# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_kir9-final
_database_code_depnum_ccdc_archive 'CCDC 1542634'
_audit_update_record             
;
2017-04-06 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H28 F2 N2 O2 P'
_chemical_formula_weight         601.58

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   38.86(2)
_cell_length_b                   8.799(5)
_cell_length_c                   17.269(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.512(7)
_cell_angle_gamma                90
_cell_volume                     5878(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1744
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             2504
_exptl_transmission_factor_min   0.966
_exptl_transmission_factor_max   0.983
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus X-ray tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28391
_diffrn_reflns_av_unetI/netI     0.1799
_diffrn_reflns_av_R_equivalents  0.1310
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.106
_diffrn_reflns_theta_max         26.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6119
_reflns_number_gt                1891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6119
_refine_ls_number_parameters     406
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1981
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_restrained_S_all      0.737
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.83119(2) 0.78639(12) 0.97434(5) 0.0517(3) Uani 1 1 d . . . . .
H1 H 0.7947(6) 0.733(3) 0.9501(14) 0.065(9) Uiso 1 1 d . . . . .
O1 O 0.82096(6) 0.8158(3) 1.06834(11) 0.0542(6) Uani 1 1 d . . . . .
C2 C 0.79993(9) 0.9356(5) 1.08565(19) 0.0491(9) Uani 1 1 d . . . . .
C3 C 0.77305(9) 0.9045(5) 1.13255(19) 0.0611(11) Uani 1 1 d . . . . .
H3A H 0.7689 0.8059 1.1487 0.073 Uiso 1 1 calc R U . . .
C4 C 0.75334(9) 1.0218(5) 1.15351(19) 0.0645(11) Uani 1 1 d . . . . .
H4A H 0.7358 1.0026 1.1853 0.077 Uiso 1 1 calc R U . . .
C5 C 0.75852(9) 1.1721(5) 1.1288(2) 0.0535(10) Uani 1 1 d . . . . .
C6 C 0.73778(9) 1.2919(5) 1.1509(2) 0.0657(11) Uani 1 1 d . . . . .
H6A H 0.7203 1.2724 1.1829 0.079 Uiso 1 1 calc R U . . .
C7 C 0.74282(10) 1.4358(5) 1.1262(2) 0.0685(12) Uani 1 1 d . . . . .
H7A H 0.7291 1.5149 1.1416 0.082 Uiso 1 1 calc R U . . .
C8 C 0.76874(10) 1.4640(4) 1.0776(2) 0.0643(11) Uani 1 1 d . . . . .
H8A H 0.7720 1.5626 1.0604 0.077 Uiso 1 1 calc R U . . .
C9 C 0.78920(9) 1.3516(5) 1.05496(19) 0.0576(10) Uani 1 1 d . . . . .
H9A H 0.8060 1.3742 1.0219 0.069 Uiso 1 1 calc R U . . .
C10 C 0.78552(8) 1.2012(5) 1.08038(18) 0.0461(9) Uani 1 1 d . . . . .
C11 C 0.80630(9) 1.0769(4) 1.06030(18) 0.0470(9) Uani 1 1 d . . . . .
C12 C 0.83749(8) 1.0938(4) 1.01431(18) 0.0491(9) Uani 1 1 d . . . . .
H12A H 0.8342 1.1864 0.9830 0.059 Uiso 1 1 calc R U . . .
N13 N 0.83937(7) 0.9657(3) 0.96039(17) 0.0489(8) Uani 1 1 d . . . . .
H13 H 0.8488(7) 0.983(3) 0.9154(16) 0.067(12) Uiso 1 1 d . . . . .
O14 O 0.84107(5) 0.7574(3) 0.88052(11) 0.0548(6) Uani 1 1 d . . . . .
C15 C 0.84603(9) 0.6143(4) 0.85159(19) 0.0517(10) Uani 1 1 d . . . . .
C16 C 0.83031(8) 0.5808(4) 0.77668(18) 0.0551(10) Uani 1 1 d . . . . .
H16A H 0.8163 0.6520 0.7492 0.066 Uiso 1 1 calc R U . . .
C17 C 0.83605(9) 0.4421(5) 0.7452(2) 0.0628(11) Uani 1 1 d . . . . .
H17A H 0.8255 0.4188 0.6960 0.075 Uiso 1 1 calc R U . . .
C18 C 0.85738(9) 0.3341(5) 0.7849(2) 0.0562(10) Uani 1 1 d . . . . .
C19 C 0.86293(10) 0.1881(5) 0.7534(2) 0.0710(12) Uani 1 1 d . . . . .
H19A H 0.8519 0.1615 0.7051 0.085 Uiso 1 1 calc R U . . .
C20 C 0.88423(11) 0.0871(5) 0.7934(2) 0.0777(13) Uani 1 1 d . . . . .
H20A H 0.8874 -0.0088 0.7727 0.093 Uiso 1 1 calc R U . . .
C21 C 0.90114(10) 0.1251(5) 0.8645(2) 0.0703(11) Uani 1 1 d . . . . .
H21A H 0.9161 0.0557 0.8907 0.084 Uiso 1 1 calc R U . . .
C22 C 0.89608(9) 0.2633(4) 0.8966(2) 0.0588(10) Uani 1 1 d . . . . .
H22A H 0.9079 0.2871 0.9445 0.071 Uiso 1 1 calc R U . . .
C23 C 0.87377(9) 0.3701(4) 0.86008(19) 0.0478(9) Uani 1 1 d . . . . .
C24 C 0.86690(8) 0.5132(4) 0.89299(18) 0.0463(9) Uani 1 1 d . . . . .
C25 C 0.88257(9) 0.5591(4) 0.97316(18) 0.0517(10) Uani 1 1 d . . . . .
H25A H 0.8847 0.4654 1.0039 0.062 Uiso 1 1 calc R U . . .
N26 N 0.85826(7) 0.6575(3) 1.01090(17) 0.0533(9) Uani 1 1 d . . . . .
H26 H 0.8620(7) 0.649(3) 1.0579(16) 0.052(11) Uiso 1 1 d . . . . .
C27 C 0.87106(9) 1.1141(4) 1.06911(18) 0.0463(9) Uani 1 1 d . . . . .
C28 C 0.87375(9) 1.2330(4) 1.12153(19) 0.0545(10) Uani 1 1 d . . . . .
H28A H 0.8549 1.2971 1.1245 0.065 Uiso 1 1 calc R U . . .
C29 C 0.90349(11) 1.2594(4) 1.1695(2) 0.0670(11) Uani 1 1 d . . . . .
H29A H 0.9050 1.3402 1.2043 0.080 Uiso 1 1 calc R U . . .
C30 C 0.93066(11) 1.1635(5) 1.1643(2) 0.0660(12) Uani 1 1 d . . . . .
F30 F 0.96004(6) 1.1872(3) 1.21210(13) 0.1029(8) Uani 1 1 d . . . . .
C31 C 0.92956(10) 1.0436(5) 1.1149(2) 0.0679(11) Uani 1 1 d . . . . .
H31A H 0.9484 0.9788 1.1133 0.081 Uiso 1 1 calc R U . . .
C32 C 0.89943(10) 1.0212(4) 1.06705(19) 0.0584(10) Uani 1 1 d . . . . .
H32A H 0.8983 0.9404 1.0322 0.070 Uiso 1 1 calc R U . . .
C33 C 0.91905(9) 0.6239(4) 0.9743(2) 0.0516(9) Uani 1 1 d . . . . .
C34 C 0.94218(11) 0.6035(5) 1.0393(2) 0.0891(14) Uani 1 1 d . . . . .
H34A H 0.9355 0.5486 1.0814 0.107 Uiso 1 1 calc R U . . .
C35 C 0.97516(12) 0.6636(6) 1.0426(3) 0.1090(18) Uani 1 1 d . . . . .
H35A H 0.9908 0.6477 1.0860 0.131 Uiso 1 1 calc R U . . .
C36 C 0.98419(11) 0.7452(6) 0.9824(3) 0.0916(15) Uani 1 1 d . . . . .
F36 F 1.01643(7) 0.8038(3) 0.98680(15) 0.1414(11) Uani 1 1 d . . . . .
C37 C 0.96281(11) 0.7697(5) 0.9170(2) 0.0845(13) Uani 1 1 d . . . . .
H37A H 0.9699 0.8260 0.8759 0.101 Uiso 1 1 calc R U . . .
C38 C 0.92990(10) 0.7075(4) 0.9139(2) 0.0696(11) Uani 1 1 d . . . . .
H38A H 0.9147 0.7230 0.8696 0.084 Uiso 1 1 calc R U . . .
C1A C 1.03317(6) 0.7144(2) 1.2392(4) 0.076(2) Uiso 0.5 1 d D . P A -1
H1A H 1.0557 0.7417 1.2319 0.091 Uiso 0.5 1 calc R U P A -1
C2A C 1.02446(6) 0.5610(2) 1.2462(4) 0.079(2) Uiso 0.5 1 d D . P A -1
H2A H 1.0410 0.4861 1.2415 0.095 Uiso 0.5 1 calc R U P A -1
C3A C 0.99079(6) 0.52021(18) 1.2602(4) 0.083(3) Uiso 0.5 1 d D . P A -1
H3A1 H 0.9850 0.4183 1.2647 0.100 Uiso 0.5 1 calc R U P A -1
C4A C 0.96589(6) 0.6330(2) 1.2675(4) 0.078(2) Uiso 0.5 1 d D . P A -1
H4A1 H 0.9438 0.6062 1.2793 0.094 Uiso 0.5 1 calc R U P A -1
C5A C 0.97420(5) 0.7859(2) 1.2570(4) 0.075(2) Uiso 0.5 1 d D . P A -1
H5A H 0.9573 0.8604 1.2593 0.090 Uiso 0.5 1 calc R U P A -1
C6A C 1.00788(6) 0.8268(2) 1.2432(4) 0.076(2) Uiso 0.5 1 d D . P A -1
H6A1 H 1.0135 0.9284 1.2367 0.092 Uiso 0.5 1 calc R U P A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N13 1.632(3) . ?
P1 N26 1.632(3) . ?
P1 O14 1.720(2) . ?
P1 O1 1.727(2) . ?
P1 H1 1.51(3) . ?
O1 C2 1.385(4) . ?
C2 C11 1.349(4) . ?
C2 C3 1.409(4) . ?
C3 C4 1.355(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.410(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.402(4) . ?
C5 C10 1.426(4) . ?
C6 C7 1.356(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.394(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.350(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.406(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.422(4) . ?
C11 C12 1.519(4) . ?
C12 N13 1.468(4) . ?
C12 C27 1.547(4) . ?
C12 H12A 0.9800 . ?
N13 H13 0.90(3) . ?
O14 C15 1.375(4) . ?
C15 C24 1.360(4) . ?
C15 C16 1.408(4) . ?
C16 C17 1.363(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.397(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.420(5) . ?
C18 C23 1.426(4) . ?
C19 C20 1.358(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.377(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.359(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.388(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.418(4) . ?
C24 C25 1.513(4) . ?
C25 N26 1.478(4) . ?
C25 C33 1.526(4) . ?
C25 H25A 0.9800 . ?
N26 H26 0.81(3) . ?
C27 C32 1.376(4) . ?
C27 C28 1.381(4) . ?
C28 C29 1.375(4) . ?
C28 H28A 0.9300 . ?
C29 C30 1.361(5) . ?
C29 H29A 0.9300 . ?
C30 C31 1.355(5) . ?
C30 F30 1.359(4) . ?
C31 C32 1.381(4) . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9300 . ?
C33 C38 1.375(4) . ?
C33 C34 1.381(4) . ?
C34 C35 1.383(5) . ?
C34 H34A 0.9300 . ?
C35 C36 1.338(5) . ?
C35 H35A 0.9300 . ?
C36 F36 1.350(4) . ?
C36 C37 1.352(5) . ?
C37 C38 1.387(4) . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
C1A C2A 1.4000(8) . ?
C1A C6A 1.4000(6) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.4000(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.4000(6) . ?
C3A H3A1 0.9300 . ?
C4A C5A 1.4000(7) . ?
C4A H4A1 0.9300 . ?
C5A C6A 1.4000(7) . ?
C5A H5A 0.9300 . ?
C6A H6A1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N13 P1 N26 126.99(15) . . ?
N13 P1 O14 86.55(14) . . ?
N26 P1 O14 93.87(14) . . ?
N13 P1 O1 93.43(14) . . ?
N26 P1 O1 86.47(14) . . ?
O14 P1 O1 179.59(12) . . ?
N13 P1 H1 116.7(9) . . ?
N26 P1 H1 116.3(9) . . ?
O14 P1 H1 89.0(9) . . ?
O1 P1 H1 90.7(9) . . ?
C2 O1 P1 120.7(2) . . ?
C11 C2 O1 120.1(3) . . ?
C11 C2 C3 122.3(4) . . ?
O1 C2 C3 117.5(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C3 C4 C5 122.2(4) . . ?
C3 C4 H4A 118.9 . . ?
C5 C4 H4A 118.9 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 C10 120.0(4) . . ?
C4 C5 C10 118.7(4) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 119.4(4) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C9 C10 C11 124.8(4) . . ?
C9 C10 C5 117.0(3) . . ?
C11 C10 C5 118.1(4) . . ?
C2 C11 C10 120.2(3) . . ?
C2 C11 C12 116.1(3) . . ?
C10 C11 C12 123.6(3) . . ?
N13 C12 C11 110.3(3) . . ?
N13 C12 C27 112.7(3) . . ?
C11 C12 C27 111.1(3) . . ?
N13 C12 H12A 107.5 . . ?
C11 C12 H12A 107.5 . . ?
C27 C12 H12A 107.5 . . ?
C12 N13 P1 128.8(2) . . ?
C12 N13 H13 118(2) . . ?
P1 N13 H13 113(2) . . ?
C15 O14 P1 122.0(2) . . ?
C24 C15 O14 120.4(3) . . ?
C24 C15 C16 122.0(4) . . ?
O14 C15 C16 117.5(3) . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17A 119.1 . . ?
C18 C17 H17A 119.1 . . ?
C17 C18 C19 122.2(4) . . ?
C17 C18 C23 119.2(4) . . ?
C19 C18 C23 118.6(4) . . ?
C20 C19 C18 120.3(4) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 C21 120.7(4) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 121.9(4) . . ?
C21 C22 H22A 119.1 . . ?
C23 C22 H22A 119.1 . . ?
C22 C23 C24 123.5(3) . . ?
C22 C23 C18 118.0(4) . . ?
C24 C23 C18 118.5(4) . . ?
C15 C24 C23 119.8(3) . . ?
C15 C24 C25 118.3(3) . . ?
C23 C24 C25 121.9(3) . . ?
N26 C25 C24 110.0(3) . . ?
N26 C25 C33 114.1(3) . . ?
C24 C25 C33 113.7(3) . . ?
N26 C25 H25A 106.1 . . ?
C24 C25 H25A 106.1 . . ?
C33 C25 H25A 106.1 . . ?
C25 N26 P1 130.7(2) . . ?
C25 N26 H26 109(2) . . ?
P1 N26 H26 120(2) . . ?
C32 C27 C28 117.2(3) . . ?
C32 C27 C12 123.1(3) . . ?
C28 C27 C12 119.7(3) . . ?
C29 C28 C27 121.9(3) . . ?
C29 C28 H28A 119.0 . . ?
C27 C28 H28A 119.0 . . ?
C30 C29 C28 117.9(4) . . ?
C30 C29 H29A 121.0 . . ?
C28 C29 H29A 121.0 . . ?
C31 C30 F30 118.4(4) . . ?
C31 C30 C29 123.1(4) . . ?
F30 C30 C29 118.5(4) . . ?
C30 C31 C32 117.5(4) . . ?
C30 C31 H31A 121.3 . . ?
C32 C31 H31A 121.3 . . ?
C27 C32 C31 122.4(3) . . ?
C27 C32 H32A 118.8 . . ?
C31 C32 H32A 118.8 . . ?
C38 C33 C34 117.6(4) . . ?
C38 C33 C25 122.9(3) . . ?
C34 C33 C25 119.5(3) . . ?
C33 C34 C35 120.8(4) . . ?
C33 C34 H34A 119.6 . . ?
C35 C34 H34A 119.6 . . ?
C36 C35 C34 119.0(4) . . ?
C36 C35 H35A 120.5 . . ?
C34 C35 H35A 120.5 . . ?
C35 C36 F36 118.2(5) . . ?
C35 C36 C37 123.2(4) . . ?
F36 C36 C37 118.6(5) . . ?
C36 C37 C38 117.4(4) . . ?
C36 C37 H37A 121.3 . . ?
C38 C37 H37A 121.3 . . ?
C33 C38 C37 122.0(4) . . ?
C33 C38 H38A 119.0 . . ?
C37 C38 H38A 119.0 . . ?
C2A C1A C6A 120.01(10) . . ?
C2A C1A H1A 120.0 . . ?
C6A C1A H1A 120.0 . . ?
C1A C2A C3A 119.97(6) . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A C2A 119.97(6) . . ?
C4A C3A H3A1 120.0 . . ?
C2A C3A H3A1 120.0 . . ?
C3A C4A C5A 119.98(6) . . ?
C3A C4A H4A1 120.0 . . ?
C5A C4A H4A1 120.0 . . ?
C6A C5A C4A 119.98(6) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C1A C6A C5A 119.96(10) . . ?
C1A C6A H6A1 120.0 . . ?
C5A C6A H6A1 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N13 P1 O1 C2 44.9(3) . . . . ?
N26 P1 O1 C2 171.8(3) . . . . ?
P1 O1 C2 C11 -48.9(4) . . . . ?
P1 O1 C2 C3 133.6(2) . . . . ?
C11 C2 C3 C4 -0.9(5) . . . . ?
O1 C2 C3 C4 176.6(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C3 C4 C5 C10 -0.3(5) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C10 C5 C6 C7 0.6(5) . . . . ?
C5 C6 C7 C8 0.7(5) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C8 C9 C10 C11 -179.0(3) . . . . ?
C8 C9 C10 C5 2.1(5) . . . . ?
C6 C5 C10 C9 -2.0(4) . . . . ?
C4 C5 C10 C9 178.1(3) . . . . ?
C6 C5 C10 C11 179.1(3) . . . . ?
C4 C5 C10 C11 -0.9(4) . . . . ?
O1 C2 C11 C10 -177.7(3) . . . . ?
C3 C2 C11 C10 -0.2(5) . . . . ?
O1 C2 C11 C12 -1.0(4) . . . . ?
C3 C2 C11 C12 176.5(3) . . . . ?
C9 C10 C11 C2 -177.8(3) . . . . ?
C5 C10 C11 C2 1.1(5) . . . . ?
C9 C10 C11 C12 5.8(5) . . . . ?
C5 C10 C11 C12 -175.3(3) . . . . ?
C2 C11 C12 N13 41.3(4) . . . . ?
C10 C11 C12 N13 -142.1(3) . . . . ?
C2 C11 C12 C27 -84.5(4) . . . . ?
C10 C11 C12 C27 92.1(4) . . . . ?
C11 C12 N13 P1 -39.3(4) . . . . ?
C27 C12 N13 P1 85.6(3) . . . . ?
N26 P1 N13 C12 -88.2(3) . . . . ?
O14 P1 N13 C12 179.5(3) . . . . ?
O1 P1 N13 C12 -0.1(3) . . . . ?
N13 P1 O14 C15 167.8(3) . . . . ?
N26 P1 O14 C15 40.9(3) . . . . ?
P1 O14 C15 C24 -47.9(4) . . . . ?
P1 O14 C15 C16 135.4(2) . . . . ?
C24 C15 C16 C17 0.5(5) . . . . ?
O14 C15 C16 C17 177.1(3) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 C19 178.6(3) . . . . ?
C16 C17 C18 C23 -0.4(5) . . . . ?
C17 C18 C19 C20 179.2(3) . . . . ?
C23 C18 C19 C20 -1.8(5) . . . . ?
C18 C19 C20 C21 -1.0(6) . . . . ?
C19 C20 C21 C22 1.7(6) . . . . ?
C20 C21 C22 C23 0.6(6) . . . . ?
C21 C22 C23 C24 177.7(3) . . . . ?
C21 C22 C23 C18 -3.3(5) . . . . ?
C17 C18 C23 C22 -177.1(3) . . . . ?
C19 C18 C23 C22 3.9(5) . . . . ?
C17 C18 C23 C24 1.9(5) . . . . ?
C19 C18 C23 C24 -177.1(3) . . . . ?
O14 C15 C24 C23 -175.5(3) . . . . ?
C16 C15 C24 C23 1.1(5) . . . . ?
O14 C15 C24 C25 3.7(5) . . . . ?
C16 C15 C24 C25 -179.8(3) . . . . ?
C22 C23 C24 C15 176.7(3) . . . . ?
C18 C23 C24 C15 -2.3(5) . . . . ?
C22 C23 C24 C25 -2.4(5) . . . . ?
C18 C23 C24 C25 178.6(3) . . . . ?
C15 C24 C25 N26 33.8(4) . . . . ?
C23 C24 C25 N26 -147.1(3) . . . . ?
C15 C24 C25 C33 -95.5(4) . . . . ?
C23 C24 C25 C33 83.6(4) . . . . ?
C24 C25 N26 P1 -35.6(4) . . . . ?
C33 C25 N26 P1 93.5(4) . . . . ?
N13 P1 N26 C25 -86.9(3) . . . . ?
O14 P1 N26 C25 1.7(3) . . . . ?
O1 P1 N26 C25 -178.5(3) . . . . ?
N13 C12 C27 C32 -0.1(4) . . . . ?
C11 C12 C27 C32 124.3(3) . . . . ?
N13 C12 C27 C28 177.9(3) . . . . ?
C11 C12 C27 C28 -57.7(4) . . . . ?
C32 C27 C28 C29 0.6(5) . . . . ?
C12 C27 C28 C29 -177.5(3) . . . . ?
C27 C28 C29 C30 -0.3(5) . . . . ?
C28 C29 C30 C31 -0.6(6) . . . . ?
C28 C29 C30 F30 -179.1(3) . . . . ?
F30 C30 C31 C32 179.8(3) . . . . ?
C29 C30 C31 C32 1.2(6) . . . . ?
C28 C27 C32 C31 0.1(5) . . . . ?
C12 C27 C32 C31 178.1(3) . . . . ?
C30 C31 C32 C27 -0.9(5) . . . . ?
N26 C25 C33 C38 -94.1(4) . . . . ?
C24 C25 C33 C38 33.1(5) . . . . ?
N26 C25 C33 C34 83.5(4) . . . . ?
C24 C25 C33 C34 -149.2(3) . . . . ?
C38 C33 C34 C35 -0.9(6) . . . . ?
C25 C33 C34 C35 -178.6(4) . . . . ?
C33 C34 C35 C36 1.5(7) . . . . ?
C34 C35 C36 F36 179.6(4) . . . . ?
C34 C35 C36 C37 -1.4(8) . . . . ?
C35 C36 C37 C38 0.7(7) . . . . ?
F36 C36 C37 C38 179.7(4) . . . . ?
C34 C33 C38 C37 0.2(6) . . . . ?
C25 C33 C38 C37 177.9(3) . . . . ?
C36 C37 C38 C33 -0.1(6) . . . . ?
C6A C1A C2A C3A -2.5(8) . . . . ?
C1A C2A C3A C4A -0.2(8) . . . . ?
C2A C3A C4A C5A 3.1(9) . . . . ?
C3A C4A C5A C6A -3.2(9) . . . . ?
C2A C1A C6A C5A 2.4(10) . . . . ?
C4A C5A C6A C1A 0.5(9) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_alf1a
_database_code_depnum_ccdc_archive 'CCDC 1542633'
_audit_update_record             
;
2017-04-06 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H27 N2 O2 P'
_chemical_formula_sum            'C34 H27 N2 O2 P'
_chemical_formula_weight         526.54

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.6029(2)
_cell_length_b                   15.2183(3)
_cell_length_c                   20.4343(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2675.29(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9792
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   0.6975
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.389
_exptl_crystal_size_min          0.152
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus X-ray tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49141
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.668
_diffrn_reflns_theta_max         31.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             8492
_reflns_number_gt                7309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.976

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2788 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8492
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.89015(6) 0.79597(3) 0.40739(2) 0.02051(10) Uani 1 1 d . . . . .
H1 H 0.758(2) 0.7605(13) 0.4182(9) 0.023(5) Uiso 1 1 d . . . . .
O1 O 0.87498(16) 0.84058(8) 0.48409(6) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.9650(2) 0.90991(12) 0.50404(9) 0.0224(4) Uani 1 1 d . . . . .
C3 C 1.0380(2) 0.90507(13) 0.56574(9) 0.0282(4) Uani 1 1 d . . . . .
H3A H 1.0350 0.8522 0.5904 0.034 Uiso 1 1 calc R U . . .
C4 C 1.1131(3) 0.97735(14) 0.58951(10) 0.0320(4) Uani 1 1 d . . . . .
H4A H 1.1632 0.9741 0.6309 0.038 Uiso 1 1 calc R U . . .
C5 C 1.1180(2) 1.05699(13) 0.55394(10) 0.0295(4) Uani 1 1 d . . . . .
C6 C 1.1867(3) 1.13418(15) 0.58003(11) 0.0388(5) Uani 1 1 d . . . . .
H6A H 1.2349 1.1320 0.6218 0.047 Uiso 1 1 calc R U . . .
C7 C 1.1851(3) 1.21082(16) 0.54652(12) 0.0447(6) Uani 1 1 d . . . . .
H7A H 1.2301 1.2620 0.5652 0.054 Uiso 1 1 calc R U . . .
C8 C 1.1171(3) 1.21484(14) 0.48434(12) 0.0403(5) Uani 1 1 d . . . . .
H8A H 1.1164 1.2689 0.4611 0.048 Uiso 1 1 calc R U . . .
C9 C 1.0517(3) 1.14202(13) 0.45663(10) 0.0312(4) Uani 1 1 d . . . . .
H9A H 1.0074 1.1459 0.4142 0.037 Uiso 1 1 calc R U . . .
C10 C 1.0491(2) 1.06018(12) 0.49057(9) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.9754(2) 0.98359(12) 0.46578(8) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.9028(2) 0.98109(11) 0.39876(8) 0.0203(3) Uani 1 1 d . . . . .
H12A H 0.9702 1.0178 0.3697 0.024 Uiso 1 1 calc R U . . .
N13 N 0.9052(2) 0.89184(10) 0.37159(7) 0.0228(3) Uani 1 1 d . . . . .
H13 H 0.909(3) 0.8890(14) 0.3330(10) 0.023(5) Uiso 1 1 d . . . . .
O14 O 0.89086(17) 0.75200(8) 0.32956(6) 0.0239(3) Uani 1 1 d . . . . .
C15 C 0.9153(2) 0.66501(11) 0.31800(8) 0.0216(4) Uani 1 1 d . . . . .
C16 C 0.8164(2) 0.62101(13) 0.27367(9) 0.0263(4) Uani 1 1 d . . . . .
H16A H 0.7340 0.6517 0.2529 0.032 Uiso 1 1 calc R U . . .
C17 C 0.8401(2) 0.53401(13) 0.26092(9) 0.0272(4) Uani 1 1 d . . . . .
H17A H 0.7740 0.5044 0.2309 0.033 Uiso 1 1 calc R U . . .
C18 C 0.9619(2) 0.48725(12) 0.29187(9) 0.0244(4) Uani 1 1 d . . . . .
C19 C 0.9831(3) 0.39574(13) 0.28248(9) 0.0307(4) Uani 1 1 d . . . . .
H19A H 0.9119 0.3644 0.2557 0.037 Uiso 1 1 calc R U . . .
C20 C 1.1028(3) 0.35192(13) 0.31097(10) 0.0360(5) Uani 1 1 d . . . . .
H20A H 1.1142 0.2905 0.3042 0.043 Uiso 1 1 calc R U . . .
C21 C 1.2103(3) 0.39744(13) 0.35059(10) 0.0341(5) Uani 1 1 d . . . . .
H21A H 1.2952 0.3668 0.3696 0.041 Uiso 1 1 calc R U . . .
C22 C 1.1928(3) 0.48579(13) 0.36175(9) 0.0269(4) Uani 1 1 d . . . . .
H22A H 1.2665 0.5158 0.3882 0.032 Uiso 1 1 calc R U . . .
C23 C 1.0661(2) 0.53312(11) 0.33436(8) 0.0218(4) Uani 1 1 d . . . . .
C24 C 1.0389(2) 0.62368(11) 0.34689(8) 0.0199(3) Uani 1 1 d . . . . .
C25 C 1.1383(2) 0.68059(11) 0.39041(8) 0.0198(3) Uani 1 1 d . . . . .
H25A H 1.1978 0.6406 0.4201 0.024 Uiso 1 1 calc R U . . .
N26 N 1.03794(19) 0.73524(10) 0.43169(7) 0.0220(3) Uani 1 1 d . . . . .
H26 H 1.062(3) 0.7388(13) 0.4726(10) 0.021(5) Uiso 1 1 d . . . . .
C27 C 0.7403(2) 1.02071(11) 0.39547(9) 0.0217(3) Uani 1 1 d . . . . .
C28 C 0.6814(2) 1.04227(13) 0.33453(10) 0.0297(4) Uani 1 1 d . . . . .
H28A H 0.7442 1.0342 0.2968 0.036 Uiso 1 1 calc R U . . .
C29 C 0.5327(3) 1.07540(15) 0.32770(12) 0.0391(5) Uani 1 1 d . . . . .
H29A H 0.4933 1.0889 0.2855 0.047 Uiso 1 1 calc R U . . .
C30 C 0.4424(3) 1.08875(15) 0.38195(13) 0.0436(6) Uani 1 1 d . . . . .
H30A H 0.3406 1.1121 0.3773 0.052 Uiso 1 1 calc R U . . .
C31 C 0.4984(3) 1.06854(16) 0.44343(13) 0.0418(5) Uani 1 1 d . . . . .
H31A H 0.4353 1.0778 0.4810 0.050 Uiso 1 1 calc R U . . .
C32 C 0.6480(2) 1.03440(14) 0.45022(10) 0.0318(4) Uani 1 1 d . . . . .
H32A H 0.6868 1.0205 0.4925 0.038 Uiso 1 1 calc R U . . .
C33 C 1.2571(2) 0.73603(11) 0.35270(9) 0.0216(3) Uani 1 1 d . . . . .
C34 C 1.2944(2) 0.72016(12) 0.28824(10) 0.0287(4) Uani 1 1 d . . . . .
H34A H 1.2428 0.6745 0.2652 0.034 Uiso 1 1 calc R U . . .
C35 C 1.4072(3) 0.77033(14) 0.25634(11) 0.0372(5) Uani 1 1 d . . . . .
H35A H 1.4310 0.7593 0.2117 0.045 Uiso 1 1 calc R U . . .
C36 C 1.4839(3) 0.83587(14) 0.28970(13) 0.0404(5) Uani 1 1 d . . . . .
H36A H 1.5614 0.8697 0.2682 0.048 Uiso 1 1 calc R U . . .
C37 C 1.4481(3) 0.85237(15) 0.35421(12) 0.0402(5) Uani 1 1 d . . . . .
H37A H 1.5015 0.8975 0.3772 0.048 Uiso 1 1 calc R U . . .
C38 C 1.3348(2) 0.80352(13) 0.38572(10) 0.0311(4) Uani 1 1 d . . . . .
H38A H 1.3097 0.8159 0.4300 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N13 1.6372(16) . ?
P1 N26 1.6484(16) . ?
P1 O1 1.7129(13) . ?
P1 O14 1.7256(12) . ?
P1 H1 1.28(2) . ?
O1 C2 1.371(2) . ?
C2 C11 1.370(2) . ?
C2 C3 1.410(3) . ?
C3 C4 1.365(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.414(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.419(3) . ?
C5 C10 1.425(3) . ?
C6 C7 1.353(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.400(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.366(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.426(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.420(2) . ?
C11 C12 1.506(2) . ?
C12 N13 1.467(2) . ?
C12 C27 1.524(3) . ?
C12 H12A 1.0000 . ?
N13 H13 0.79(2) . ?
O14 C15 1.361(2) . ?
C15 C24 1.369(3) . ?
C15 C16 1.412(2) . ?
C16 C17 1.365(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.415(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.418(3) . ?
C18 C23 1.430(3) . ?
C19 C20 1.358(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.411(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.372(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.421(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.421(2) . ?
C24 C25 1.507(2) . ?
C25 N26 1.466(2) . ?
C25 C33 1.534(3) . ?
C25 H25A 1.0000 . ?
N26 H26 0.86(2) . ?
C27 C28 1.384(3) . ?
C27 C32 1.388(3) . ?
C28 C29 1.382(3) . ?
C28 H28A 0.9500 . ?
C29 C30 1.369(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.380(4) . ?
C30 H30A 0.9500 . ?
C31 C32 1.395(3) . ?
C31 H31A 0.9500 . ?
C32 H32A 0.9500 . ?
C33 C34 1.377(3) . ?
C33 C38 1.399(3) . ?
C34 C35 1.396(3) . ?
C34 H34A 0.9500 . ?
C35 C36 1.376(3) . ?
C35 H35A 0.9500 . ?
C36 C37 1.377(3) . ?
C36 H36A 0.9500 . ?
C37 C38 1.385(3) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N13 P1 N26 124.98(9) . . ?
N13 P1 O1 93.54(7) . . ?
N26 P1 O1 90.31(7) . . ?
N13 P1 O14 86.18(7) . . ?
N26 P1 O14 93.29(7) . . ?
O1 P1 O14 175.79(8) . . ?
N13 P1 H1 121.6(9) . . ?
N26 P1 H1 113.4(9) . . ?
O1 P1 H1 86.6(9) . . ?
O14 P1 H1 90.0(9) . . ?
C2 O1 P1 122.28(11) . . ?
C11 C2 O1 119.80(16) . . ?
C11 C2 C3 121.60(17) . . ?
O1 C2 C3 118.51(16) . . ?
C4 C3 C2 119.12(18) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 121.47(17) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C4 C5 C6 121.93(18) . . ?
C4 C5 C10 118.94(17) . . ?
C6 C5 C10 119.12(19) . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C11 C10 C5 118.80(17) . . ?
C11 C10 C9 123.41(17) . . ?
C5 C10 C9 117.72(17) . . ?
C2 C11 C10 119.82(16) . . ?
C2 C11 C12 118.13(16) . . ?
C10 C11 C12 122.02(16) . . ?
N13 C12 C11 111.22(14) . . ?
N13 C12 C27 111.24(14) . . ?
C11 C12 C27 114.22(15) . . ?
N13 C12 H12A 106.5 . . ?
C11 C12 H12A 106.5 . . ?
C27 C12 H12A 106.5 . . ?
C12 N13 P1 130.89(12) . . ?
C12 N13 H13 115.4(15) . . ?
P1 N13 H13 113.6(15) . . ?
C15 O14 P1 122.52(11) . . ?
O14 C15 C24 119.47(16) . . ?
O14 C15 C16 118.65(17) . . ?
C24 C15 C16 121.79(16) . . ?
C17 C16 C15 119.51(18) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.87(17) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C17 C18 C19 121.92(18) . . ?
C17 C18 C23 119.33(16) . . ?
C19 C18 C23 118.75(19) . . ?
C20 C19 C18 121.46(18) . . ?
C20 C19 H19A 119.3 . . ?
C18 C19 H19A 119.3 . . ?
C19 C20 C21 120.13(18) . . ?
C19 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 121.01(19) . . ?
C21 C22 H22A 119.5 . . ?
C23 C22 H22A 119.5 . . ?
C24 C23 C22 123.13(16) . . ?
C24 C23 C18 118.67(17) . . ?
C22 C23 C18 118.20(16) . . ?
C15 C24 C23 119.70(16) . . ?
C15 C24 C25 115.52(15) . . ?
C23 C24 C25 124.78(16) . . ?
N26 C25 C24 109.37(15) . . ?
N26 C25 C33 111.70(13) . . ?
C24 C25 C33 113.44(14) . . ?
N26 C25 H25A 107.3 . . ?
C24 C25 H25A 107.3 . . ?
C33 C25 H25A 107.3 . . ?
C25 N26 P1 126.80(12) . . ?
C25 N26 H26 116.8(14) . . ?
P1 N26 H26 116.2(14) . . ?
C28 C27 C32 118.69(18) . . ?
C28 C27 C12 117.99(17) . . ?
C32 C27 C12 123.30(17) . . ?
C29 C28 C27 121.1(2) . . ?
C29 C28 H28A 119.5 . . ?
C27 C28 H28A 119.5 . . ?
C30 C29 C28 119.9(2) . . ?
C30 C29 H29A 120.1 . . ?
C28 C29 H29A 120.1 . . ?
C29 C30 C31 120.4(2) . . ?
C29 C30 H30A 119.8 . . ?
C31 C30 H30A 119.8 . . ?
C30 C31 C32 119.7(2) . . ?
C30 C31 H31A 120.1 . . ?
C32 C31 H31A 120.1 . . ?
C27 C32 C31 120.3(2) . . ?
C27 C32 H32A 119.9 . . ?
C31 C32 H32A 119.9 . . ?
C34 C33 C38 118.61(18) . . ?
C34 C33 C25 122.65(16) . . ?
C38 C33 C25 118.70(16) . . ?
C33 C34 C35 120.84(19) . . ?
C33 C34 H34A 119.6 . . ?
C35 C34 H34A 119.6 . . ?
C36 C35 C34 119.9(2) . . ?
C36 C35 H35A 120.1 . . ?
C34 C35 H35A 120.1 . . ?
C35 C36 C37 120.0(2) . . ?
C35 C36 H36A 120.0 . . ?
C37 C36 H36A 120.0 . . ?
C36 C37 C38 120.3(2) . . ?
C36 C37 H37A 119.8 . . ?
C38 C37 H37A 119.8 . . ?
C37 C38 C33 120.4(2) . . ?
C37 C38 H38A 119.8 . . ?
C33 C38 H38A 119.8 . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.050

