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

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1427664'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            YR1
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10.50 N P0.50'
_chemical_formula_iupac          ?
_chemical_formula_weight         244.25

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -z-1/2'

_cell_length_a                   15.8239(8)
_cell_length_b                   19.3822(10)
_cell_length_c                   7.8312(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2401.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.5745
_cell_measurement_theta_max      33.7105
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'irregular rhombic shard'
_exptl_crystal_colour            'translucent intense red-purple'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016

_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'BRUKER APEX II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            52792
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         36.37
_diffrn_reflns_theta_full        36.37
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12

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

_reflns_number_total             5933
_reflns_number_gt                4817
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1312
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.944
_refine_ls_number_reflns         5933
_refine_ls_number_parameters     220
_refine_ls_number_restraints     84
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0598P)²+2.2881P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.439
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.75166(2) 0.25 0.70796(5) 0.01177(8) Uani d . . S 1 . .
N N1 0.73097(5) 0.31828(5) 0.57524(12) 0.01551(15) Uani d . . . 1 . .
C C1 0.78364(6) 0.37605(5) 0.56738(14) 0.01674(17) Uani d . . D 1 . .
C C2 0.86182(7) 0.38680(5) 0.64444(16) 0.01930(19) Uani d . . D 1 . .
H H2 0.8875 0.3526 0.7141 0.023 Uiso calc . . R 1 . .
C C3 0.90061(8) 0.45005(6) 0.61446(19) 0.0259(2) Uani d . . D 1 . .
H H3 0.954 0.4594 0.6651 0.031 Uiso calc . . R 1 . .
C C4 0.86254(10) 0.50049(6) 0.5109(2) 0.0315(3) Uani d . . D 1 . .
H H4 0.8911 0.5429 0.4916 0.038 Uiso calc . . R 1 . .
C C5 0.78470(10) 0.48976(6) 0.43676(19) 0.0309(3) Uani d . . D 1 . .
H H5 0.7594 0.5243 0.3675 0.037 Uiso calc . . R 1 . .
C C6 0.74351(8) 0.42661(6) 0.46580(15) 0.0224(2) Uani d . . D 1 . .
C C7 0.66421(8) 0.39854(7) 0.41388(16) 0.0252(2) Uani d . . . 1 . .
H H7 0.6234 0.421 0.3442 0.03 Uiso calc . . R 1 . .
C C8 0.65696(6) 0.33344(6) 0.48201(14) 0.01941(19) Uani d . . . 1 . .
C C9 0.58711(6) 0.28568(7) 0.46689(13) 0.0222(2) Uani d . . . 1 . .
C C10A 0.50138(19) 0.31956(15) 0.4413(4) 0.0150(5) Uani d U P D 0.5 . 1
C C11A 0.46462(18) 0.38352(16) 0.4299(4) 0.0196(5) Uani d U P D 0.5 . 1
H H11A 0.497 0.4243 0.4451 0.024 Uiso calc . P R 0.5 . 1
C C12A 0.37616(17) 0.38676(17) 0.3945(4) 0.0233(5) Uani d U P D 0.5 . 1
H H12A 0.3503 0.4308 0.3853 0.028 Uiso calc . P R 0.5 . 1
C C13A 0.32692(17) 0.32946(17) 0.3733(4) 0.0225(5) Uani d U P D 0.5 . 1
H H13A 0.2685 0.3344 0.3483 0.027 Uiso calc . P R 0.5 . 1
C C10B 0.49675(19) 0.29989(15) 0.4390(4) 0.0145(5) Uani d U P D 0.5 . 2
C C11B 0.45529(18) 0.36234(16) 0.4242(4) 0.0201(5) Uani d U P D 0.5 . 2
H H11B 0.4847 0.4047 0.4384 0.024 Uiso calc . P R 0.5 . 2
C C12B 0.36632(18) 0.36140(17) 0.3866(4) 0.0245(5) Uani d U P D 0.5 . 2
H H12B 0.3374 0.4041 0.3742 0.029 Uiso calc . P R 0.5 . 2
C C13B 0.32206(16) 0.30181(17) 0.3681(4) 0.0223(4) Uani d U P D 0.5 . 2
H H13B 0.258(2) 0.2995(18) 0.336(5) 0.027 Uiso d . P . 0.5 A 2
C C14 0.36264(12) 0.2375(2) 0.3886(3) 0.0257(11) Uani d U P D 0.5 . .
C C15 0.44973(12) 0.2397(2) 0.4239(2) 0.0201(10) Uani d U P D 0.5 . .
C C16 0.65559(8) 0.25 0.83553(17) 0.0124(2) Uani d . . S 1 . .
C C17 0.62012(7) 0.18788(5) 0.88889(14) 0.01672(17) Uani d . . . 1 . .
H H17 0.646 0.1454 0.8584 0.02 Uiso calc . . R 1 . .
C C18 0.54674(7) 0.18805(6) 0.98683(15) 0.0208(2) Uani d . . . 1 . .
H H18 0.5225 0.1457 1.023 0.025 Uiso calc . . R 1 . .
C C19 0.50898(10) 0.25 1.03167(19) 0.0214(3) Uani d . . S 1 . .
H H19 0.4572 0.25 1.0931 0.026 Uiso calc . . SR 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 N1 . 1.7143(9) ?
P1 N1 7_565 1.7143(9) ?
P1 C16 . 1.8190(13) ?
N1 C1 . 1.3972(14) ?
N1 C8 . 1.4110(13) ?
C1 C2 . 1.3922(16) ?
C1 C6 . 1.4129(15) ?
C2 C3 . 1.3910(15) ?
C2 H2 . 0.95 ?
C3 C4 . 1.406(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.377(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.4053(18) ?
C5 H5 . 0.95 ?
C6 C7 . 1.4269(19) ?
C7 C8 . 1.3747(17) ?
C7 H7 . 0.95 ?
C8 C9 . 1.4467(17) ?
C9 C9 7_565 1.383(3) ?
C9 C10B . 1.472(3) ?
C9 C10A . 1.520(3) ?
C10A C11A . 1.372(4) ?
C10A C15 7_565 1.417(5) ?
C10A C15 . 1.755(5) ?
C11A C12A . 1.428(4) ?
C11A H11A . 0.95 ?
C12A C13A . 1.367(4) ?
C12A H12A . 0.95 ?
C13A C14 7_565 1.421(5) ?
C13A C14 . 1.874(5) ?
C13A H13A . 0.95 ?
C13A H13B . 1.27(3) ?
C10B C15 7_565 1.076(4) ?
C10B C11B . 1.382(4) ?
C10B C15 . 1.388(5) ?
C10B C10B 7_565 1.934(6) ?
C11B C12B . 1.438(4) ?
C11B C15 7_565 1.981(5) ?
C11B H11B . 0.95 ?
C12B C13B . 1.359(4) ?
C12B C14 7_565 1.918(5) ?
C12B H12B . 0.95 ?
C13B C14 7_565 1.009(4) ?
C13B C14 . 1.411(5) ?
C13B C13B 7_565 2.008(7) ?
C13B H13B . 1.05(3) ?
C14 C14 7_565 0.485(8) ?
C14 C13B 7_565 1.009(4) ?
C14 C15 . 1.406(3) ?
C14 C13A 7_565 1.421(5) ?
C14 C15 7_565 1.473(3) ?
C14 C12B 7_565 1.918(5) ?
C15 C15 7_565 0.397(9) ?
C15 C10B 7_565 1.076(4) ?
C15 C10A 7_565 1.417(5) ?
C15 C14 7_565 1.473(3) ?
C15 C11B 7_565 1.981(5) ?
C16 C17 . 1.3925(12) ?
C16 C17 7_565 1.3926(12) ?
C17 C18 . 1.3916(15) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3864(14) ?
C18 H18 . 0.95 ?
C19 C18 7_565 1.3863(14) ?
C19 H19 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 P1 N1 . 7_565 101.06(7) ?
N1 P1 C16 . . 99.99(4) ?
N1 P1 C16 7_565 . 99.99(4) ?
C1 N1 C8 . . 107.78(9) ?
C1 N1 P1 . . 122.10(7) ?
C8 N1 P1 . . 129.27(8) ?
C2 C1 N1 . . 129.12(9) ?
C2 C1 C6 . . 122.65(10) ?
N1 C1 C6 . . 108.22(10) ?
C3 C2 C1 . . 116.80(11) ?
C3 C2 H2 . . 121.6 ?
C1 C2 H2 . . 121.6 ?
C2 C3 C4 . . 121.41(13) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 121.42(12) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 118.56(12) ?
C4 C5 H5 . . 120.7 ?
C6 C5 H5 . . 120.7 ?
C5 C6 C1 . . 119.13(12) ?
C5 C6 C7 . . 133.94(12) ?
C1 C6 C7 . . 106.93(10) ?
C8 C7 C6 . . 108.22(10) ?
C8 C7 H7 . . 125.9 ?
C6 C7 H7 . . 125.9 ?
C7 C8 N1 . . 108.83(11) ?
C7 C8 C9 . . 128.26(10) ?
N1 C8 C9 . . 122.91(10) ?
C9 C9 C8 7_565 . 129.78(6) ?
C9 C9 C10B 7_565 . 100.79(13) ?
C8 C9 C10B . . 129.38(15) ?
C9 C9 C10A 7_565 . 115.59(12) ?
C8 C9 C10A . . 114.59(15) ?
C10B C9 C10A . . 14.81(12) ?
C11A C10A C15 . 7_565 118.8(3) ?
C11A C10A C9 . . 141.0(3) ?
C15 C10A C9 7_565 . 100.2(2) ?
C11A C10A C15 . . 126.4(3) ?
C15 C10A C15 7_565 . 7.61(17) ?
C9 C10A C15 . . 92.59(18) ?
C10A C11A C12A . . 117.9(3) ?
C10A C11A H11A . . 121.1 ?
C12A C11A H11A . . 121.1 ?
C13A C12A C11A . . 123.1(3) ?
C13A C12A H12A . . 118.4 ?
C11A C12A H12A . . 118.4 ?
C12A C13A C14 . 7_565 120.3(2) ?
C12A C13A C14 . . 126.4(2) ?
C14 C13A C14 7_565 . 6.04(11) ?
C12A C13A H13A . . 119.8 ?
C14 C13A H13A 7_565 . 119.8 ?
C14 C13A H13A . . 113.8 ?
C12A C13A H13B . . 152.7(16) ?
C14 C13A H13B 7_565 . 86.8(16) ?
C14 C13A H13B . . 80.8(16) ?
H13A C13A H13B . . 33.1 ?
C15 C10B C11B 7_565 . 106.7(3) ?
C15 C10B C15 7_565 . 11.6(3) ?
C11B C10B C15 . . 118.3(3) ?
C15 C10B C9 7_565 . 123.7(3) ?
C11B C10B C9 . . 129.6(2) ?
C15 C10B C9 . . 112.1(2) ?
C15 C10B C10B 7_565 7_565 44.4(2) ?
C11B C10B C10B . 7_565 151.17(17) ?
C15 C10B C10B . 7_565 32.88(16) ?
C9 C10B C10B . 7_565 79.22(12) ?
C10B C11B C12B . . 118.1(3) ?
C10B C11B C15 . 7_565 31.35(15) ?
C12B C11B C15 . 7_565 86.8(2) ?
C10B C11B H11B . . 121.0 ?
C12B C11B H11B . . 121.0 ?
C15 C11B H11B 7_565 . 152.2 ?
C13B C12B C11B . . 122.5(3) ?
C13B C12B C14 . 7_565 30.17(14) ?
C11B C12B C14 . 7_565 92.3(2) ?
C13B C12B H12B . . 118.8 ?
C11B C12B H12B . . 118.8 ?
C14 C12B H12B 7_565 . 148.9 ?
C14 C13B C12B 7_565 . 107.3(3) ?
C14 C13B C14 7_565 . 13.0(2) ?
C12B C13B C14 . . 120.3(2) ?
C14 C13B C13B 7_565 7_565 41.0(2) ?
C12B C13B C13B . 7_565 148.23(16) ?
C14 C13B C13B . 7_565 27.97(15) ?
C14 C13B H13B 7_565 . 129.(2) ?
C12B C13B H13B . . 124.1(19) ?
C14 C13B H13B . . 115.6(19) ?
C13B C13B H13B 7_565 . 87.6(19) ?
C14 C14 C13B 7_565 7_565 139.0(2) ?
C14 C14 C15 7_565 . 88.2(2) ?
C13B C14 C15 7_565 . 132.7(4) ?
C14 C14 C13B 7_565 . 27.98(15) ?
C13B C14 C13B 7_565 . 111.0(3) ?
C15 C14 C13B . . 116.2(3) ?
C14 C14 C13A 7_565 7_565 156.00(16) ?
C13B C14 C13A 7_565 7_565 17.0(2) ?
C15 C14 C13A . 7_565 115.8(3) ?
C13B C14 C13A . 7_565 128.0(2) ?
C14 C14 C15 7_565 7_565 72.6(2) ?
C13B C14 C15 7_565 7_565 148.3(4) ?
C15 C14 C15 . 7_565 15.6(3) ?
C13B C14 C15 . 7_565 100.5(3) ?
C13A C14 C15 7_565 7_565 131.4(3) ?
C14 C14 C13A 7_565 . 17.97(11) ?
C13B C14 C13A 7_565 . 121.1(3) ?
C15 C14 C13A . . 106.2(3) ?
C13B C14 C13A . . 10.04(15) ?
C13A C14 C13A 7_565 . 138.0(2) ?
C15 C14 C13A 7_565 . 90.5(3) ?
C14 C14 C12B 7_565 7_565 178.18(11) ?
C13B C14 C12B 7_565 7_565 42.6(2) ?
C15 C14 C12B . 7_565 90.2(3) ?
C13B C14 C12B . 7_565 153.6(2) ?
C13A C14 C12B 7_565 7_565 25.62(16) ?
C15 C14 C12B 7_565 7_565 105.8(2) ?
C13A C14 C12B . 7_565 163.62(18) ?
C15 C15 C10B 7_565 7_565 135.6(2) ?
C15 C15 C10B 7_565 . 32.87(16) ?
C10B C15 C10B 7_565 . 102.7(3) ?
C15 C15 C14 7_565 . 91.8(2) ?
C10B C15 C14 7_565 . 132.6(4) ?
C10B C15 C14 . . 124.6(3) ?
C15 C15 C10A 7_565 7_565 144.21(17) ?
C10B C15 C10A 7_565 7_565 8.7(2) ?
C10B C15 C10A . 7_565 111.34(18) ?
C14 C15 C10A . 7_565 124.0(3) ?
C15 C15 C14 7_565 7_565 72.6(2) ?
C10B C15 C14 7_565 7_565 151.8(4) ?
C10B C15 C14 . 7_565 105.4(3) ?
C14 C15 C14 . 7_565 19.2(3) ?
C10A C15 C14 7_565 7_565 143.2(3) ?
C15 C15 C10A 7_565 . 28.17(13) ?
C10B C15 C10A 7_565 . 107.4(2) ?
C10B C15 C10A . . 4.7(2) ?
C14 C15 C10A . . 119.9(3) ?
C10A C15 C10A 7_565 . 116.0(2) ?
C14 C15 C10A 7_565 . 100.7(3) ?
C15 C15 C11B 7_565 7_565 177.45(10) ?
C10B C15 C11B 7_565 7_565 41.9(2) ?
C10B C15 C11B . 7_565 144.6(2) ?
C14 C15 C11B . 7_565 90.7(3) ?
C10A C15 C11B 7_565 7_565 33.27(17) ?
C14 C15 C11B 7_565 7_565 109.9(2) ?
C10A C15 C11B . 7_565 149.30(18) ?
C17 C16 C17 . 7_565 119.67(13) ?
C17 C16 P1 . . 120.11(6) ?
C17 C16 P1 7_565 . 120.11(6) ?
C18 C17 C16 . . 119.98(10) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C19 C18 C17 . . 120.08(10) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 C18 7_565 . 120.02(14) ?
C18 C19 H19 7_565 . 120.0 ?
C18 C19 H19 . . 120.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 P1 N1 C1 7_565 . . . -136.59(7) ?
C16 P1 N1 C1 . . . . 121.06(8) ?
N1 P1 N1 C8 7_565 . . . 55.27(11) ?
C16 P1 N1 C8 . . . . -47.08(10) ?
C8 N1 C1 C2 . . . . 177.40(11) ?
P1 N1 C1 C2 . . . . 7.02(16) ?
C8 N1 C1 C6 . . . . -1.44(12) ?
P1 N1 C1 C6 . . . . -171.83(8) ?
N1 C1 C2 C3 . . . . -179.91(11) ?
C6 C1 C2 C3 . . . . -1.21(16) ?
C1 C2 C3 C4 . . . . -0.15(18) ?
C2 C3 C4 C5 . . . . 0.9(2) ?
C3 C4 C5 C6 . . . . -0.4(2) ?
C4 C5 C6 C1 . . . . -0.95(18) ?
C4 C5 C6 C7 . . . . 178.86(13) ?
C2 C1 C6 C5 . . . . 1.80(17) ?
N1 C1 C6 C5 . . . . -179.26(10) ?
C2 C1 C6 C7 . . . . -178.06(10) ?
N1 C1 C6 C7 . . . . 0.87(12) ?
C5 C6 C7 C8 . . . . -179.79(13) ?
C1 C6 C7 C8 . . . . 0.04(13) ?
C6 C7 C8 N1 . . . . -0.93(13) ?
C6 C7 C8 C9 . . . . 178.78(11) ?
C1 N1 C8 C7 . . . . 1.48(12) ?
P1 N1 C8 C7 . . . . 170.95(8) ?
C1 N1 C8 C9 . . . . -178.25(10) ?
P1 N1 C8 C9 . . . . -8.78(16) ?
C7 C8 C9 C9 . . . 7_565 149.82(9) ?
N1 C8 C9 C9 . . . 7_565 -30.50(13) ?
C7 C8 C9 C10B . . . . -26.9(2) ?
N1 C8 C9 C10B . . . . 152.77(19) ?
C7 C8 C9 C10A . . . . -27.9(2) ?
N1 C8 C9 C10A . . . . 151.77(16) ?
C9 C9 C10A C11A 7_565 . . . -179.8(4) ?
C8 C9 C10A C11A . . . . -1.7(5) ?
C10B C9 C10A C11A . . . . -178.7(12) ?
C9 C9 C10A C15 7_565 . . 7_565 -0.6(2) ?
C8 C9 C10A C15 . . . 7_565 177.42(14) ?
C10B C9 C10A C15 . . . 7_565 0.4(7) ?
C9 C9 C10A C15 7_565 . . . -0.51(18) ?
C8 C9 C10A C15 . . . . 177.56(11) ?
C10B C9 C10A C15 . . . . 0.6(8) ?
C15 C10A C11A C12A 7_565 . . . -2.3(4) ?
C9 C10A C11A C12A . . . . 176.7(3) ?
C15 C10A C11A C12A . . . . -2.3(5) ?
C10A C11A C12A C13A . . . . 0.6(5) ?
C11A C12A C13A C14 . . . 7_565 1.0(4) ?
C11A C12A C13A C14 . . . . 1.0(4) ?
C9 C9 C10B C15 7_565 . . 7_565 -0.3(3) ?
C8 C9 C10B C15 . . . 7_565 177.1(2) ?
C10A C9 C10B C15 . . . 7_565 -179.3(11) ?
C9 C9 C10B C11B 7_565 . . . -179.1(3) ?
C8 C9 C10B C11B . . . . -1.7(4) ?
C10A C9 C10B C11B . . . . 1.9(6) ?
C9 C9 C10B C15 7_565 . . . -0.2(2) ?
C8 C9 C10B C15 . . . . 177.23(15) ?
C10A C9 C10B C15 . . . . -179.2(10) ?
C9 C9 C10B C10B 7_565 . . 7_565 0 ?
C8 C9 C10B C10B . . . 7_565 177.45(17) ?
C10A C9 C10B C10B . . . 7_565 -179.0(8) ?
C15 C10B C11B C12B 7_565 . . . -2.7(4) ?
C15 C10B C11B C12B . . . . -2.6(4) ?
C9 C10B C11B C12B . . . . 176.3(3) ?
C10B C10B C11B C12B 7_565 . . . -2.0(6) ?
C15 C10B C11B C15 . . . 7_565 0.11(4) ?
C9 C10B C11B C15 . . . 7_565 179.0(5) ?
C10B C10B C11B C15 7_565 . . 7_565 0.7(2) ?
C10B C11B C12B C13B . . . . 1.1(5) ?
C15 C11B C12B C13B 7_565 . . . -0.4(3) ?
C10B C11B C12B C14 . . . 7_565 1.8(3) ?
C15 C11B C12B C14 7_565 . . 7_565 0.37(15) ?
C11B C12B C13B C14 . . . 7_565 1.4(4) ?
C11B C12B C13B C14 . . . . 1.1(4) ?
C14 C12B C13B C14 7_565 . . . -0.35(4) ?
C11B C12B C13B C13B . . . 7_565 -0.2(5) ?
C14 C12B C13B C13B 7_565 . . 7_565 -1.6(2) ?
C12B C13B C14 C14 . . . 7_565 1.46(19) ?
C13B C13B C14 C14 7_565 . . 7_565 180.004(2) ?
C14 C13B C14 C13B 7_565 . . 7_565 179.996(2) ?
C12B C13B C14 C13B . . . 7_565 -178.54(19) ?
C14 C13B C14 C15 7_565 . . . -3.0(4) ?
C12B C13B C14 C15 . . . . -1.6(4) ?
C13B C13B C14 C15 7_565 . . . 177.0(4) ?
C14 C13B C14 C13A 7_565 . . 7_565 178.9(2) ?
C12B C13B C14 C13A . . . 7_565 -179.6(3) ?
C13B C13B C14 C13A 7_565 . . 7_565 -1.1(2) ?
C14 C13B C14 C15 7_565 . . 7_565 -2.6(3) ?
C12B C13B C14 C15 . . . 7_565 -1.2(3) ?
C13B C13B C14 C15 7_565 . . 7_565 177.4(3) ?
C14 C13B C14 C13A 7_565 . . . 3.7(8) ?
C12B C13B C14 C13A . . . . 5.1(8) ?
C13B C13B C14 C13A 7_565 . . . -176.3(8) ?
C14 C13B C14 C12B 7_565 . . 7_565 -178.0(3) ?
C12B C13B C14 C12B . . . 7_565 -176.5(4) ?
C13B C13B C14 C12B 7_565 . . 7_565 2.0(3) ?
C12A C13A C14 C14 . . . 7_565 0.0(2) ?
C12A C13A C14 C13B . . . 7_565 -178.5(3) ?
C14 C13A C14 C13B 7_565 . . 7_565 -178.4(3) ?
C12A C13A C14 C15 . . . . -0.7(3) ?
C14 C13A C14 C15 7_565 . . . -0.7(4) ?
C12A C13A C14 C13B . . . . -174.5(11) ?
C14 C13A C14 C13B 7_565 . . . -174.4(11) ?
C12A C13A C14 C13A . . . 7_565 180.0(2) ?
C14 C13A C14 C13A 7_565 . . 7_565 179.994(2) ?
C12A C13A C14 C15 . . . 7_565 -0.7(3) ?
C14 C13A C14 C15 7_565 . . 7_565 -0.6(4) ?
C12A C13A C14 C12B . . . 7_565 -177.1(5) ?
C14 C13A C14 C12B 7_565 . . 7_565 -177.0(4) ?
C11B C10B C15 C15 . . . 7_565 -0.55(17) ?
C9 C10B C15 C15 . . . 7_565 -179.6(4) ?
C10B C10B C15 C15 7_565 . . 7_565 -179.992(2) ?
C15 C10B C15 C10B 7_565 . . 7_565 179.9920(10) ?
C11B C10B C15 C10B . . . 7_565 179.45(17) ?
C9 C10B C15 C10B . . . 7_565 0.4(4) ?
C15 C10B C15 C14 7_565 . . . 2.8(4) ?
C11B C10B C15 C14 . . . . 2.2(4) ?
C9 C10B C15 C14 . . . . -176.85(18) ?
C10B C10B C15 C14 7_565 . . . -177.2(4) ?
C15 C10B C15 C10A 7_565 . . 7_565 -179.7(3) ?
C11B C10B C15 C10A . . . 7_565 179.7(3) ?
C9 C10B C15 C10A . . . 7_565 0.7(2) ?
C10B C10B C15 C10A 7_565 . . 7_565 0.3(3) ?
C15 C10B C15 C14 7_565 . . 7_565 2.2(3) ?
C11B C10B C15 C14 . . . 7_565 1.7(3) ?
C9 C10B C15 C14 . . . 7_565 -177.36(19) ?
C10B C10B C15 C14 7_565 . . 7_565 -177.7(3) ?
C15 C10B C15 C10A 7_565 . . . -3.(2) ?
C11B C10B C15 C10A . . . . -3.(2) ?
C9 C10B C15 C10A . . . . 178.(3) ?
C10B C10B C15 C10A 7_565 . . . 177.(2) ?
C15 C10B C15 C11B 7_565 . . 7_565 179.41(18) ?
C11B C10B C15 C11B . . . 7_565 178.9(3) ?
C9 C10B C15 C11B . . . 7_565 -0.2(5) ?
C10B C10B C15 C11B 7_565 . . 7_565 -0.58(18) ?
C14 C14 C15 C15 7_565 . . 7_565 0 ?
C13B C14 C15 C15 7_565 . . 7_565 177.6(3) ?
C13B C14 C15 C15 . . . 7_565 1.41(19) ?
C13A C14 C15 C15 7_565 . . 7_565 179.71(18) ?
C13A C14 C15 C15 . . . 7_565 0.20(13) ?
C12B C14 C15 C15 7_565 . . 7_565 179.18(11) ?
C14 C14 C15 C10B 7_565 . . 7_565 -177.8(3) ?
C13B C14 C15 C10B 7_565 . . 7_565 -0.2(5) ?
C13B C14 C15 C10B . . . 7_565 -176.4(3) ?
C13A C14 C15 C10B 7_565 . . 7_565 1.9(4) ?
C15 C14 C15 C10B 7_565 . . 7_565 -177.8(3) ?
C13A C14 C15 C10B . . . 7_565 -177.6(3) ?
C12B C14 C15 C10B 7_565 . . 7_565 1.4(4) ?
C14 C14 C15 C10B 7_565 . . . -1.5(2) ?
C13B C14 C15 C10B 7_565 . . . 176.1(3) ?
C13B C14 C15 C10B . . . . -0.1(3) ?
C13A C14 C15 C10B 7_565 . . . 178.2(2) ?
C15 C14 C15 C10B 7_565 . . . -1.5(2) ?
C13A C14 C15 C10B . . . . -1.3(3) ?
C12B C14 C15 C10B 7_565 . . . 177.7(2) ?
C14 C14 C15 C10A 7_565 . . 7_565 -178.7(2) ?
C13B C14 C15 C10A 7_565 . . 7_565 -1.1(4) ?
C13B C14 C15 C10A . . . 7_565 -177.3(2) ?
C13A C14 C15 C10A 7_565 . . 7_565 1.0(3) ?
C15 C14 C15 C10A 7_565 . . 7_565 -178.7(2) ?
C13A C14 C15 C10A . . . 7_565 -178.5(2) ?
C12B C14 C15 C10A 7_565 . . 7_565 0.5(3) ?
C13B C14 C15 C14 7_565 . . 7_565 177.6(3) ?
C13B C14 C15 C14 . . . 7_565 1.42(19) ?
C13A C14 C15 C14 7_565 . . 7_565 179.71(18) ?
C15 C14 C15 C14 7_565 . . 7_565 0 ?
C13A C14 C15 C14 . . . 7_565 0.21(13) ?
C12B C14 C15 C14 7_565 . . 7_565 179.18(11) ?
C14 C14 C15 C10A 7_565 . . . -1.01(17) ?
C13B C14 C15 C10A 7_565 . . . 176.6(3) ?
C13B C14 C15 C10A . . . . 0.4(3) ?
C13A C14 C15 C10A 7_565 . . . 178.7(2) ?
C15 C14 C15 C10A 7_565 . . . -1.00(17) ?
C13A C14 C15 C10A . . . . -0.8(2) ?
C12B C14 C15 C10A 7_565 . . . 178.18(19) ?
C14 C14 C15 C11B 7_565 . . 7_565 -179.56(11) ?
C13B C14 C15 C11B 7_565 . . 7_565 -2.0(4) ?
C13B C14 C15 C11B . . . 7_565 -178.1(2) ?
C13A C14 C15 C11B 7_565 . . 7_565 0.1(2) ?
C15 C14 C15 C11B 7_565 . . 7_565 -179.56(11) ?
C13A C14 C15 C11B . . . 7_565 -179.35(16) ?
C12B C14 C15 C11B 7_565 . . 7_565 -0.38(15) ?
C11A C10A C15 C15 . . . 7_565 0.41(18) ?
C9 C10A C15 C15 . . . 7_565 -179.0(3) ?
C11A C10A C15 C10B . . . 7_565 -179.9(4) ?
C15 C10A C15 C10B 7_565 . . 7_565 179.7(3) ?
C9 C10A C15 C10B . . . 7_565 0.65(19) ?
C11A C10A C15 C10B . . . . 178.(3) ?
C15 C10A C15 C10B 7_565 . . . 177.(3) ?
C9 C10A C15 C10B . . . . -2.(3) ?
C11A C10A C15 C14 . . . . 2.5(4) ?
C15 C10A C15 C14 7_565 . . . 2.1(4) ?
C9 C10A C15 C14 . . . . -176.90(17) ?
C11A C10A C15 C10A . . . 7_565 -179.60(18) ?
C15 C10A C15 C10A 7_565 . . 7_565 179.993(2) ?
C9 C10A C15 C10A . . . 7_565 1.0(3) ?
C11A C10A C15 C14 . . . 7_565 2.2(3) ?
C15 C10A C15 C14 7_565 . . 7_565 1.8(3) ?
C9 C10A C15 C14 . . . 7_565 -177.23(16) ?
C11A C10A C15 C11B . . . 7_565 179.7(2) ?
C15 C10A C15 C11B 7_565 . . 7_565 179.3(2) ?
C9 C10A C15 C11B . . . 7_565 0.3(4) ?
N1 P1 C16 C17 . . . . 143.56(10) ?
N1 P1 C16 C17 7_565 . . . 40.33(11) ?
N1 P1 C16 C17 . . . 7_565 -40.33(11) ?
N1 P1 C16 C17 7_565 . . 7_565 -143.56(10) ?
C17 C16 C17 C18 7_565 . . . 3.7(2) ?
P1 C16 C17 C18 . . . . 179.84(9) ?
C16 C17 C18 C19 . . . . -0.14(18) ?
C17 C18 C19 C18 . . . 7_565 -3.5(2) ?

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1427665'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            YR5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34.50 H21.50 Cl1.50 N2 O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         564.18

_chemical_melting_point          ?

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

_cell_length_a                   11.925(5)
_cell_length_b                   12.375(6)
_cell_length_c                   18.662(9)
_cell_angle_alpha                87.764(14)
_cell_angle_beta                 76.460(9)
_cell_angle_gamma                83.562(10)
_cell_volume                     2660.(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.2485
_cell_measurement_theta_max      29.5586
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            'translucent intense red'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1164

_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'BRUKER APEX II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            55541
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         29.59
_diffrn_reflns_theta_full        29.59
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

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

_reflns_number_total             14874
_reflns_number_gt                11710
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1286
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         14874
_refine_ls_number_parameters     758
_refine_ls_number_restraints     60
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0716P)²+1.0398P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.568
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 -0.08528(3) 0.13567(3) 0.70513(2) 0.01274(8) Uani d . . . 1.0 . .
C C1 -0.04190(15) -0.03535(12) 0.60671(8) 0.0179(3) Uani d . . . 1.0 . .
N N1 -0.00300(12) 0.04358(10) 0.64529(7) 0.0150(2) Uani d . . . 1.0 . .
O O1 -0.21052(10) 0.13372(9) 0.71123(6) 0.0184(2) Uani d . . . 1.0 . .
C C2 -0.15311(17) -0.04949(13) 0.60069(9) 0.0223(3) Uani d . . . 1.0 . .
H H2 -0.2189 -0.0035 0.6253 0.027 Uiso calc . . R 1.0 . .
P P2 0.76834(3) 0.27729(3) 0.069121(19) 0.01010(8) Uani d . . . 1.0 . .
N N2 -0.03822(11) 0.25518(10) 0.67135(7) 0.0135(2) Uani d . . . 1.0 . .
O O2 0.89252(9) 0.27210(8) 0.06755(6) 0.0142(2) Uani d . . . 1.0 . .
N N3 0.68651(11) 0.31635(10) 0.15220(6) 0.0116(2) Uani d . . . 1.0 . .
C C3 -0.16325(19) -0.13472(14) 0.55660(10) 0.0283(4) Uani d . . . 1.0 . .
H H3 -0.238 -0.1469 0.551 0.034 Uiso calc . . R 1.0 . .
N N4 0.72654(10) 0.37310(9) 0.01091(6) 0.0105(2) Uani d . . . 1.0 . .
C C4 -0.06623(19) -0.20296(14) 0.52030(9) 0.0291(4) Uani d . . . 1.0 . .
H H4 -0.0765 -0.2602 0.4907 0.035 Uiso calc . . R 1.0 . .
C C5 0.04305(19) -0.18826(13) 0.52686(9) 0.0269(4) Uani d . . . 1.0 . .
H H5 0.1083 -0.2347 0.502 0.032 Uiso calc . . R 1.0 . .
C C6 0.05726(16) -0.10326(13) 0.57095(8) 0.0206(3) Uani d . . . 1.0 . .
C C7 0.15616(16) -0.06558(13) 0.58835(9) 0.0209(3) Uani d . . . 1.0 . .
H H7 0.2342 -0.0967 0.5721 0.025 Uiso calc . . R 1.0 . .
C C8 0.11900(14) 0.02358(12) 0.63269(8) 0.0159(3) Uani d . . . 1.0 . .
C C9 0.18878(14) 0.09159(12) 0.66194(8) 0.0152(3) Uani d . . . 1.0 . .
C C10 0.29968(14) 0.04907(13) 0.68059(8) 0.0174(3) Uani d . . . 1.0 . .
C C19 0.34494(14) 0.13861(13) 0.70338(8) 0.0177(3) Uani d . . . 1.0 . .
C C18 0.26899(14) 0.23458(13) 0.70228(8) 0.0158(3) Uani d . . . 1.0 . .
C C17 0.29925(15) 0.33007(13) 0.72490(8) 0.0189(3) Uani d . . . 1.0 . .
H H17 0.2494 0.3959 0.7264 0.023 Uiso calc . . R 1.0 . .
C C16 0.40701(15) 0.32748(15) 0.74583(9) 0.0230(3) Uani d . . . 1.0 . .
H H16 0.4287 0.3933 0.7604 0.028 Uiso calc . . R 1.0 . .
C C15 0.48140(16) 0.23333(16) 0.74581(9) 0.0250(4) Uani d . . . 1.0 . .
H H15 0.5526 0.2353 0.76 0.03 Uiso calc . . R 1.0 . .
C C14 0.45076(15) 0.13341(15) 0.72438(9) 0.0217(3) Uani d . . . 1.0 . .
C C13 0.51473(15) 0.02867(16) 0.72176(9) 0.0263(4) Uani d . . . 1.0 . .
H H13 0.5882 0.0199 0.734 0.032 Uiso calc . . R 1.0 . .
C C12 0.46944(17) -0.05980(16) 0.70136(10) 0.0278(4) Uani d . . . 1.0 . .
H H12 0.5128 -0.1292 0.7008 0.033 Uiso calc . . R 1.0 . .
C C11 0.36099(15) -0.05249(14) 0.68112(9) 0.0222(3) Uani d . . . 1.0 . .
H H11 0.3316 -0.1155 0.6684 0.027 Uiso calc . . R 1.0 . .
C C20 0.17072(13) 0.20281(12) 0.67484(8) 0.0144(3) Uani d . . . 1.0 . .
C C22 0.08222(14) 0.38747(12) 0.63899(8) 0.0165(3) Uani d . . . 1.0 . .
H H22 0.1493 0.4254 0.6292 0.02 Uiso calc . . R 1.0 . .
C C21 0.07691(13) 0.28123(12) 0.66227(8) 0.0137(3) Uani d . . . 1.0 . .
C C23 -0.03085(15) 0.43103(12) 0.63201(8) 0.0169(3) Uani d . . . 1.0 . .
C C24 -0.07632(17) 0.53390(13) 0.61067(10) 0.0236(3) Uani d . . . 1.0 . .
H H24 -0.0278 0.5907 0.5967 0.028 Uiso calc . . R 1.0 . .
C C25 -0.19228(17) 0.55090(14) 0.61033(10) 0.0267(4) Uani d . . . 1.0 . .
H H25 -0.224 0.6203 0.5965 0.032 Uiso calc . . R 1.0 . .
C C34 -0.02251(13) 0.19703(12) 0.83034(8) 0.0143(3) Uani d . . . 1.0 . .
H H34 -0.0447 0.2698 0.8171 0.017 Uiso calc . . R 1.0 . .
C C33 0.02132(14) 0.17554(12) 0.89288(8) 0.0165(3) Uani d . . . 1.0 . .
H H33 0.0303 0.234 0.9219 0.02 Uiso calc . . R 1.0 . .
C C32 0.05209(14) 0.06887(13) 0.91309(8) 0.0173(3) Uani d . . . 1.0 . .
H H32 0.0828 0.0547 0.9555 0.021 Uiso calc . . R 1.0 . .
C C31 0.03796(15) -0.01687(13) 0.87137(9) 0.0190(3) Uani d . . . 1.0 . .
H H31 0.0569 -0.0897 0.886 0.023 Uiso calc . . R 1.0 . .
C C30 -0.00389(15) 0.00403(12) 0.80811(8) 0.0177(3) Uani d . . . 1.0 . .
H H30 -0.0122 -0.0546 0.779 0.021 Uiso calc . . R 1.0 . .
C C29 -0.03375(13) 0.11098(12) 0.78723(8) 0.0127(3) Uani d . . . 1.0 . .
C C28 -0.10507(14) 0.34826(12) 0.65204(8) 0.0142(3) Uani d . . . 1.0 . .
C C27 -0.22220(14) 0.36450(13) 0.65128(8) 0.0178(3) Uani d . . . 1.0 . .
H H27 -0.2712 0.308 0.6646 0.021 Uiso calc . . R 1.0 . .
C C26 -0.26407(16) 0.46721(14) 0.63010(9) 0.0229(3) Uani d . . . 1.0 . .
H H26 -0.3436 0.481 0.629 0.027 Uiso calc . . R 1.0 . .
C C37 0.84735(15) 0.33539(14) 0.30043(9) 0.0208(3) Uani d . . . 1.0 . .
H H37 0.922 0.3251 0.311 0.025 Uiso calc . . R 1.0 . .
C C36 0.83633(14) 0.31796(13) 0.22925(8) 0.0173(3) Uani d . . . 1.0 . .
H H36 0.9022 0.2976 0.1907 0.021 Uiso calc . . R 1.0 . .
C C35 0.72508(13) 0.33150(11) 0.21678(8) 0.0128(3) Uani d . . . 1.0 . .
C C38 0.75005(16) 0.36792(14) 0.35698(9) 0.0227(3) Uani d . . . 1.0 . .
H H38 0.7601 0.3796 0.405 0.027 Uiso calc . . R 1.0 . .
C C39 0.63996(15) 0.38311(14) 0.34373(8) 0.0210(3) Uani d . . . 1.0 . .
H H39 0.5748 0.4062 0.382 0.025 Uiso calc . . R 1.0 . .
C C40 0.62599(14) 0.36386(12) 0.27291(8) 0.0148(3) Uani d . . . 1.0 . .
C C41 0.52694(14) 0.36789(12) 0.24132(8) 0.0154(3) Uani d . . . 1.0 . .
H H41 0.4486 0.3876 0.2663 0.019 Uiso calc . . R 1.0 . .
C C42 0.56473(12) 0.33835(11) 0.16887(8) 0.0122(3) Uani d . . . 1.0 . .
C C43 0.49452(13) 0.32517(11) 0.11646(8) 0.0120(3) Uani d . . . 1.0 . .
C C44 0.37730(13) 0.29017(11) 0.14240(8) 0.0126(3) Uani d . . . 1.0 . .
C C45 0.31346(14) 0.25307(12) 0.20848(8) 0.0161(3) Uani d . . . 1.0 . .
H H45 0.3442 0.2479 0.2512 0.019 Uiso calc . . R 1.0 . .
C C46 0.20101(14) 0.22276(13) 0.21138(9) 0.0189(3) Uani d . . . 1.0 . .
H H46 0.1572 0.1966 0.2567 0.023 Uiso calc . . R 1.0 . .
C C54 0.51534(12) 0.34386(11) 0.04046(8) 0.0113(3) Uani d . . . 1.0 . .
C C53 0.32897(13) 0.29377(11) 0.08022(8) 0.0126(3) Uani d . . . 1.0 . .
C C52 0.40934(13) 0.32480(11) 0.01637(8) 0.0123(3) Uani d . . . 1.0 . .
C C51 0.37441(14) 0.32924(12) -0.04948(8) 0.0169(3) Uani d . . . 1.0 . .
H H51 0.4258 0.3481 -0.0941 0.02 Uiso calc . . R 1.0 . .
C C50 0.26071(15) 0.30524(13) -0.04936(9) 0.0197(3) Uani d . . . 1.0 . .
H H50 0.2367 0.3102 -0.0946 0.024 Uiso calc . . R 1.0 . .
C C49 0.18386(14) 0.27510(13) 0.01357(9) 0.0180(3) Uani d . . . 1.0 . .
H H49 0.1082 0.2603 0.0115 0.022 Uiso calc . . R 1.0 . .
C C48 0.21821(13) 0.26630(12) 0.08158(8) 0.0148(3) Uani d . . . 1.0 . .
C C47 0.15350(14) 0.23013(12) 0.15044(9) 0.0175(3) Uani d . . . 1.0 . .
H H47 0.0773 0.2109 0.1546 0.021 Uiso calc . . R 1.0 . .
C C55 0.61833(13) 0.37712(11) -0.00938(8) 0.0115(3) Uani d . . . 1.0 . .
C C56 0.63177(13) 0.41794(11) -0.08014(8) 0.0131(3) Uani d . . . 1.0 . .
H H56 0.5728 0.4289 -0.107 0.016 Uiso calc . . R 1.0 . .
C C57 0.74917(13) 0.44116(11) -0.10663(8) 0.0124(3) Uani d . . . 1.0 . .
C C58 0.81073(14) 0.48333(12) -0.17374(8) 0.0155(3) Uani d . . . 1.0 . .
H H58 0.7743 0.4993 -0.2136 0.019 Uiso calc . . R 1.0 . .
C C59 0.92501(14) 0.50099(12) -0.18041(8) 0.0166(3) Uani d . . . 1.0 . .
H H59 0.9676 0.5289 -0.2255 0.02 Uiso calc . . R 1.0 . .
C C68 0.66746(14) 0.08388(12) 0.10240(9) 0.0173(3) Uani d . . . 1.0 . .
H H68 0.6605 0.0993 0.1528 0.021 Uiso calc . . R 1.0 . .
C C67 0.62894(16) -0.01042(13) 0.08298(10) 0.0230(3) Uani d . . . 1.0 . .
H H67 0.5951 -0.0592 0.1203 0.028 Uiso calc . . R 1.0 . .
C C66 0.63966(15) -0.03347(13) 0.00937(10) 0.0223(3) Uani d . . . 1.0 . .
H H66 0.6124 -0.0976 -0.0035 0.027 Uiso calc . . R 1.0 . .
C C65 0.69020(15) 0.03686(13) -0.04570(9) 0.0208(3) Uani d . . . 1.0 . .
H H65 0.6984 0.0202 -0.0961 0.025 Uiso calc . . R 1.0 . .
C C64 0.72863(14) 0.13150(12) -0.02701(8) 0.0161(3) Uani d . . . 1.0 . .
H H64 0.7631 0.1797 -0.0646 0.019 Uiso calc . . R 1.0 . .
C C63 0.71652(13) 0.15580(11) 0.04726(8) 0.0121(3) Uani d . . . 1.0 . .
C C62 0.80715(13) 0.41507(11) -0.04937(8) 0.0116(3) Uani d . . . 1.0 . .
C C61 0.92132(13) 0.43521(11) -0.05498(8) 0.0140(3) Uani d . . . 1.0 . .
H H61 0.958 0.4201 -0.0151 0.017 Uiso calc . . R 1.0 . .
C C60 0.97952(14) 0.47839(12) -0.12149(8) 0.0165(3) Uani d . . . 1.0 . .
H H60 1.0577 0.4929 -0.1272 0.02 Uiso calc . . R 1.0 . .
C C69A 0.4680(13) 0.2442(10) 0.5372(8) 0.048(3) Uani d U P . 0.353(11) A 1
H H69A 0.4249 0.2141 0.585 0.058 Uiso calc . P R 0.353(11) A 1
Cl Cl1A 0.6026(6) 0.2738(11) 0.5452(4) 0.116(3) Uani d U P . 0.353(11) A 1
Cl Cl2A 0.3936(7) 0.3816(5) 0.5175(3) 0.099(2) Uani d U P . 0.353(11) A 1
Cl Cl3A 0.4746(6) 0.1616(8) 0.4718(6) 0.080(2) Uani d U P . 0.353(11) A 1
C C69B 0.4673(4) 0.2638(4) 0.5407(3) 0.0201(9) Uani d U P . 0.647(11) A 2
H H69B 0.4278 0.2472 0.5928 0.024 Uiso calc . P R 0.647(11) A 2
Cl Cl1B 0.60382(16) 0.29817(19) 0.54175(12) 0.0406(6) Uani d U P . 0.647(11) A
2
Cl Cl2B 0.37895(16) 0.3611(3) 0.50835(14) 0.0590(7) Uani d U P . 0.647(11) A 2
Cl Cl3B 0.4835(4) 0.1416(4) 0.4900(3) 0.0852(14) Uani d U P . 0.647(11) A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . 1.4739(13) ?
P1 N1 . 1.6863(14) ?
P1 N2 . 1.6874(15) ?
P1 C29 . 1.7835(16) ?
C1 C2 . 1.387(2) ?
C1 N1 . 1.414(2) ?
C1 C6 . 1.415(2) ?
N1 C8 . 1.413(2) ?
C2 C3 . 1.395(2) ?
C2 H2 . 0.95 ?
P2 O2 . 1.4685(13) ?
P2 N3 . 1.6835(14) ?
P2 N4 . 1.6896(13) ?
P2 C63 . 1.7841(16) ?
N2 C28 . 1.4101(19) ?
N2 C21 . 1.416(2) ?
N3 C42 . 1.4093(19) ?
N3 C35 . 1.4126(19) ?
C3 C4 . 1.403(3) ?
C3 H3 . 0.95 ?
N4 C62 . 1.4211(18) ?
N4 C55 . 1.4227(19) ?
C4 C5 . 1.370(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.409(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.424(3) ?
C7 C8 . 1.374(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.451(2) ?
C9 C20 . 1.391(2) ?
C9 C10 . 1.481(2) ?
C10 C11 . 1.382(2) ?
C10 C19 . 1.407(2) ?
C19 C14 . 1.400(2) ?
C19 C18 . 1.413(2) ?
C18 C17 . 1.382(2) ?
C18 C20 . 1.480(2) ?
C17 C16 . 1.425(2) ?
C17 H17 . 0.95 ?
C16 C15 . 1.383(3) ?
C16 H16 . 0.95 ?
C15 C14 . 1.425(3) ?
C15 H15 . 0.95 ?
C14 C13 . 1.425(3) ?
C13 C12 . 1.377(3) ?
C13 H13 . 0.95 ?
C12 C11 . 1.422(3) ?
C12 H12 . 0.95 ?
C11 H11 . 0.95 ?
C20 C21 . 1.453(2) ?
C22 C21 . 1.372(2) ?
C22 C23 . 1.428(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.407(2) ?
C23 C28 . 1.411(2) ?
C24 C25 . 1.377(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.401(3) ?
C25 H25 . 0.95 ?
C34 C33 . 1.392(2) ?
C34 C29 . 1.396(2) ?
C34 H34 . 0.95 ?
C33 C32 . 1.392(2) ?
C33 H33 . 0.95 ?
C32 C31 . 1.388(2) ?
C32 H32 . 0.95 ?
C31 C30 . 1.390(2) ?
C31 H31 . 0.95 ?
C30 C29 . 1.396(2) ?
C30 H30 . 0.95 ?
C28 C27 . 1.392(2) ?
C27 C26 . 1.390(2) ?
C27 H27 . 0.95 ?
C26 H26 . 0.95 ?
C37 C36 . 1.392(2) ?
C37 C38 . 1.406(3) ?
C37 H37 . 0.95 ?
C36 C35 . 1.391(2) ?
C36 H36 . 0.95 ?
C35 C40 . 1.415(2) ?
C38 C39 . 1.383(2) ?
C38 H38 . 0.95 ?
C39 C40 . 1.403(2) ?
C39 H39 . 0.95 ?
C40 C41 . 1.434(2) ?
C41 C42 . 1.372(2) ?
C41 H41 . 0.95 ?
C42 C43 . 1.453(2) ?
C43 C54 . 1.396(2) ?
C43 C44 . 1.476(2) ?
C44 C45 . 1.380(2) ?
C44 C53 . 1.409(2) ?
C45 C46 . 1.421(2) ?
C45 H45 . 0.95 ?
C46 C47 . 1.380(2) ?
C46 H46 . 0.95 ?
C54 C55 . 1.446(2) ?
C54 C52 . 1.482(2) ?
C53 C48 . 1.395(2) ?
C53 C52 . 1.414(2) ?
C52 C51 . 1.384(2) ?
C51 C50 . 1.420(2) ?
C51 H51 . 0.95 ?
C50 C49 . 1.377(2) ?
C50 H50 . 0.95 ?
C49 C48 . 1.419(2) ?
C49 H49 . 0.95 ?
C48 C47 . 1.420(2) ?
C47 H47 . 0.95 ?
C55 C56 . 1.375(2) ?
C56 C57 . 1.429(2) ?
C56 H56 . 0.95 ?
C57 C58 . 1.409(2) ?
C57 C62 . 1.412(2) ?
C58 C59 . 1.381(2) ?
C58 H58 . 0.95 ?
C59 C60 . 1.407(2) ?
C59 H59 . 0.95 ?
C68 C67 . 1.391(2) ?
C68 C63 . 1.399(2) ?
C68 H68 . 0.95 ?
C67 C66 . 1.387(3) ?
C67 H67 . 0.95 ?
C66 C65 . 1.391(2) ?
C66 H66 . 0.95 ?
C65 C64 . 1.390(2) ?
C65 H65 . 0.95 ?
C64 C63 . 1.400(2) ?
C64 H64 . 0.95 ?
C62 C61 . 1.391(2) ?
C61 C60 . 1.391(2) ?
C61 H61 . 0.95 ?
C60 H60 . 0.95 ?
C69A Cl3A . 1.604(15) ?
C69A Cl1A . 1.726(16) ?
C69A Cl2A . 1.891(14) ?
C69A H69A . 1.0 ?
C69B Cl2B . 1.697(6) ?
C69B Cl1B . 1.733(5) ?
C69B Cl3B . 1.784(6) ?
C69B H69B . 1.0 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N1 . . 112.83(7) ?
O1 P1 N2 . . 112.51(7) ?
N1 P1 N2 . . 103.57(7) ?
O1 P1 C29 . . 117.37(7) ?
N1 P1 C29 . . 104.16(7) ?
N2 P1 C29 . . 105.09(7) ?
C2 C1 N1 . . 130.18(15) ?
C2 C1 C6 . . 122.68(15) ?
N1 C1 C6 . . 107.13(15) ?
C8 N1 C1 . . 107.89(13) ?
C8 N1 P1 . . 124.38(10) ?
C1 N1 P1 . . 127.27(12) ?
C1 C2 C3 . . 116.55(17) ?
C1 C2 H2 . . 121.7 ?
C3 C2 H2 . . 121.7 ?
O2 P2 N3 . . 111.21(6) ?
O2 P2 N4 . . 112.61(6) ?
N3 P2 N4 . . 103.48(7) ?
O2 P2 C63 . . 116.92(7) ?
N3 P2 C63 . . 106.54(7) ?
N4 P2 C63 . . 104.99(7) ?
C28 N2 C21 . . 107.79(12) ?
C28 N2 P1 . . 127.39(11) ?
C21 N2 P1 . . 124.69(10) ?
C42 N3 C35 . . 108.14(12) ?
C42 N3 P2 . . 124.57(10) ?
C35 N3 P2 . . 127.28(11) ?
C2 C3 C4 . . 121.88(19) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C62 N4 C55 . . 107.66(12) ?
C62 N4 P2 . . 121.94(10) ?
C55 N4 P2 . . 122.51(9) ?
C5 C4 C3 . . 120.97(16) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 119.04(18) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 118.87(17) ?
C5 C6 C7 . . 133.21(17) ?
C1 C6 C7 . . 107.91(14) ?
C8 C7 C6 . . 108.08(15) ?
C8 C7 H7 . . 126.0 ?
C6 C7 H7 . . 126.0 ?
C7 C8 N1 . . 108.99(14) ?
C7 C8 C9 . . 128.03(16) ?
N1 C8 C9 . . 122.96(13) ?
C20 C9 C8 . . 129.21(14) ?
C20 C9 C10 . . 108.04(14) ?
C8 C9 C10 . . 122.70(14) ?
C11 C10 C19 . . 118.42(16) ?
C11 C10 C9 . . 135.02(16) ?
C19 C10 C9 . . 106.55(14) ?
C14 C19 C10 . . 124.66(15) ?
C14 C19 C18 . . 124.61(15) ?
C10 C19 C18 . . 110.73(15) ?
C17 C18 C19 . . 118.21(15) ?
C17 C18 C20 . . 135.70(15) ?
C19 C18 C20 . . 106.10(14) ?
C18 C17 C16 . . 118.42(15) ?
C18 C17 H17 . . 120.8 ?
C16 C17 H17 . . 120.8 ?
C15 C16 C17 . . 122.87(16) ?
C15 C16 H16 . . 118.6 ?
C17 C16 H16 . . 118.6 ?
C16 C15 C14 . . 119.70(16) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C19 C14 C13 . . 115.97(16) ?
C19 C14 C15 . . 116.17(16) ?
C13 C14 C15 . . 127.86(17) ?
C12 C13 C14 . . 119.63(17) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C12 C11 . . 123.26(16) ?
C13 C12 H12 . . 118.4 ?
C11 C12 H12 . . 118.4 ?
C10 C11 C12 . . 117.99(17) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
C9 C20 C21 . . 128.93(14) ?
C9 C20 C18 . . 108.55(13) ?
C21 C20 C18 . . 122.47(14) ?
C21 C22 C23 . . 107.97(14) ?
C21 C22 H22 . . 126.0 ?
C23 C22 H22 . . 126.0 ?
C22 C21 N2 . . 109.01(13) ?
C22 C21 C20 . . 128.14(15) ?
N2 C21 C20 . . 122.83(13) ?
C24 C23 C28 . . 119.16(16) ?
C24 C23 C22 . . 133.04(16) ?
C28 C23 C22 . . 107.80(14) ?
C25 C24 C23 . . 118.89(16) ?
C25 C24 H24 . . 120.6 ?
C23 C24 H24 . . 120.6 ?
C24 C25 C26 . . 120.86(15) ?
C24 C25 H25 . . 119.6 ?
C26 C25 H25 . . 119.6 ?
C33 C34 C29 . . 119.60(14) ?
C33 C34 H34 . . 120.2 ?
C29 C34 H34 . . 120.2 ?
C34 C33 C32 . . 120.30(14) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C31 C32 C33 . . 120.11(14) ?
C31 C32 H32 . . 119.9 ?
C33 C32 H32 . . 119.9 ?
C32 C31 C30 . . 119.91(14) ?
C32 C31 H31 . . 120.0 ?
C30 C31 H31 . . 120.0 ?
C31 C30 C29 . . 120.14(14) ?
C31 C30 H30 . . 119.9 ?
C29 C30 H30 . . 119.9 ?
C34 C29 C30 . . 119.90(14) ?
C34 C29 P1 . . 120.85(11) ?
C30 C29 P1 . . 119.25(11) ?
C27 C28 N2 . . 130.27(14) ?
C27 C28 C23 . . 122.31(14) ?
N2 C28 C23 . . 107.42(14) ?
C26 C27 C28 . . 116.89(15) ?
C26 C27 H27 . . 121.6 ?
C28 C27 H27 . . 121.6 ?
C27 C26 C25 . . 121.88(17) ?
C27 C26 H26 . . 119.1 ?
C25 C26 H26 . . 119.1 ?
C36 C37 C38 . . 121.24(16) ?
C36 C37 H37 . . 119.4 ?
C38 C37 H37 . . 119.4 ?
C35 C36 C37 . . 117.37(15) ?
C35 C36 H36 . . 121.3 ?
C37 C36 H36 . . 121.3 ?
C36 C35 N3 . . 130.35(13) ?
C36 C35 C40 . . 122.30(14) ?
N3 C35 C40 . . 107.35(13) ?
C39 C38 C37 . . 120.98(15) ?
C39 C38 H38 . . 119.5 ?
C37 C38 H38 . . 119.5 ?
C38 C39 C40 . . 119.00(15) ?
C38 C39 H39 . . 120.5 ?
C40 C39 H39 . . 120.5 ?
C39 C40 C35 . . 119.09(15) ?
C39 C40 C41 . . 133.56(15) ?
C35 C40 C41 . . 107.34(13) ?
C42 C41 C40 . . 108.23(14) ?
C42 C41 H41 . . 125.9 ?
C40 C41 H41 . . 125.9 ?
C41 C42 N3 . . 108.94(13) ?
C41 C42 C43 . . 127.58(14) ?
N3 C42 C43 . . 123.41(13) ?
C54 C43 C42 . . 131.23(14) ?
C54 C43 C44 . . 108.73(12) ?
C42 C43 C44 . . 120.00(13) ?
C45 C44 C53 . . 118.36(14) ?
C45 C44 C43 . . 135.36(14) ?
C53 C44 C43 . . 106.21(13) ?
C44 C45 C46 . . 118.80(14) ?
C44 C45 H45 . . 120.6 ?
C46 C45 H45 . . 120.6 ?
C47 C46 C45 . . 122.06(14) ?
C47 C46 H46 . . 119.0 ?
C45 C46 H46 . . 119.0 ?
C43 C54 C55 . . 128.96(13) ?
C43 C54 C52 . . 107.80(13) ?
C55 C54 C52 . . 123.23(13) ?
C48 C53 C44 . . 124.15(14) ?
C48 C53 C52 . . 124.96(14) ?
C44 C53 C52 . . 110.85(13) ?
C51 C52 C53 . . 117.18(14) ?
C51 C52 C54 . . 136.47(14) ?
C53 C52 C54 . . 106.36(13) ?
C52 C51 C50 . . 119.10(14) ?
C52 C51 H51 . . 120.5 ?
C50 C51 H51 . . 120.5 ?
C49 C50 C51 . . 122.69(15) ?
C49 C50 H50 . . 118.7 ?
C51 C50 H50 . . 118.7 ?
C50 C49 C48 . . 119.65(15) ?
C50 C49 H49 . . 120.2 ?
C48 C49 H49 . . 120.2 ?
C53 C48 C49 . . 116.36(14) ?
C53 C48 C47 . . 116.40(14) ?
C49 C48 C47 . . 127.23(15) ?
C46 C47 C48 . . 120.18(15) ?
C46 C47 H47 . . 119.9 ?
C48 C47 H47 . . 119.9 ?
C56 C55 N4 . . 108.50(13) ?
C56 C55 C54 . . 129.15(14) ?
N4 C55 C54 . . 122.34(13) ?
C55 C56 C57 . . 108.73(13) ?
C55 C56 H56 . . 125.6 ?
C57 C56 H56 . . 125.6 ?
C58 C57 C62 . . 119.10(14) ?
C58 C57 C56 . . 133.39(14) ?
C62 C57 C56 . . 107.50(13) ?
C59 C58 C57 . . 118.70(14) ?
C59 C58 H58 . . 120.7 ?
C57 C58 H58 . . 120.7 ?
C58 C59 C60 . . 121.11(14) ?
C58 C59 H59 . . 119.4 ?
C60 C59 H59 . . 119.4 ?
C67 C68 C63 . . 119.62(15) ?
C67 C68 H68 . . 120.2 ?
C63 C68 H68 . . 120.2 ?
C66 C67 C68 . . 120.29(15) ?
C66 C67 H67 . . 119.9 ?
C68 C67 H67 . . 119.9 ?
C67 C66 C65 . . 120.31(15) ?
C67 C66 H66 . . 119.8 ?
C65 C66 H66 . . 119.8 ?
C64 C65 C66 . . 119.94(15) ?
C64 C65 H65 . . 120.0 ?
C66 C65 H65 . . 120.0 ?
C65 C64 C63 . . 119.91(14) ?
C65 C64 H64 . . 120.0 ?
C63 C64 H64 . . 120.0 ?
C68 C63 C64 . . 119.92(14) ?
C68 C63 P2 . . 121.42(12) ?
C64 C63 P2 . . 118.64(11) ?
C61 C62 C57 . . 122.49(13) ?
C61 C62 N4 . . 129.86(13) ?
C57 C62 N4 . . 107.57(13) ?
C62 C61 C60 . . 117.12(14) ?
C62 C61 H61 . . 121.4 ?
C60 C61 H61 . . 121.4 ?
C61 C60 C59 . . 121.39(15) ?
C61 C60 H60 . . 119.3 ?
C59 C60 H60 . . 119.3 ?
Cl3A C69A Cl1A . . 113.1(9) ?
Cl3A C69A Cl2A . . 110.5(9) ?
Cl1A C69A Cl2A . . 103.3(7) ?
Cl3A C69A H69A . . 109.9 ?
Cl1A C69A H69A . . 109.9 ?
Cl2A C69A H69A . . 109.9 ?
Cl2B C69B Cl1B . . 116.0(3) ?
Cl2B C69B Cl3B . . 110.3(3) ?
Cl1B C69B Cl3B . . 108.7(3) ?
Cl2B C69B H69B . . 107.1 ?
Cl1B C69B H69B . . 107.1 ?
Cl3B C69B H69B . . 107.1 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 N1 C8 . . . . -178.94(15) ?
C6 C1 N1 C8 . . . . 0.16(16) ?
C2 C1 N1 P1 . . . . 8.6(2) ?
C6 C1 N1 P1 . . . . -172.29(11) ?
O1 P1 N1 C8 . . . . -175.70(11) ?
N2 P1 N1 C8 . . . . 62.37(13) ?
C29 P1 N1 C8 . . . . -47.34(13) ?
O1 P1 N1 C1 . . . . -4.41(15) ?
N2 P1 N1 C1 . . . . -126.34(13) ?
C29 P1 N1 C1 . . . . 123.96(13) ?
N1 C1 C2 C3 . . . . 178.55(15) ?
C6 C1 C2 C3 . . . . -0.4(2) ?
O1 P1 N2 C28 . . . . 2.10(14) ?
N1 P1 N2 C28 . . . . 124.24(13) ?
C29 P1 N2 C28 . . . . -126.75(12) ?
O1 P1 N2 C21 . . . . 177.48(11) ?
N1 P1 N2 C21 . . . . -60.37(13) ?
C29 P1 N2 C21 . . . . 48.64(13) ?
O2 P2 N3 C42 . . . . 173.99(11) ?
N4 P2 N3 C42 . . . . 52.85(13) ?
C63 P2 N3 C42 . . . . -57.56(13) ?
O2 P2 N3 C35 . . . . -6.91(14) ?
N4 P2 N3 C35 . . . . -128.05(12) ?
C63 P2 N3 C35 . . . . 121.54(12) ?
C1 C2 C3 C4 . . . . 0.2(2) ?
O2 P2 N4 C62 . . . . 20.38(13) ?
N3 P2 N4 C62 . . . . 140.57(11) ?
C63 P2 N4 C62 . . . . -107.88(11) ?
O2 P2 N4 C55 . . . . 165.61(10) ?
N3 P2 N4 C55 . . . . -74.20(12) ?
C63 P2 N4 C55 . . . . 37.34(12) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
C4 C5 C6 C1 . . . . -0.4(2) ?
C4 C5 C6 C7 . . . . -179.03(17) ?
C2 C1 C6 C5 . . . . 0.5(2) ?
N1 C1 C6 C5 . . . . -178.64(13) ?
C2 C1 C6 C7 . . . . 179.52(14) ?
N1 C1 C6 C7 . . . . 0.33(17) ?
C5 C6 C7 C8 . . . . 178.05(17) ?
C1 C6 C7 C8 . . . . -0.72(18) ?
C6 C7 C8 N1 . . . . 0.83(17) ?
C6 C7 C8 C9 . . . . -177.49(14) ?
C1 N1 C8 C7 . . . . -0.62(16) ?
P1 N1 C8 C7 . . . . 172.11(11) ?
C1 N1 C8 C9 . . . . 177.80(13) ?
P1 N1 C8 C9 . . . . -9.5(2) ?
C7 C8 C9 C20 . . . . 145.58(17) ?
N1 C8 C9 C20 . . . . -32.5(2) ?
C7 C8 C9 C10 . . . . -31.7(2) ?
N1 C8 C9 C10 . . . . 150.22(14) ?
C20 C9 C10 C11 . . . . 178.01(17) ?
C8 C9 C10 C11 . . . . -4.2(3) ?
C20 C9 C10 C19 . . . . -0.77(16) ?
C8 C9 C10 C19 . . . . 176.99(13) ?
C11 C10 C19 C14 . . . . 2.4(2) ?
C9 C10 C19 C14 . . . . -178.57(14) ?
C11 C10 C19 C18 . . . . -177.53(14) ?
C9 C10 C19 C18 . . . . 1.49(17) ?
C14 C19 C18 C17 . . . . -1.4(2) ?
C10 C19 C18 C17 . . . . 178.50(13) ?
C14 C19 C18 C20 . . . . 178.46(14) ?
C10 C19 C18 C20 . . . . -1.60(17) ?
C19 C18 C17 C16 . . . . 2.0(2) ?
C20 C18 C17 C16 . . . . -177.87(16) ?
C18 C17 C16 C15 . . . . -1.3(2) ?
C17 C16 C15 C14 . . . . -0.2(2) ?
C10 C19 C14 C13 . . . . 0.0(2) ?
C18 C19 C14 C13 . . . . 179.95(15) ?
C10 C19 C14 C15 . . . . -179.94(15) ?
C18 C19 C14 C15 . . . . 0.0(2) ?
C16 C15 C14 C19 . . . . 0.8(2) ?
C16 C15 C14 C13 . . . . -179.13(16) ?
C19 C14 C13 C12 . . . . -1.7(2) ?
C15 C14 C13 C12 . . . . 178.23(17) ?
C14 C13 C12 C11 . . . . 1.1(3) ?
C19 C10 C11 C12 . . . . -3.0(2) ?
C9 C10 C11 C12 . . . . 178.33(16) ?
C13 C12 C11 C10 . . . . 1.4(3) ?
C8 C9 C20 C21 . . . . -0.2(3) ?
C10 C9 C20 C21 . . . . 177.38(14) ?
C8 C9 C20 C18 . . . . -177.76(14) ?
C10 C9 C20 C18 . . . . -0.19(16) ?
C17 C18 C20 C9 . . . . -179.04(17) ?
C19 C18 C20 C9 . . . . 1.08(16) ?
C17 C18 C20 C21 . . . . 3.2(3) ?
C19 C18 C20 C21 . . . . -176.69(13) ?
C23 C22 C21 N2 . . . . -0.62(17) ?
C23 C22 C21 C20 . . . . 177.86(14) ?
C28 N2 C21 C22 . . . . 0.77(16) ?
P1 N2 C21 C22 . . . . -175.38(11) ?
C28 N2 C21 C20 . . . . -177.81(13) ?
P1 N2 C21 C20 . . . . 6.0(2) ?
C9 C20 C21 C22 . . . . -143.91(17) ?
C18 C20 C21 C22 . . . . 33.4(2) ?
C9 C20 C21 N2 . . . . 34.4(2) ?
C18 C20 C21 N2 . . . . -148.34(14) ?
C21 C22 C23 C24 . . . . 179.93(17) ?
C21 C22 C23 C28 . . . . 0.25(17) ?
C28 C23 C24 C25 . . . . 0.3(2) ?
C22 C23 C24 C25 . . . . -179.33(17) ?
C23 C24 C25 C26 . . . . -0.7(3) ?
C29 C34 C33 C32 . . . . -1.0(2) ?
C34 C33 C32 C31 . . . . -0.7(2) ?
C33 C32 C31 C30 . . . . 1.8(2) ?
C32 C31 C30 C29 . . . . -1.2(3) ?
C33 C34 C29 C30 . . . . 1.7(2) ?
C33 C34 C29 P1 . . . . -178.01(12) ?
C31 C30 C29 C34 . . . . -0.6(2) ?
C31 C30 C29 P1 . . . . 179.11(13) ?
O1 P1 C29 C34 . . . . -93.71(13) ?
N1 P1 C29 C34 . . . . 140.76(13) ?
N2 P1 C29 C34 . . . . 32.17(14) ?
O1 P1 C29 C30 . . . . 86.60(14) ?
N1 P1 C29 C30 . . . . -38.93(14) ?
N2 P1 C29 C30 . . . . -147.52(13) ?
C21 N2 C28 C27 . . . . 179.74(15) ?
P1 N2 C28 C27 . . . . -4.2(2) ?
C21 N2 C28 C23 . . . . -0.60(15) ?
P1 N2 C28 C23 . . . . 175.41(11) ?
C24 C23 C28 C27 . . . . 0.2(2) ?
C22 C23 C28 C27 . . . . 179.92(14) ?
C24 C23 C28 N2 . . . . -179.51(14) ?
C22 C23 C28 N2 . . . . 0.23(16) ?
N2 C28 C27 C26 . . . . 179.26(15) ?
C23 C28 C27 C26 . . . . -0.4(2) ?
C28 C27 C26 C25 . . . . 0.0(2) ?
C24 C25 C26 C27 . . . . 0.5(3) ?
C38 C37 C36 C35 . . . . -1.5(2) ?
C37 C36 C35 N3 . . . . -177.65(15) ?
C37 C36 C35 C40 . . . . 1.3(2) ?
C42 N3 C35 C36 . . . . 178.57(15) ?
P2 N3 C35 C36 . . . . -0.7(2) ?
C42 N3 C35 C40 . . . . -0.50(15) ?
P2 N3 C35 C40 . . . . -179.72(10) ?
C36 C37 C38 C39 . . . . 0.4(3) ?
C37 C38 C39 C40 . . . . 1.0(2) ?
C38 C39 C40 C35 . . . . -1.2(2) ?
C38 C39 C40 C41 . . . . 177.63(16) ?
C36 C35 C40 C39 . . . . 0.0(2) ?
N3 C35 C40 C39 . . . . 179.18(13) ?
C36 C35 C40 C41 . . . . -179.08(14) ?
N3 C35 C40 C41 . . . . 0.08(16) ?
C39 C40 C41 C42 . . . . -178.53(17) ?
C35 C40 C41 C42 . . . . 0.38(17) ?
C40 C41 C42 N3 . . . . -0.70(16) ?
C40 C41 C42 C43 . . . . 176.39(14) ?
C35 N3 C42 C41 . . . . 0.75(16) ?
P2 N3 C42 C41 . . . . 180.00(10) ?
C35 N3 C42 C43 . . . . -176.48(13) ?
P2 N3 C42 C43 . . . . 2.77(19) ?
C41 C42 C43 C54 . . . . 146.94(16) ?
N3 C42 C43 C54 . . . . -36.4(2) ?
C41 C42 C43 C44 . . . . -30.4(2) ?
N3 C42 C43 C44 . . . . 146.32(14) ?
C54 C43 C44 C45 . . . . 173.95(16) ?
C42 C43 C44 C45 . . . . -8.2(2) ?
C54 C43 C44 C53 . . . . -2.56(16) ?
C42 C43 C44 C53 . . . . 175.31(12) ?
C53 C44 C45 C46 . . . . -1.5(2) ?
C43 C44 C45 C46 . . . . -177.72(15) ?
C44 C45 C46 C47 . . . . -0.5(2) ?
C42 C43 C54 C55 . . . . 3.7(3) ?
C44 C43 C54 C55 . . . . -178.72(13) ?
C42 C43 C54 C52 . . . . -175.57(14) ?
C44 C43 C54 C52 . . . . 1.98(15) ?
C45 C44 C53 C48 . . . . 2.7(2) ?
C43 C44 C53 C48 . . . . 179.93(13) ?
C45 C44 C53 C52 . . . . -175.06(13) ?
C43 C44 C53 C52 . . . . 2.15(16) ?
C48 C53 C52 C51 . . . . 0.7(2) ?
C44 C53 C52 C51 . . . . 178.50(13) ?
C48 C53 C52 C54 . . . . -178.73(13) ?
C44 C53 C52 C54 . . . . -0.98(16) ?
C43 C54 C52 C51 . . . . -179.99(16) ?
C55 C54 C52 C51 . . . . 0.7(3) ?
C43 C54 C52 C53 . . . . -0.67(15) ?
C55 C54 C52 C53 . . . . 179.98(13) ?
C53 C52 C51 C50 . . . . 1.4(2) ?
C54 C52 C51 C50 . . . . -179.34(16) ?
C52 C51 C50 C49 . . . . -1.5(2) ?
C51 C50 C49 C48 . . . . -0.5(2) ?
C44 C53 C48 C49 . . . . 179.83(14) ?
C52 C53 C48 C49 . . . . -2.7(2) ?
C44 C53 C48 C47 . . . . -1.7(2) ?
C52 C53 C48 C47 . . . . 175.81(13) ?
C50 C49 C48 C53 . . . . 2.5(2) ?
C50 C49 C48 C47 . . . . -175.82(15) ?
C45 C46 C47 C48 . . . . 1.6(2) ?
C53 C48 C47 C46 . . . . -0.5(2) ?
C49 C48 C47 C46 . . . . 177.80(15) ?
C62 N4 C55 C56 . . . . 1.18(15) ?
P2 N4 C55 C56 . . . . -148.30(10) ?
C62 N4 C55 C54 . . . . -177.81(12) ?
P2 N4 C55 C54 . . . . 32.72(18) ?
C43 C54 C55 C56 . . . . -164.48(15) ?
C52 C54 C55 C56 . . . . 14.7(2) ?
C43 C54 C55 N4 . . . . 14.3(2) ?
C52 C54 C55 N4 . . . . -166.51(12) ?
N4 C55 C56 C57 . . . . -0.11(15) ?
C54 C55 C56 C57 . . . . 178.78(14) ?
C55 C56 C57 C58 . . . . -179.99(15) ?
C55 C56 C57 C62 . . . . -1.01(16) ?
C62 C57 C58 C59 . . . . -2.0(2) ?
C56 C57 C58 C59 . . . . 176.86(15) ?
C57 C58 C59 C60 . . . . -0.5(2) ?
C63 C68 C67 C66 . . . . 0.4(3) ?
C68 C67 C66 C65 . . . . 0.7(3) ?
C67 C66 C65 C64 . . . . -1.0(3) ?
C66 C65 C64 C63 . . . . 0.1(2) ?
C67 C68 C63 C64 . . . . -1.3(2) ?
C67 C68 C63 P2 . . . . -179.49(13) ?
C65 C64 C63 C68 . . . . 1.0(2) ?
C65 C64 C63 P2 . . . . 179.31(12) ?
O2 P2 C63 C68 . . . . 95.10(13) ?
N3 P2 C63 C68 . . . . -29.94(14) ?
N4 P2 C63 C68 . . . . -139.29(13) ?
O2 P2 C63 C64 . . . . -83.16(13) ?
N3 P2 C63 C64 . . . . 151.80(12) ?
N4 P2 C63 C64 . . . . 42.45(14) ?
C58 C57 C62 C61 . . . . 3.8(2) ?
C56 C57 C62 C61 . . . . -175.36(13) ?
C58 C57 C62 N4 . . . . -179.13(12) ?
C56 C57 C62 N4 . . . . 1.72(15) ?
C55 N4 C62 C61 . . . . 175.00(14) ?
P2 N4 C62 C61 . . . . -35.3(2) ?
C55 N4 C62 C57 . . . . -1.79(14) ?
P2 N4 C62 C57 . . . . 147.90(10) ?
C57 C62 C61 C60 . . . . -2.8(2) ?
N4 C62 C61 C60 . . . . -179.19(14) ?
C62 C61 C60 C59 . . . . 0.2(2) ?
C58 C59 C60 C61 . . . . 1.5(2) ?

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1427666'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_I                   
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.84 Report
RESPONSE: The largest peaks in the difference (electron density) map are along the covalent bonds between atoms
;

# Added during the CSD deposition process: Friday 25th of September 2015 01:59:27 PM
# end Validation Reply Form

_chemical_name_systematic        ?
_chemical_name_common            YR4
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H17 N4 P S'
_chemical_formula_iupac          ?
_chemical_formula_weight         472.48

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
'x-1/2, y-1/2, -z'

_cell_length_a                   17.008(8)
_cell_length_b                   32.243(12)
_cell_length_c                   7.688(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4216.(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9166
_cell_measurement_theta_min      2.7036
_cell_measurement_theta_max      33.1012
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'rectangular rod'
_exptl_crystal_colour            'translucent intense yellow'
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.148
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952

_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'BRUKER APEX II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            98307
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         32.09
_diffrn_reflns_theta_full        32.09
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             7382
_reflns_number_gt                6489
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1021
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_number_reflns         7382
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+2.1210P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v4.2.4'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.63952(2) 0.06657(2) 0.73864(3) 0.01770(7) Uani d . . . 1 . .
N N1 0.52104(5) 0.15615(3) -0.08677(11) 0.01146(15) Uani d . . . 1 . .
C C1 0.55719(6) 0.17934(3) -0.21785(13) 0.01127(17) Uani d . . . 1 . .
P P1 0.42275(2) 0.14674(2) -0.09060(3) 0.01027(6) Uani d . . . 1 . .
C C2 0.52388(6) 0.19766(3) -0.36451(14) 0.01428(19) Uani d . . . 1 . .
H H2 0.4693 0.1954 -0.3885 0.017 Uiso calc U . R 1 . .
N N2 0.42225(5) 0.09450(3) -0.06687(12) 0.01140(15) Uani d . . . 1 . .
N N3 0.67138(6) 0.09971(3) 0.59836(12) 0.01696(18) Uani d . . . 1 . .
C C3 0.57395(7) 0.21934(3) -0.47393(14) 0.01590(19) Uani d . . . 1 . .
H H3 0.5533 0.2323 -0.5752 0.019 Uiso calc U . R 1 . .
N N4 0.56045(6) 0.04988(3) 0.64584(12) 0.01659(18) Uani d . . . 1 . .
C C4 0.65468(7) 0.22250(3) -0.43755(14) 0.01598(19) Uani d . . . 1 . .
H H4 0.6874 0.2381 -0.5134 0.019 Uiso calc U . R 1 . .
C C6 0.63816(6) 0.18119(3) -0.18171(13) 0.01128(17) Uani d . . . 1 . .
C C5 0.68737(6) 0.20352(3) -0.29419(14) 0.01394(18) Uani d . . . 1 . .
H H5 0.7422 0.2055 -0.272 0.017 Uiso calc U . R 1 . .
C C9 0.56635(6) 0.11717(3) 0.18439(13) 0.01094(17) Uani d . . . 1 . .
C C8 0.57994(6) 0.14242(3) 0.02784(13) 0.01067(17) Uani d . . . 1 . .
C C7 0.65111(6) 0.15735(3) -0.02813(13) 0.01211(17) Uani d . . . 1 . .
H H7 0.7005 0.1526 0.0261 0.015 Uiso calc U . R 1 . .
C C10 0.62119(6) 0.12310(3) 0.31462(13) 0.01335(18) Uani d . . . 1 . .
H H10 0.6608 0.1436 0.3013 0.016 Uiso calc U . R 1 . .
C C11 0.61875(6) 0.09889(3) 0.46680(13) 0.01327(18) Uani d . . . 1 . .
C C12 0.55602(6) 0.07031(3) 0.49318(13) 0.01303(18) Uani d . . . 1 . .
C C16 0.42974(6) 0.03016(3) 0.04667(14) 0.01266(18) Uani d . . . 1 . .
H H16 0.4419 0.0076 0.1217 0.015 Uiso calc U . R 1 . .
C C15 0.45353(6) 0.07041(3) 0.06842(13) 0.01130(17) Uani d . . . 1 . .
C C14 0.50529(6) 0.08587(3) 0.20681(13) 0.01129(17) Uani d . . . 1 . .
C C13 0.49921(6) 0.06452(3) 0.36226(13) 0.01335(18) Uani d . . . 1 . .
H H13 0.4567 0.0459 0.3807 0.016 Uiso calc U . R 1 . .
C C17 0.38338(6) 0.02780(3) -0.10819(14) 0.01223(17) Uani d . . . 1 . .
C C20 0.30505(6) 0.04489(4) -0.41773(15) 0.0167(2) Uani d . . . 1 . .
H H20 0.2782 0.0501 -0.5238 0.02 Uiso calc U . R 1 . .
C C19 0.30706(6) 0.00435(3) -0.35077(15) 0.0167(2) Uani d . . . 1 . .
H H19 0.2812 -0.0173 -0.4119 0.02 Uiso calc U . R 1 . .
C C18 0.34607(6) -0.00459(3) -0.19731(15) 0.01504(19) Uani d . . . 1 . .
H H18 0.3475 -0.0321 -0.1533 0.018 Uiso calc U . R 1 . .
C C21 0.34149(6) 0.07735(3) -0.33207(14) 0.01431(18) Uani d . . . 1 . .
H H21 0.3403 0.1048 -0.3773 0.017 Uiso calc U . R 1 . .
C C22 0.37991(6) 0.06821(3) -0.17699(13) 0.01165(17) Uani d . . . 1 . .
C C23 0.39068(6) 0.16409(3) 0.12269(13) 0.01176(17) Uani d . . . 1 . .
C C24 0.33410(6) 0.14188(3) 0.21517(14) 0.01510(19) Uani d . . . 1 . .
H H24 0.3208 0.1145 0.1803 0.018 Uiso calc U . R 1 . .
C C26 0.31585(8) 0.19964(4) 0.40947(16) 0.0252(3) Uani d . . . 1 . .
H H26 0.29 0.2117 0.5066 0.03 Uiso calc U . R 1 . .
C C27 0.37236(8) 0.22190(4) 0.31875(17) 0.0243(2) Uani d . . . 1 . .
H H27 0.3853 0.2493 0.3539 0.029 Uiso calc U . R 1 . .
C C28 0.41001(7) 0.20421(3) 0.17674(15) 0.0173(2) Uani d . . . 1 . .
H H28 0.4491 0.2195 0.116 0.021 Uiso calc U . R 1 . .
C C25 0.29727(7) 0.15950(4) 0.35721(15) 0.0204(2) Uani d . . . 1 . .
H H25 0.259 0.1441 0.4197 0.024 Uiso calc U . R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 N3 . 1.6120(11) ?
S1 N4 . 1.6146(12) ?
N1 C1 . 1.3973(13) ?
N1 C8 . 1.4058(13) ?
N1 P1 . 1.6992(12) ?
C1 C2 . 1.3933(14) ?
C1 C6 . 1.4061(15) ?
P1 N2 . 1.6943(11) ?
P1 C23 . 1.8163(12) ?
C2 C3 . 1.3863(15) ?
C2 H2 . 0.95 ?
N2 C22 . 1.3977(13) ?
N2 C15 . 1.4030(13) ?
N3 C11 . 1.3509(14) ?
C3 C4 . 1.4050(17) ?
C3 H3 . 0.95 ?
N4 C12 . 1.3479(14) ?
C4 C5 . 1.3779(16) ?
C4 H4 . 0.95 ?
C6 C5 . 1.4023(14) ?
C6 C7 . 1.4261(15) ?
C5 H5 . 0.95 ?
C9 C10 . 1.3816(15) ?
C9 C14 . 1.4584(14) ?
C9 C8 . 1.4713(14) ?
C8 C7 . 1.3719(14) ?
C7 H7 . 0.95 ?
C10 C11 . 1.4071(15) ?
C10 H10 . 0.95 ?
C11 C12 . 1.4243(15) ?
C12 C13 . 1.4076(15) ?
C16 C15 . 1.3699(15) ?
C16 C17 . 1.4300(15) ?
C16 H16 . 0.95 ?
C15 C14 . 1.4680(14) ?
C14 C13 . 1.3830(14) ?
C13 H13 . 0.95 ?
C17 C18 . 1.4011(15) ?
C17 C22 . 1.4073(15) ?
C20 C21 . 1.3830(15) ?
C20 C19 . 1.4051(17) ?
C20 H20 . 0.95 ?
C19 C18 . 1.3840(16) ?
C19 H19 . 0.95 ?
C18 H18 . 0.95 ?
C21 C22 . 1.3912(15) ?
C21 H21 . 0.95 ?
C23 C24 . 1.3945(15) ?
C23 C28 . 1.3979(15) ?
C24 C25 . 1.3812(16) ?
C24 H24 . 0.95 ?
C26 C27 . 1.388(2) ?
C26 C25 . 1.391(2) ?
C26 H26 . 0.95 ?
C27 C28 . 1.3883(17) ?
C27 H27 . 0.95 ?
C28 H28 . 0.95 ?
C25 H25 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 S1 N4 . . 101.84(5) ?
C1 N1 C8 . . 107.87(9) ?
C1 N1 P1 . . 121.07(7) ?
C8 N1 P1 . . 130.97(7) ?
C2 C1 N1 . . 129.16(10) ?
C2 C1 C6 . . 122.69(9) ?
N1 C1 C6 . . 108.14(9) ?
N2 P1 N1 . . 100.41(4) ?
N2 P1 C23 . . 101.98(5) ?
N1 P1 C23 . . 102.99(5) ?
C3 C2 C1 . . 117.07(10) ?
C3 C2 H2 . . 121.5 ?
C1 C2 H2 . . 121.5 ?
C22 N2 C15 . . 107.98(8) ?
C22 N2 P1 . . 122.71(7) ?
C15 N2 P1 . . 128.92(7) ?
C11 N3 S1 . . 105.38(8) ?
C2 C3 C4 . . 121.07(10) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C12 N4 S1 . . 105.58(8) ?
C5 C4 C3 . . 121.43(10) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C5 C6 C1 . . 118.98(10) ?
C5 C6 C7 . . 134.03(10) ?
C1 C6 C7 . . 106.97(9) ?
C4 C5 C6 . . 118.71(10) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C10 C9 C14 . . 119.40(9) ?
C10 C9 C8 . . 114.21(9) ?
C14 C9 C8 . . 126.26(9) ?
C7 C8 N1 . . 108.77(9) ?
C7 C8 C9 . . 126.11(9) ?
N1 C8 C9 . . 125.11(9) ?
C8 C7 C6 . . 108.21(9) ?
C8 C7 H7 . . 125.9 ?
C6 C7 H7 . . 125.9 ?
C9 C10 C11 . . 120.38(10) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
N3 C11 C10 . . 126.31(10) ?
N3 C11 C12 . . 113.73(9) ?
C10 C11 C12 . . 119.96(9) ?
N4 C12 C13 . . 126.60(10) ?
N4 C12 C11 . . 113.46(10) ?
C13 C12 C11 . . 119.88(9) ?
C15 C16 C17 . . 108.35(9) ?
C15 C16 H16 . . 125.8 ?
C17 C16 H16 . . 125.8 ?
C16 C15 N2 . . 108.79(9) ?
C16 C15 C14 . . 125.96(9) ?
N2 C15 C14 . . 125.22(9) ?
C13 C14 C9 . . 119.98(9) ?
C13 C14 C15 . . 114.36(9) ?
C9 C14 C15 . . 125.19(9) ?
C14 C13 C12 . . 120.04(10) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C18 C17 C22 . . 119.17(10) ?
C18 C17 C16 . . 134.14(10) ?
C22 C17 C16 . . 106.68(9) ?
C21 C20 C19 . . 121.23(10) ?
C21 C20 H20 . . 119.4 ?
C19 C20 H20 . . 119.4 ?
C18 C19 C20 . . 121.18(10) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C19 C18 C17 . . 118.60(10) ?
C19 C18 H18 . . 120.7 ?
C17 C18 H18 . . 120.7 ?
C20 C21 C22 . . 117.28(10) ?
C20 C21 H21 . . 121.4 ?
C22 C21 H21 . . 121.4 ?
C21 C22 N2 . . 129.25(9) ?
C21 C22 C17 . . 122.53(9) ?
N2 C22 C17 . . 108.19(9) ?
C24 C23 C28 . . 119.08(10) ?
C24 C23 P1 . . 120.62(8) ?
C28 C23 P1 . . 118.86(8) ?
C25 C24 C23 . . 120.32(11) ?
C25 C24 H24 . . 119.8 ?
C23 C24 H24 . . 119.8 ?
C27 C26 C25 . . 119.55(11) ?
C27 C26 H26 . . 120.2 ?
C25 C26 H26 . . 120.2 ?
C26 C27 C28 . . 120.15(12) ?
C26 C27 H27 . . 119.9 ?
C28 C27 H27 . . 119.9 ?
C27 C28 C23 . . 120.36(11) ?
C27 C28 H28 . . 119.8 ?
C23 C28 H28 . . 119.8 ?
C24 C25 C26 . . 120.53(11) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 C1 C2 . . . . 176.75(10) ?
P1 N1 C1 C2 . . . . -0.18(15) ?
C8 N1 C1 C6 . . . . -1.93(11) ?
P1 N1 C1 C6 . . . . -178.86(7) ?
C1 N1 P1 N2 . . . . 127.98(8) ?
C8 N1 P1 N2 . . . . -48.14(10) ?
C1 N1 P1 C23 . . . . -127.02(8) ?
C8 N1 P1 C23 . . . . 56.86(10) ?
N1 C1 C2 C3 . . . . 179.65(10) ?
C6 C1 C2 C3 . . . . -1.84(16) ?
N1 P1 N2 C22 . . . . -129.64(8) ?
C23 P1 N2 C22 . . . . 124.55(9) ?
N1 P1 N2 C15 . . . . 58.43(10) ?
C23 P1 N2 C15 . . . . -47.39(10) ?
N4 S1 N3 C11 . . . . -0.10(9) ?
C1 C2 C3 C4 . . . . 0.06(16) ?
N3 S1 N4 C12 . . . . 0.58(8) ?
C2 C3 C4 C5 . . . . 1.37(17) ?
C2 C1 C6 C5 . . . . 2.20(15) ?
N1 C1 C6 C5 . . . . -179.02(9) ?
C2 C1 C6 C7 . . . . -176.85(10) ?
N1 C1 C6 C7 . . . . 1.93(11) ?
C3 C4 C5 C6 . . . . -1.01(16) ?
C1 C6 C5 C4 . . . . -0.71(15) ?
C7 C6 C5 C4 . . . . 178.03(11) ?
C1 N1 C8 C7 . . . . 1.18(11) ?
P1 N1 C8 C7 . . . . 177.70(8) ?
C1 N1 C8 C9 . . . . 179.62(9) ?
P1 N1 C8 C9 . . . . -3.87(15) ?
C10 C9 C8 C7 . . . . 26.65(15) ?
C14 C9 C8 C7 . . . . -149.21(11) ?
C10 C9 C8 N1 . . . . -151.52(10) ?
C14 C9 C8 N1 . . . . 32.62(16) ?
N1 C8 C7 C6 . . . . 0.02(11) ?
C9 C8 C7 C6 . . . . -178.40(9) ?
C5 C6 C7 C8 . . . . 179.95(11) ?
C1 C6 C7 C8 . . . . -1.21(11) ?
C14 C9 C10 C11 . . . . 0.68(15) ?
C8 C9 C10 C11 . . . . -175.49(9) ?
S1 N3 C11 C10 . . . . 179.21(9) ?
S1 N3 C11 C12 . . . . -0.41(11) ?
C9 C10 C11 N3 . . . . 175.55(10) ?
C9 C10 C11 C12 . . . . -4.85(16) ?
S1 N4 C12 C13 . . . . 176.30(9) ?
S1 N4 C12 C11 . . . . -0.88(11) ?
N3 C11 C12 N4 . . . . 0.89(14) ?
C10 C11 C12 N4 . . . . -178.75(10) ?
N3 C11 C12 C13 . . . . -176.50(10) ?
C10 C11 C12 C13 . . . . 3.86(15) ?
C17 C16 C15 N2 . . . . 1.27(12) ?
C17 C16 C15 C14 . . . . -176.93(9) ?
C22 N2 C15 C16 . . . . -1.58(11) ?
P1 N2 C15 C16 . . . . 171.29(8) ?
C22 N2 C15 C14 . . . . 176.64(9) ?
P1 N2 C15 C14 . . . . -10.49(15) ?
C10 C9 C14 C13 . . . . 4.61(15) ?
C8 C9 C14 C13 . . . . -179.73(10) ?
C10 C9 C14 C15 . . . . -167.11(10) ?
C8 C9 C14 C15 . . . . 8.56(16) ?
C16 C15 C14 C13 . . . . -31.23(15) ?
N2 C15 C14 C13 . . . . 150.85(10) ?
C16 C15 C14 C9 . . . . 140.89(11) ?
N2 C15 C14 C9 . . . . -37.03(15) ?
C9 C14 C13 C12 . . . . -5.60(15) ?
C15 C14 C13 C12 . . . . 166.97(9) ?
N4 C12 C13 C14 . . . . -175.59(10) ?
C11 C12 C13 C14 . . . . 1.43(15) ?
C15 C16 C17 C18 . . . . 177.76(11) ?
C15 C16 C17 C22 . . . . -0.49(12) ?
C21 C20 C19 C18 . . . . -0.48(17) ?
C20 C19 C18 C17 . . . . 0.50(16) ?
C22 C17 C18 C19 . . . . 0.11(15) ?
C16 C17 C18 C19 . . . . -177.96(11) ?
C19 C20 C21 C22 . . . . -0.17(16) ?
C20 C21 C22 N2 . . . . 178.67(10) ?
C20 C21 C22 C17 . . . . 0.81(16) ?
C15 N2 C22 C21 . . . . -176.84(10) ?
P1 N2 C22 C21 . . . . 9.75(16) ?
C15 N2 C22 C17 . . . . 1.26(11) ?
P1 N2 C22 C17 . . . . -172.15(7) ?
C18 C17 C22 C21 . . . . -0.79(16) ?
C16 C17 C22 C21 . . . . 177.77(10) ?
C18 C17 C22 N2 . . . . -179.04(9) ?
C16 C17 C22 N2 . . . . -0.49(11) ?
N2 P1 C23 C24 . . . . -36.73(9) ?
N1 P1 C23 C24 . . . . -140.53(8) ?
N2 P1 C23 C28 . . . . 157.07(8) ?
N1 P1 C23 C28 . . . . 53.27(9) ?
C28 C23 C24 C25 . . . . 0.57(16) ?
P1 C23 C24 C25 . . . . -165.59(8) ?
C25 C26 C27 C28 . . . . 0.05(19) ?
C26 C27 C28 C23 . . . . 0.78(18) ?
C24 C23 C28 C27 . . . . -1.09(16) ?
P1 C23 C28 C27 . . . . 165.32(9) ?
C23 C24 C25 C26 . . . . 0.26(17) ?
C27 C26 C25 C24 . . . . -0.58(18) ?

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1427667'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            YR3
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H19 N2 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         414.44

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5379(4)
_cell_length_b                   12.3661(6)
_cell_length_c                   20.2417(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.9180(10)
_cell_angle_gamma                90
_cell_volume                     2105.19(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      4.2066
_cell_measurement_theta_max      72.2067
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864

_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'ImuS micro--focus source'
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'BRUKER APEX II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            34226
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         72.21
_diffrn_reflns_theta_full        72.21
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             4150
_reflns_number_gt                3981
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1000
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_number_reflns         4150
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.9597P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.007
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_computing_data_collection       'Bruker Instrument Service v4.2.4'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.50699(4) 0.66719(2) 0.08528(2) 0.01391(11) Uani d . . . 1 . .
N N1 0.45373(12) 0.78218(8) 0.12308(5) 0.0149(2) Uani d . . . 1 . .
C C1 0.36398(14) 0.86484(10) 0.08786(6) 0.0158(3) Uani d . . . 1 . .
C C2 0.28687(16) 0.86777(11) 0.02119(7) 0.0200(3) Uani d . . . 1 . .
H H2 0.2887 0.8075 -0.0078 0.024 Uiso calc U . R 1 . .
N N2 0.45774(13) 0.57174(8) 0.13957(5) 0.0156(2) Uani d . . . 1 . .
C C3 0.20786(17) 0.96204(12) -0.00081(7) 0.0240(3) Uani d . . . 1 . .
H H3 0.1551 0.9668 -0.046 0.029 Uiso calc U . R 1 . .
C C4 0.20370(18) 1.05097(11) 0.04206(7) 0.0252(3) Uani d . . . 1 . .
H H4 0.1483 1.1146 0.0253 0.03 Uiso calc U . R 1 . .
C C6 0.36146(15) 0.95286(10) 0.13179(6) 0.0182(3) Uani d . . . 1 . .
C C5 0.27885(17) 1.04740(11) 0.10809(7) 0.0228(3) Uani d . . . 1 . .
H H5 0.2749 1.1076 0.1369 0.027 Uiso calc U . R 1 . .
C C9 0.61446(15) 0.75714(11) 0.24053(6) 0.0162(3) Uani d . . . 1 . .
C C8 0.50893(15) 0.81958(10) 0.18876(6) 0.0160(3) Uani d . . . 1 . .
C C7 0.45340(16) 0.92214(10) 0.19472(6) 0.0187(3) Uani d . . . 1 . .
H H7 0.4727 0.9656 0.234 0.022 Uiso calc U . R 1 . .
C C10 0.72583(16) 0.81734(11) 0.28455(7) 0.0202(3) Uani d . . . 1 . .
H H10 0.7324 0.8931 0.2777 0.024 Uiso calc U . R 1 . .
C C11 0.82695(16) 0.77013(12) 0.33781(7) 0.0227(3) Uani d . . . 1 . .
H H11 0.9012 0.8131 0.3669 0.027 Uiso calc U . R 1 . .
C C12 0.81853(17) 0.65943(12) 0.34815(7) 0.0220(3) Uani d . . . 1 . .
H H12 0.8866 0.6261 0.3845 0.026 Uiso calc U . R 1 . .
C C13 0.71016(16) 0.59801(11) 0.30499(6) 0.0197(3) Uani d . . . 1 . .
H H13 0.7054 0.5223 0.3124 0.024 Uiso calc U . R 1 . .
C C14 0.60708(15) 0.64395(11) 0.25066(6) 0.0166(3) Uani d . . . 1 . .
C C21 0.26926(16) 0.46112(11) 0.05540(7) 0.0201(3) Uani d . . . 1 . .
H H21 0.2876 0.4996 0.0168 0.024 Uiso calc U . R 1 . .
C C20 0.16176(17) 0.37639(11) 0.05021(7) 0.0233(3) Uani d . . . 1 . .
H H20 0.1039 0.3574 0.0074 0.028 Uiso calc U . R 1 . .
C C19 0.13654(17) 0.31790(11) 0.10707(7) 0.0226(3) Uani d . . . 1 . .
H H19 0.0621 0.2601 0.1021 0.027 Uiso calc U . R 1 . .
C C18 0.21869(16) 0.34342(10) 0.17018(7) 0.0205(3) Uani d . . . 1 . .
H H18 0.2034 0.3024 0.2083 0.025 Uiso calc U . R 1 . .
C C17 0.32487(15) 0.43085(10) 0.17691(7) 0.0174(3) Uani d . . . 1 . .
C C16 0.41771(15) 0.48392(10) 0.23319(6) 0.0181(3) Uani d . . . 1 . .
H H16 0.4242 0.4635 0.2788 0.022 Uiso calc U . R 1 . .
C C15 0.49536(15) 0.56888(10) 0.21029(6) 0.0162(3) Uani d . . . 1 . .
C C22 0.34955(15) 0.48789(10) 0.11920(6) 0.0162(3) Uani d . . . 1 . .
C C23 0.72217(15) 0.67620(10) 0.10940(6) 0.0151(3) Uani d . . . 1 . .
C C24 0.79639(16) 0.77591(11) 0.10444(6) 0.0186(3) Uani d . . . 1 . .
H H24 0.7338 0.8387 0.0923 0.022 Uiso calc U . R 1 . .
C C25 0.96091(16) 0.78371(12) 0.11708(7) 0.0223(3) Uani d . . . 1 . .
H H25 1.0108 0.8516 0.1136 0.027 Uiso calc U . R 1 . .
C C28 0.81502(16) 0.58399(11) 0.12524(6) 0.0195(3) Uani d . . . 1 . .
H H28 0.7656 0.5155 0.1271 0.023 Uiso calc U . R 1 . .
C C27 0.97964(17) 0.59210(12) 0.13835(7) 0.0250(3) Uani d . . . 1 . .
H H27 1.0426 0.5293 0.1498 0.03 Uiso calc U . R 1 . .
C C26 1.05255(17) 0.69201(13) 0.13479(7) 0.0253(3) Uani d . . . 1 . .
H H26 1.1652 0.6975 0.1445 0.03 Uiso calc U . R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 N2 . 1.7136(11) ?
P1 N1 . 1.7130(11) ?
P1 C23 . 1.8212(13) ?
N1 C1 . 1.3972(16) ?
N1 C8 . 1.4099(16) ?
C1 C2 . 1.3963(18) ?
C1 C6 . 1.4080(18) ?
C2 C3 . 1.3816(19) ?
C2 H2 . 0.95 ?
N2 C22 . 1.4026(16) ?
N2 C15 . 1.4126(16) ?
C3 C4 . 1.405(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.380(2) ?
C4 H4 . 0.95 ?
C6 C5 . 1.4064(18) ?
C6 C7 . 1.4278(18) ?
C5 H5 . 0.95 ?
C9 C10 . 1.4002(19) ?
C9 C14 . 1.4176(18) ?
C9 C8 . 1.4767(17) ?
C8 C7 . 1.3665(18) ?
C7 H7 . 0.95 ?
C10 C11 . 1.3884(19) ?
C10 H10 . 0.95 ?
C11 C12 . 1.389(2) ?
C11 H11 . 0.95 ?
C12 C13 . 1.385(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.4048(18) ?
C13 H13 . 0.95 ?
C14 C15 . 1.4734(18) ?
C21 C20 . 1.3850(19) ?
C21 C22 . 1.3937(18) ?
C21 H21 . 0.95 ?
C20 C19 . 1.407(2) ?
C20 H20 . 0.95 ?
C19 C18 . 1.384(2) ?
C19 H19 . 0.95 ?
C18 C17 . 1.4025(19) ?
C18 H18 . 0.95 ?
C17 C22 . 1.4111(18) ?
C17 C16 . 1.4303(18) ?
C16 C15 . 1.3653(18) ?
C16 H16 . 0.95 ?
C23 C28 . 1.3943(18) ?
C23 C24 . 1.3978(18) ?
C24 C25 . 1.3871(19) ?
C24 H24 . 0.95 ?
C25 C26 . 1.389(2) ?
C25 H25 . 0.95 ?
C28 C27 . 1.388(2) ?
C28 H28 . 0.95 ?
C27 C26 . 1.391(2) ?
C27 H27 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 P1 N1 . . 99.91(5) ?
N2 P1 C23 . . 102.59(5) ?
N1 P1 C23 . . 99.36(5) ?
C1 N1 C8 . . 107.82(10) ?
C1 N1 P1 . . 122.95(9) ?
C8 N1 P1 . . 128.48(9) ?
C2 C1 N1 . . 129.64(12) ?
C2 C1 C6 . . 122.30(12) ?
N1 C1 C6 . . 108.06(11) ?
C3 C2 C1 . . 117.14(12) ?
C3 C2 H2 . . 121.4 ?
C1 C2 H2 . . 121.4 ?
C22 N2 C15 . . 107.62(10) ?
C22 N2 P1 . . 122.87(9) ?
C15 N2 P1 . . 128.98(9) ?
C2 C3 C4 . . 121.62(13) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 121.07(13) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C5 C6 C1 . . 119.24(12) ?
C5 C6 C7 . . 133.78(12) ?
C1 C6 C7 . . 106.97(11) ?
C4 C5 C6 . . 118.63(13) ?
C4 C5 H5 . . 120.7 ?
C6 C5 H5 . . 120.7 ?
C10 C9 C14 . . 118.36(12) ?
C10 C9 C8 . . 115.98(12) ?
C14 C9 C8 . . 125.59(12) ?
C7 C8 N1 . . 108.84(11) ?
C7 C8 C9 . . 126.96(12) ?
N1 C8 C9 . . 124.17(11) ?
C8 C7 C6 . . 108.30(11) ?
C8 C7 H7 . . 125.8 ?
C6 C7 H7 . . 125.8 ?
C11 C10 C9 . . 122.28(13) ?
C11 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
C10 C11 C12 . . 119.35(13) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C13 C12 C11 . . 119.47(13) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C14 . . 122.17(13) ?
C12 C13 H13 . . 118.9 ?
C14 C13 H13 . . 118.9 ?
C13 C14 C9 . . 118.37(12) ?
C13 C14 C15 . . 115.96(12) ?
C9 C14 C15 . . 125.63(12) ?
C20 C21 C22 . . 117.63(12) ?
C20 C21 H21 . . 121.2 ?
C22 C21 H21 . . 121.2 ?
C21 C20 C19 . . 121.31(13) ?
C21 C20 H20 . . 119.3 ?
C19 C20 H20 . . 119.3 ?
C18 C19 C20 . . 120.88(13) ?
C18 C19 H19 . . 119.6 ?
C20 C19 H19 . . 119.6 ?
C19 C18 C17 . . 118.81(12) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C18 C17 C22 . . 119.41(12) ?
C18 C17 C16 . . 133.74(12) ?
C22 C17 C16 . . 106.78(11) ?
C15 C16 C17 . . 108.52(11) ?
C15 C16 H16 . . 125.7 ?
C17 C16 H16 . . 125.7 ?
C16 C15 N2 . . 108.93(11) ?
C16 C15 C14 . . 127.04(11) ?
N2 C15 C14 . . 123.97(11) ?
C21 C22 N2 . . 129.93(12) ?
C21 C22 C17 . . 121.91(12) ?
N2 C22 C17 . . 108.11(11) ?
C28 C23 C24 . . 119.42(12) ?
C28 C23 P1 . . 121.26(10) ?
C24 C23 P1 . . 118.92(10) ?
C25 C24 C23 . . 120.35(12) ?
C25 C24 H24 . . 119.8 ?
C23 C24 H24 . . 119.8 ?
C24 C25 C26 . . 119.89(13) ?
C24 C25 H25 . . 120.1 ?
C26 C25 H25 . . 120.1 ?
C27 C28 C23 . . 120.11(13) ?
C27 C28 H28 . . 119.9 ?
C23 C28 H28 . . 119.9 ?
C26 C27 C28 . . 120.11(13) ?
C26 C27 H27 . . 119.9 ?
C28 C27 H27 . . 119.9 ?
C27 C26 C25 . . 120.08(13) ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 P1 N1 C1 . . . . -133.02(10) ?
C23 P1 N1 C1 . . . . 122.33(10) ?
N2 P1 N1 C8 . . . . 58.17(11) ?
C23 P1 N1 C8 . . . . -46.48(12) ?
C8 N1 C1 C2 . . . . 178.85(13) ?
P1 N1 C1 C2 . . . . 8.03(19) ?
C8 N1 C1 C6 . . . . -0.82(13) ?
P1 N1 C1 C6 . . . . -171.64(9) ?
N1 C1 C2 C3 . . . . -179.01(12) ?
C6 C1 C2 C3 . . . . 0.62(19) ?
N1 P1 N2 C22 . . . . 122.09(10) ?
C23 P1 N2 C22 . . . . -135.90(10) ?
N1 P1 N2 C15 . . . . -48.39(12) ?
C23 P1 N2 C15 . . . . 53.62(12) ?
C1 C2 C3 C4 . . . . -0.6(2) ?
C2 C3 C4 C5 . . . . 0.0(2) ?
C2 C1 C6 C5 . . . . -0.09(19) ?
N1 C1 C6 C5 . . . . 179.61(11) ?
C2 C1 C6 C7 . . . . -179.18(12) ?
N1 C1 C6 C7 . . . . 0.52(14) ?
C3 C4 C5 C6 . . . . 0.5(2) ?
C1 C6 C5 C4 . . . . -0.5(2) ?
C7 C6 C5 C4 . . . . 178.29(14) ?
C1 N1 C8 C7 . . . . 0.82(14) ?
P1 N1 C8 C7 . . . . 170.98(9) ?
C1 N1 C8 C9 . . . . -177.08(11) ?
P1 N1 C8 C9 . . . . -6.93(18) ?
C10 C9 C8 C7 . . . . -32.61(18) ?
C14 C9 C8 C7 . . . . 144.49(14) ?
C10 C9 C8 N1 . . . . 144.90(12) ?
C14 C9 C8 N1 . . . . -37.99(19) ?
N1 C8 C7 C6 . . . . -0.49(14) ?
C9 C8 C7 C6 . . . . 177.34(12) ?
C5 C6 C7 C8 . . . . -178.92(14) ?
C1 C6 C7 C8 . . . . -0.02(15) ?
C14 C9 C10 C11 . . . . -0.80(19) ?
C8 C9 C10 C11 . . . . 176.52(12) ?
C9 C10 C11 C12 . . . . 0.1(2) ?
C10 C11 C12 C13 . . . . 0.4(2) ?
C11 C12 C13 C14 . . . . -0.2(2) ?
C12 C13 C14 C9 . . . . -0.52(19) ?
C12 C13 C14 C15 . . . . -178.35(12) ?
C10 C9 C14 C13 . . . . 0.97(17) ?
C8 C9 C14 C13 . . . . -176.07(11) ?
C10 C9 C14 C15 . . . . 178.57(12) ?
C8 C9 C14 C15 . . . . 1.5(2) ?
C22 C21 C20 C19 . . . . -1.2(2) ?
C21 C20 C19 C18 . . . . 0.0(2) ?
C20 C19 C18 C17 . . . . 1.7(2) ?
C19 C18 C17 C22 . . . . -2.28(19) ?
C19 C18 C17 C16 . . . . 174.38(13) ?
C18 C17 C16 C15 . . . . -177.21(14) ?
C22 C17 C16 C15 . . . . -0.25(14) ?
C17 C16 C15 N2 . . . . -1.08(14) ?
C17 C16 C15 C14 . . . . -178.33(12) ?
C22 N2 C15 C16 . . . . 2.01(14) ?
P1 N2 C15 C16 . . . . 173.63(9) ?
C22 N2 C15 C14 . . . . 179.36(11) ?
P1 N2 C15 C14 . . . . -9.02(18) ?
C13 C14 C15 C16 . . . . 38.03(18) ?
C9 C14 C15 C16 . . . . -139.63(14) ?
C13 C14 C15 N2 . . . . -138.83(12) ?
C9 C14 C15 N2 . . . . 43.51(18) ?
C20 C21 C22 N2 . . . . -176.70(13) ?
C20 C21 C22 C17 . . . . 0.65(19) ?
C15 N2 C22 C21 . . . . 175.49(13) ?
P1 N2 C22 C21 . . . . 3.24(19) ?
C15 N2 C22 C17 . . . . -2.14(13) ?
P1 N2 C22 C17 . . . . -174.39(8) ?
C18 C17 C22 C21 . . . . 1.11(19) ?
C16 C17 C22 C21 . . . . -176.37(12) ?
C18 C17 C22 N2 . . . . 178.97(11) ?
C16 C17 C22 N2 . . . . 1.49(14) ?
N2 P1 C23 C28 . . . . 40.84(11) ?
N1 P1 C23 C28 . . . . 143.28(10) ?
N2 P1 C23 C24 . . . . -146.53(10) ?
N1 P1 C23 C24 . . . . -44.09(11) ?
C28 C23 C24 C25 . . . . -1.89(19) ?
P1 C23 C24 C25 . . . . -174.66(10) ?
C23 C24 C25 C26 . . . . 0.0(2) ?
C24 C23 C28 C27 . . . . 2.36(19) ?
P1 C23 C28 C27 . . . . 174.95(10) ?
C23 C28 C27 C26 . . . . -0.9(2) ?
C28 C27 C26 C25 . . . . -1.0(2) ?
C24 C25 C26 C27 . . . . 1.5(2) ?

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1427668'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_I                   
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.10 Report
RESPONSE:  a small amount of negative difference density at both Phosphorus atoms
;

# Added during the CSD deposition process: Friday 25th of September 2015 01:59:27 PM
# end Validation Reply Form

_chemical_name_systematic        ?
_chemical_name_common            YR6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H36 N6 O6 P2'
_chemical_formula_iupac          ?
_chemical_formula_weight         926.83

_chemical_melting_point          ?

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

_cell_length_a                   10.2381(6)
_cell_length_b                   13.0126(8)
_cell_length_c                   17.4162(11)
_cell_angle_alpha                89.311(2)
_cell_angle_beta                 88.175(2)
_cell_angle_gamma                67.8250(10)
_cell_volume                     2147.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      2.1758
_cell_measurement_theta_max      34.3208
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'elongated prism'
_exptl_crystal_colour            'translucent intense red-green'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960

_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'BRUKER APEX II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            120588
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         33.73
_diffrn_reflns_theta_full        33.73
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

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

_reflns_number_total             17096
_reflns_number_gt                14842
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1036
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         17096
_refine_ls_number_parameters     615
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0580P)²+0.6492P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.21376(2) 0.076034(16) 0.609095(11) 0.01053(4) Uani d . . . 1 . .
O O1 0.33764(6) 0.08295(5) 0.56828(4) 0.01535(11) Uani d . . . 1 . .
N N1 0.07546(7) 0.19892(5) 0.60842(4) 0.01218(11) Uani d . . . 1 . .
C C1 0.09345(8) 0.30061(6) 0.59631(5) 0.01302(12) Uani d . . . 1 . .
P P2 0.28024(2) 0.282684(17) 0.105549(12) 0.01340(4) Uani d . . . 1 . .
O O2 -0.31645(7) 0.26467(6) 0.74490(4) 0.02028(12) Uani d . . . 1 . .
N N2 -0.29602(7) 0.09029(6) 0.70732(4) 0.01587(12) Uani d . . . 1 . .
C C2 0.18917(9) 0.32493(7) 0.54790(5) 0.01615(14) Uani d . . . 1 . .
H H2 0.2583 0.2691 0.5177 0.019 Uiso calc . . R 1 . .
N N3 0.15427(7) -0.01414(5) 0.56829(4) 0.01158(11) Uani d . . . 1 . .
O O3 -0.21792(7) -0.08060(6) 0.65009(4) 0.02029(12) Uani d . . . 1 . .
C C3 0.17873(10) 0.43458(7) 0.54587(6) 0.02037(16) Uani d . . . 1 . .
H H3 0.2428 0.4538 0.5137 0.024 Uiso calc . . R 1 . .
O O4 0.40559(7) 0.21666(6) 0.05936(4) 0.02052(13) Uani d . . . 1 . .
N N4 0.18966(8) 0.40531(6) 0.06324(4) 0.01519(12) Uani d . . . 1 . .
C C4 0.07638(10) 0.51782(7) 0.58989(6) 0.02093(16) Uani d . . . 1 . .
H H4 0.0737 0.5916 0.5878 0.025 Uiso calc . . R 1 . .
O O5 -0.17845(8) 0.66351(6) 0.17449(5) 0.02764(16) Uani d . . . 1 . .
N N5 -0.22111(8) 0.52089(7) 0.23376(5) 0.02032(14) Uani d . . . 1 . .
C C5 -0.02072(10) 0.49379(7) 0.63626(5) 0.01848(15) Uani d . . . 1 . .
H H5 -0.091 0.5504 0.6653 0.022 Uiso calc . . R 1 . .
N N6 0.16528(7) 0.21881(6) 0.11567(4) 0.01406(12) Uani d . . . 1 . .
C C35 0.06378(10) 0.59162(7) 0.06864(6) 0.02020(16) Uani d . . . 1 . .
H H35 -0.0061 0.6619 0.0819 0.024 Uiso calc . . R 1 . .
C C6 -0.01275(9) 0.38354(7) 0.63924(5) 0.01465(13) Uani d . . . 1 . .
O O6 -0.20706(8) 0.34711(7) 0.27126(5) 0.02598(15) Uani d . . . 1 . .
C C17 0.25058(10) -0.29106(7) 0.49305(5) 0.01828(15) Uani d . . . 1 . .
H H17 0.21 -0.3457 0.4944 0.022 Uiso calc . . R 1 . .
C C18 0.37754(10) -0.31048(7) 0.45436(5) 0.01927(15) Uani d . . . 1 . .
H H18 0.425 -0.3794 0.429 0.023 Uiso calc . . R 1 . .
C C7 -0.09903(9) 0.33279(7) 0.67674(5) 0.01561(14) Uani d . . . 1 . .
H H7 -0.1784 0.3688 0.7099 0.019 Uiso calc . . R 1 . .
C C8 -0.04706(8) 0.22257(6) 0.65648(5) 0.01312(13) Uani d . . . 1 . .
C C9 -0.11140(8) 0.14311(6) 0.66893(5) 0.01288(12) Uani d . . . 1 . .
C C10 -0.25152(8) 0.17769(7) 0.71218(5) 0.01496(13) Uani d . . . 1 . .
C C11 -0.43122(9) 0.09134(8) 0.73607(6) 0.02139(17) Uani d . . . 1 . .
H H11A -0.4862 0.0837 0.693 0.032 Uiso calc . . R 1 . .
H H11B -0.4829 0.1616 0.7628 0.032 Uiso calc . . R 1 . .
H H11C -0.4158 0.0294 0.7719 0.032 Uiso calc . . R 1 . .
C C14 0.03668(8) -0.03782(6) 0.59649(4) 0.01221(12) Uani d . . . 1 . .
C C13 -0.07899(8) 0.03769(6) 0.64153(5) 0.01254(12) Uani d . . . 1 . .
C C12 -0.20040(8) 0.00392(7) 0.66501(5) 0.01458(13) Uani d . . . 1 . .
C C26 0.32415(10) -0.11661(8) 0.79858(5) 0.01935(15) Uani d . . . 1 . .
H H26 0.3571 -0.1935 0.8106 0.023 Uiso calc . . R 1 . .
C C15 0.05300(9) -0.14281(7) 0.57291(5) 0.01516(13) Uani d . . . 1 . .
H H15 -0.0114 -0.1784 0.5833 0.018 Uiso calc . . R 1 . .
C C16 0.18291(9) -0.18875(7) 0.53032(5) 0.01424(13) Uani d . . . 1 . .
C C30 0.37297(10) 0.41054(8) -0.03775(5) 0.02107(16) Uani d . . . 1 . .
H H30 0.4225 0.3325 -0.0411 0.025 Uiso calc . . R 1 . .
C C28 0.23904(8) 0.03223(6) 0.70672(4) 0.01191(12) Uani d . . . 1 . .
C C19 0.43747(9) -0.22927(7) 0.45207(5) 0.01719(14) Uani d . . . 1 . .
H H19 0.5246 -0.2447 0.4248 0.021 Uiso calc . . R 1 . .
C C29 0.25603(9) 0.45702(7) 0.01183(5) 0.01701(14) Uani d . . . 1 . .
C C34 0.17915(10) 0.57249(7) 0.01560(5) 0.02000(16) Uani d . . . 1 . .
C C38 -0.14634(9) 0.56483(7) 0.18576(6) 0.01910(16) Uani d . . . 1 . .
C C36 0.07099(9) 0.49051(7) 0.09736(5) 0.01596(14) Uani d . . . 1 . .
C C20 0.37321(8) -0.12726(7) 0.48843(5) 0.01448(13) Uani d . . . 1 . .
H H20 0.4143 -0.0729 0.4867 0.017 Uiso calc . . R 1 . .
C C37 -0.02467(9) 0.46906(7) 0.15135(5) 0.01518(13) Uani d . . . 1 . .
C C21 0.24510(8) -0.10864(6) 0.52775(4) 0.01203(12) Uani d . . . 1 . .
C C39 -0.34475(10) 0.58747(10) 0.27930(7) 0.0292(2) Uani d . . . 1 . .
H H39A -0.4263 0.6169 0.2462 0.044 Uiso calc . . R 1 . .
H H39B -0.3278 0.6492 0.3028 0.044 Uiso calc . . R 1 . .
H H39C -0.3637 0.5413 0.3196 0.044 Uiso calc . . R 1 . .
C C40 -0.16262(9) 0.40608(8) 0.23347(5) 0.01827(15) Uani d . . . 1 . .
C C41 -0.03647(8) 0.37358(7) 0.17858(5) 0.01423(13) Uani d . . . 1 . .
C C31 0.41397(12) 0.48331(10) -0.08206(6) 0.0261(2) Uani d . . . 1 . .
H H31 0.4936 0.4542 -0.1162 0.031 Uiso calc . . R 1 . .
C C42 0.03809(8) 0.25876(6) 0.16048(5) 0.01359(13) Uani d . . . 1 . .
C C25 0.31430(10) -0.03997(9) 0.85557(5) 0.02235(17) Uani d . . . 1 . .
H H25 0.3408 -0.0647 0.9064 0.027 Uiso calc . . R 1 . .
C C24 0.26586(10) 0.07286(8) 0.83866(5) 0.02120(16) Uani d . . . 1 . .
H H24 0.2584 0.125 0.8779 0.025 Uiso calc . . R 1 . .
C C23 0.22844(9) 0.10914(7) 0.76420(5) 0.01599(14) Uani d . . . 1 . .
H H23 0.1957 0.1861 0.7524 0.019 Uiso calc . . R 1 . .
C C27 0.28589(9) -0.08117(7) 0.72401(5) 0.01496(13) Uani d . . . 1 . .
H H27 0.2915 -0.1334 0.6851 0.018 Uiso calc . . R 1 . .
C C54 0.37103(10) 0.25672(8) 0.33152(5) 0.02031(16) Uani d . . . 1 . .
H H54 0.3739 0.2076 0.3728 0.024 Uiso calc . . R 1 . .
C C55 0.32033(9) 0.24234(7) 0.26087(5) 0.01620(14) Uani d . . . 1 . .
H H55 0.289 0.1831 0.2539 0.019 Uiso calc . . R 1 . .
C C53 0.41740(10) 0.34304(9) 0.34145(6) 0.02356(17) Uani d . . . 1 . .
H H53 0.4548 0.3515 0.3891 0.028 Uiso calc . . R 1 . .
C C52 0.40930(11) 0.41744(9) 0.28172(6) 0.02395(18) Uani d . . . 1 . .
H H52 0.4388 0.4775 0.2893 0.029 Uiso calc . . R 1 . .
C C51 0.35808(9) 0.40389(8) 0.21107(6) 0.01927(15) Uani d . . . 1 . .
H H51 0.3521 0.4547 0.1705 0.023 Uiso calc . . R 1 . .
C C50 0.31539(8) 0.31488(7) 0.20019(5) 0.01407(13) Uani d . . . 1 . .
C C49 0.20042(9) 0.10386(7) 0.10439(5) 0.01537(14) Uani d . . . 1 . .
C C48 0.31524(11) 0.02511(7) 0.06543(5) 0.02244(17) Uani d . . . 1 . .
H H48 0.3872 0.0445 0.0412 0.027 Uiso calc . . R 1 . .
C C47 0.31956(13) -0.08295(8) 0.06363(6) 0.0273(2) Uani d . . . 1 . .
H H47 0.397 -0.1386 0.0381 0.033 Uiso calc . . R 1 . .
C C46 0.21280(14) -0.11224(8) 0.09842(6) 0.0274(2) Uani d . . . 1 . .
H H46 0.2189 -0.1868 0.0956 0.033 Uiso calc . . R 1 . .
C C45 0.09932(12) -0.03420(8) 0.13661(6) 0.02298(17) Uani d . . . 1 . .
H H45 0.0267 -0.0539 0.1597 0.028 Uiso calc . . R 1 . .
C C33 0.22343(12) 0.64410(9) -0.03016(6) 0.0261(2) Uani d . . . 1 . .
H H33 0.1732 0.7221 -0.0282 0.031 Uiso calc . . R 1 . .
C C44 0.09370(10) 0.07529(7) 0.14063(5) 0.01656(14) Uani d . . . 1 . .
C C43 -0.00544(9) 0.17278(7) 0.17606(5) 0.01668(14) Uani d . . . 1 . .
H H43 -0.0874 0.1775 0.2054 0.02 Uiso calc . . R 1 . .
C C32 0.34095(13) 0.59860(10) -0.07780(6) 0.0289(2) Uani d . . . 1 . .
H H32 0.373 0.646 -0.1082 0.035 Uiso calc . . R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . 1.4661(6) ?
P1 N3 . 1.6852(7) ?
P1 N1 . 1.6892(7) ?
P1 C28 . 1.7821(8) ?
N1 C1 . 1.4156(10) ?
N1 C8 . 1.4202(10) ?
C1 C2 . 1.3951(11) ?
C1 C6 . 1.4098(11) ?
P2 O4 . 1.4666(7) ?
P2 N6 . 1.6819(7) ?
P2 N4 . 1.6874(7) ?
P2 C50 . 1.7861(9) ?
O2 C10 . 1.2128(11) ?
N2 C10 . 1.3799(11) ?
N2 C12 . 1.3813(11) ?
N2 C11 . 1.4521(11) ?
C2 C3 . 1.3901(12) ?
C2 H2 . 0.95 ?
N3 C21 . 1.4111(10) ?
N3 C14 . 1.4228(10) ?
O3 C12 . 1.2116(11) ?
C3 C4 . 1.4039(14) ?
C3 H3 . 0.95 ?
N4 C29 . 1.4172(11) ?
N4 C36 . 1.4182(11) ?
C4 C5 . 1.3840(13) ?
C4 H4 . 0.95 ?
O5 C38 . 1.2144(11) ?
N5 C38 . 1.3747(13) ?
N5 C40 . 1.3840(12) ?
N5 C39 . 1.4514(12) ?
C5 C6 . 1.4063(11) ?
C5 H5 . 0.95 ?
N6 C49 . 1.4148(10) ?
N6 C42 . 1.4173(10) ?
C35 C36 . 1.3784(12) ?
C35 C34 . 1.4228(14) ?
C35 H35 . 0.95 ?
C6 C7 . 1.4268(12) ?
O6 C40 . 1.2089(12) ?
C17 C18 . 1.3812(13) ?
C17 C16 . 1.4035(12) ?
C17 H17 . 0.95 ?
C18 C19 . 1.4077(13) ?
C18 H18 . 0.95 ?
C7 C8 . 1.3743(11) ?
C7 H7 . 0.95 ?
C8 C9 . 1.4318(11) ?
C9 C13 . 1.3717(11) ?
C9 C10 . 1.5099(11) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C14 C15 . 1.3783(11) ?
C14 C13 . 1.4368(11) ?
C13 C12 . 1.5104(11) ?
C26 C25 . 1.3898(14) ?
C26 C27 . 1.3908(12) ?
C26 H26 . 0.95 ?
C15 C16 . 1.4227(12) ?
C15 H15 . 0.95 ?
C16 C21 . 1.4115(11) ?
C30 C31 . 1.3894(13) ?
C30 C29 . 1.3946(13) ?
C30 H30 . 0.95 ?
C28 C23 . 1.3967(11) ?
C28 C27 . 1.4009(11) ?
C19 C20 . 1.3893(12) ?
C19 H19 . 0.95 ?
C29 C34 . 1.4099(13) ?
C34 C33 . 1.4096(13) ?
C38 C37 . 1.5041(12) ?
C36 C37 . 1.4362(12) ?
C20 C21 . 1.3982(11) ?
C20 H20 . 0.95 ?
C37 C41 . 1.3707(11) ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C40 C41 . 1.5097(12) ?
C41 C42 . 1.4316(11) ?
C31 C32 . 1.4028(17) ?
C31 H31 . 0.95 ?
C42 C43 . 1.3731(11) ?
C25 C24 . 1.3920(14) ?
C25 H25 . 0.95 ?
C24 C23 . 1.3900(12) ?
C24 H24 . 0.95 ?
C23 H23 . 0.95 ?
C27 H27 . 0.95 ?
C54 C53 . 1.3890(14) ?
C54 C55 . 1.3922(13) ?
C54 H54 . 0.95 ?
C55 C50 . 1.3977(11) ?
C55 H55 . 0.95 ?
C53 C52 . 1.3954(15) ?
C53 H53 . 0.95 ?
C52 C51 . 1.3915(14) ?
C52 H52 . 0.95 ?
C51 C50 . 1.4005(12) ?
C51 H51 . 0.95 ?
C49 C48 . 1.3960(12) ?
C49 C44 . 1.4099(12) ?
C48 C47 . 1.3908(14) ?
C48 H48 . 0.95 ?
C47 C46 . 1.4050(17) ?
C47 H47 . 0.95 ?
C46 C45 . 1.3783(15) ?
C46 H46 . 0.95 ?
C45 C44 . 1.4065(12) ?
C45 H45 . 0.95 ?
C33 C32 . 1.3773(18) ?
C33 H33 . 0.95 ?
C44 C43 . 1.4238(12) ?
C43 H43 . 0.95 ?
C32 H32 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N3 . . 112.89(4) ?
O1 P1 N1 . . 111.51(4) ?
N3 P1 N1 . . 104.80(3) ?
O1 P1 C28 . . 115.53(4) ?
N3 P1 C28 . . 104.24(3) ?
N1 P1 C28 . . 107.02(4) ?
C1 N1 C8 . . 106.75(6) ?
C1 N1 P1 . . 121.99(5) ?
C8 N1 P1 . . 123.25(5) ?
C2 C1 C6 . . 121.95(7) ?
C2 C1 N1 . . 129.74(7) ?
C6 C1 N1 . . 108.18(7) ?
O4 P2 N6 . . 111.79(4) ?
O4 P2 N4 . . 111.55(4) ?
N6 P2 N4 . . 105.31(4) ?
O4 P2 C50 . . 114.85(4) ?
N6 P2 C50 . . 106.55(4) ?
N4 P2 C50 . . 106.16(4) ?
C10 N2 C12 . . 111.13(7) ?
C10 N2 C11 . . 125.17(8) ?
C12 N2 C11 . . 123.46(8) ?
C3 C2 C1 . . 116.94(8) ?
C3 C2 H2 . . 121.5 ?
C1 C2 H2 . . 121.5 ?
C21 N3 C14 . . 107.38(6) ?
C21 N3 P1 . . 122.06(5) ?
C14 N3 P1 . . 124.65(6) ?
C2 C3 C4 . . 121.98(8) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C29 N4 C36 . . 107.23(7) ?
C29 N4 P2 . . 121.92(6) ?
C36 N4 P2 . . 124.36(6) ?
C5 C4 C3 . . 120.83(8) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C38 N5 C40 . . 111.43(7) ?
C38 N5 C39 . . 123.79(9) ?
C40 N5 C39 . . 124.78(9) ?
C4 C5 C6 . . 118.36(8) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C49 N6 C42 . . 107.17(7) ?
C49 N6 P2 . . 124.41(6) ?
C42 N6 P2 . . 125.15(6) ?
C36 C35 C34 . . 108.15(8) ?
C36 C35 H35 . . 125.9 ?
C34 C35 H35 . . 125.9 ?
C5 C6 C1 . . 119.89(8) ?
C5 C6 C7 . . 132.51(8) ?
C1 C6 C7 . . 107.54(7) ?
C18 C17 C16 . . 118.55(8) ?
C18 C17 H17 . . 120.7 ?
C16 C17 H17 . . 120.7 ?
C17 C18 C19 . . 120.75(8) ?
C17 C18 H18 . . 119.6 ?
C19 C18 H18 . . 119.6 ?
C8 C7 C6 . . 107.97(7) ?
C8 C7 H7 . . 126.0 ?
C6 C7 H7 . . 126.0 ?
C7 C8 N1 . . 109.47(7) ?
C7 C8 C9 . . 128.20(7) ?
N1 C8 C9 . . 121.65(7) ?
C13 C9 C8 . . 132.33(7) ?
C13 C9 C10 . . 107.97(7) ?
C8 C9 C10 . . 119.27(7) ?
O2 C10 N2 . . 124.89(8) ?
O2 C10 C9 . . 128.42(8) ?
N2 C10 C9 . . 106.69(7) ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C15 C14 N3 . . 108.78(7) ?
C15 C14 C13 . . 126.86(7) ?
N3 C14 C13 . . 124.36(7) ?
C9 C13 C14 . . 134.09(7) ?
C9 C13 C12 . . 106.91(7) ?
C14 C13 C12 . . 118.96(7) ?
O3 C12 N2 . . 123.80(8) ?
O3 C12 C13 . . 128.92(8) ?
N2 C12 C13 . . 107.26(7) ?
C25 C26 C27 . . 120.22(8) ?
C25 C26 H26 . . 119.9 ?
C27 C26 H26 . . 119.9 ?
C14 C15 C16 . . 108.24(7) ?
C14 C15 H15 . . 125.9 ?
C16 C15 H15 . . 125.9 ?
C17 C16 C21 . . 119.86(8) ?
C17 C16 C15 . . 132.42(8) ?
C21 C16 C15 . . 107.70(7) ?
C31 C30 C29 . . 117.11(10) ?
C31 C30 H30 . . 121.4 ?
C29 C30 H30 . . 121.4 ?
C23 C28 C27 . . 120.25(7) ?
C23 C28 P1 . . 119.90(6) ?
C27 C28 P1 . . 119.42(6) ?
C20 C19 C18 . . 122.10(8) ?
C20 C19 H19 . . 118.9 ?
C18 C19 H19 . . 118.9 ?
C30 C29 C34 . . 121.98(8) ?
C30 C29 N4 . . 130.19(8) ?
C34 C29 N4 . . 107.81(8) ?
C33 C34 C29 . . 119.49(10) ?
C33 C34 C35 . . 132.74(9) ?
C29 C34 C35 . . 107.76(8) ?
O5 C38 N5 . . 124.11(9) ?
O5 C38 C37 . . 128.68(9) ?
N5 C38 C37 . . 107.20(7) ?
C35 C36 N4 . . 109.04(8) ?
C35 C36 C37 . . 127.82(8) ?
N4 C36 C37 . . 123.12(7) ?
C19 C20 C21 . . 116.70(8) ?
C19 C20 H20 . . 121.6 ?
C21 C20 H20 . . 121.6 ?
C41 C37 C36 . . 133.26(8) ?
C41 C37 C38 . . 107.19(8) ?
C36 C37 C38 . . 119.46(7) ?
C20 C21 N3 . . 130.06(7) ?
C20 C21 C16 . . 122.03(7) ?
N3 C21 C16 . . 107.88(7) ?
N5 C39 H39A . . 109.5 ?
N5 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
N5 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
O6 C40 N5 . . 124.79(8) ?
O6 C40 C41 . . 128.95(8) ?
N5 C40 C41 . . 106.26(8) ?
C37 C41 C42 . . 132.82(8) ?
C37 C41 C40 . . 107.87(7) ?
C42 C41 C40 . . 119.12(7) ?
C30 C31 C32 . . 121.77(10) ?
C30 C31 H31 . . 119.1 ?
C32 C31 H31 . . 119.1 ?
C43 C42 N6 . . 109.25(7) ?
C43 C42 C41 . . 127.08(8) ?
N6 C42 C41 . . 123.39(7) ?
C26 C25 C24 . . 120.39(8) ?
C26 C25 H25 . . 119.8 ?
C24 C25 H25 . . 119.8 ?
C23 C24 C25 . . 119.88(8) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
C24 C23 C28 . . 119.84(8) ?
C24 C23 H23 . . 120.1 ?
C28 C23 H23 . . 120.1 ?
C26 C27 C28 . . 119.41(8) ?
C26 C27 H27 . . 120.3 ?
C28 C27 H27 . . 120.3 ?
C53 C54 C55 . . 119.82(9) ?
C53 C54 H54 . . 120.1 ?
C55 C54 H54 . . 120.1 ?
C54 C55 C50 . . 120.12(8) ?
C54 C55 H55 . . 119.9 ?
C50 C55 H55 . . 119.9 ?
C54 C53 C52 . . 120.31(9) ?
C54 C53 H53 . . 119.8 ?
C52 C53 H53 . . 119.8 ?
C51 C52 C53 . . 120.15(9) ?
C51 C52 H52 . . 119.9 ?
C53 C52 H52 . . 119.9 ?
C52 C51 C50 . . 119.61(8) ?
C52 C51 H51 . . 120.2 ?
C50 C51 H51 . . 120.2 ?
C55 C50 C51 . . 119.94(8) ?
C55 C50 P2 . . 119.94(6) ?
C51 C50 P2 . . 119.46(6) ?
C48 C49 C44 . . 121.61(8) ?
C48 C49 N6 . . 130.62(8) ?
C44 C49 N6 . . 107.77(7) ?
C47 C48 C49 . . 117.05(9) ?
C47 C48 H48 . . 121.5 ?
C49 C48 H48 . . 121.5 ?
C48 C47 C46 . . 121.96(9) ?
C48 C47 H47 . . 119.0 ?
C46 C47 H47 . . 119.0 ?
C45 C46 C47 . . 120.84(9) ?
C45 C46 H46 . . 119.6 ?
C47 C46 H46 . . 119.6 ?
C46 C45 C44 . . 118.39(10) ?
C46 C45 H45 . . 120.8 ?
C44 C45 H45 . . 120.8 ?
C32 C33 C34 . . 118.65(10) ?
C32 C33 H33 . . 120.7 ?
C34 C33 H33 . . 120.7 ?
C45 C44 C49 . . 120.13(8) ?
C45 C44 C43 . . 132.15(9) ?
C49 C44 C43 . . 107.72(7) ?
C42 C43 C44 . . 108.06(8) ?
C42 C43 H43 . . 126.0 ?
C44 C43 H43 . . 126.0 ?
C33 C32 C31 . . 120.96(9) ?
C33 C32 H32 . . 119.5 ?
C31 C32 H32 . . 119.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 P1 N1 C1 . . . . -21.72(8) ?
N3 P1 N1 C1 . . . . -144.18(6) ?
C28 P1 N1 C1 . . . . 105.52(7) ?
O1 P1 N1 C8 . . . . -166.42(6) ?
N3 P1 N1 C8 . . . . 71.13(7) ?
C28 P1 N1 C8 . . . . -39.17(7) ?
C8 N1 C1 C2 . . . . -173.23(8) ?
P1 N1 C1 C2 . . . . 37.09(12) ?
C8 N1 C1 C6 . . . . 2.63(8) ?
P1 N1 C1 C6 . . . . -147.06(6) ?
C6 C1 C2 C3 . . . . 2.32(12) ?
N1 C1 C2 C3 . . . . 177.67(8) ?
O1 P1 N3 C21 . . . . 29.86(7) ?
N1 P1 N3 C21 . . . . 151.41(6) ?
C28 P1 N3 C21 . . . . -96.29(6) ?
O1 P1 N3 C14 . . . . 179.32(6) ?
N1 P1 N3 C14 . . . . -59.13(7) ?
C28 P1 N3 C14 . . . . 53.17(7) ?
C1 C2 C3 C4 . . . . -0.41(13) ?
O4 P2 N4 C29 . . . . -26.19(8) ?
N6 P2 N4 C29 . . . . -147.65(7) ?
C50 P2 N4 C29 . . . . 99.60(7) ?
O4 P2 N4 C36 . . . . -174.27(7) ?
N6 P2 N4 C36 . . . . 64.26(8) ?
C50 P2 N4 C36 . . . . -48.49(8) ?
C2 C3 C4 C5 . . . . -1.32(15) ?
C3 C4 C5 C6 . . . . 1.12(14) ?
O4 P2 N6 C49 . . . . 19.51(8) ?
N4 P2 N6 C49 . . . . 140.81(7) ?
C50 P2 N6 C49 . . . . -106.71(7) ?
O4 P2 N6 C42 . . . . 176.42(6) ?
N4 P2 N6 C42 . . . . -62.28(7) ?
C50 P2 N6 C42 . . . . 50.20(7) ?
C4 C5 C6 C1 . . . . 0.75(13) ?
C4 C5 C6 C7 . . . . -175.92(9) ?
C2 C1 C6 C5 . . . . -2.54(12) ?
N1 C1 C6 C5 . . . . -178.78(7) ?
C2 C1 C6 C7 . . . . 174.88(8) ?
N1 C1 C6 C7 . . . . -1.36(9) ?
C16 C17 C18 C19 . . . . -0.29(14) ?
C5 C6 C7 C8 . . . . 176.48(9) ?
C1 C6 C7 C8 . . . . -0.48(9) ?
C6 C7 C8 N1 . . . . 2.15(9) ?
C6 C7 C8 C9 . . . . -168.39(8) ?
C1 N1 C8 C7 . . . . -2.98(9) ?
P1 N1 C8 C7 . . . . 146.23(6) ?
C1 N1 C8 C9 . . . . 168.30(7) ?
P1 N1 C8 C9 . . . . -42.49(10) ?
C7 C8 C9 C13 . . . . 168.81(9) ?
N1 C8 C9 C13 . . . . -0.70(14) ?
C7 C8 C9 C10 . . . . -2.70(13) ?
N1 C8 C9 C10 . . . . -172.22(7) ?
C12 N2 C10 O2 . . . . 178.76(8) ?
C11 N2 C10 O2 . . . . 4.30(14) ?
C12 N2 C10 C9 . . . . -0.62(9) ?
C11 N2 C10 C9 . . . . -175.08(8) ?
C13 C9 C10 O2 . . . . 179.99(9) ?
C8 C9 C10 O2 . . . . -6.59(13) ?
C13 C9 C10 N2 . . . . -0.66(9) ?
C8 C9 C10 N2 . . . . 172.76(7) ?
C21 N3 C14 C15 . . . . -1.08(9) ?
P1 N3 C14 C15 . . . . -154.26(6) ?
C21 N3 C14 C13 . . . . 179.37(7) ?
P1 N3 C14 C13 . . . . 26.19(11) ?
C8 C9 C13 C14 . . . . 6.99(16) ?
C10 C9 C13 C14 . . . . 179.21(8) ?
C8 C9 C13 C12 . . . . -170.68(8) ?
C10 C9 C13 C12 . . . . 1.54(8) ?
C15 C14 C13 C9 . . . . -179.49(9) ?
N3 C14 C13 C9 . . . . -0.03(14) ?
C15 C14 C13 C12 . . . . -2.03(12) ?
N3 C14 C13 C12 . . . . 177.43(7) ?
C10 N2 C12 O3 . . . . -177.18(8) ?
C11 N2 C12 O3 . . . . -2.61(13) ?
C10 N2 C12 C13 . . . . 1.55(9) ?
C11 N2 C12 C13 . . . . 176.12(7) ?
C9 C13 C12 O3 . . . . 176.71(9) ?
C14 C13 C12 O3 . . . . -1.38(13) ?
C9 C13 C12 N2 . . . . -1.93(9) ?
C14 C13 C12 N2 . . . . 179.98(7) ?
N3 C14 C15 C16 . . . . 1.04(9) ?
C13 C14 C15 C16 . . . . -179.43(8) ?
C18 C17 C16 C21 . . . . -0.09(13) ?
C18 C17 C16 C15 . . . . 178.62(9) ?
C14 C15 C16 C17 . . . . -179.43(9) ?
C14 C15 C16 C21 . . . . -0.60(9) ?
O1 P1 C28 C23 . . . . 83.13(7) ?
N3 P1 C28 C23 . . . . -152.40(6) ?
N1 P1 C28 C23 . . . . -41.71(7) ?
O1 P1 C28 C27 . . . . -89.28(7) ?
N3 P1 C28 C27 . . . . 35.19(7) ?
N1 P1 C28 C27 . . . . 145.89(6) ?
C17 C18 C19 C20 . . . . 0.36(14) ?
C31 C30 C29 C34 . . . . 1.96(13) ?
C31 C30 C29 N4 . . . . 179.77(9) ?
C36 N4 C29 C30 . . . . -177.33(9) ?
P2 N4 C29 C30 . . . . 29.86(13) ?
C36 N4 C29 C34 . . . . 0.72(9) ?
P2 N4 C29 C34 . . . . -152.10(6) ?
C30 C29 C34 C33 . . . . -1.98(13) ?
N4 C29 C34 C33 . . . . 179.78(8) ?
C30 C29 C34 C35 . . . . 177.33(8) ?
N4 C29 C34 C35 . . . . -0.92(10) ?
C36 C35 C34 C33 . . . . 179.94(10) ?
C36 C35 C34 C29 . . . . 0.77(10) ?
C40 N5 C38 O5 . . . . 178.05(9) ?
C39 N5 C38 O5 . . . . -2.56(15) ?
C40 N5 C38 C37 . . . . -1.03(10) ?
C39 N5 C38 C37 . . . . 178.36(8) ?
C34 C35 C36 N4 . . . . -0.33(10) ?
C34 C35 C36 C37 . . . . -178.68(8) ?
C29 N4 C36 C35 . . . . -0.24(9) ?
P2 N4 C36 C35 . . . . 151.74(7) ?
C29 N4 C36 C37 . . . . 178.21(8) ?
P2 N4 C36 C37 . . . . -29.81(12) ?
C18 C19 C20 C21 . . . . -0.03(13) ?
C35 C36 C37 C41 . . . . 172.96(9) ?
N4 C36 C37 C41 . . . . -5.19(15) ?
C35 C36 C37 C38 . . . . -2.98(13) ?
N4 C36 C37 C38 . . . . 178.88(7) ?
O5 C38 C37 C41 . . . . -176.96(9) ?
N5 C38 C37 C41 . . . . 2.06(10) ?
O5 C38 C37 C36 . . . . -0.06(14) ?
N5 C38 C37 C36 . . . . 178.96(8) ?
C19 C20 C21 N3 . . . . -178.49(8) ?
C19 C20 C21 C16 . . . . -0.36(12) ?
C14 N3 C21 C20 . . . . 179.04(8) ?
P1 N3 C21 C20 . . . . -26.94(11) ?
C14 N3 C21 C16 . . . . 0.70(8) ?
P1 N3 C21 C16 . . . . 154.73(6) ?
C17 C16 C21 C20 . . . . 0.43(12) ?
C15 C16 C21 C20 . . . . -178.58(7) ?
C17 C16 C21 N3 . . . . 178.93(7) ?
C15 C16 C21 N3 . . . . -0.08(9) ?
C38 N5 C40 O6 . . . . 179.17(9) ?
C39 N5 C40 O6 . . . . -0.21(15) ?
C38 N5 C40 C41 . . . . -0.29(10) ?
C39 N5 C40 C41 . . . . -179.67(8) ?
C36 C37 C41 C42 . . . . -3.76(17) ?
C38 C37 C41 C42 . . . . 172.53(9) ?
C36 C37 C41 C40 . . . . -178.50(9) ?
C38 C37 C41 C40 . . . . -2.20(9) ?
O6 C40 C41 C37 . . . . -177.81(10) ?
N5 C40 C41 C37 . . . . 1.63(9) ?
O6 C40 C41 C42 . . . . 6.61(14) ?
N5 C40 C41 C42 . . . . -173.95(7) ?
C29 C30 C31 C32 . . . . -0.38(14) ?
C49 N6 C42 C43 . . . . -0.53(9) ?
P2 N6 C42 C43 . . . . -160.74(6) ?
C49 N6 C42 C41 . . . . -174.88(8) ?
P2 N6 C42 C41 . . . . 24.91(11) ?
C37 C41 C42 C43 . . . . -161.29(9) ?
C40 C41 C42 C43 . . . . 12.98(13) ?
C37 C41 C42 N6 . . . . 12.03(14) ?
C40 C41 C42 N6 . . . . -173.71(7) ?
C27 C26 C25 C24 . . . . 0.12(15) ?
C26 C25 C24 C23 . . . . -0.65(15) ?
C25 C24 C23 C28 . . . . 0.27(14) ?
C27 C28 C23 C24 . . . . 0.64(12) ?
P1 C28 C23 C24 . . . . -171.71(7) ?
C25 C26 C27 C28 . . . . 0.78(13) ?
C23 C28 C27 C26 . . . . -1.16(12) ?
P1 C28 C27 C26 . . . . 171.22(7) ?
C53 C54 C55 C50 . . . . -0.33(13) ?
C55 C54 C53 C52 . . . . 2.01(15) ?
C54 C53 C52 C51 . . . . -1.69(15) ?
C53 C52 C51 C50 . . . . -0.30(15) ?
C54 C55 C50 C51 . . . . -1.65(13) ?
C54 C55 C50 P2 . . . . 168.99(7) ?
C52 C51 C50 C55 . . . . 1.97(13) ?
C52 C51 C50 P2 . . . . -168.72(7) ?
O4 P2 C50 C55 . . . . -89.22(7) ?
N6 P2 C50 C55 . . . . 35.14(8) ?
N4 P2 C50 C55 . . . . 147.04(7) ?
O4 P2 C50 C51 . . . . 81.47(8) ?
N6 P2 C50 C51 . . . . -154.17(7) ?
N4 P2 C50 C51 . . . . -42.28(8) ?
C42 N6 C49 C48 . . . . -179.16(9) ?
P2 N6 C49 C48 . . . . -18.77(13) ?
C42 N6 C49 C44 . . . . 1.28(9) ?
P2 N6 C49 C44 . . . . 161.66(6) ?
C44 C49 C48 C47 . . . . 0.26(14) ?
N6 C49 C48 C47 . . . . -179.26(9) ?
C49 C48 C47 C46 . . . . 0.80(15) ?
C48 C47 C46 C45 . . . . -0.61(16) ?
C47 C46 C45 C44 . . . . -0.66(15) ?
C29 C34 C33 C32 . . . . 0.34(14) ?
C35 C34 C33 C32 . . . . -178.75(10) ?
C46 C45 C44 C49 . . . . 1.68(14) ?
C46 C45 C44 C43 . . . . -178.79(10) ?
C48 C49 C44 C45 . . . . -1.51(13) ?
N6 C49 C44 C45 . . . . 178.10(8) ?
C48 C49 C44 C43 . . . . 178.86(8) ?
N6 C49 C44 C43 . . . . -1.53(9) ?
N6 C42 C43 C44 . . . . -0.42(10) ?
C41 C42 C43 C44 . . . . 173.67(8) ?
C45 C44 C43 C42 . . . . -178.36(9) ?
C49 C44 C43 C42 . . . . 1.21(10) ?
C34 C33 C32 C31 . . . . 1.20(15) ?
C30 C31 C32 C33 . . . . -1.21(15) ?

