) . ?
C8 C9 1.389(5) . ?
C8 H8 0.95 . ?
C9 C10 1.372(5) . ?
C9 H9 0.95 . ?
C10 C11 1.384(5) . ?
C10 H10 0.95 . ?
C11 C12 1.394(5) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C15 1.516(5) . ?
C13 C14 1.521(5) . ?
C13 C16 1.553(4) . ?
C13 P2 1.912(3) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 C20 1.510(5) . ?
C17 C18 1.520(5) . ?
C17 C19 1.537(5) . ?
C17 P2 1.902(3) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
P1 P2 2.2368(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.8(3) . . ?
C2 C1 P1 116.9(2) . . ?
C6 C1 P1 124.3(2) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C12 C7 C8 118.3(3) . . ?
C12 C7 P1 126.9(2) . . ?
C8 C7 P1 114.8(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C15 C13 C14 110.1(3) . . ?
C15 C13 C16 108.1(3) . . ?
C14 C13 C16 106.6(3) . . ?
C15 C13 P2 116.4(2) . . ?
C14 C13 P2 110.1(2) . . ?
C16 C13 P2 105.0(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C17 C18 109.0(3) . . ?
C20 C17 C19 109.7(3) . . ?
C18 C17 C19 105.7(3) . . ?
C20 C17 P2 117.4(2) . . ?
C18 C17 P2 108.3(2) . . ?
C19 C17 P2 106.1(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 P1 C1 99.29(13) . . ?
C7 P1 P2 102.22(11) . . ?
C1 P1 P2 101.01(10) . . ?
C17 P2 C13 108.54(14) . . ?
C17 P2 P1 100.04(11) . . ?
C13 P2 P1 101.46(11) . . ?

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 C3 -0.2(5) . . . . ?
P1 C1 C2 C3 -177.9(3) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
P1 C1 C6 C5 176.7(3) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
P1 C7 C8 C9 179.5(2) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C8 C7 C12 C11 1.0(4) . . . . ?
P1 C7 C12 C11 -179.2(2) . . . . ?
C12 C7 P1 C1 72.1(3) . . . . ?
C8 C7 P1 C1 -108.1(2) . . . . ?
C12 C7 P1 P2 -31.3(3) . . . . ?
C8 C7 P1 P2 148.4(2) . . . . ?
C2 C1 P1 C7 129.8(3) . . . . ?
C6 C1 P1 C7 -47.8(3) . . . . ?
C2 C1 P1 P2 -125.7(2) . . . . ?
C6 C1 P1 P2 56.7(3) . . . . ?


# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_global
_database_code_depnum_ccdc_archive 'CCDC 1560641'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2018-06-10
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C18  H41  N1  P2'
_chemical_formula_sum            'C18 H41 N P2'
_chemical_formula_weight         333.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5271(5)
_cell_length_b                   9.5290(5)
_cell_length_c                   13.9449(9)
_cell_angle_alpha                93.186(5)
_cell_angle_beta                 90.722(5)
_cell_angle_gamma                110.634(4)
_cell_volume                     1058.13(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6370
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.047
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.97

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 211 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_number            8763
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.554
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             4545
_reflns_number_gt                3254
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        'STOE X-Area'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4545
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.953
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.072

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.1344(3) 0.7619(2) 0.37756(18) 0.0231(5) Uani 1 1 d . . . . .
C2 C 0.1144(3) 0.8781(3) 0.45315(19) 0.0324(6) Uani 1 1 d . . . . .
H2A H 0.0228 0.91043 0.43253 0.049 Uiso 1 1 calc R U . . .
H2B H 0.088691 0.832646 0.515044 0.049 Uiso 1 1 calc R U . . .
H2C H 0.218898 0.965281 0.459939 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0305(3) 0.6271(3) 0.3757(2) 0.0347(6) Uani 1 1 d . . . . .
H3A H -0.122746 0.657754 0.35395 0.052 Uiso 1 1 calc R U . . .
H3B H -0.022487 0.546532 0.331435 0.052 Uiso 1 1 calc R U . . .
H3C H -0.051805 0.590948 0.440349 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2778(3) 0.7135(3) 0.4115(2) 0.0342(6) Uani 1 1 d . . . . .
H4A H 0.383482 0.799455 0.412773 0.051 Uiso 1 1 calc R U . . .
H4B H 0.256313 0.677262 0.476139 0.051 Uiso 1 1 calc R U . . .
H4C H 0.285631 0.632847 0.367225 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1240(3) 0.7100(2) 0.15526(18) 0.0226(5) Uani 1 1 d . . . . .
C6 C -0.0659(3) 0.6238(3) 0.1418(2) 0.0369(6) Uani 1 1 d . . . . .
H6A H -0.107515 0.567725 0.198668 0.055 Uiso 1 1 calc R U . . .
H6B H -0.123482 0.695126 0.133248 0.055 Uiso 1 1 calc R U . . .
H6C H -0.087635 0.553585 0.084943 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2153(4) 0.5981(3) 0.1639(2) 0.0352(6) Uani 1 1 d . . . . .
H7A H 0.181688 0.544122 0.222396 0.053 Uiso 1 1 calc R U . . .
H7B H 0.185788 0.52609 0.107767 0.053 Uiso 1 1 calc R U . . .
H7C H 0.33668 0.652535 0.167075 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1773(3) 0.7932(2) 0.06400(18) 0.0247(5) Uani 1 1 d . . . . .
H8A H 0.119543 0.864969 0.057964 0.037 Uiso 1 1 calc R U . . .
H8B H 0.298807 0.847291 0.067368 0.037 Uiso 1 1 calc R U . . .
H8C H 0.147915 0.720846 0.00806 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6085(2) 1.0173(3) 0.23852(18) 0.0231(5) Uani 1 1 d . . . . .
C10 C 0.6472(3) 0.9019(3) 0.2971(2) 0.0341(6) Uani 1 1 d . . . . .
H10A H 0.642081 0.927426 0.365721 0.051 Uiso 1 1 calc R U . . .
H10B H 0.564614 0.801751 0.280057 0.051 Uiso 1 1 calc R U . . .
H10C H 0.759756 0.902612 0.282951 0.051 Uiso 1 1 calc R U . . .
C11 C 0.6170(3) 0.9759(3) 0.1324(2) 0.0337(6) Uani 1 1 d . . . . .
H11A H 0.592392 1.049246 0.094013 0.05 Uiso 1 1 calc R U . . .
H11B H 0.729678 0.976391 0.118793 0.05 Uiso 1 1 calc R U . . .
H11C H 0.534536 0.87553 0.115899 0.05 Uiso 1 1 calc R U . . .
C12 C 0.7456(3) 1.1718(3) 0.2632(2) 0.0355(6) Uani 1 1 d . . . . .
H12A H 0.742266 1.200686 0.331452 0.053 Uiso 1 1 calc R U . . .
H12B H 0.855741 1.166128 0.249509 0.053 Uiso 1 1 calc R U . . .
H12C H 0.72605 1.24694 0.224205 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3500(3) 1.1880(2) 0.12884(18) 0.0231(5) Uani 1 1 d . . . . .
H13 H 0.365316 1.097427 0.096776 0.028 Uiso 1 1 calc R U . . .
C14 C 0.1684(3) 1.1729(2) 0.1075(2) 0.0298(6) Uani 1 1 d . . . . .
H14A H 0.150021 1.173903 0.038081 0.045 Uiso 1 1 calc R U . . .
H14B H 0.092784 1.078006 0.130352 0.045 Uiso 1 1 calc R U . . .
H14C H 0.145765 1.256978 0.140432 0.045 Uiso 1 1 calc R U . . .
C15 C 0.4712(3) 1.3240(3) 0.0829(2) 0.0320(6) Uani 1 1 d . . . . .
H15A H 0.439872 1.320035 0.014655 0.048 Uiso 1 1 calc R U . . .
H15B H 0.466101 1.416243 0.1152 0.048 Uiso 1 1 calc R U . . .
H15C H 0.585442 1.323244 0.089253 0.048 Uiso 1 1 calc R U . . .
C16 C 0.3664(3) 1.3108(2) 0.29289(18) 0.0231(5) Uani 1 1 d . . . . .
H16 H 0.338528 1.378028 0.248402 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5256(3) 1.4057(3) 0.3484(2) 0.0439(8) Uani 1 1 d . . . . .
H17A H 0.504724 1.485443 0.387665 0.066 Uiso 1 1 calc R U . . .
H17B H 0.561288 1.342372 0.390257 0.066 Uiso 1 1 calc R U . . .
H17C H 0.613937 1.450664 0.303357 0.066 Uiso 1 1 calc R U . . .
C18 C 0.2217(3) 1.2576(3) 0.3609(2) 0.0350(6) Uani 1 1 d . . . . .
H18A H 0.213087 1.344317 0.398642 0.053 Uiso 1 1 calc R U . . .
H18B H 0.116924 1.206449 0.323549 0.053 Uiso 1 1 calc R U . . .
H18C H 0.242022 1.187874 0.404263 0.053 Uiso 1 1 calc R U . . .
N1 N 0.3908(2) 1.18765(18) 0.23195(14) 0.0180(4) Uani 1 1 d . . . . .
P1 P 0.15765(6) 0.85652(6) 0.25947(4) 0.01632(15) Uani 1 1 d . . . . .
P2 P 0.40925(6) 1.03998(6) 0.28682(4) 0.01756(16) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C4 1.530(3) . ?
C1 C3 1.533(3) . ?
C1 C2 1.541(3) . ?
C1 P1 1.900(2) . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C8 1.526(3) . ?
C5 C7 1.534(3) . ?
C5 C6 1.540(3) . ?
C5 P1 1.904(2) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C11 1.520(3) . ?
C9 C10 1.527(3) . ?
C9 C12 1.540(3) . ?
C9 P2 1.913(2) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 N1 1.475(3) . ?
C13 C15 1.524(3) . ?
C13 C14 1.528(3) . ?
C13 H13 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 N1 1.486(3) . ?
C16 C17 1.514(3) . ?
C16 C18 1.524(3) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
N1 P2 1.6922(17) . ?
P1 P2 2.2508(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C3 109.26(19) . . ?
C4 C1 C2 108.4(2) . . ?
C3 C1 C2 105.81(19) . . ?
C4 C1 P1 117.66(16) . . ?
C3 C1 P1 110.12(17) . . ?
C2 C1 P1 104.88(15) . . ?
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 . . ?
C8 C5 C7 109.0(2) . . ?
C8 C5 C6 105.8(2) . . ?
C7 C5 C6 109.58(19) . . ?
C8 C5 P1 107.72(14) . . ?
C7 C5 P1 116.51(17) . . ?
C6 C5 P1 107.72(16) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C9 C10 108.7(2) . . ?
C11 C9 C12 108.1(2) . . ?
C10 C9 C12 108.07(19) . . ?
C11 C9 P2 119.86(15) . . ?
C10 C9 P2 107.65(16) . . ?
C12 C9 P2 103.88(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C15 112.04(19) . . ?
N1 C13 C14 113.77(19) . . ?
C15 C13 C14 110.85(19) . . ?
N1 C13 H13 106.6 . . ?
C15 C13 H13 106.6 . . ?
C14 C13 H13 106.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 111.85(18) . . ?
N1 C16 C18 113.94(18) . . ?
C17 C16 C18 110.1(2) . . ?
N1 C16 H16 106.8 . . ?
C17 C16 H16 106.8 . . ?
C18 C16 H16 106.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 N1 C16 114.48(17) . . ?
C13 N1 P2 125.18(14) . . ?
C16 N1 P2 118.12(16) . . ?
C1 P1 C5 109.51(10) . . ?
C1 P1 P2 100.16(7) . . ?
C5 P1 P2 120.36(8) . . ?
N1 P2 C9 105.27(10) . . ?
N1 P2 P1 104.12(6) . . ?
C9 P2 P1 120.85(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
C15 C13 N1 C16 66.9(2) . . . . ?
C14 C13 N1 C16 -59.8(2) . . . . ?
C15 C13 N1 P2 -130.43(17) . . . . ?
C14 C13 N1 P2 102.84(19) . . . . ?
C17 C16 N1 C13 -123.1(2) . . . . ?
C18 C16 N1 C13 111.3(2) . . . . ?
C17 C16 N1 P2 73.0(2) . . . . ?
C18 C16 N1 P2 -52.7(2) . . . . ?
C13 N1 P2 C9 69.27(18) . . . . ?
C16 N1 P2 C9 -128.64(15) . . . . ?
C13 N1 P2 P1 -58.81(17) . . . . ?
C16 N1 P2 P1 103.28(14) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 1576835'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-28T21:44:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H38 N2 P2'
_chemical_formula_sum            'C16 H38 N2 P2'
_chemical_formula_weight         320.42

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5142(8)
_cell_length_b                   9.8037(10)
_cell_length_c                   12.7706(12)
_cell_angle_alpha                100.535(8)
_cell_angle_beta                 96.438(8)
_cell_angle_gamma                109.184(7)
_cell_volume                     972.63(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4016
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      29.67
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.955

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 206 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_number            7567
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         26.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             4193
_reflns_number_gt                3633
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        'STOE X-Area'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0871P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4193
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.073

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.47523(5) 0.53571(4) 0.31143(3) 0.01266(13) Uani 1 1 d . . . . .
P2 P 0.50166(5) 0.38511(4) 0.16312(3) 0.01410(13) Uani 1 1 d . . . . .
N1 N 0.35630(16) 0.62344(13) 0.25744(10) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.68064(16) 0.65232(13) 0.35362(10) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.2767(2) 0.24431(16) 0.11519(12) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.1672(2) 0.32701(19) 0.07372(15) 0.0300(4) Uani 1 1 d . . . . .
H2A H 0.217081 0.375884 0.018673 0.045 Uiso 1 1 calc R U . . .
H2B H 0.0528 0.256163 0.041761 0.045 Uiso 1 1 calc R U . . .
H2C H 0.161741 0.40184 0.134206 0.045 Uiso 1 1 calc R U . . .
C3 C 0.1970(2) 0.1690(2) 0.20077(15) 0.0321(4) Uani 1 1 d . . . . .
H3A H 0.265937 0.115681 0.227963 0.048 Uiso 1 1 calc R U . . .
H3B H 0.191457 0.244335 0.260855 0.048 Uiso 1 1 calc R U . . .
H3C H 0.082515 0.098658 0.16841 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2733(2) 0.12681(18) 0.01600(13) 0.0271(4) Uani 1 1 d . . . . .
H4A H 0.324668 0.17637 -0.038319 0.041 Uiso 1 1 calc R U . . .
H4B H 0.337048 0.066724 0.038337 0.041 Uiso 1 1 calc R U . . .
H4C H 0.155822 0.0625 -0.0152 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6368(2) 0.29517(16) 0.23434(12) 0.0189(3) Uani 1 1 d . . . . .
C6 C 0.8208(2) 0.39298(19) 0.23797(13) 0.0247(3) Uani 1 1 d . . . . .
H6A H 0.836911 0.403501 0.164678 0.037 Uiso 1 1 calc R U . . .
H6B H 0.845791 0.491202 0.285196 0.037 Uiso 1 1 calc R U . . .
H6C H 0.897058 0.346686 0.266346 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6130(2) 0.27947(18) 0.34945(13) 0.0244(4) Uani 1 1 d . . . . .
H7A H 0.495689 0.217102 0.347757 0.037 Uiso 1 1 calc R U . . .
H7B H 0.689634 0.233377 0.377631 0.037 Uiso 1 1 calc R U . . .
H7C H 0.638366 0.377893 0.396481 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6092(3) 0.14073(18) 0.16507(14) 0.0289(4) Uani 1 1 d . . . . .
H8A H 0.62382 0.148172 0.091033 0.043 Uiso 1 1 calc R U . . .
H8B H 0.691722 0.102361 0.196322 0.043 Uiso 1 1 calc R U . . .
H8C H 0.494416 0.073144 0.163655 0.043 Uiso 1 1 calc R U . . .
C9 C 0.3903(2) 0.69461(17) 0.16678(12) 0.0197(3) Uani 1 1 d . . . . .
H9A H 0.433856 0.634829 0.114641 0.024 Uiso 1 1 calc R U . . .
H9B H 0.479629 0.794013 0.194558 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2343(2) 0.7117(2) 0.10739(14) 0.0295(4) Uani 1 1 d . . . . .
H10A H 0.264841 0.759769 0.047935 0.044 Uiso 1 1 calc R U . . .
H10B H 0.146169 0.613556 0.078085 0.044 Uiso 1 1 calc R U . . .
H10C H 0.191973 0.772848 0.158056 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2664(2) 0.68561(16) 0.33357(12) 0.0190(3) Uani 1 1 d . . . . .
H11A H 0.242657 0.624593 0.387724 0.023 Uiso 1 1 calc R U . . .
H11B H 0.156259 0.677428 0.293053 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3611(2) 0.84733(17) 0.39346(14) 0.0264(4) Uani 1 1 d . . . . .
H12A H 0.292545 0.879725 0.44225 0.04 Uiso 1 1 calc R U . . .
H12B H 0.469029 0.856612 0.435735 0.04 Uiso 1 1 calc R U . . .
H12C H 0.382462 0.90955 0.34088 0.04 Uiso 1 1 calc R U . . .
C13 C 0.7422(2) 0.70141(16) 0.47146(11) 0.0191(3) Uani 1 1 d . . . . .
H13A H 0.660938 0.637347 0.507725 0.023 Uiso 1 1 calc R U . . .
H13B H 0.745799 0.804333 0.496312 0.023 Uiso 1 1 calc R U . . .
C14 C 0.9161(2) 0.6966(2) 0.50582(13) 0.0261(4) Uani 1 1 d . . . . .
H14A H 0.949712 0.730487 0.58482 0.039 Uiso 1 1 calc R U . . .
H14B H 0.913025 0.594619 0.48314 0.039 Uiso 1 1 calc R U . . .
H14C H 0.997957 0.761744 0.471717 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7835(2) 0.73928(16) 0.28764(12) 0.0192(3) Uani 1 1 d . . . . .
H15A H 0.723933 0.702967 0.211199 0.023 Uiso 1 1 calc R U . . .
H15B H 0.891973 0.72202 0.291271 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8212(2) 0.90594(18) 0.32218(15) 0.0283(4) Uani 1 1 d . . . . .
H16A H 0.890224 0.956571 0.274549 0.042 Uiso 1 1 calc R U . . .
H16B H 0.714715 0.924617 0.316995 0.042 Uiso 1 1 calc R U . . .
H16C H 0.882989 0.943696 0.397179 0.042 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.6951(12) . ?
P1 N2 1.7045(13) . ?
P1 P2 2.2604(5) . ?
P2 C1 1.9075(16) . ?
P2 C5 1.9114(15) . ?
N1 C9 1.4658(18) . ?
N1 C11 1.4696(19) . ?
N2 C15 1.4631(19) . ?
N2 C13 1.4710(18) . ?
C1 C3 1.527(2) . ?
C1 C2 1.533(2) . ?
C1 C4 1.539(2) . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C7 1.535(2) . ?
C5 C6 1.535(2) . ?
C5 C8 1.536(2) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C10 1.528(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C12 1.525(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14 1.514(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C16 1.525(2) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 N2 110.61(6) . . ?
N1 P1 P2 102.55(4) . . ?
N2 P1 P2 99.74(5) . . ?
C1 P2 C5 108.73(7) . . ?
C1 P2 P1 102.11(5) . . ?
C5 P2 P1 98.29(5) . . ?
C9 N1 C11 115.58(12) . . ?
C9 N1 P1 124.76(11) . . ?
C11 N1 P1 114.25(10) . . ?
C15 N2 C13 115.98(12) . . ?
C15 N2 P1 125.20(10) . . ?
C13 N2 P1 116.41(10) . . ?
C3 C1 C2 108.67(15) . . ?
C3 C1 C4 110.20(13) . . ?
C2 C1 C4 105.70(13) . . ?
C3 C1 P2 115.60(11) . . ?
C2 C1 P2 107.05(10) . . ?
C4 C1 P2 109.12(11) . . ?
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 . . ?
C7 C5 C6 109.02(13) . . ?
C7 C5 C8 108.09(13) . . ?
C6 C5 C8 106.84(14) . . ?
C7 C5 P2 117.02(11) . . ?
C6 C5 P2 105.26(10) . . ?
C8 C5 P2 110.16(11) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 113.25(14) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 114.82(13) . . ?
N1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 113.44(13) . . ?
N2 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 114.14(13) . . ?
N2 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
N2 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 P1 N1 C9 56.70(13) . . . . ?
P2 P1 N1 C9 -48.90(12) . . . . ?
N2 P1 N1 C11 -96.07(11) . . . . ?
P2 P1 N1 C11 158.33(9) . . . . ?
N1 P1 N2 C15 -51.56(13) . . . . ?
P2 P1 N2 C15 55.90(12) . . . . ?
N1 P1 N2 C13 110.05(11) . . . . ?
P2 P1 N2 C13 -142.49(10) . . . . ?
C11 N1 C9 C10 -49.57(17) . . . . ?
P1 N1 C9 C10 157.97(11) . . . . ?
C9 N1 C11 C12 -62.63(18) . . . . ?
P1 N1 C11 C12 92.75(14) . . . . ?
C15 N2 C13 C14 -60.76(17) . . . . ?
P1 N2 C13 C14 135.91(12) . . . . ?
C13 N2 C15 C16 -52.53(18) . . . . ?
P1 N2 C15 C16 109.15(14) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 1576834'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-30T21:23:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H38 N2 O3 P2'
_chemical_formula_sum            'C24 H38 N2 O3 P2'
_chemical_formula_weight         464.5
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_Int_Tables_number      43
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   23.2044(13)
_cell_length_b                   28.9097(17)
_cell_length_c                   7.4145(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4973.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1999
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      29.25
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.959

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 95 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_number            4704
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         29.162
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.811
_reflns_Friedel_fraction_full    0.622
_reflns_Friedel_fraction_max     0.607
_reflns_Friedel_coverage         0.53
_reflns_number_total             2728
_reflns_number_gt                1840
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        'STOE X-Area'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2993
_refine_ls_wR_factor_gt          0.2154
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 432 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.169

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.1094(2) -0.01008(19) 0.1780(7) 0.0271(18) Uani 1 1 d G . . . .
C2 C 0.1676(2) -0.01041(19) 0.1341(7) 0.0312(19) Uani 1 1 d G . . . .
H2 H 0.179755 -0.00131 0.016985 0.037 Uiso 1 1 calc R U . . .
C3 C 0.20814(19) -0.0240(2) 0.2616(9) 0.040(2) Uani 1 1 d G . . . .
H3 H 0.247938 -0.024274 0.231577 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1904(2) -0.03736(19) 0.4330(8) 0.037(2) Uani 1 1 d G . . . .
H4 H 0.218087 -0.046682 0.52009 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1322(3) -0.03703(19) 0.4769(6) 0.040(2) Uani 1 1 d G . . . .
H5 H 0.120052 -0.046126 0.594013 0.048 Uiso 1 1 calc R U . . .
C6 C 0.0917(2) -0.0234(2) 0.3494(8) 0.032(2) Uani 1 1 d G . . . .
H6 H 0.051868 -0.023162 0.379422 0.039 Uiso 1 1 calc R U . . .
C7 C 0.0629(4) 0.0923(2) 0.1612(10) 0.0216(16) Uani 1 1 d . . . . .
H7 H 0.057033 0.069456 0.260861 0.026 Uiso 1 1 calc R U . . .
C8 C 0.1188(4) 0.1189(3) 0.2046(13) 0.033(2) Uani 1 1 d . . . . .
H8A H 0.113662 0.136535 0.316395 0.05 Uiso 1 1 calc R U . . .
H8B H 0.150595 0.096925 0.219583 0.05 Uiso 1 1 calc R U . . .
H8C H 0.127684 0.140176 0.105542 0.05 Uiso 1 1 calc R U . . .
C9 C 0.0106(4) 0.1234(3) 0.1598(13) 0.0305(19) Uani 1 1 d . . . . .
H9A H 0.008351 0.140362 0.27402 0.046 Uiso 1 1 calc R U . . .
H9B H 0.013639 0.145426 0.059725 0.046 Uiso 1 1 calc R U . . .
H9C H -0.024266 0.104624 0.144603 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0784(4) 0.0911(3) -0.1774(12) 0.0267(18) Uani 1 1 d . . . . .
H10 H 0.078295 0.124734 -0.145699 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0295(4) 0.0836(3) -0.3121(12) 0.0307(19) Uani 1 1 d . . . . .
H11A H 0.037322 0.10131 -0.422118 0.046 Uiso 1 1 calc R U . . .
H11B H 0.02679 0.050637 -0.341728 0.046 Uiso 1 1 calc R U . . .
H11C H -0.006878 0.094026 -0.258885 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1372(4) 0.0806(3) -0.2604(14) 0.0343(18) Uani 1 1 d . . . . .
H12A H 0.141732 0.098232 -0.372459 0.051 Uiso 1 1 calc R U . . .
H12B H 0.167678 0.089406 -0.17546 0.051 Uiso 1 1 calc R U . . .
H12C H 0.140037 0.04746 -0.286614 0.051 Uiso 1 1 calc R U . . .
N1 N 0.0694(3) 0.06529(19) -0.0074(10) 0.0215(12) Uani 1 1 d . . . . .
P1 P 0.06128(8) 0.00892(6) -0.0006(3) 0.0207(5) Uani 1 1 d . . . . .
O1 O 0.0716(5) -0.0136(4) -0.1651(14) 0.079(3) Uani 1 1 d . . . . .
O2 O 0 0 0.1026(11) 0.0255(17) Uani 1 2 d S T P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.39 . ?
C1 C6 1.39 . ?
C1 P1 1.818(5) . ?
C2 C3 1.39 . ?
C2 H2 0.95 . ?
C3 C4 1.39 . ?
C3 H3 0.95 . ?
C4 C5 1.39 . ?
C4 H4 0.95 . ?
C5 C6 1.39 . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.482(10) . ?
C7 C9 1.511(11) . ?
C7 C8 1.543(12) . ?
C7 H7 1 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 N1 1.479(11) . ?
C10 C11 1.527(13) . ?
C10 C12 1.528(13) . ?
C10 H10 1 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
N1 P1 1.641(6) . ?
P1 O1 1.403(11) . ?
P1 O2 1.635(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120 . . ?
C2 C1 P1 115.4(3) . . ?
C6 C1 P1 124.6(3) . . ?
C1 C2 C3 120 . . ?
C1 C2 H2 120 . . ?
C3 C2 H2 120 . . ?
C2 C3 C4 120 . . ?
C2 C3 H3 120 . . ?
C4 C3 H3 120 . . ?
C5 C4 C3 120 . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
C6 C5 C4 120 . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C1 120 . . ?
C5 C6 H6 120 . . ?
C1 C6 H6 120 . . ?
N1 C7 C9 113.0(7) . . ?
N1 C7 C8 110.6(7) . . ?
C9 C7 C8 112.4(7) . . ?
N1 C7 H7 106.8 . . ?
C9 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 112.4(7) . . ?
N1 C10 C12 111.6(7) . . ?
C11 C10 C12 111.8(8) . . ?
N1 C10 H10 106.9 . . ?
C11 C10 H10 106.9 . . ?
C12 C10 H10 106.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 N1 C7 117.9(5) . . ?
C10 N1 P1 122.9(6) . . ?
C7 N1 P1 119.0(5) . . ?
O1 P1 O2 118.8(5) . . ?
O1 P1 N1 114.5(5) . . ?
O2 P1 N1 105.8(3) . . ?
O1 P1 C1 112.8(5) . . ?
O2 P1 C1 98.4(3) . . ?
N1 P1 C1 104.6(3) . . ?
P1 O2 P1 124.2(5) 2 . ?

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 C3 0 . . . . ?
P1 C1 C2 C3 179.5(4) . . . . ?
C1 C2 C3 C4 0 . . . . ?
C2 C3 C4 C5 0 . . . . ?
C3 C4 C5 C6 0 . . . . ?
C4 C5 C6 C1 0 . . . . ?
C2 C1 C6 C5 0 . . . . ?
P1 C1 C6 C5 -179.5(4) . . . . ?
C11 C10 N1 C7 -117.1(8) . . . . ?
C12 C10 N1 C7 116.3(8) . . . . ?
C11 C10 N1 P1 57.8(9) . . . . ?
C12 C10 N1 P1 -68.8(9) . . . . ?
C9 C7 N1 C10 62.5(9) . . . . ?
C8 C7 N1 C10 -64.5(9) . . . . ?
C9 C7 N1 P1 -112.6(7) . . . . ?
C8 C7 N1 P1 120.5(6) . . . . ?
C10 N1 P1 O1 8.6(9) . . . . ?
C7 N1 P1 O1 -176.6(8) . . . . ?
C10 N1 P1 O2 -124.1(7) . . . . ?
C7 N1 P1 O2 50.7(7) . . . . ?
C10 N1 P1 C1 132.6(6) . . . . ?
C7 N1 P1 C1 -52.6(6) . . . . ?
C2 C1 P1 O1 49.6(6) . . . . ?
C6 C1 P1 O1 -130.8(6) . . . . ?
C2 C1 P1 O2 175.8(3) . . . . ?
C6 C1 P1 O2 -4.6(3) . . . . ?
C2 C1 P1 N1 -75.4(4) . . . . ?
C6 C1 P1 N1 104.1(4) . . . . ?
O1 P1 O2 P1 -33.8(5) . . . 2 ?
N1 P1 O2 P1 96.5(3) . . . 2 ?
C1 P1 O2 P1 -155.7(2) . . . 2 ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 1576836'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-28T21:20:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22 H33 N P2'
_chemical_formula_sum            'C22 H33 N P2'
_chemical_formula_weight         373.43

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3935(5)
_cell_length_b                   11.1597(6)
_cell_length_c                   11.2752(6)
_cell_angle_alpha                110.014(4)
_cell_angle_beta                 100.623(4)
_cell_angle_gamma                95.397(4)
_cell_volume                     1075.63(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8920
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      29.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.958

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 213 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.071
_diffrn_reflns_number            8525
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             4624
_reflns_number_gt                3589
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        'STOE X-Area'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4624
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1669
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.86
_refine_diff_density_rms         0.097

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.3957(2) 0.31317(19) 0.57504(19) 0.0218(4) Uani 1 1 d . . . . .
C2 C 0.5338(2) 0.3690(2) 0.65678(19) 0.0254(4) Uani 1 1 d . . . . .
H2 H 0.547278 0.387334 0.747217 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6513(2) 0.3982(2) 0.6084(2) 0.0264(4) Uani 1 1 d . . . . .
H3 H 0.744777 0.436729 0.665629 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6338(2) 0.3715(2) 0.4763(2) 0.0269(5) Uani 1 1 d . . . . .
H4 H 0.714954 0.391982 0.443256 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4993(2) 0.3155(2) 0.39425(19) 0.0274(5) Uani 1 1 d . . . . .
H5 H 0.487075 0.297151 0.303897 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3803(2) 0.28532(19) 0.44213(19) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.287599 0.245393 0.384039 0.028 Uiso 1 1 calc R U . . .
C7 C 0.1994(2) 0.4467(2) 0.7086(2) 0.0255(4) Uani 1 1 d . . . . .
C8 C 0.3007(3) 0.5404(2) 0.8125(2) 0.0327(5) Uani 1 1 d . . . . .
H8 H 0.390129 0.519034 0.848139 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2714(3) 0.6657(2) 0.8645(3) 0.0429(6) Uani 1 1 d . . . . .
H9 H 0.340677 0.728987 0.935975 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1424(3) 0.6985(3) 0.8129(3) 0.0468(7) Uani 1 1 d . . . . .
H10 H 0.123231 0.784095 0.848622 0.056 Uiso 1 1 calc R U . . .
C11 C 0.0422(3) 0.6070(3) 0.7098(3) 0.0464(7) Uani 1 1 d . . . . .
H11 H -0.046415 0.629457 0.67404 0.056 Uiso 1 1 calc R U . . .
C12 C 0.0699(3) 0.4817(2) 0.6576(2) 0.0340(5) Uani 1 1 d . . . . .
H12 H -0.000246 0.419032 0.586291 0.041 Uiso 1 1 calc R U . . .
C13 C 0.0027(2) 0.1414(2) 0.7606(2) 0.0251(4) Uani 1 1 d . . . . .
H13 H 0.018337 0.104401 0.670659 0.03 Uiso 1 1 calc R U . . .
C14 C -0.1074(2) 0.2335(2) 0.7589(2) 0.0291(5) Uani 1 1 d . . . . .
H14A H -0.201235 0.184798 0.699977 0.044 Uiso 1 1 calc R U . . .
H14B H -0.122336 0.274517 0.846621 0.044 Uiso 1 1 calc R U . . .
H14C H -0.069303 0.300145 0.729121 0.044 Uiso 1 1 calc R U . . .
C15 C -0.0620(3) 0.0283(2) 0.7927(3) 0.0375(5) Uani 1 1 d . . . . .
H15A H -0.157597 -0.013074 0.732835 0.056 Uiso 1 1 calc R U . . .
H15B H 0.004788 -0.035029 0.783866 0.056 Uiso 1 1 calc R U . . .
H15C H -0.074553 0.06045 0.881977 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1454(2) 0.2796(2) 0.98443(19) 0.0284(5) Uani 1 1 d . . . . .
H16 H 0.043079 0.258154 0.993218 0.034 Uiso 1 1 calc R U . . .
C17 C 0.1784(3) 0.4262(2) 1.0240(2) 0.0392(6) Uani 1 1 d . . . . .
H17A H 0.175505 0.467831 1.115222 0.059 Uiso 1 1 calc R U . . .
H17B H 0.276213 0.451362 1.012502 0.059 Uiso 1 1 calc R U . . .
H17C H 0.104603 0.453566 0.969652 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2458(3) 0.2368(3) 1.0785(2) 0.0447(6) Uani 1 1 d . . . . .
H18A H 0.240655 0.286954 1.167473 0.067 Uiso 1 1 calc R U . . .
H18B H 0.214325 0.144589 1.059322 0.067 Uiso 1 1 calc R U . . .
H18C H 0.347065 0.251283 1.069414 0.067 Uiso 1 1 calc R U . . .
C19 C 0.3486(2) 0.0597(2) 0.7219(2) 0.0259(4) Uani 1 1 d . . . . .
C20 C 0.3654(3) 0.0010(2) 0.8276(2) 0.0361(5) Uani 1 1 d . . . . .
H20A H 0.43621 0.0608 0.905687 0.054 Uiso 1 1 calc R U . . .
H20B H 0.270052 -0.013692 0.848394 0.054 Uiso 1 1 calc R U . . .
H20C H 0.400774 -0.081463 0.796324 0.054 Uiso 1 1 calc R U . . .
C21 C 0.5007(3) 0.0771(2) 0.6914(2) 0.0379(6) Uani 1 1 d . . . . .
H21A H 0.571489 0.136573 0.769654 0.057 Uiso 1 1 calc R U . . .
H21B H 0.533243 -0.006893 0.662405 0.057 Uiso 1 1 calc R U . . .
H21C H 0.494281 0.112869 0.622736 0.057 Uiso 1 1 calc R U . . .
C22 C 0.2392(3) -0.0323(2) 0.6007(2) 0.0448(6) Uani 1 1 d . . . . .
H22A H 0.228882 0.005541 0.533561 0.067 Uiso 1 1 calc R U . . .
H22B H 0.27438 -0.114838 0.56909 0.067 Uiso 1 1 calc R U . . .
H22C H 0.143659 -0.047066 0.621159 0.067 Uiso 1 1 calc R U . . .
N1 N 0.14731(19) 0.20802(17) 0.84766(16) 0.0226(4) Uani 1 1 d . . . . .
P1 P 0.22614(6) 0.27909(5) 0.62649(5) 0.02227(18) Uani 1 1 d . . . . .
P2 P 0.30581(5) 0.22758(5) 0.80007(5) 0.02009(18) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.391(3) . ?
C1 C6 1.399(3) . ?
C1 P1 1.8425(19) . ?
C2 C3 1.378(3) . ?
C2 H2 0.95 . ?
C3 C4 1.389(3) . ?
C3 H3 0.95 . ?
C4 C5 1.367(3) . ?
C4 H4 0.95 . ?
C5 C6 1.390(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.391(3) . ?
C7 C12 1.396(3) . ?
C7 P1 1.846(2) . ?
C8 C9 1.394(3) . ?
C8 H8 0.95 . ?
C9 C10 1.382(4) . ?
C9 H9 0.95 . ?
C10 C11 1.372(4) . ?
C10 H10 0.95 . ?
C11 C12 1.390(3) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 N1 1.477(3) . ?
C13 C14 1.527(3) . ?
C13 C15 1.531(3) . ?
C13 H13 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 N1 1.479(3) . ?
C16 C18 1.518(3) . ?
C16 C17 1.524(3) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C22 1.517(3) . ?
C19 C20 1.536(3) . ?
C19 C21 1.540(3) . ?
C19 P2 1.895(2) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
N1 P2 1.6929(17) . ?
P1 P2 2.2433(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.06(17) . . ?
C2 C1 P1 125.84(15) . . ?
C6 C1 P1 116.02(15) . . ?
C3 C2 C1 120.91(18) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.64(19) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.41(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.62(19) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C12 118.5(2) . . ?
C8 C7 P1 124.89(16) . . ?
C12 C7 P1 116.56(18) . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
N1 C13 C14 112.61(17) . . ?
N1 C13 C15 112.17(17) . . ?
C14 C13 C15 110.24(17) . . ?
N1 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C15 C13 H13 107.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C18 112.61(18) . . ?
N1 C16 C17 113.46(16) . . ?
C18 C16 C17 110.4(2) . . ?
N1 C16 H16 106.6 . . ?
C18 C16 H16 106.6 . . ?
C17 C16 H16 106.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C19 C20 109.80(19) . . ?
C22 C19 C21 109.43(19) . . ?
C20 C19 C21 106.89(18) . . ?
C22 C19 P2 117.35(15) . . ?
C20 C19 P2 105.86(14) . . ?
C21 C19 P2 106.99(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 N1 C16 115.49(16) . . ?
C13 N1 P2 125.57(13) . . ?
C16 N1 P2 118.23(14) . . ?
C1 P1 C7 99.23(9) . . ?
C1 P1 P2 103.52(6) . . ?
C7 P1 P2 99.79(7) . . ?
N1 P2 C19 106.67(9) . . ?
N1 P2 P1 100.79(6) . . ?
C19 P2 P1 101.73(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 C3 1.2(3) . . . . ?
P1 C1 C2 C3 -175.57(15) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
P1 C1 C6 C5 175.65(15) . . . . ?
C12 C7 C8 C9 0.7(3) . . . . ?
P1 C7 C8 C9 177.74(16) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
P1 C7 C12 C11 -177.67(15) . . . . ?
C14 C13 N1 C16 57.2(2) . . . . ?
C15 C13 N1 C16 -67.9(2) . . . . ?
C14 C13 N1 P2 -112.95(18) . . . . ?
C15 C13 N1 P2 122.00(18) . . . . ?
C18 C16 N1 C13 124.0(2) . . . . ?
C17 C16 N1 C13 -109.7(2) . . . . ?
C18 C16 N1 P2 -65.1(2) . . . . ?
C17 C16 N1 P2 61.2(2) . . . . ?
C2 C1 P1 C7 68.46(19) . . . . ?
C6 C1 P1 C7 -108.32(16) . . . . ?
C2 C1 P1 P2 -34.02(19) . . . . ?
C6 C1 P1 P2 149.19(13) . . . . ?
C8 C7 P1 C1 -58.24(19) . . . . ?
C12 C7 P1 C1 118.81(16) . . . . ?
C8 C7 P1 P2 47.32(18) . . . . ?
C12 C7 P1 P2 -135.62(15) . . . . ?
C13 N1 P2 C19 -63.70(18) . . . . ?
C16 N1 P2 C19 126.44(15) . . . . ?
C13 N1 P2 P1 42.15(17) . . . . ?
C16 N1 P2 P1 -127.71(14) . . . . ?
C22 C19 P2 N1 62.52(19) . . . . ?
C20 C19 P2 N1 -60.39(17) . . . . ?
C21 C19 P2 N1 -174.13(13) . . . . ?
C22 C19 P2 P1 -42.66(18) . . . . ?
C20 C19 P2 P1 -165.57(14) . . . . ?
C21 C19 P2 P1 80.69(14) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 1585541'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-28T20:39:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H37 N P2'
_chemical_formula_sum            'C20 H37 N P2'
_chemical_formula_weight         353.45
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_Int_Tables_number      29
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   14.3144(10)
_cell_length_b                   12.1120(9)
_cell_length_c                   12.1179(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2101.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4488
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      66.34
_cell_measurement_wavelength     1.54186

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.86
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.4883
_exptl_absorpt_correction_T_max  0.6765
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0840
0 0 -1 0.1610
0 1 0 0.2290
0 -1 0 0.2880
-1 0 0 0.1380
1 0 0 0.1080

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Cu, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 512 frames, detector distance = 50 mm
;
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_number            9628
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.649
_diffrn_reflns_theta_max         65.998
_diffrn_reflns_theta_full        65.998
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.88
_diffrn_reflns_point_group_measured_fraction_max 0.88
_reflns_Friedel_fraction_full    0.784
_reflns_Friedel_fraction_max     0.784
_reflns_Friedel_coverage         0.729
_reflns_number_total             3235
_reflns_number_gt                2948
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1207P)²+1.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3235
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1785
_refine_ls_wR_factor_gt          0.162
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.105

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.6998(4) 0.9322(5) 0.7355(5) 0.0286(13) Uani 1 1 d . . . . .
C2 C 0.6823(4) 1.0175(5) 0.8100(6) 0.0329(13) Uani 1 1 d . . . . .
H2 H 0.675322 1.000829 0.88618 0.04 Uiso 1 1 calc R U . . .
C3 C 0.6749(4) 1.1260(5) 0.7750(6) 0.0362(15) Uani 1 1 d . . . . .
H3 H 0.663009 1.182663 0.827453 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6844(4) 1.1528(5) 0.6650(6) 0.0382(14) Uani 1 1 d . . . . .
H4 H 0.679697 1.2274 0.641476 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7011(4) 1.0695(5) 0.5892(6) 0.0337(14) Uani 1 1 d . . . . .
H5 H 0.707412 1.08702 0.513195 0.04 Uiso 1 1 calc R U . . .
C6 C 0.7087(4) 0.9595(4) 0.6240(6) 0.0294(13) Uani 1 1 d . . . . .
H6 H 0.720004 0.903008 0.571233 0.035 Uiso 1 1 calc R U . . .
C7 C 0.8435(4) 0.7673(5) 0.7618(5) 0.0304(14) Uani 1 1 d . . . . .
C8 C 0.8941(4) 0.8686(5) 0.8109(6) 0.0382(15) Uani 1 1 d . . . . .
H8A H 0.877432 0.87626 0.888925 0.057 Uiso 1 1 calc R U . . .
H8B H 0.96178 0.858536 0.804076 0.057 Uiso 1 1 calc R U . . .
H8C H 0.875189 0.935171 0.770745 0.057 Uiso 1 1 calc R U . . .
C9 C 0.8712(4) 0.7584(5) 0.6408(5) 0.0334(14) Uani 1 1 d . . . . .
H9A H 0.850327 0.824561 0.601256 0.05 Uiso 1 1 calc R U . . .
H9B H 0.9393 0.752052 0.635049 0.05 Uiso 1 1 calc R U . . .
H9C H 0.841917 0.692989 0.608166 0.05 Uiso 1 1 calc R U . . .
C10 C 0.8743(4) 0.6660(5) 0.8279(6) 0.0365(15) Uani 1 1 d . . . . .
H10A H 0.85527 0.674733 0.905125 0.055 Uiso 1 1 calc R U . . .
H10B H 0.845048 0.599703 0.797093 0.055 Uiso 1 1 calc R U . . .
H10C H 0.942431 0.658766 0.823976 0.055 Uiso 1 1 calc R U . . .
C11 C 0.6339(4) 0.5520(5) 0.6968(6) 0.0350(15) Uani 1 1 d . . . . .
C12 C 0.7190(4) 0.5132(5) 0.6318(7) 0.0455(18) Uani 1 1 d . . . . .
H12A H 0.7131 0.536912 0.554808 0.068 Uiso 1 1 calc R U . . .
H12B H 0.775628 0.545323 0.663961 0.068 Uiso 1 1 calc R U . . .
H12C H 0.722884 0.432505 0.634914 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6413(5) 0.5162(5) 0.8173(6) 0.0412(16) Uani 1 1 d . . . . .
H13A H 0.586101 0.54176 0.857774 0.062 Uiso 1 1 calc R U . . .
H13B H 0.644837 0.435466 0.821176 0.062 Uiso 1 1 calc R U . . .
H13C H 0.697581 0.548283 0.850223 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5485(4) 0.4966(5) 0.6444(7) 0.0442(17) Uani 1 1 d . . . . .
H14A H 0.491901 0.519406 0.683844 0.066 Uiso 1 1 calc R U . . .
H14B H 0.543675 0.518802 0.566796 0.066 Uiso 1 1 calc R U . . .
H14C H 0.555158 0.416218 0.648916 0.066 Uiso 1 1 calc R U . . .
C15 C 0.4454(4) 0.7969(4) 0.6517(6) 0.0314(14) Uani 1 1 d . . . . .
H15 H 0.390098 0.814193 0.699175 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4107(5) 0.7196(5) 0.5611(6) 0.0404(16) Uani 1 1 d . . . . .
H16A H 0.364608 0.758205 0.515427 0.061 Uiso 1 1 calc R U . . .
H16B H 0.463525 0.696633 0.515086 0.061 Uiso 1 1 calc R U . . .
H16C H 0.38174 0.654442 0.594641 0.061 Uiso 1 1 calc R U . . .
C17 C 0.4781(4) 0.9057(5) 0.6031(6) 0.0345(14) Uani 1 1 d . . . . .
H17A H 0.4288 0.936341 0.556 0.052 Uiso 1 1 calc R U . . .
H17B H 0.492042 0.95763 0.662804 0.052 Uiso 1 1 calc R U . . .
H17C H 0.534466 0.893278 0.558919 0.052 Uiso 1 1 calc R U . . .
C18 C 0.4918(4) 0.7380(5) 0.8429(5) 0.0291(13) Uani 1 1 d . . . . .
H18 H 0.546177 0.70414 0.882114 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4059(4) 0.6635(5) 0.8643(6) 0.0399(16) Uani 1 1 d . . . . .
H19A H 0.392319 0.661992 0.943567 0.06 Uiso 1 1 calc R U . . .
H19B H 0.351801 0.692937 0.824431 0.06 Uiso 1 1 calc R U . . .
H19C H 0.419197 0.588465 0.838535 0.06 Uiso 1 1 calc R U . . .
C20 C 0.4758(4) 0.8518(5) 0.8930(6) 0.0351(14) Uani 1 1 d . . . . .
H20A H 0.460044 0.843972 0.9713 0.053 Uiso 1 1 calc R U . . .
H20B H 0.532756 0.896077 0.885561 0.053 Uiso 1 1 calc R U . . .
H20C H 0.424313 0.888513 0.85435 0.053 Uiso 1 1 calc R U . . .
N1 N 0.5159(3) 0.7438(4) 0.7248(5) 0.0306(11) Uani 1 1 d . . . . .
P1 P 0.71465(9) 0.79183(10) 0.79295(13) 0.0274(4) Uani 1 1 d . . . . .
P2 P 0.62055(9) 0.70626(11) 0.66934(13) 0.0271(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.394(8) . ?
C1 C6 1.398(9) . ?
C1 P1 1.849(6) . ?
C2 C3 1.385(8) . ?
C2 H2 0.95 . ?
C3 C4 1.379(10) . ?
C3 H3 0.95 . ?
C4 C5 1.385(9) . ?
C4 H4 0.95 . ?
C5 C6 1.401(8) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C9 1.523(9) . ?
C7 C10 1.531(8) . ?
C7 C8 1.544(8) . ?
C7 P1 1.905(6) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C12 1.524(9) . ?
C11 C13 1.526(10) . ?
C11 C14 1.533(8) . ?
C11 P2 1.907(6) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 N1 1.489(8) . ?
C15 C17 1.518(8) . ?
C15 C16 1.525(9) . ?
C15 H15 1 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 N1 1.474(8) . ?
C18 C20 1.523(8) . ?
C18 C19 1.547(8) . ?
C18 H18 1 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
N1 P2 1.704(5) . ?
P1 P2 2.265(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
C2 C1 C6 117.9(6) . . ?
C2 C1 P1 117.3(5) . . ?
C6 C1 P1 124.8(4) . . ?
C3 C2 C1 121.2(7) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.1(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.5(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.5(6) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C9 C7 C10 111.9(5) . . ?
C9 C7 C8 107.7(5) . . ?
C10 C7 C8 107.4(5) . . ?
C9 C7 P1 117.0(4) . . ?
C10 C7 P1 107.5(4) . . ?
C8 C7 P1 104.7(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 110.6(5) . . ?
C12 C11 C14 106.7(5) . . ?
C13 C11 C14 109.1(5) . . ?
C12 C11 P2 107.0(4) . . ?
C13 C11 P2 116.9(4) . . ?
C14 C11 P2 106.0(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C17 113.4(4) . . ?
N1 C15 C16 112.6(5) . . ?
C17 C15 C16 110.7(6) . . ?
N1 C15 H15 106.6 . . ?
C17 C15 H15 106.6 . . ?
C16 C15 H15 106.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C20 112.3(5) . . ?
N1 C18 C19 112.1(5) . . ?
C20 C18 C19 109.9(5) . . ?
N1 C18 H18 107.4 . . ?
C20 C18 H18 107.4 . . ?
C19 C18 H18 107.4 . . ?
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 N1 C15 116.1(5) . . ?
C18 N1 P2 125.2(4) . . ?
C15 N1 P2 118.5(4) . . ?
C1 P1 C7 100.4(2) . . ?
C1 P1 P2 95.94(19) . . ?
C7 P1 P2 111.9(2) . . ?
N1 P2 C11 106.3(3) . . ?
N1 P2 P1 98.0(2) . . ?
C11 P2 P1 105.8(2) . . ?

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 C3 -0.7(8) . . . . ?
P1 C1 C2 C3 176.7(4) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C2 C1 C6 C5 0.7(8) . . . . ?
P1 C1 C6 C5 -176.5(4) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
C20 C18 N1 C15 -59.4(6) . . . . ?
C19 C18 N1 C15 64.9(6) . . . . ?
C20 C18 N1 P2 114.4(5) . . . . ?
C19 C18 N1 P2 -121.2(5) . . . . ?
C17 C15 N1 C18 112.5(6) . . . . ?
C16 C15 N1 C18 -120.9(6) . . . . ?
C17 C15 N1 P2 -61.7(6) . . . . ?
C16 C15 N1 P2 64.9(6) . . . . ?
C2 C1 P1 C7 -112.6(4) . . . . ?
C6 C1 P1 C7 64.6(5) . . . . ?
C2 C1 P1 P2 133.9(4) . . . . ?
C6 C1 P1 P2 -48.9(5) . . . . ?
C18 N1 P2 C11 63.2(5) . . . . ?
C15 N1 P2 C11 -123.1(4) . . . . ?
C18 N1 P2 P1 -46.0(5) . . . . ?
C15 N1 P2 P1 127.7(4) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-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_shelx_CCDC12
_database_code_depnum_ccdc_archive 'CCDC 1560640'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_date             2018-08-30T11:01:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H38 N2 P2'
_chemical_formula_sum            'C20 H38 N2 P2'
_chemical_formula_weight         368.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   9.9020(5)
_cell_length_b                   18.9837(7)
_cell_length_c                   11.9159(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.506(4)
_cell_angle_gamma                90
_cell_volume                     2229.58(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1654
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      20.06
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_absorpt_coefficient_mu    0.2
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.967

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 210 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.1058
_diffrn_reflns_number            19942
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         29.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             6009
_reflns_number_gt                2831
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+0.1436P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6009
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1872
_refine_ls_wR_factor_gt          0.149
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
N1 N 0.2940(2) 0.29845(12) 0.5803(2) 0.0401(6) Uani 1 1 d . . . . .
N2 N 0.2081(3) 0.39599(13) 0.7375(2) 0.0530(7) Uani 1 1 d . . . . .
P1 P 0.47174(9) 0.42336(4) 0.64491(7) 0.0433(2) Uani 1 1 d . . . . .
P2 P 0.33436(8) 0.34111(4) 0.70385(7) 0.0405(2) Uani 1 1 d . . . . .
C1 C 0.6030(3) 0.36699(15) 0.5934(3) 0.0405(7) Uani 1 1 d . . . . .
C2 C 0.6645(3) 0.39137(17) 0.5004(3) 0.0482(8) Uani 1 1 d . . . . .
H2 H 0.641234 0.436605 0.47036 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7582(4) 0.3511(2) 0.4512(3) 0.0586(9) Uani 1 1 d . . . . .
H3 H 0.79911 0.368418 0.387755 0.07 Uiso 1 1 calc R U . . .
C4 C 0.7924(3) 0.2858(2) 0.4942(3) 0.0566(9) Uani 1 1 d . . . . .
H4 H 0.855767 0.257489 0.459416 0.068 Uiso 1 1 calc R U . . .
C5 C 0.7352(3) 0.26085(18) 0.5878(3) 0.0510(8) Uani 1 1 d . . . . .
H5 H 0.760524 0.215988 0.618264 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6414(3) 0.30136(16) 0.6367(3) 0.0441(7) Uani 1 1 d . . . . .
H6 H 0.602343 0.284075 0.701056 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5604(4) 0.46015(15) 0.7802(3) 0.0496(8) Uani 1 1 d . . . . .
C8 C 0.4634(5) 0.51294(17) 0.8266(3) 0.0690(11) Uani 1 1 d . . . . .
H8A H 0.432796 0.546899 0.76765 0.103 Uiso 1 1 calc R U . . .
H8B H 0.3848 0.487833 0.851037 0.103 Uiso 1 1 calc R U . . .
H8C H 0.510277 0.537925 0.890983 0.103 Uiso 1 1 calc R U . . .
C9 C 0.6811(5) 0.5017(2) 0.7425(4) 0.0857(14) Uani 1 1 d . . . . .
H9A H 0.648478 0.535976 0.684628 0.129 Uiso 1 1 calc R U . . .
H9B H 0.727161 0.526595 0.807426 0.129 Uiso 1 1 calc R U . . .
H9C H 0.744834 0.469208 0.711547 0.129 Uiso 1 1 calc R U . . .
C10 C 0.6090(4) 0.40731(17) 0.8692(3) 0.0581(9) Uani 1 1 d . . . . .
H10A H 0.671024 0.373929 0.838044 0.087 Uiso 1 1 calc R U . . .
H10B H 0.656536 0.431836 0.933753 0.087 Uiso 1 1 calc R U . . .
H10C H 0.531059 0.381745 0.893807 0.087 Uiso 1 1 calc R U . . .
C11 C 0.2864(3) 0.32746(16) 0.4648(3) 0.0465(8) Uani 1 1 d . . . . .
H11 H 0.321163 0.376898 0.471514 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1442(3) 0.33129(19) 0.4066(3) 0.0594(9) Uani 1 1 d . . . . .
H12A H 0.147073 0.350945 0.330777 0.089 Uiso 1 1 calc R U . . .
H12B H 0.104913 0.283891 0.400963 0.089 Uiso 1 1 calc R U . . .
H12C H 0.088313 0.361525 0.450151 0.089 Uiso 1 1 calc R U . . .
C13 C 0.3795(3) 0.28747(17) 0.3911(3) 0.0505(8) Uani 1 1 d . . . . .
H13A H 0.371929 0.30805 0.315382 0.076 Uiso 1 1 calc R U . . .
H13B H 0.473561 0.290958 0.424622 0.076 Uiso 1 1 calc R U . . .
H13C H 0.35234 0.237829 0.386339 0.076 Uiso 1 1 calc R U . . .
C14 C 0.2477(3) 0.22453(16) 0.5884(3) 0.0501(8) Uani 1 1 d . . . . .
H14 H 0.218645 0.208851 0.509606 0.06 Uiso 1 1 calc R U . . .
C15 C 0.3603(4) 0.17532(15) 0.6332(3) 0.0567(9) Uani 1 1 d . . . . .
H15A H 0.3246 0.127315 0.636926 0.085 Uiso 1 1 calc R U . . .
H15B H 0.433057 0.176244 0.583022 0.085 Uiso 1 1 calc R U . . .
H15C H 0.396184 0.19053 0.70888 0.085 Uiso 1 1 calc R U . . .
C16 C 0.1251(3) 0.21693(18) 0.6539(3) 0.0591(9) Uani 1 1 d . . . . .
H16A H 0.099233 0.167175 0.656442 0.089 Uiso 1 1 calc R U . . .
H16B H 0.14721 0.234421 0.730872 0.089 Uiso 1 1 calc R U . . .
H16C H 0.049564 0.244271 0.616939 0.089 Uiso 1 1 calc R U . . .
C18 C 0.1215(19) 0.3673(10) 0.8251(16) 0.061(4) Uani 0.599(10) 1 d . . P A 1
H18A H 0.024273 0.36954 0.796742 0.073 Uiso 0.599(10) 1 calc R U P A 1
H18B H 0.145371 0.317538 0.842233 0.073 Uiso 0.599(10) 1 calc R U P A 1
C19 C 0.148(2) 0.4112(7) 0.9283(16) 0.083(5) Uani 0.599(10) 1 d . . P A 1
H19A H 0.092799 0.393758 0.98664 0.125 Uiso 0.599(10) 1 calc R U P A 1
H19B H 0.244019 0.408417 0.955731 0.125 Uiso 0.599(10) 1 calc R U P A 1
H19C H 0.123402 0.460213 0.91042 0.125 Uiso 0.599(10) 1 calc R U P A 1
C20 C 0.1202(8) 0.4353(4) 0.6466(7) 0.0478(19) Uani 0.599(10) 1 d . . P A 1
H20A H 0.173496 0.443886 0.581732 0.057 Uiso 0.599(10) 1 calc R U P A 1
H20B H 0.041617 0.405467 0.619974 0.057 Uiso 0.599(10) 1 calc R U P A 1
C21 C 0.0694(7) 0.5044(3) 0.6867(6) 0.066(2) Uani 0.599(10) 1 d . . P A 1
H21A H 0.013566 0.527448 0.624954 0.099 Uiso 0.599(10) 1 calc R U P A 1
H21B H 0.014784 0.496255 0.749817 0.099 Uiso 0.599(10) 1 calc R U P A 1
H21C H 0.146715 0.534688 0.71156 0.099 Uiso 0.599(10) 1 calc R U P A 1
C18A C 0.148(3) 0.3810(13) 0.840(3) 0.058(6) Uani 0.401(10) 1 d . . P A 2
H18C H 0.192857 0.338315 0.8737 0.07 Uiso 0.401(10) 1 calc R U P A 2
H18D H 0.051789 0.368296 0.818969 0.07 Uiso 0.401(10) 1 calc R U P A 2
C19A C 0.148(3) 0.4362(11) 0.935(2) 0.064(5) Uani 0.401(10) 1 d . . P A 2
H19D H 0.103244 0.41676 0.99821 0.096 Uiso 0.401(10) 1 calc R U P A 2
H19E H 0.242368 0.448409 0.961846 0.096 Uiso 0.401(10) 1 calc R U P A 2
H19F H 0.100314 0.4786 0.906733 0.096 Uiso 0.401(10) 1 calc R U P A 2
C20A C 0.1650(13) 0.4593(6) 0.6797(10) 0.049(3) Uani 0.401(10) 1 d . . P A 2
H20C H 0.211607 0.464679 0.610347 0.059 Uiso 0.401(10) 1 calc R U P A 2
H20D H 0.18667 0.500767 0.728628 0.059 Uiso 0.401(10) 1 calc R U P A 2
C21A C 0.0098(12) 0.4535(6) 0.6498(9) 0.071(4) Uani 0.401(10) 1 d . . P A 2
H21D H -0.023492 0.496199 0.609891 0.107 Uiso 0.401(10) 1 calc R U P A 2
H21E H -0.010267 0.412396 0.601329 0.107 Uiso 0.401(10) 1 calc R U P A 2
H21F H -0.035095 0.448326 0.719094 0.107 Uiso 0.401(10) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N1 C11 1.477(4) . ?
N1 C14 1.482(4) . ?
N1 P2 1.694(3) . ?
N2 C20A 1.430(12) . ?
N2 C18A 1.44(3) . ?
N2 C18 1.515(15) . ?
N2 C20 1.519(8) . ?
N2 P2 1.705(3) . ?
P1 C1 1.834(3) . ?
P1 C7 1.894(3) . ?
P1 P2 2.2284(11) . ?
C1 C6 1.387(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.377(5) . ?
C2 H2 0.95 . ?
C3 C4 1.371(5) . ?
C3 H3 0.95 . ?
C4 C5 1.382(5) . ?
C4 H4 0.95 . ?
C5 C6 1.378(4) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C10 1.505(4) . ?
C7 C8 1.529(5) . ?
C7 C9 1.535(5) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C12 1.511(5) . ?
C11 C13 1.533(4) . ?
C11 H11 1 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 C16 1.512(4) . ?
C14 C15 1.513(4) . ?
C14 H14 1 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C18 C19 1.49(2) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 C21 1.499(11) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C18A C19A 1.54(3) . ?
C18A H18C 0.99 . ?
C18A H18D 0.99 . ?
C19A H19D 0.98 . ?
C19A H19E 0.98 . ?
C19A H19F 0.98 . ?
C20A C21A 1.548(19) . ?
C20A H20C 0.99 . ?
C20A H20D 0.99 . ?
C21A H21D 0.98 . ?
C21A H21E 0.98 . ?
C21A H21F 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C14 115.1(3) . . ?
C11 N1 P2 128.2(2) . . ?
C14 N1 P2 116.4(2) . . ?
C20A N2 C18A 116.5(11) . . ?
C18 N2 C20 110.2(9) . . ?
C20A N2 P2 126.3(5) . . ?
C18A N2 P2 116.9(11) . . ?
C18 N2 P2 114.8(7) . . ?
C20 N2 P2 121.0(3) . . ?
C1 P1 C7 102.38(15) . . ?
C1 P1 P2 99.80(10) . . ?
C7 P1 P2 103.74(10) . . ?
N1 P2 N2 112.30(14) . . ?
N1 P2 P1 99.29(8) . . ?
N2 P2 P1 97.45(9) . . ?
C6 C1 C2 117.9(3) . . ?
C6 C1 P1 125.3(2) . . ?
C2 C1 P1 116.7(2) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C10 C7 C8 110.6(3) . . ?
C10 C7 C9 110.1(3) . . ?
C8 C7 C9 107.6(3) . . ?
C10 C7 P1 116.4(2) . . ?
C8 C7 P1 107.1(3) . . ?
C9 C7 P1 104.6(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 114.0(3) . . ?
N1 C11 C13 111.7(2) . . ?
C12 C11 C13 110.2(3) . . ?
N1 C11 H11 106.8 . . ?
C12 C11 H11 106.8 . . ?
C13 C11 H11 106.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C16 113.1(3) . . ?
N1 C14 C15 112.7(3) . . ?
C16 C14 C15 111.1(3) . . ?
N1 C14 H14 106.5 . . ?
C16 C14 H14 106.5 . . ?
C15 C14 H14 106.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C18 N2 107.6(14) . . ?
C19 C18 H18A 110.2 . . ?
N2 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
N2 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
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 . . ?
C21 C20 N2 112.9(7) . . ?
C21 C20 H20A 109 . . ?
N2 C20 H20A 109 . . ?
C21 C20 H20B 109 . . ?
N2 C20 H20B 109 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C18A C19A 121(2) . . ?
N2 C18A H18C 107 . . ?
C19A C18A H18C 107 . . ?
N2 C18A H18D 107 . . ?
C19A C18A H18D 107 . . ?
H18C C18A H18D 106.8 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
N2 C20A C21A 107.1(10) . . ?
N2 C20A H20C 110.3 . . ?
C21A C20A H20C 110.3 . . ?
N2 C20A H20D 110.3 . . ?
C21A C20A H20D 110.3 . . ?
H20C C20A H20D 108.5 . . ?
C20A C21A H21D 109.5 . . ?
C20A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
C20A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 P2 N2 72.8(3) . . . . ?
C14 N1 P2 N2 -100.9(2) . . . . ?
C11 N1 P2 P1 -29.3(3) . . . . ?
C14 N1 P2 P1 157.1(2) . . . . ?
C20A N2 P2 N1 -68.3(7) . . . . ?
C18A N2 P2 N1 118.2(13) . . . . ?
C18 N2 P2 N1 101.4(9) . . . . ?
C20 N2 P2 N1 -34.7(4) . . . . ?
C20A N2 P2 P1 35.0(7) . . . . ?
C18A N2 P2 P1 -138.5(13) . . . . ?
C18 N2 P2 P1 -155.3(9) . . . . ?
C20 N2 P2 P1 68.5(4) . . . . ?
C7 P1 C1 C6 75.7(3) . . . . ?
P2 P1 C1 C6 -30.8(3) . . . . ?
C7 P1 C1 C2 -107.1(3) . . . . ?
P2 P1 C1 C2 146.4(2) . . . . ?
C6 C1 C2 C3 1.4(5) . . . . ?
P1 C1 C2 C3 -176.1(2) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
P1 C1 C6 C5 175.9(2) . . . . ?
C1 P1 C7 C10 -60.0(3) . . . . ?
P2 P1 C7 C10 43.5(3) . . . . ?
C1 P1 C7 C8 175.7(2) . . . . ?
P2 P1 C7 C8 -80.8(2) . . . . ?
C1 P1 C7 C9 61.7(3) . . . . ?
P2 P1 C7 C9 165.2(2) . . . . ?
C14 N1 C11 C12 62.8(3) . . . . ?
P2 N1 C11 C12 -110.9(3) . . . . ?
C14 N1 C11 C13 -63.0(3) . . . . ?
P2 N1 C11 C13 123.3(3) . . . . ?
C11 N1 C14 C16 -117.1(3) . . . . ?
P2 N1 C14 C16 57.4(3) . . . . ?
C11 N1 C14 C15 116.0(3) . . . . ?
P2 N1 C14 C15 -69.6(3) . . . . ?
C20 N2 C18 C19 -106.4(14) . . . . ?
P2 N2 C18 C19 112.9(12) . . . . ?
C18 N2 C20 C21 71.9(10) . . . . ?
P2 N2 C20 C21 -150.2(4) . . . . ?
C20A N2 C18A C19A -52(3) . . . . ?
P2 N2 C18A C19A 121.8(19) . . . . ?
C18A N2 C20A C21A -59.7(17) . . . . ?
P2 N2 C20A C21A 126.9(7) . . . . ?



# END of CIF
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
