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

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

data_final_a
_database_code_depnum_ccdc_archive 'CCDC 1848994'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-15 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            'C22 H39 N2 O2 P'
_chemical_formula_weight         394.52

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

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

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

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

_cell_length_a                   7.7213(8)
_cell_length_b                   16.7703(18)
_cell_length_c                   9.1967(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.326(4)
_cell_angle_gamma                90
_cell_volume                     1116.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2944
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.34

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10544
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4852
_reflns_number_gt                4072
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.990

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4852
_refine_ls_number_parameters     400
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.38197(11) 0.44266(5) 0.41598(9) 0.0142(2) Uani 1 1 d . . . . .
O1 O -0.2943(4) 0.54789(19) -0.0985(3) 0.0372(8) Uani 1 1 d . . . . .
O2 O -0.0441(4) 0.61780(16) 0.0409(3) 0.0282(7) Uani 1 1 d . . . . .
N1 N 0.1756(4) 0.42469(16) 0.2882(3) 0.0186(7) Uani 1 1 d . . . . .
N2 N 0.0984(4) 0.49130(18) 0.2114(3) 0.0188(7) Uani 1 1 d . . . . .
C1 C -0.0650(5) 0.4839(2) 0.1070(4) 0.0218(8) Uani 1 1 d . . . . .
C2 C -0.1468(5) 0.5517(2) 0.0078(4) 0.0244(9) Uani 1 1 d . . . . .
C3 C -0.1188(7) 0.6864(3) -0.0547(5) 0.0357(11) Uani 1 1 d . . . . .
C4 C 0.0232(8) 0.7504(3) -0.0097(7) 0.0443(13) Uani 1 1 d . . . . .
C5 C 0.4816(5) 0.5362(2) 0.3806(4) 0.0166(8) Uani 1 1 d . . . . .
C6 C 0.5001(6) 0.5422(3) 0.2205(5) 0.0244(9) Uani 1 1 d . . . . .
C7 C 0.5531(6) 0.6268(3) 0.1922(5) 0.0273(9) Uani 1 1 d . . . . .
C8 C 0.7337(6) 0.6509(2) 0.3168(5) 0.0271(9) Uani 1 1 d . . . . .
C9 C 0.7175(7) 0.6452(3) 0.4758(5) 0.0299(10) Uani 1 1 d . . . . .
C10 C 0.6614(6) 0.5618(3) 0.5071(5) 0.0280(9) Uani 1 1 d . . . . .
C11 C 0.5159(5) 0.3543(2) 0.4104(4) 0.0182(8) Uani 1 1 d . . . . .
C12 C 0.5211(6) 0.3355(3) 0.2488(5) 0.0242(9) Uani 1 1 d . . . . .
C13 C 0.6088(6) 0.2544(3) 0.2472(5) 0.0301(10) Uani 1 1 d . . . . .
C14 C 0.8029(6) 0.2503(3) 0.3698(6) 0.0318(10) Uani 1 1 d . . . . .
C15 C 0.7984(6) 0.2695(3) 0.5294(5) 0.0327(10) Uani 1 1 d . . . . .
C16 C 0.7096(6) 0.3504(3) 0.5331(5) 0.0258(9) Uani 1 1 d . . . . .
C17 C 0.3731(5) 0.4492(2) 0.6117(4) 0.0172(7) Uani 1 1 d . . . . .
C18 C 0.2402(6) 0.5164(3) 0.6185(5) 0.0275(9) Uani 1 1 d . . . . .
C19 C 0.2239(7) 0.5226(3) 0.7789(5) 0.0319(10) Uani 1 1 d . . . . .
C20 C 0.1709(6) 0.4436(3) 0.8317(4) 0.0319(9) Uani 1 1 d . . . . .
C21 C 0.3050(7) 0.3784(3) 0.8262(5) 0.0316(10) Uani 1 1 d . . . . .
C22 C 0.3173(7) 0.3703(2) 0.6654(5) 0.0259(9) Uani 1 1 d . . . . .
H7B H 0.564(5) 0.629(2) 0.092(5) 0.019(10) Uiso 1 1 d . . . . .
H12B H 0.599(5) 0.375(2) 0.220(4) 0.014(9) Uiso 1 1 d . . . . .
H21B H 0.443(6) 0.395(2) 0.905(5) 0.028(11) Uiso 1 1 d . . . . .
H20A H 0.159(5) 0.450(3) 0.931(4) 0.029(10) Uiso 1 1 d . . . . .
H5 H 0.386(6) 0.571(3) 0.375(5) 0.030(12) Uiso 1 1 d . . . . .
H17 H 0.498(6) 0.461(2) 0.681(4) 0.030(12) Uiso 1 1 d . . . . .
H19A H 0.345(6) 0.538(3) 0.852(5) 0.033(12) Uiso 1 1 d . . . . .
H11 H 0.445(5) 0.311(2) 0.433(4) 0.014(9) Uiso 1 1 d . . . . .
H1A H -0.130(5) 0.431(3) 0.082(4) 0.028(11) Uiso 1 1 d . . . . .
H20B H 0.048(6) 0.432(3) 0.773(5) 0.037(12) Uiso 1 1 d . . . . .
H6B H 0.596(6) 0.506(3) 0.210(5) 0.039(13) Uiso 1 1 d . . . . .
H15A H 0.732(5) 0.230(2) 0.568(4) 0.016(10) Uiso 1 1 d . . . . .
H10B H 0.645(5) 0.558(2) 0.604(4) 0.019(10) Uiso 1 1 d . . . . .
H7A H 0.452(7) 0.663(3) 0.181(5) 0.034(12) Uiso 1 1 d . . . . .
H14B H 0.875(6) 0.287(3) 0.345(5) 0.030(12) Uiso 1 1 d . . . . .
H6A H 0.391(6) 0.527(3) 0.147(5) 0.029(12) Uiso 1 1 d . . . . .
H18A H 0.127(6) 0.509(2) 0.545(5) 0.021(10) Uiso 1 1 d . . . . .
H10A H 0.757(6) 0.527(3) 0.508(5) 0.029(12) Uiso 1 1 d . . . . .
H13B H 0.614(6) 0.247(3) 0.143(6) 0.039(13) Uiso 1 1 d . . . . .
H21A H 0.271(6) 0.328(3) 0.864(5) 0.037(12) Uiso 1 1 d . . . . .
H12A H 0.394(5) 0.338(2) 0.175(4) 0.014(10) Uiso 1 1 d . . . . .
H13A H 0.531(5) 0.213(2) 0.268(4) 0.014(9) Uiso 1 1 d . . . . .
H8B H 0.828(6) 0.619(3) 0.296(5) 0.029(11) Uiso 1 1 d . . . . .
H3A H -0.237(6) 0.702(3) -0.034(5) 0.036(12) Uiso 1 1 d . . . . .
H22B H 0.209(6) 0.359(3) 0.600(5) 0.029(12) Uiso 1 1 d . . . . .
H8A H 0.773(6) 0.706(3) 0.292(5) 0.042(13) Uiso 1 1 d . . . . .
H16A H 0.792(7) 0.392(3) 0.520(5) 0.045(14) Uiso 1 1 d . . . . .
H16B H 0.715(6) 0.367(3) 0.634(5) 0.030(11) Uiso 1 1 d . . . . .
H9B H 0.625(6) 0.680(3) 0.486(5) 0.030(12) Uiso 1 1 d . . . . .
H15B H 0.922(6) 0.270(3) 0.608(5) 0.035(12) Uiso 1 1 d . . . . .
H18B H 0.274(7) 0.572(3) 0.588(5) 0.039(12) Uiso 1 1 d . . . . .
H14A H 0.855(6) 0.197(3) 0.366(5) 0.035(12) Uiso 1 1 d . . . . .
H22A H 0.413(6) 0.328(3) 0.668(5) 0.031(12) Uiso 1 1 d . . . . .
H4A H -0.020(7) 0.794(4) -0.065(6) 0.053(15) Uiso 1 1 d . . . . .
H19B H 0.136(6) 0.562(3) 0.782(5) 0.030(11) Uiso 1 1 d . . . . .
H9A H 0.835(8) 0.660(3) 0.553(6) 0.046(14) Uiso 1 1 d . . . . .
H4B H 0.058(8) 0.766(4) 0.108(8) 0.079(19) Uiso 1 1 d . . . . .
H4C H 0.133(9) 0.737(3) -0.023(7) 0.069(19) Uiso 1 1 d . . . . .
H3B H -0.136(7) 0.669(3) -0.147(6) 0.047(15) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.646(3) . ?
P1 C11 1.818(4) . ?
P1 C5 1.825(4) . ?
P1 C17 1.828(3) . ?
O1 C2 1.218(4) . ?
O2 C2 1.335(5) . ?
O2 C3 1.441(5) . ?
N1 N2 1.345(4) . ?
N2 C1 1.299(5) . ?
C1 C2 1.457(5) . ?
C1 H1A 1.01(4) . ?
C3 C4 1.487(7) . ?
C3 H3A 1.03(5) . ?
C3 H3B 0.87(5) . ?
C4 H4A 0.89(6) . ?
C4 H4B 1.06(7) . ?
C4 H4C 0.93(6) . ?
C5 C10 1.531(5) . ?
C5 C6 1.531(5) . ?
C5 H5 0.93(4) . ?
C6 C7 1.524(6) . ?
C6 H6B 0.99(5) . ?
C6 H6A 0.92(4) . ?
C7 C8 1.521(6) . ?
C7 H7B 0.95(4) . ?
C7 H7A 0.97(5) . ?
C8 C9 1.513(6) . ?
C8 H8B 0.97(5) . ?
C8 H8A 1.02(5) . ?
C9 C10 1.521(6) . ?
C9 H9B 0.95(4) . ?
C9 H9A 0.97(5) . ?
C10 H10B 0.95(4) . ?
C10 H10A 0.95(4) . ?
C11 C16 1.530(5) . ?
C11 C12 1.534(5) . ?
C11 H11 0.98(4) . ?
C12 C13 1.522(6) . ?
C12 H12B 1.00(4) . ?
C12 H12A 0.98(4) . ?
C13 C14 1.533(6) . ?
C13 H13B 0.98(5) . ?
C13 H13A 0.98(4) . ?
C14 C15 1.515(7) . ?
C14 H14B 0.91(5) . ?
C14 H14A 0.98(5) . ?
C15 C16 1.525(6) . ?
C15 H15A 0.97(4) . ?
C15 H15B 0.98(5) . ?
C16 H16A 0.98(5) . ?
C16 H16B 0.95(5) . ?
C17 C22 1.525(5) . ?
C17 C18 1.540(5) . ?
C17 H17 0.98(4) . ?
C18 C19 1.526(6) . ?
C18 H18A 0.91(4) . ?
C18 H18B 1.03(5) . ?
C19 C20 1.515(7) . ?
C19 H19A 0.98(5) . ?
C19 H19B 0.95(4) . ?
C20 C21 1.518(7) . ?
C20 H20A 0.95(4) . ?
C20 H20B 0.93(4) . ?
C21 C22 1.521(5) . ?
C21 H21B 1.09(4) . ?
C21 H21A 0.98(5) . ?
C22 H22B 0.86(5) . ?
C22 H22A 1.01(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C11 104.47(16) . . ?
N1 P1 C5 113.16(15) . . ?
C11 P1 C5 114.58(16) . . ?
N1 P1 C17 110.85(16) . . ?
C11 P1 C17 107.04(18) . . ?
C5 P1 C17 106.64(18) . . ?
C2 O2 C3 116.4(3) . . ?
N2 N1 P1 111.4(2) . . ?
C1 N2 N1 116.7(3) . . ?
N2 C1 C2 119.1(4) . . ?
N2 C1 H1A 122(2) . . ?
C2 C1 H1A 118(2) . . ?
O1 C2 O2 122.8(4) . . ?
O1 C2 C1 122.9(4) . . ?
O2 C2 C1 114.3(3) . . ?
O2 C3 C4 107.9(4) . . ?
O2 C3 H3A 106(2) . . ?
C4 C3 H3A 112(3) . . ?
O2 C3 H3B 102(3) . . ?
C4 C3 H3B 112(4) . . ?
H3A C3 H3B 115(4) . . ?
C3 C4 H4A 110(4) . . ?
C3 C4 H4B 111(3) . . ?
H4A C4 H4B 107(5) . . ?
C3 C4 H4C 114(4) . . ?
H4A C4 H4C 108(5) . . ?
H4B C4 H4C 106(5) . . ?
C10 C5 C6 110.5(3) . . ?
C10 C5 P1 115.6(3) . . ?
C6 C5 P1 114.5(3) . . ?
C10 C5 H5 111(3) . . ?
C6 C5 H5 104(3) . . ?
P1 C5 H5 100(3) . . ?
C7 C6 C5 110.2(3) . . ?
C7 C6 H6B 107(3) . . ?
C5 C6 H6B 112(3) . . ?
C7 C6 H6A 112(3) . . ?
C5 C6 H6A 109(3) . . ?
H6B C6 H6A 106(4) . . ?
C8 C7 C6 110.5(3) . . ?
C8 C7 H7B 110(2) . . ?
C6 C7 H7B 109(2) . . ?
C8 C7 H7A 114(3) . . ?
C6 C7 H7A 110(3) . . ?
H7B C7 H7A 102(3) . . ?
C9 C8 C7 110.4(3) . . ?
C9 C8 H8B 118(2) . . ?
C7 C8 H8B 105(2) . . ?
C9 C8 H8A 114(3) . . ?
C7 C8 H8A 110(3) . . ?
H8B C8 H8A 99(4) . . ?
C8 C9 C10 111.5(4) . . ?
C8 C9 H9B 112(3) . . ?
C10 C9 H9B 106(3) . . ?
C8 C9 H9A 108(3) . . ?
C10 C9 H9A 111(3) . . ?
H9B C9 H9A 108(4) . . ?
C9 C10 C5 110.9(4) . . ?
C9 C10 H10B 113(2) . . ?
C5 C10 H10B 108(2) . . ?
C9 C10 H10A 108(3) . . ?
C5 C10 H10A 109(3) . . ?
H10B C10 H10A 108(4) . . ?
C16 C11 C12 111.0(3) . . ?
C16 C11 P1 115.7(3) . . ?
C12 C11 P1 113.7(3) . . ?
C16 C11 H11 107(2) . . ?
C12 C11 H11 105(2) . . ?
P1 C11 H11 104(2) . . ?
C13 C12 C11 110.8(3) . . ?
C13 C12 H12B 107(2) . . ?
C11 C12 H12B 110(2) . . ?
C13 C12 H12A 112(2) . . ?
C11 C12 H12A 108(2) . . ?
H12B C12 H12A 110(3) . . ?
C12 C13 C14 111.0(4) . . ?
C12 C13 H13B 107(3) . . ?
C14 C13 H13B 111(3) . . ?
C12 C13 H13A 109(2) . . ?
C14 C13 H13A 109(2) . . ?
H13B C13 H13A 110(4) . . ?
C15 C14 C13 110.9(4) . . ?
C15 C14 H14B 109(3) . . ?
C13 C14 H14B 108(3) . . ?
C15 C14 H14A 112(3) . . ?
C13 C14 H14A 109(3) . . ?
H14B C14 H14A 108(4) . . ?
C14 C15 C16 111.9(4) . . ?
C14 C15 H15A 114(2) . . ?
C16 C15 H15A 107(2) . . ?
C14 C15 H15B 112(3) . . ?
C16 C15 H15B 108(3) . . ?
H15A C15 H15B 104(3) . . ?
C15 C16 C11 110.7(3) . . ?
C15 C16 H16A 108(3) . . ?
C11 C16 H16A 113(3) . . ?
C15 C16 H16B 114(3) . . ?
C11 C16 H16B 114(3) . . ?
H16A C16 H16B 96(4) . . ?
C22 C17 C18 110.7(3) . . ?
C22 C17 P1 112.2(3) . . ?
C18 C17 P1 109.7(3) . . ?
C22 C17 H17 107(2) . . ?
C18 C17 H17 110(2) . . ?
P1 C17 H17 107(2) . . ?
C19 C18 C17 111.6(4) . . ?
C19 C18 H18A 110(3) . . ?
C17 C18 H18A 111(2) . . ?
C19 C18 H18B 108(2) . . ?
C17 C18 H18B 114(3) . . ?
H18A C18 H18B 101(3) . . ?
C20 C19 C18 111.9(4) . . ?
C20 C19 H19A 108(3) . . ?
C18 C19 H19A 108(3) . . ?
C20 C19 H19B 109(3) . . ?
C18 C19 H19B 112(3) . . ?
H19A C19 H19B 108(4) . . ?
C19 C20 C21 110.8(3) . . ?
C19 C20 H20A 109(3) . . ?
C21 C20 H20A 114(3) . . ?
C19 C20 H20B 109(3) . . ?
C21 C20 H20B 114(3) . . ?
H20A C20 H20B 99(3) . . ?
C20 C21 C22 111.8(4) . . ?
C20 C21 H21B 109(2) . . ?
C22 C21 H21B 107(2) . . ?
C20 C21 H21A 110(3) . . ?
C22 C21 H21A 113(3) . . ?
H21B C21 H21A 107(3) . . ?
C21 C22 C17 111.0(3) . . ?
C21 C22 H22B 109(3) . . ?
C17 C22 H22B 106(3) . . ?
C21 C22 H22A 109(2) . . ?
C17 C22 H22A 109(2) . . ?
H22B C22 H22A 113(4) . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_cas
_database_code_depnum_ccdc_archive 'CCDC 1848996'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-15 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            'C34 H35 B F15 N2 O3 P'
_chemical_formula_weight         846.42

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'
B B 0.0013 0.0007 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.9153(11)
_cell_length_b                   13.8962(11)
_cell_length_c                   22.195(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.783(4)
_cell_angle_gamma                90
_cell_volume                     3667.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4561
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      22.23

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30433
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.713
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8081
_reflns_number_gt                5068
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-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)+(0.0890P)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         8081
_refine_ls_number_parameters     519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.34558(6) 0.75329(5) 0.17854(3) 0.02319(18) Uani 1 1 d . . . . .
F5 F 0.96909(13) 0.90615(11) 0.07881(7) 0.0286(4) Uani 1 1 d . . . . .
F4 F 1.05703(14) 1.07775(12) 0.05654(8) 0.0364(4) Uani 1 1 d . . . . .
F6 F 0.90183(15) 0.94870(12) 0.20093(7) 0.0347(4) Uani 1 1 d . . . . .
F10 F 0.69912(14) 0.66785(11) 0.14083(8) 0.0326(4) Uani 1 1 d . . . . .
O3 O 0.61806(17) 0.85803(16) 0.10902(10) 0.0274(5) Uani 1 1 d . . . . .
F2 F 0.70058(17) 1.21974(12) 0.06719(9) 0.0461(5) Uani 1 1 d . . . . .
F1 F 0.61206(14) 1.05161(12) 0.09188(9) 0.0391(5) Uani 1 1 d . . . . .
F11 F 0.90880(14) 0.69413(12) 0.08262(8) 0.0378(4) Uani 1 1 d . . . . .
F9 F 0.78147(18) 0.57995(14) 0.23981(9) 0.0534(6) Uani 1 1 d . . . . .
F3 F 0.92348(17) 1.23722(12) 0.04961(9) 0.0481(5) Uani 1 1 d . . . . .
O2 O 0.34512(17) 0.58054(15) -0.01532(9) 0.0352(5) Uani 1 1 d . . . . .
F15 F 0.63263(16) 0.89304(14) -0.01623(8) 0.0485(5) Uani 1 1 d . . . . .
F7 F 0.98645(17) 0.85778(16) 0.29740(8) 0.0511(5) Uani 1 1 d . . . . .
F12 F 0.9313(2) 0.60068(14) -0.01943(10) 0.0610(6) Uani 1 1 d . . . . .
N2 N 0.4121(2) 0.67819(16) 0.08118(11) 0.0265(5) Uani 1 1 d . . . . .
C18 C 0.8991(2) 0.98299(19) 0.07658(12) 0.0222(6) Uani 1 1 d . . . . .
F8 F 0.92719(18) 0.67289(16) 0.32006(9) 0.0590(6) Uani 1 1 d . . . . .
F14 F 0.6616(2) 0.79968(19) -0.11889(9) 0.0766(8) Uani 1 1 d . . . . .
F13 F 0.8074(2) 0.65099(16) -0.12172(9) 0.0786(8) Uani 1 1 d . . . . .
C13 C 0.7869(2) 0.96907(19) 0.08774(12) 0.0216(6) Uani 1 1 d . . . . .
O1 O 0.5116(2) 0.6033(2) -0.05467(11) 0.0537(7) Uani 1 1 d . . . . .
C26 C 0.8425(2) 0.7225(2) 0.03451(13) 0.0283(7) Uani 1 1 d . . . . .
C25 C 0.7660(2) 0.7969(2) 0.03959(12) 0.0239(6) Uani 1 1 d . . . . .
C16 C 0.8799(3) 1.1512(2) 0.06223(13) 0.0313(7) Uani 1 1 d . . . . .
C19 C 0.7977(2) 0.81236(19) 0.16362(12) 0.0216(6) Uani 1 1 d . . . . .
C20 C 0.8695(2) 0.8561(2) 0.20688(12) 0.0267(6) Uani 1 1 d . . . . .
N1 N 0.44620(19) 0.72774(16) 0.13294(10) 0.0263(5) Uani 1 1 d . . . . .
H1A H 0.5167 0.7447 0.1412 0.032 Uiso 1 1 calc R U . . .
C17 C 0.9467(2) 1.0705(2) 0.06496(12) 0.0263(6) Uani 1 1 d . . . . .
C14 C 0.7245(2) 1.0532(2) 0.08413(12) 0.0257(6) Uani 1 1 d . . . . .
C15 C 0.7680(3) 1.1423(2) 0.07150(13) 0.0302(7) Uani 1 1 d . . . . .
C23 C 0.8120(3) 0.6713(2) 0.22949(15) 0.0353(8) Uani 1 1 d . . . . .
B1 B 0.7399(2) 0.8603(2) 0.10087(14) 0.0213(6) Uani 1 1 d . . . . .
C24 C 0.7700(2) 0.7190(2) 0.17863(13) 0.0263(6) Uani 1 1 d . . . . .
C22 C 0.8849(3) 0.7182(3) 0.27007(13) 0.0376(8) Uani 1 1 d . . . . .
C40 C 0.4809(2) 0.6719(2) 0.03969(13) 0.0288(7) Uani 1 1 d . . . . .
H40A H 0.5519 0.7031 0.0439 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2770(2) 0.8675(2) 0.15148(13) 0.0302(7) Uani 1 1 d . . . . .
C28 C 0.7951(3) 0.6981(3) -0.06959(15) 0.0478(10) Uani 1 1 d . . . . .
C5 C 0.2459(3) 0.6484(2) 0.17566(16) 0.0396(8) Uani 1 1 d . . . . .
C42 C 0.3066(3) 0.5170(2) -0.06445(15) 0.0380(8) Uani 1 1 d . . . . .
H42A H 0.3075 0.4494 -0.0503 0.046 Uiso 1 1 calc R U . . .
H42B H 0.3569 0.5223 -0.0980 0.046 Uiso 1 1 calc R U . . .
C30 C 0.7079(3) 0.8197(2) -0.01444(14) 0.0328(7) Uani 1 1 d . . . . .
C21 C 0.9142(3) 0.8113(2) 0.25873(13) 0.0338(7) Uani 1 1 d . . . . .
C41 C 0.4482(2) 0.6151(2) -0.01509(14) 0.0297(7) Uani 1 1 d . . . . .
C10 C 0.2582(3) 0.8628(2) 0.08231(13) 0.0394(8) Uani 1 1 d . . . . .
H10A H 0.2181 0.9206 0.0676 0.059 Uiso 1 1 calc R U . . .
H10B H 0.2135 0.8057 0.0709 0.059 Uiso 1 1 calc R U . . .
H10C H 0.3311 0.8591 0.0644 0.059 Uiso 1 1 calc R U . . .
C29 C 0.7207(3) 0.7725(3) -0.06832(14) 0.0468(10) Uani 1 1 d . . . . .
C11 C 0.1659(2) 0.8872(2) 0.17976(14) 0.0355(7) Uani 1 1 d . . . . .
H11A H 0.1369 0.9502 0.1664 0.053 Uiso 1 1 calc R U . . .
H11B H 0.1781 0.8869 0.2239 0.053 Uiso 1 1 calc R U . . .
H11C H 0.1113 0.8372 0.1672 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1646(3) 0.6499(3) 0.11850(17) 0.0489(9) Uani 1 1 d . . . . .
H8A H 0.1151 0.5935 0.1185 0.073 Uiso 1 1 calc R U . . .
H8B H 0.2079 0.6485 0.0825 0.073 Uiso 1 1 calc R U . . .
H8C H 0.1190 0.7086 0.1182 0.073 Uiso 1 1 calc R U . . .
C27 C 0.8568(3) 0.6724(2) -0.01864(16) 0.0390(8) Uani 1 1 d . . . . .
C43 C 0.1900(3) 0.5454(2) -0.08554(16) 0.0444(9) Uani 1 1 d . . . . .
H43A H 0.1609 0.5007 -0.1169 0.067 Uiso 1 1 calc R U . . .
H43B H 0.1906 0.6108 -0.1021 0.067 Uiso 1 1 calc R U . . .
H43C H 0.1417 0.5435 -0.0515 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5319(3) 0.8244(3) 0.24944(15) 0.0442(9) Uani 1 1 d . . . . .
H4A H 0.5708 0.8299 0.2896 0.066 Uiso 1 1 calc R U . . .
H4B H 0.5141 0.8889 0.2336 0.066 Uiso 1 1 calc R U . . .
H4C H 0.5805 0.7911 0.2222 0.066 Uiso 1 1 calc R U . . .
C12 C 0.3571(3) 0.9531(2) 0.16508(16) 0.0390(8) Uani 1 1 d . . . . .
H12A H 0.3252 1.0113 0.1458 0.058 Uiso 1 1 calc R U . . .
H12B H 0.4303 0.9393 0.1493 0.058 Uiso 1 1 calc R U . . .
H12C H 0.3668 0.9630 0.2088 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3098(3) 0.5524(2) 0.17485(19) 0.0544(10) Uani 1 1 d . . . . .
H6A H 0.2564 0.4990 0.1765 0.082 Uiso 1 1 calc R U . . .
H6B H 0.3643 0.5492 0.2098 0.082 Uiso 1 1 calc R U . . .
H6C H 0.3494 0.5478 0.1376 0.082 Uiso 1 1 calc R U . . .
C2 C 0.3516(3) 0.8182(3) 0.29961(15) 0.0500(10) Uani 1 1 d . . . . .
H2B H 0.3928 0.8191 0.3393 0.075 Uiso 1 1 calc R U . . .
H2C H 0.2804 0.7838 0.3024 0.075 Uiso 1 1 calc R U . . .
H2D H 0.3363 0.8844 0.2862 0.075 Uiso 1 1 calc R U . . .
C1 C 0.4226(3) 0.7672(3) 0.25399(14) 0.0382(8) Uani 1 1 d . . . . .
C3 C 0.4585(4) 0.6673(3) 0.27859(18) 0.0645(12) Uani 1 1 d . . . . .
H3B H 0.5028 0.6749 0.3171 0.097 Uiso 1 1 calc R U . . .
H3C H 0.5041 0.6349 0.2495 0.097 Uiso 1 1 calc R U . . .
H3D H 0.3915 0.6287 0.2848 0.097 Uiso 1 1 calc R U . . .
C7 C 0.1745(3) 0.6518(3) 0.23132(18) 0.0560(10) Uani 1 1 d . . . . .
H7A H 0.1131 0.6049 0.2262 0.084 Uiso 1 1 calc R U . . .
H7B H 0.1431 0.7165 0.2353 0.084 Uiso 1 1 calc R U . . .
H7C H 0.2220 0.6361 0.2677 0.084 Uiso 1 1 calc R U . . .
H3 H 0.591(3) 0.891(2) 0.0919(14) 0.023(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.658(2) . ?
P1 C1 1.866(3) . ?
P1 C9 1.866(3) . ?
P1 C5 1.879(3) . ?
F5 C18 1.353(3) . ?
F4 C17 1.344(3) . ?
F6 C20 1.352(3) . ?
F10 C24 1.352(3) . ?
O3 B1 1.475(4) . ?
F2 C15 1.343(3) . ?
F1 C14 1.362(3) . ?
F11 C26 1.345(3) . ?
F9 C23 1.345(4) . ?
F3 C16 1.340(3) . ?
O2 C41 1.319(4) . ?
O2 C42 1.454(3) . ?
F15 C30 1.356(4) . ?
F7 C21 1.341(3) . ?
F12 C27 1.335(4) . ?
N2 C40 1.276(4) . ?
N2 N1 1.378(3) . ?
C18 C17 1.373(4) . ?
C18 C13 1.390(4) . ?
F8 C22 1.345(3) . ?
F14 C29 1.340(4) . ?
F13 C28 1.346(4) . ?
C13 C14 1.386(4) . ?
C13 B1 1.644(4) . ?
O1 C41 1.207(4) . ?
C26 C25 1.388(4) . ?
C26 C27 1.390(4) . ?
C25 C30 1.382(4) . ?
C25 B1 1.667(4) . ?
C16 C15 1.368(4) . ?
C16 C17 1.374(4) . ?
C19 C20 1.384(4) . ?
C19 C24 1.385(4) . ?
C19 B1 1.653(4) . ?
C20 C21 1.383(4) . ?
C14 C15 1.378(4) . ?
C23 C22 1.374(5) . ?
C23 C24 1.375(4) . ?
C22 C21 1.367(5) . ?
C40 C41 1.480(4) . ?
C9 C11 1.528(4) . ?
C9 C10 1.538(4) . ?
C9 C12 1.542(4) . ?
C28 C27 1.355(5) . ?
C28 C29 1.363(6) . ?
C5 C6 1.537(5) . ?
C5 C8 1.545(5) . ?
C5 C7 1.546(5) . ?
C42 C43 1.490(5) . ?
C30 C29 1.382(5) . ?
C4 C1 1.535(5) . ?
C2 C1 1.536(5) . ?
C1 C3 1.541(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C1 103.72(13) . . ?
N1 P1 C9 107.73(13) . . ?
C1 P1 C9 112.32(15) . . ?
N1 P1 C5 107.11(14) . . ?
C1 P1 C5 112.53(15) . . ?
C9 P1 C5 112.76(15) . . ?
C41 O2 C42 118.2(2) . . ?
C40 N2 N1 117.9(2) . . ?
F5 C18 C17 116.4(2) . . ?
F5 C18 C13 118.8(2) . . ?
C17 C18 C13 124.8(3) . . ?
C14 C13 C18 113.1(2) . . ?
C14 C13 B1 126.7(2) . . ?
C18 C13 B1 120.2(2) . . ?
F11 C26 C25 120.6(3) . . ?
F11 C26 C27 115.4(3) . . ?
C25 C26 C27 124.0(3) . . ?
C30 C25 C26 113.3(3) . . ?
C30 C25 B1 118.5(3) . . ?
C26 C25 B1 128.2(2) . . ?
F3 C16 C15 120.4(3) . . ?
F3 C16 C17 120.4(3) . . ?
C15 C16 C17 119.1(3) . . ?
C20 C19 C24 113.0(2) . . ?
C20 C19 B1 127.7(2) . . ?
C24 C19 B1 119.2(2) . . ?
F6 C20 C21 114.4(3) . . ?
F6 C20 C19 121.1(2) . . ?
C21 C20 C19 124.5(3) . . ?
N2 N1 P1 115.52(18) . . ?
F4 C17 C18 120.8(3) . . ?
F4 C17 C16 120.1(2) . . ?
C18 C17 C16 119.1(3) . . ?
F1 C14 C15 115.3(2) . . ?
F1 C14 C13 120.5(2) . . ?
C15 C14 C13 124.2(3) . . ?
F2 C15 C16 120.1(3) . . ?
F2 C15 C14 120.2(3) . . ?
C16 C15 C14 119.7(3) . . ?
F9 C23 C22 120.2(3) . . ?
F9 C23 C24 120.4(3) . . ?
C22 C23 C24 119.4(3) . . ?
O3 B1 C13 113.0(2) . . ?
O3 B1 C19 104.3(2) . . ?
C13 B1 C19 113.1(2) . . ?
O3 B1 C25 109.1(2) . . ?
C13 B1 C25 104.9(2) . . ?
C19 B1 C25 112.6(2) . . ?
F10 C24 C23 115.8(3) . . ?
F10 C24 C19 119.5(2) . . ?
C23 C24 C19 124.7(3) . . ?
F8 C22 C21 120.6(3) . . ?
F8 C22 C23 120.3(3) . . ?
C21 C22 C23 119.1(3) . . ?
N2 C40 C41 118.9(3) . . ?
C11 C9 C10 110.2(3) . . ?
C11 C9 C12 108.9(2) . . ?
C10 C9 C12 106.0(3) . . ?
C11 C9 P1 113.1(2) . . ?
C10 C9 P1 108.4(2) . . ?
C12 C9 P1 109.9(2) . . ?
F13 C28 C27 120.4(4) . . ?
F13 C28 C29 119.6(4) . . ?
C27 C28 C29 120.0(3) . . ?
C6 C5 C8 106.7(3) . . ?
C6 C5 C7 109.6(3) . . ?
C8 C5 C7 107.9(3) . . ?
C6 C5 P1 111.2(2) . . ?
C8 C5 P1 112.2(2) . . ?
C7 C5 P1 109.2(2) . . ?
O2 C42 C43 108.4(3) . . ?
F15 C30 C25 119.4(3) . . ?
F15 C30 C29 116.3(3) . . ?
C25 C30 C29 124.3(3) . . ?
F7 C21 C22 119.9(3) . . ?
F7 C21 C20 120.7(3) . . ?
C22 C21 C20 119.4(3) . . ?
O1 C41 O2 125.1(3) . . ?
O1 C41 C40 121.8(3) . . ?
O2 C41 C40 113.1(3) . . ?
F14 C29 C28 120.2(3) . . ?
F14 C29 C30 120.6(4) . . ?
C28 C29 C30 119.2(3) . . ?
F12 C27 C28 120.7(3) . . ?
F12 C27 C26 120.3(3) . . ?
C28 C27 C26 119.1(3) . . ?
C4 C1 C2 108.1(3) . . ?
C4 C1 C3 105.9(3) . . ?
C2 C1 C3 109.5(3) . . ?
C4 C1 P1 111.3(2) . . ?
C2 C1 P1 112.3(2) . . ?
C3 C1 P1 109.5(2) . . ?

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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_final_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1848998'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-15 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            'C52 H45 B F15 N2 O4 P'
_chemical_formula_weight         1088.68

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'
B B 0.0013 0.0007 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.6815(4)
_cell_length_b                   25.0825(8)
_cell_length_c                   17.9044(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.974(2)
_cell_angle_gamma                90
_cell_volume                     5017.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2944
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.34

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             2232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            84250
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.440
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11537
_reflns_number_gt                8717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0915P)²+0.8175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11537
_refine_ls_number_parameters     716
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.104
_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
O4 O -0.0832(3) 0.78413(11) -0.06186(16) 0.0547(9) Uani 0.700(5) 1 d . U P A 1
C47 C -0.0874(7) 0.83434(16) -0.0321(4) 0.0362(11) Uani 0.700(5) 1 d G U P A 1
C48 C -0.0972(6) 0.87919(17) -0.0792(3) 0.0332(10) Uani 0.700(5) 1 d G U P A 1
C49 C -0.0996(5) 0.92970(16) -0.0477(3) 0.0340(11) Uani 0.700(5) 1 d G U P A 1
C50 C -0.0922(6) 0.9354(2) 0.0308(3) 0.0357(11) Uani 0.700(5) 1 d G U P A 1
C51 C -0.0824(8) 0.8905(3) 0.0778(3) 0.0396(13) Uani 0.700(5) 1 d G U P A 1
C52 C -0.0800(8) 0.8400(2) 0.0464(3) 0.0373(12) Uani 0.700(5) 1 d G U P A 1
O4B O -0.0871(5) 0.7910(2) 0.0846(3) 0.0472(18) Uani 0.300(5) 1 d . U P A 2
C47B C -0.0908(17) 0.8220(5) -0.0363(10) 0.049(3) Uani 0.300(5) 1 d G U P A 2
C48B C -0.0969(15) 0.8634(5) -0.0888(8) 0.053(3) Uani 0.300(5) 1 d G U P A 2
C49B C -0.1012(14) 0.9159(5) -0.0649(8) 0.050(3) Uani 0.300(5) 1 d G U P A 2
C50B C -0.0994(16) 0.9270(5) 0.0115(8) 0.049(3) Uani 0.300(5) 1 d G U P A 2
C51B C -0.093(2) 0.8855(7) 0.0640(8) 0.044(3) Uani 0.300(5) 1 d G U P A 2
C52B C -0.089(2) 0.8330(6) 0.0401(9) 0.045(2) Uani 0.300(5) 1 d G U P A 2
P1 P 0.34064(4) 0.79529(2) 0.20875(3) 0.01559(12) Uani 1 1 d . . . . .
B1 B 0.45465(19) 0.57621(8) 0.25559(12) 0.0193(4) Uani 1 1 d . . . . .
F1 F 0.28625(11) 0.65068(4) 0.28825(7) 0.0259(3) Uani 1 1 d . . . . .
F2 F 0.06502(12) 0.63327(6) 0.29178(9) 0.0451(4) Uani 1 1 d . . . . .
F3 F -0.02491(13) 0.53184(7) 0.27756(11) 0.0603(5) Uani 1 1 d . . . . .
F4 F 0.11262(15) 0.44965(6) 0.25369(10) 0.0563(4) Uani 1 1 d . . . . .
F5 F 0.33108(13) 0.46654(4) 0.24399(8) 0.0382(3) Uani 1 1 d . . . . .
F6 F 0.32939(11) 0.52993(5) 0.10787(7) 0.0338(3) Uani 1 1 d . . . . .
F7 F 0.41171(13) 0.46189(5) 0.02196(7) 0.0388(3) Uani 1 1 d . . . . .
F8 F 0.64135(14) 0.42617(5) 0.07255(8) 0.0424(3) Uani 1 1 d . . . . .
F9 F 0.78548(11) 0.45834(5) 0.21367(8) 0.0347(3) Uani 1 1 d . . . . .
F10 F 0.70526(10) 0.52478(4) 0.30220(7) 0.0268(3) Uani 1 1 d . . . . .
F11 F 0.53110(12) 0.68405(4) 0.33216(7) 0.0342(3) Uani 1 1 d . . . . .
F12 F 0.61379(13) 0.70144(5) 0.48375(8) 0.0424(4) Uani 1 1 d . . . . .
F13 F 0.66092(12) 0.61841(5) 0.58717(7) 0.0381(3) Uani 1 1 d . . . . .
F14 F 0.62949(12) 0.51713(5) 0.53273(7) 0.0317(3) Uani 1 1 d . . . . .
F15 F 0.53557(11) 0.49818(4) 0.37931(6) 0.0248(3) Uani 1 1 d . . . . .
O1 O -0.02534(14) 0.69217(6) 0.03904(10) 0.0424(4) Uani 1 1 d . . . . .
O2 O 0.03403(15) 0.60802(6) 0.06767(11) 0.0476(5) Uani 1 1 d . . . . .
O3 O 0.43711(12) 0.62413(5) 0.20292(8) 0.0218(3) Uani 1 1 d . . . . .
N1 N 0.31517(14) 0.73171(6) 0.18180(9) 0.0192(3) Uani 1 1 d . . . . .
H1A H 0.3702 0.7068 0.1969 0.023 Uiso 1 1 calc R U . . .
N2 N 0.20190(15) 0.72103(6) 0.13436(9) 0.0212(3) Uani 1 1 d . . . . .
C1 C 0.28948(17) 0.83300(7) 0.11946(10) 0.0180(4) Uani 1 1 d . . . . .
H1B H 0.2024 0.8246 0.0978 0.022 Uiso 1 1 calc R U . . .
C2 C 0.34698(19) 0.81617(8) 0.05621(11) 0.0239(4) Uani 1 1 d . . . . .
H2B H 0.4322 0.8270 0.0717 0.029 Uiso 1 1 calc R U . . .
H2C H 0.3430 0.7769 0.0501 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2803(2) 0.84279(8) -0.02086(12) 0.0302(5) Uani 1 1 d . . . . .
H3A H 0.1960 0.8306 -0.0374 0.036 Uiso 1 1 calc R U . . .
H3B H 0.3176 0.8325 -0.0618 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2842(2) 0.90346(8) -0.01146(11) 0.0271(4) Uani 1 1 d . . . . .
H4B H 0.3681 0.9158 0.0006 0.033 Uiso 1 1 calc R U . . .
H4C H 0.2380 0.9202 -0.0612 0.033 Uiso 1 1 calc R U . . .
C5 C 0.23279(19) 0.92091(7) 0.05304(11) 0.0242(4) Uani 1 1 d . . . . .
H5A H 0.1465 0.9120 0.0382 0.029 Uiso 1 1 calc R U . . .
H5B H 0.2408 0.9601 0.0594 0.029 Uiso 1 1 calc R U . . .
C6 C 0.29646(19) 0.89385(7) 0.13090(11) 0.0215(4) Uani 1 1 d . . . . .
H6A H 0.2577 0.9042 0.1710 0.026 Uiso 1 1 calc R U . . .
H6B H 0.3812 0.9053 0.1489 0.026 Uiso 1 1 calc R U . . .
C7 C 0.25512(16) 0.81496(7) 0.27424(10) 0.0179(4) Uani 1 1 d . . . . .
H7A H 0.2792 0.8523 0.2912 0.022 Uiso 1 1 calc R U . . .
C8 C 0.11979(18) 0.81564(9) 0.23374(12) 0.0285(5) Uani 1 1 d . . . . .
H8A H 0.1021 0.8397 0.1880 0.034 Uiso 1 1 calc R U . . .
H8B H 0.0925 0.7794 0.2150 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0525(2) 0.83464(10) 0.29017(13) 0.0348(5) Uani 1 1 d . . . . .
H9A H -0.0346 0.8333 0.2639 0.042 Uiso 1 1 calc R U . . .
H9B H 0.0744 0.8721 0.3050 0.042 Uiso 1 1 calc R U . . .
C10 C 0.0820(2) 0.80015(10) 0.36355(14) 0.0375(5) Uani 1 1 d . . . . .
H10A H 0.0399 0.8143 0.4000 0.045 Uiso 1 1 calc R U . . .
H10B H 0.0537 0.7633 0.3493 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2155(2) 0.79962(9) 0.40348(12) 0.0287(5) Uani 1 1 d . . . . .
H11A H 0.2328 0.7758 0.4496 0.034 Uiso 1 1 calc R U . . .
H11B H 0.2422 0.8360 0.4220 0.034 Uiso 1 1 calc R U . . .
C12 C 0.28538(19) 0.78046(8) 0.34838(11) 0.0246(4) Uani 1 1 d . . . . .
H12A H 0.2650 0.7428 0.3340 0.030 Uiso 1 1 calc R U . . .
H12B H 0.3723 0.7825 0.3752 0.030 Uiso 1 1 calc R U . . .
C13 C 0.49826(16) 0.79873(7) 0.26236(11) 0.0177(4) Uani 1 1 d . . . . .
H13A H 0.5118 0.7704 0.3034 0.021 Uiso 1 1 calc R U . . .
C14 C 0.53146(17) 0.85176(8) 0.30667(13) 0.0259(4) Uani 1 1 d . . . . .
H14A H 0.5246 0.8813 0.2690 0.031 Uiso 1 1 calc R U . . .
H14B H 0.4757 0.8589 0.3378 0.031 Uiso 1 1 calc R U . . .
C15 C 0.65982(18) 0.84860(9) 0.36060(13) 0.0321(5) Uani 1 1 d . . . . .
H15A H 0.6824 0.8834 0.3868 0.039 Uiso 1 1 calc R U . . .
H15B H 0.6639 0.8215 0.4015 0.039 Uiso 1 1 calc R U . . .
C16 C 0.74810(19) 0.83428(9) 0.31644(14) 0.0308(5) Uani 1 1 d . . . . .
H16A H 0.8287 0.8299 0.3539 0.037 Uiso 1 1 calc R U . . .
H16B H 0.7520 0.8637 0.2804 0.037 Uiso 1 1 calc R U . . .
C17 C 0.71252(18) 0.78302(9) 0.26998(14) 0.0307(5) Uani 1 1 d . . . . .
H17A H 0.7182 0.7528 0.3065 0.037 Uiso 1 1 calc R U . . .
H17B H 0.7689 0.7762 0.2391 0.037 Uiso 1 1 calc R U . . .
C18 C 0.58508(18) 0.78629(8) 0.21501(12) 0.0262(4) Uani 1 1 d . . . . .
H18A H 0.5630 0.7520 0.1872 0.031 Uiso 1 1 calc R U . . .
H18B H 0.5803 0.8146 0.1757 0.031 Uiso 1 1 calc R U . . .
C19 C 0.17510(18) 0.67220(7) 0.11694(11) 0.0225(4) Uani 1 1 d . . . . .
H19A H 0.2327 0.6446 0.1335 0.027 Uiso 1 1 calc R U . . .
C20 C 0.05041(19) 0.66034(8) 0.06992(12) 0.0276(5) Uani 1 1 d . . . . .
C21 C -0.0847(2) 0.58748(11) 0.02568(19) 0.0588(9) Uani 1 1 d . . . . .
H21A H -0.1472 0.6133 0.0290 0.071 Uiso 1 1 calc R U . . .
H21B H -0.0907 0.5820 -0.0301 0.071 Uiso 1 1 calc R U . . .
C22 C -0.1018(4) 0.53692(17) 0.0615(3) 0.1044(17) Uani 1 1 d . . . . .
H22A H -0.1809 0.5224 0.0343 0.157 Uiso 1 1 calc R U . . .
H22B H -0.0398 0.5116 0.0578 0.157 Uiso 1 1 calc R U . . .
H22C H -0.0961 0.5428 0.1166 0.157 Uiso 1 1 calc R U . . .
C23 C 0.52230(18) 0.63966(7) 0.16817(11) 0.0219(4) Uani 1 1 d . . . . .
C24 C 0.4821(2) 0.65830(8) 0.09180(12) 0.0273(4) Uani 1 1 d . . . . .
H24A H 0.3990 0.6576 0.0648 0.033 Uiso 1 1 calc R U . . .
C25 C 0.5615(2) 0.67773(9) 0.05518(13) 0.0367(5) Uani 1 1 d . . . . .
H25A H 0.5327 0.6908 0.0032 0.044 Uiso 1 1 calc R U . . .
C26 C 0.6834(2) 0.67854(9) 0.09325(14) 0.0371(5) Uani 1 1 d . . . . .
H26A H 0.7382 0.6924 0.0680 0.045 Uiso 1 1 calc R U . . .
C27 C 0.7238(2) 0.65876(9) 0.16866(14) 0.0339(5) Uani 1 1 d . . . . .
H27A H 0.8073 0.6583 0.1948 0.041 Uiso 1 1 calc R U . . .
C28 C 0.64452(19) 0.63963(8) 0.20641(13) 0.0277(4) Uani 1 1 d . . . . .
H28A H 0.6734 0.6265 0.2583 0.033 Uiso 1 1 calc R U . . .
C29 C 0.32018(18) 0.56033(7) 0.26155(11) 0.0212(4) Uani 1 1 d . . . . .
C30 C 0.24559(18) 0.59990(7) 0.27604(11) 0.0220(4) Uani 1 1 d . . . . .
C31 C 0.1316(2) 0.59185(9) 0.28011(12) 0.0306(5) Uani 1 1 d . . . . .
C32 C 0.0858(2) 0.54085(10) 0.27270(14) 0.0369(5) Uani 1 1 d . . . . .
C33 C 0.1561(2) 0.49979(9) 0.26127(14) 0.0356(5) Uani 1 1 d . . . . .
C34 C 0.2693(2) 0.50983(8) 0.25598(12) 0.0280(4) Uani 1 1 d . . . . .
C35 C 0.51138(17) 0.53003(7) 0.21122(11) 0.0207(4) Uani 1 1 d . . . . .
C36 C 0.44335(18) 0.51256(8) 0.13769(11) 0.0244(4) Uani 1 1 d . . . . .
C37 C 0.4838(2) 0.47779(8) 0.09165(11) 0.0271(5) Uani 1 1 d . . . . .
C38 C 0.5998(2) 0.45957(8) 0.11682(12) 0.0287(5) Uani 1 1 d . . . . .
C39 C 0.67198(18) 0.47579(7) 0.18857(12) 0.0246(4) Uani 1 1 d . . . . .
C40 C 0.62689(18) 0.51014(7) 0.23355(11) 0.0217(4) Uani 1 1 d . . . . .
C41 C 0.52959(17) 0.58954(7) 0.34711(11) 0.0193(4) Uani 1 1 d . . . . .
C42 C 0.55698(17) 0.54927(7) 0.40296(11) 0.0197(4) Uani 1 1 d . . . . .
C43 C 0.60324(18) 0.55788(8) 0.48223(11) 0.0229(4) Uani 1 1 d . . . . .
C44 C 0.62111(18) 0.60952(8) 0.50980(12) 0.0264(4) Uani 1 1 d . . . . .
C45 C 0.59697(18) 0.65071(8) 0.45816(13) 0.0267(4) Uani 1 1 d . . . . .
C46 C 0.55311(18) 0.64024(7) 0.37876(12) 0.0227(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C47 1.374(5) . ?
C47 C48 1.3900 . ?
C47 C52 1.3900 . ?
C48 C49 1.3900 . ?
C49 C50 1.3900 . ?
C50 C51 1.3900 . ?
C51 C52 1.3900 . ?
O4B C52B 1.317(14) . ?
C47B C48B 1.3900 . ?
C47B C52B 1.3900 . ?
C48B C49B 1.3900 . ?
C49B C50B 1.3900 . ?
C50B C51B 1.3900 . ?
C51B C52B 1.3900 . ?
P1 N1 1.6675(15) . ?
P1 C1 1.8027(18) . ?
P1 C13 1.8132(19) . ?
P1 C7 1.8167(19) . ?
B1 O3 1.504(2) . ?
B1 C35 1.649(3) . ?
B1 C41 1.651(3) . ?
B1 C29 1.654(3) . ?
F1 C30 1.355(2) . ?
F2 C31 1.350(3) . ?
F3 C32 1.340(3) . ?
F4 C33 1.348(2) . ?
F5 C34 1.355(2) . ?
F6 C36 1.354(2) . ?
F7 C37 1.346(2) . ?
F8 C38 1.338(2) . ?
F9 C39 1.343(2) . ?
F10 C40 1.352(2) . ?
F11 C46 1.358(2) . ?
F12 C45 1.347(2) . ?
F13 C44 1.345(2) . ?
F14 C43 1.340(2) . ?
F15 C42 1.350(2) . ?
O1 C20 1.200(3) . ?
O2 C20 1.325(2) . ?
O2 C21 1.465(3) . ?
O3 C23 1.375(2) . ?
N1 N2 1.374(2) . ?
N1 H1A 0.8800 . ?
N2 C19 1.280(2) . ?
C1 C2 1.535(3) . ?
C1 C6 1.539(2) . ?
C1 H1B 1.0000 . ?
C2 C3 1.526(3) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.513(3) . ?
C4 H4B 0.9900 . ?
C4 H4C 0.9900 . ?
C5 C6 1.534(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.535(3) . ?
C7 C12 1.537(3) . ?
C7 H7A 1.0000 . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.526(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.530(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.532(3) . ?
C13 C14 1.539(2) . ?
C13 H13A 1.0000 . ?
C14 C15 1.530(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.514(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.528(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.484(3) . ?
C19 H19A 0.9500 . ?
C21 C22 1.461(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.391(3) . ?
C23 C28 1.392(3) . ?
C24 C25 1.372(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.388(4) . ?
C25 H25A 0.9500 . ?
C26 C27 1.386(3) . ?
C26 H26A 0.9500 . ?
C27 C28 1.382(3) . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?
C29 C34 1.391(3) . ?
C29 C30 1.394(3) . ?
C30 C31 1.370(3) . ?
C31 C32 1.378(3) . ?
C32 C33 1.369(4) . ?
C33 C34 1.376(3) . ?
C35 C40 1.384(3) . ?
C35 C36 1.395(3) . ?
C36 C37 1.375(3) . ?
C37 C38 1.375(3) . ?
C38 C39 1.376(3) . ?
C39 C40 1.384(3) . ?
C41 C46 1.387(2) . ?
C41 C42 1.391(3) . ?
C42 C43 1.380(3) . ?
C43 C44 1.380(3) . ?
C44 C45 1.360(3) . ?
C45 C46 1.388(3) . ?

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
O4 C47 C48 120.9(4) . . ?
O4 C47 C52 119.1(4) . . ?
C48 C47 C52 120.0 . . ?
C47 C48 C49 120.0 . . ?
C50 C49 C48 120.0 . . ?
C49 C50 C51 120.0 . . ?
C52 C51 C50 120.0 . . ?
C51 C52 C47 120.0 . . ?
C48B C47B C52B 120.0 . . ?
C49B C48B C47B 120.0 . . ?
C50B C49B C48B 120.0 . . ?
C49B C50B C51B 120.0 . . ?
C52B C51B C50B 120.0 . . ?
O4B C52B C51B 124.6(12) . . ?
O4B C52B C47B 115.3(12) . . ?
C51B C52B C47B 120.0 . . ?
N1 P1 C1 105.09(8) . . ?
N1 P1 C13 105.46(8) . . ?
C1 P1 C13 117.84(9) . . ?
N1 P1 C7 111.18(9) . . ?
C1 P1 C7 109.11(8) . . ?
C13 P1 C7 108.06(9) . . ?
O3 B1 C35 105.05(15) . . ?
O3 B1 C41 113.33(15) . . ?
C35 B1 C41 116.69(15) . . ?
O3 B1 C29 105.94(14) . . ?
C35 B1 C29 112.63(15) . . ?
C41 B1 C29 102.89(15) . . ?
C20 O2 C21 118.08(18) . . ?
C23 O3 B1 121.72(15) . . ?
N2 N1 P1 115.06(12) . . ?
N2 N1 H1A 122.5 . . ?
P1 N1 H1A 122.5 . . ?
C19 N2 N1 117.38(16) . . ?
C2 C1 C6 110.70(15) . . ?
C2 C1 P1 114.00(13) . . ?
C6 C1 P1 114.30(12) . . ?
C2 C1 H1B 105.7 . . ?
C6 C1 H1B 105.7 . . ?
P1 C1 H1B 105.7 . . ?
C3 C2 C1 109.20(16) . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2C 109.8 . . ?
C1 C2 H2C 109.8 . . ?
H2B C2 H2C 108.3 . . ?
C2 C3 C4 110.16(16) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.46(17) . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4C 109.3 . . ?
C3 C4 H4C 109.3 . . ?
H4B C4 H4C 108.0 . . ?
C4 C5 C6 111.75(16) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C1 108.98(15) . . ?
C5 C6 H6A 109.9 . . ?
C1 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C1 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C12 111.09(16) . . ?
C8 C7 P1 112.50(13) . . ?
C12 C7 P1 111.93(13) . . ?
C8 C7 H7A 107.0 . . ?
C12 C7 H7A 107.0 . . ?
P1 C7 H7A 107.0 . . ?
C9 C8 C7 110.42(17) . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 111.26(19) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 110.74(19) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 111.59(18) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C7 110.40(16) . . ?
C11 C12 H12A 109.6 . . ?
C7 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C7 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C18 C13 C14 110.70(16) . . ?
C18 C13 P1 115.55(13) . . ?
C14 C13 P1 112.22(13) . . ?
C18 C13 H13A 105.9 . . ?
C14 C13 H13A 105.9 . . ?
P1 C13 H13A 105.9 . . ?
C15 C14 C13 109.48(16) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 111.97(18) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 111.52(18) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.47(17) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 C13 109.41(17) . . ?
C17 C18 H18A 109.8 . . ?
C13 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
C13 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
N2 C19 C20 117.36(17) . . ?
N2 C19 H19A 121.3 . . ?
C20 C19 H19A 121.3 . . ?
O1 C20 O2 124.35(19) . . ?
O1 C20 C19 126.71(18) . . ?
O2 C20 C19 108.95(17) . . ?
C22 C21 O2 108.1(2) . . ?
C22 C21 H21A 110.1 . . ?
O2 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
O2 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 C24 117.33(18) . . ?
O3 C23 C28 123.46(17) . . ?
C24 C23 C28 119.16(19) . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C24 C25 C26 120.7(2) . . ?
C24 C25 H25A 119.7 . . ?
C26 C25 H25A 119.7 . . ?
C27 C26 C25 118.8(2) . . ?
C27 C26 H26A 120.6 . . ?
C25 C26 H26A 120.6 . . ?
C28 C27 C26 120.9(2) . . ?
C28 C27 H27A 119.5 . . ?
C26 C27 H27A 119.5 . . ?
C27 C28 C23 119.8(2) . . ?
C27 C28 H28A 120.1 . . ?
C23 C28 H28A 120.1 . . ?
C34 C29 C30 112.60(19) . . ?
C34 C29 B1 127.53(18) . . ?
C30 C29 B1 119.84(16) . . ?
F1 C30 C31 115.50(18) . . ?
F1 C30 C29 119.38(17) . . ?
C31 C30 C29 125.11(18) . . ?
F2 C31 C30 120.50(19) . . ?
F2 C31 C32 120.3(2) . . ?
C30 C31 C32 119.2(2) . . ?
F3 C32 C33 121.0(2) . . ?
F3 C32 C31 120.3(2) . . ?
C33 C32 C31 118.7(2) . . ?
F4 C33 C32 119.5(2) . . ?
F4 C33 C34 120.3(2) . . ?
C32 C33 C34 120.2(2) . . ?
F5 C34 C33 115.55(18) . . ?
F5 C34 C29 120.30(19) . . ?
C33 C34 C29 124.1(2) . . ?
C40 C35 C36 113.47(18) . . ?
C40 C35 B1 127.53(17) . . ?
C36 C35 B1 118.49(17) . . ?
F6 C36 C37 116.01(17) . . ?
F6 C36 C35 119.66(18) . . ?
C37 C36 C35 124.33(19) . . ?
F7 C37 C38 119.70(19) . . ?
F7 C37 C36 120.8(2) . . ?
C38 C37 C36 119.52(19) . . ?
F8 C38 C37 120.47(19) . . ?
F8 C38 C39 120.6(2) . . ?
C37 C38 C39 118.95(19) . . ?
F9 C39 C38 119.47(19) . . ?
F9 C39 C40 120.95(18) . . ?
C38 C39 C40 119.58(19) . . ?
F10 C40 C35 120.62(17) . . ?
F10 C40 C39 115.24(17) . . ?
C35 C40 C39 124.12(18) . . ?
C46 C41 C42 113.30(17) . . ?
C46 C41 B1 125.15(16) . . ?
C42 C41 B1 120.69(15) . . ?
F15 C42 C43 116.88(16) . . ?
F15 C42 C41 118.76(16) . . ?
C43 C42 C41 124.36(17) . . ?
F14 C43 C44 119.59(17) . . ?
F14 C43 C42 121.23(17) . . ?
C44 C43 C42 119.18(17) . . ?
F13 C44 C45 120.99(18) . . ?
F13 C44 C43 119.65(19) . . ?
C45 C44 C43 119.35(18) . . ?
F12 C45 C44 120.38(18) . . ?
F12 C45 C46 120.04(19) . . ?
C44 C45 C46 119.58(17) . . ?
F11 C46 C41 120.77(17) . . ?
F11 C46 C45 115.03(16) . . ?
C41 C46 C45 124.19(18) . . ?

_refine_diff_density_max         0.807
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.171

####################################################################### 
# 
# 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_pres_sqd
_database_code_depnum_ccdc_archive 'CCDC 1848997'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT602_pres_sqd            
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info
RESPONSE: Co-crystallized solvent molecules were found to be disordered. Modelling them with constraints demonstrated that the solvents were not crystallized in any fixed position but were instead occupying a large void in the unit cell. This void contained 132 electrons and had a volume of 393 \%A3. The squeeze function was applied to this void and, by comparing the residuals between the squeezed solution and the constrained solution, the squeezed solution was found to be the more accurate representation of the molecular structure in the solid state.
;
# Added during the CSD deposition process: Tuesday 12 June 2018 08:12 PM
# end Validation Reply Form


_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            'C34 H33 B F15 N2 O2 P'
_chemical_formula_weight         828.40

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'
B B 0.0013 0.0007 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.3226(8)
_cell_length_b                   12.4212(8)
_cell_length_c                   15.8884(11)
_cell_angle_alpha                102.662(3)
_cell_angle_beta                 96.402(3)
_cell_angle_gamma                113.135(3)
_cell_volume                     2128.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4789
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      20.57

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34735
_diffrn_reflns_av_unetI/netI     0.1156
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8027
_reflns_number_gt                3925
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0878P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8027
_refine_ls_number_parameters     506
_refine_ls_number_restraints     792
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1589
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.948
_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 0.65409(9) -2.10330(9) 0.78343(6) 0.0302(3) Uani 1 1 d . U . . .
B1 B 0.1405(4) -2.6069(4) 0.6542(3) 0.0336(10) Uani 1 1 d . U . . .
C8 C 0.1434(3) -2.7277(3) 0.7684(2) 0.0326(9) Uani 1 1 d . U . . .
C2 C -0.1037(4) -2.7233(4) 0.5988(2) 0.0359(9) Uani 1 1 d . U . . .
C7 C 0.1993(3) -2.6773(3) 0.7062(2) 0.0320(9) Uani 1 1 d . U . . .
C12 C 0.2965(3) -2.7030(3) 0.6912(2) 0.0343(9) Uani 1 1 d . U . . .
C11 C 0.3358(4) -2.7698(4) 0.7347(3) 0.0378(10) Uani 1 1 d . U . . .
C4 C -0.2022(4) -2.9009(4) 0.4758(3) 0.0467(11) Uani 1 1 d . U . . .
C5 C -0.0927(4) -2.8960(4) 0.4657(3) 0.0466(11) Uani 1 1 d . U . . .
C9 C 0.1787(4) -2.7963(4) 0.8118(3) 0.0389(10) Uani 1 1 d . U . . .
C10 C 0.2765(4) -2.8167(4) 0.7945(3) 0.0407(10) Uani 1 1 d . U . . .
C6 C 0.0108(4) -2.8032(4) 0.5229(2) 0.0387(10) Uani 1 1 d . U . . .
C1 C 0.0108(3) -2.7113(3) 0.5914(2) 0.0310(9) Uani 1 1 d . U . . .
C3 C -0.2097(4) -2.8144(4) 0.5416(3) 0.0452(11) Uani 1 1 d . U . . .
F1 F -0.11863(19) -2.6440(2) 0.66425(14) 0.0439(6) Uani 1 1 d . U . . .
F5 F 0.1169(2) -2.8059(2) 0.51136(14) 0.0509(7) Uani 1 1 d . U . . .
F6 F 0.04494(19) -2.7106(2) 0.78664(13) 0.0391(6) Uani 1 1 d . U . . .
F10 F 0.3578(2) -2.6654(2) 0.63007(15) 0.0474(6) Uani 1 1 d . U . . .
F4 F -0.0842(3) -2.9818(2) 0.40155(15) 0.0686(8) Uani 1 1 d . U . . .
F9 F 0.4330(2) -2.7889(2) 0.71802(16) 0.0529(7) Uani 1 1 d . U . . .
F7 F 0.1199(2) -2.8424(3) 0.87124(16) 0.0605(7) Uani 1 1 d . U . . .
F2 F -0.3175(2) -2.8206(2) 0.55397(18) 0.0627(7) Uani 1 1 d . U . . .
F8 F 0.3135(2) -2.8834(2) 0.83745(17) 0.0649(8) Uani 1 1 d . U . . .
F3 F -0.3043(2) -2.9917(2) 0.42158(16) 0.0700(8) Uani 1 1 d . U . . .
C18 C 0.1846(4) -2.4276(4) 0.8049(2) 0.0362(10) Uani 1 1 d . U . . .
C15 C 0.0817(4) -2.3127(4) 0.7190(3) 0.0429(10) Uani 1 1 d . U . . .
C17 C 0.1853(4) -2.3203(4) 0.8502(3) 0.0472(11) Uani 1 1 d . U . . .
C13 C 0.1346(3) -2.4842(3) 0.7154(2) 0.0306(9) Uani 1 1 d . U . . .
C14 C 0.0838(4) -2.4202(4) 0.6760(2) 0.0362(10) Uani 1 1 d . U . . .
C16 C 0.1332(4) -2.2623(4) 0.8081(3) 0.0503(12) Uani 1 1 d . U . . .
F15 F 0.2413(2) -2.4759(2) 0.85285(13) 0.0471(6) Uani 1 1 d . U . . .
F11 F 0.0344(2) -2.4635(2) 0.58826(14) 0.0466(6) Uani 1 1 d . U . . .
F12 F 0.0289(3) -2.2577(2) 0.67580(16) 0.0642(8) Uani 1 1 d . U . . .
F14 F 0.2386(3) -2.2703(2) 0.93744(15) 0.0676(8) Uani 1 1 d . U . . .
F13 F 0.1325(3) -2.1561(2) 0.85151(17) 0.0747(9) Uani 1 1 d . U . . .
O1 O 0.2134(2) -2.5601(2) 0.58568(15) 0.0334(6) Uani 1 1 d . U . . .
C20 C 0.3927(3) -2.4070(4) 0.6869(2) 0.0355(9) Uani 1 1 d . U . . .
H20A H 0.3788 -2.4400 0.7354 0.043 Uiso 1 1 calc R U . . .
C19 C 0.3170(4) -2.4694(4) 0.6030(2) 0.0342(9) Uani 1 1 d . U . . .
O2 O 0.3546(2) -2.4317(2) 0.53571(16) 0.0390(7) Uani 1 1 d . U . . .
C21 C 0.2728(4) -2.4867(4) 0.4493(2) 0.0428(11) Uani 1 1 d . U . . .
H21A H 0.2080 -2.4585 0.4479 0.051 Uiso 1 1 calc R U . . .
H21B H 0.2350 -2.5769 0.4356 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3470(4) -2.4475(4) 0.3828(3) 0.0564(13) Uani 1 1 d . U . . .
H22A H 0.2940 -2.4804 0.3237 0.085 Uiso 1 1 calc R U . . .
H22B H 0.4087 -2.4788 0.3831 0.085 Uiso 1 1 calc R U . . .
H22C H 0.3863 -2.3581 0.3983 0.085 Uiso 1 1 calc R U . . .
N2 N 0.5537(3) -2.2435(3) 0.77762(19) 0.0344(8) Uani 1 1 d . U . . .
N1 N 0.4846(3) -2.3003(3) 0.6966(2) 0.0344(8) Uani 1 1 d . U . . .
C23 C 0.5739(4) -2.0026(4) 0.7990(3) 0.0633(14) Uani 1 1 d . U . . .
C26 C 0.4507(5) -2.0654(5) 0.7319(4) 0.0858(19) Uani 1 1 d . U . . .
H26A H 0.4641 -2.0797 0.6716 0.129 Uiso 1 1 calc R U . . .
H26B H 0.4087 -2.0126 0.7400 0.129 Uiso 1 1 calc R U . . .
H26C H 0.4013 -2.1437 0.7415 0.129 Uiso 1 1 calc R U . . .
C25 C 0.6472(5) -1.8749(4) 0.7898(4) 0.0919(19) Uani 1 1 d . U . . .
H25A H 0.6628 -1.8825 0.7302 0.138 Uiso 1 1 calc R U . . .
H25B H 0.7242 -1.8346 0.8335 0.138 Uiso 1 1 calc R U . . .
H25C H 0.6012 -1.8262 0.8000 0.138 Uiso 1 1 calc R U . . .
C24 C 0.5420(5) -1.9890(6) 0.8912(4) 0.0928(19) Uani 1 1 d . U . . .
H24A H 0.5034 -2.0699 0.9003 0.139 Uiso 1 1 calc R U . . .
H24B H 0.4863 -1.9503 0.8945 0.139 Uiso 1 1 calc R U . . .
H24C H 0.6160 -1.9381 0.9371 0.139 Uiso 1 1 calc R U . . .
C27 C 0.7704(4) -2.0655(4) 0.8843(3) 0.0472(11) Uani 1 1 d . U . . .
C30 C 0.8524(4) -1.9301(4) 0.9215(3) 0.0583(13) Uani 1 1 d . U . . .
H30A H 0.8050 -1.8868 0.9432 0.087 Uiso 1 1 calc R U . . .
H30B H 0.8888 -1.8988 0.8751 0.087 Uiso 1 1 calc R U . . .
H30C H 0.9164 -1.9172 0.9704 0.087 Uiso 1 1 calc R U . . .
C28 C 0.8474(5) -2.1340(5) 0.8626(4) 0.0777(16) Uani 1 1 d . U . . .
H28A H 0.7948 -2.2215 0.8373 0.117 Uiso 1 1 calc R U . . .
H28B H 0.9034 -2.1210 0.9167 0.117 Uiso 1 1 calc R U . . .
H28C H 0.8936 -2.1035 0.8197 0.117 Uiso 1 1 calc R U . . .
C29 C 0.7055(5) -2.1131(6) 0.9560(3) 0.092(2) Uani 1 1 d . U . . .
H29A H 0.6537 -2.2010 0.9323 0.138 Uiso 1 1 calc R U . . .
H29B H 0.6559 -2.0701 0.9728 0.138 Uiso 1 1 calc R U . . .
H29C H 0.7660 -2.0982 1.0080 0.138 Uiso 1 1 calc R U . . .
C31 C 0.7171(4) -2.1014(4) 0.6814(3) 0.0515(12) Uani 1 1 d . U . . .
C32 C 0.7348(5) -2.2189(4) 0.6512(3) 0.0746(16) Uani 1 1 d . U . . .
H32A H 0.6574 -2.2904 0.6407 0.112 Uiso 1 1 calc R U . . .
H32B H 0.7938 -2.2202 0.6973 0.112 Uiso 1 1 calc R U . . .
H32C H 0.7646 -2.2208 0.5965 0.112 Uiso 1 1 calc R U . . .
C33 C 0.6302(5) -2.1032(5) 0.6034(3) 0.0810(17) Uani 1 1 d . U . . .
H33A H 0.5553 -2.1788 0.5877 0.122 Uiso 1 1 calc R U . . .
H33B H 0.6683 -2.0993 0.5525 0.122 Uiso 1 1 calc R U . . .
H33C H 0.6115 -2.0327 0.6202 0.122 Uiso 1 1 calc R U . . .
C34 C 0.8382(5) -1.9864(4) 0.6990(3) 0.0709(16) Uani 1 1 d . U . . .
H34A H 0.8260 -1.9129 0.7215 0.106 Uiso 1 1 calc R U . . .
H34B H 0.8663 -1.9844 0.6438 0.106 Uiso 1 1 calc R U . . .
H34C H 0.8989 -1.9891 0.7429 0.106 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 N2 1.668(3) . ?
P1 C27 1.864(4) . ?
P1 C23 1.869(4) . ?
P1 C31 1.875(4) . ?
B1 O1 1.555(5) . ?
B1 C7 1.628(6) . ?
B1 C1 1.638(6) . ?
B1 C13 1.651(6) . ?
C8 F6 1.362(4) . ?
C8 C9 1.369(5) . ?
C8 C7 1.388(5) . ?
C2 F1 1.349(4) . ?
C2 C1 1.380(5) . ?
C2 C3 1.391(5) . ?
C7 C12 1.388(5) . ?
C12 F10 1.349(4) . ?
C12 C11 1.375(5) . ?
C11 F9 1.353(4) . ?
C11 C10 1.356(6) . ?
C4 F3 1.347(4) . ?
C4 C5 1.356(6) . ?
C4 C3 1.366(6) . ?
C5 F4 1.349(5) . ?
C5 C6 1.381(6) . ?
C9 F7 1.346(4) . ?
C9 C10 1.370(6) . ?
C10 F8 1.354(4) . ?
C6 F5 1.353(4) . ?
C6 C1 1.394(5) . ?
C3 F2 1.339(5) . ?
C18 F15 1.356(4) . ?
C18 C17 1.365(5) . ?
C18 C13 1.386(5) . ?
C15 F12 1.348(4) . ?
C15 C14 1.371(5) . ?
C15 C16 1.378(6) . ?
C17 F14 1.356(4) . ?
C17 C16 1.363(6) . ?
C13 C14 1.392(5) . ?
C14 F11 1.352(4) . ?
C16 F13 1.352(5) . ?
O1 C19 1.278(4) . ?
C20 N1 1.325(5) . ?
C20 C19 1.395(5) . ?
C19 O2 1.318(4) . ?
O2 C21 1.451(4) . ?
C21 C22 1.510(5) . ?
N2 N1 1.329(4) . ?
C23 C25 1.535(7) . ?
C23 C26 1.547(6) . ?
C23 C24 1.550(7) . ?
C27 C30 1.514(6) . ?
C27 C28 1.524(6) . ?
C27 C29 1.553(6) . ?
C31 C33 1.535(7) . ?
C31 C32 1.541(6) . ?
C31 C34 1.550(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 P1 C27 102.48(18) . . ?
N2 P1 C23 106.9(2) . . ?
C27 P1 C23 111.6(2) . . ?
N2 P1 C31 111.43(17) . . ?
C27 P1 C31 112.8(2) . . ?
C23 P1 C31 111.2(2) . . ?
O1 B1 C7 111.4(3) . . ?
O1 B1 C1 102.6(3) . . ?
C7 B1 C1 106.5(3) . . ?
O1 B1 C13 104.1(3) . . ?
C7 B1 C13 116.6(3) . . ?
C1 B1 C13 114.8(3) . . ?
F6 C8 C9 117.1(3) . . ?
F6 C8 C7 118.3(3) . . ?
C9 C8 C7 124.5(4) . . ?
F1 C2 C1 120.5(3) . . ?
F1 C2 C3 115.5(4) . . ?
C1 C2 C3 124.0(4) . . ?
C8 C7 C12 113.4(4) . . ?
C8 C7 B1 118.9(3) . . ?
C12 C7 B1 127.5(3) . . ?
F10 C12 C11 115.2(3) . . ?
F10 C12 C7 121.2(4) . . ?
C11 C12 C7 123.6(4) . . ?
F9 C11 C10 119.9(4) . . ?
F9 C11 C12 120.3(4) . . ?
C10 C11 C12 119.8(4) . . ?
F3 C4 C5 120.3(4) . . ?
F3 C4 C3 119.5(4) . . ?
C5 C4 C3 120.2(4) . . ?
F4 C5 C4 120.7(4) . . ?
F4 C5 C6 120.0(4) . . ?
C4 C5 C6 119.3(4) . . ?
F7 C9 C8 121.1(3) . . ?
F7 C9 C10 119.9(4) . . ?
C8 C9 C10 118.9(4) . . ?
F8 C10 C11 120.5(4) . . ?
F8 C10 C9 119.8(4) . . ?
C11 C10 C9 119.7(4) . . ?
F5 C6 C5 116.5(3) . . ?
F5 C6 C1 119.5(3) . . ?
C5 C6 C1 124.0(4) . . ?
C2 C1 C6 113.5(4) . . ?
C2 C1 B1 127.7(3) . . ?
C6 C1 B1 118.7(3) . . ?
F2 C3 C4 120.6(4) . . ?
F2 C3 C2 120.4(4) . . ?
C4 C3 C2 118.9(4) . . ?
F15 C18 C17 115.4(3) . . ?
F15 C18 C13 120.4(3) . . ?
C17 C18 C13 124.2(4) . . ?
F12 C15 C14 121.0(4) . . ?
F12 C15 C16 120.2(4) . . ?
C14 C15 C16 118.8(4) . . ?
F14 C17 C16 119.5(4) . . ?
F14 C17 C18 120.1(4) . . ?
C16 C17 C18 120.4(4) . . ?
C18 C13 C14 112.8(3) . . ?
C18 C13 B1 127.1(3) . . ?
C14 C13 B1 120.0(3) . . ?
F11 C14 C15 116.0(4) . . ?
F11 C14 C13 119.0(3) . . ?
C15 C14 C13 125.0(4) . . ?
F13 C16 C17 121.6(4) . . ?
F13 C16 C15 119.5(4) . . ?
C17 C16 C15 118.9(4) . . ?
C19 O1 B1 126.2(3) . . ?
N1 C20 C19 117.7(4) . . ?
O1 C19 O2 116.7(3) . . ?
O1 C19 C20 125.5(3) . . ?
O2 C19 C20 117.8(4) . . ?
C19 O2 C21 118.9(3) . . ?
O2 C21 C22 107.2(3) . . ?
N1 N2 P1 110.7(2) . . ?
C20 N1 N2 115.7(3) . . ?
C25 C23 C26 109.7(5) . . ?
C25 C23 C24 109.0(4) . . ?
C26 C23 C24 105.1(4) . . ?
C25 C23 P1 113.4(4) . . ?
C26 C23 P1 109.5(3) . . ?
C24 C23 P1 109.8(4) . . ?
C30 C27 C28 109.0(4) . . ?
C30 C27 C29 109.5(4) . . ?
C28 C27 C29 106.7(4) . . ?
C30 C27 P1 113.5(3) . . ?
C28 C27 P1 109.1(3) . . ?
C29 C27 P1 108.8(3) . . ?
C33 C31 C32 105.8(4) . . ?
C33 C31 C34 107.9(4) . . ?
C32 C31 C34 110.8(4) . . ?
C33 C31 P1 112.6(3) . . ?
C32 C31 P1 108.6(3) . . ?
C34 C31 P1 111.0(3) . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_CAS005_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1848995'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-15 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            'C22 H21 N2 O2 P'
_chemical_formula_weight         376.38

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.661(4)
_cell_length_b                   13.155(5)
_cell_length_c                   14.357(6)
_cell_angle_alpha                77.71(2)
_cell_angle_beta                 89.30(3)
_cell_angle_gamma                87.78(2)
_cell_volume                     1965.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2002
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      20.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30339
_diffrn_reflns_av_unetI/netI     0.1446
_diffrn_reflns_av_R_equivalents  0.1132
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.452
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             8279
_reflns_number_gt                4427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1020P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8279
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.2079
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.29252(9) 0.39056(7) 0.25806(7) 0.0183(3) Uani 1 1 d . . . . .
P2 P 0.20243(9) 0.80445(8) 0.69241(7) 0.0187(3) Uani 1 1 d . . . . .
O2 O -0.0960(3) 0.7374(2) 0.1857(2) 0.0281(7) Uani 1 1 d . . . . .
O4 O 0.6005(3) 1.0865(2) 0.7598(2) 0.0344(7) Uani 1 1 d . . . . .
O3 O 0.4230(3) 1.0689(3) 0.8481(2) 0.0439(9) Uani 1 1 d . . . . .
N2 N 0.1362(3) 0.5405(2) 0.2519(2) 0.0215(7) Uani 1 1 d . . . . .
N4 N 0.3492(3) 0.9318(2) 0.7322(2) 0.0221(7) Uani 1 1 d . . . . .
N3 N 0.3335(3) 0.8660(2) 0.6715(2) 0.0217(7) Uani 1 1 d . . . . .
N1 N 0.1570(3) 0.4470(2) 0.2268(2) 0.0225(8) Uani 1 1 d . . . . .
O1 O 0.0619(3) 0.7372(3) 0.2883(3) 0.0540(10) Uani 1 1 d . . . . .
C23 C 0.1865(4) 0.7229(3) 0.8105(3) 0.0203(8) Uani 1 1 d . . . . .
C41 C 0.4536(4) 0.9800(3) 0.7197(3) 0.0219(9) Uani 1 1 d . . . . .
H41A H 0.5091 0.9710 0.6695 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2925(4) 0.3080(3) 0.3758(3) 0.0194(8) Uani 1 1 d . . . . .
C19 C 0.0323(4) 0.5892(3) 0.2202(3) 0.0233(9) Uani 1 1 d . . . . .
H19A H -0.0254 0.5574 0.1864 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3259(4) 0.3142(3) 0.1703(3) 0.0205(9) Uani 1 1 d . . . . .
C8 C 0.1990(4) 0.3252(3) 0.4397(3) 0.0249(9) Uani 1 1 d . . . . .
H8A H 0.1335 0.3756 0.4191 0.030 Uiso 1 1 calc R U . . .
C1 C 0.4209(3) 0.4766(3) 0.2584(3) 0.0200(9) Uani 1 1 d . . . . .
C35 C 0.0634(3) 0.8886(3) 0.6729(3) 0.0192(8) Uani 1 1 d . . . . .
C29 C 0.2057(4) 0.7213(3) 0.6079(3) 0.0220(9) Uani 1 1 d . . . . .
C36 C 0.0740(4) 0.9905(3) 0.6219(3) 0.0244(9) Uani 1 1 d . . . . .
H36A H 0.1534 1.0144 0.5979 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2313(4) 0.2998(3) 0.1073(3) 0.0270(10) Uani 1 1 d . . . . .
H18A H 0.1500 0.3309 0.1111 0.032 Uiso 1 1 calc R U . . .
C20 C 0.0048(4) 0.6936(3) 0.2371(3) 0.0247(9) Uani 1 1 d . . . . .
C42 C 0.4857(4) 1.0484(3) 0.7832(3) 0.0258(9) Uani 1 1 d . . . . .
C26 C 0.1682(4) 0.5986(3) 0.9935(3) 0.0335(11) Uani 1 1 d . . . . .
H26A H 0.1611 0.5559 1.0555 0.040 Uiso 1 1 calc R U . . .
C28 C 0.2392(4) 0.6212(3) 0.8314(3) 0.0264(10) Uani 1 1 d . . . . .
H28A H 0.2827 0.5946 0.7830 0.032 Uiso 1 1 calc R U . . .
C40 C -0.0541(4) 0.8546(3) 0.7065(3) 0.0294(10) Uani 1 1 d . . . . .
H40A H -0.0627 0.7847 0.7402 0.035 Uiso 1 1 calc R U . . .
C37 C -0.0312(4) 1.0571(3) 0.6060(3) 0.0282(10) Uani 1 1 d . . . . .
H37A H -0.0240 1.1261 0.5700 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4446(4) 0.2689(3) 0.1621(3) 0.0298(10) Uani 1 1 d . . . . .
H14A H 0.5101 0.2788 0.2032 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2006(4) 0.2695(3) 0.5331(3) 0.0306(10) Uani 1 1 d . . . . .
H9A H 0.1370 0.2829 0.5763 0.037 Uiso 1 1 calc R U . . .
C34 C 0.2833(4) 0.7444(3) 0.5275(3) 0.0292(10) Uani 1 1 d . . . . .
H34A H 0.3367 0.8018 0.5197 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3858(4) 0.1743(3) 0.5006(3) 0.0338(11) Uani 1 1 d . . . . .
H11A H 0.4487 0.1213 0.5210 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3865(4) 0.2309(3) 0.4078(3) 0.0304(10) Uani 1 1 d . . . . .
H12A H 0.4510 0.2177 0.3653 0.037 Uiso 1 1 calc R U . . .
C38 C -0.1465(4) 1.0232(3) 0.6424(3) 0.0316(10) Uani 1 1 d . . . . .
H38A H -0.2178 1.0698 0.6339 0.038 Uiso 1 1 calc R U . . .
C27 C 0.2281(4) 0.5598(3) 0.9211(3) 0.0323(11) Uani 1 1 d . . . . .
H27A H 0.2618 0.4904 0.9338 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4574(4) 0.5394(3) 0.1725(3) 0.0324(11) Uani 1 1 d . . . . .
H2B H 0.4173 0.5349 0.1149 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4811(4) 0.4843(3) 0.3422(3) 0.0301(10) Uani 1 1 d . . . . .
H6A H 0.4574 0.4414 0.4012 0.036 Uiso 1 1 calc R U . . .
C24 C 0.1274(4) 0.7617(3) 0.8838(3) 0.0316(10) Uani 1 1 d . . . . .
H24A H 0.0929 0.8309 0.8712 0.038 Uiso 1 1 calc R U . . .
C30 C 0.1278(4) 0.6365(3) 0.6197(3) 0.0304(10) Uani 1 1 d . . . . .
H30A H 0.0743 0.6206 0.6739 0.036 Uiso 1 1 calc R U . . .
C25 C 0.1187(4) 0.7002(3) 0.9746(3) 0.0333(11) Uani 1 1 d . . . . .
H25A H 0.0788 0.7274 1.0241 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2944(4) 0.1941(3) 0.5640(3) 0.0327(11) Uani 1 1 d . . . . .
H10A H 0.2957 0.1565 0.6283 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3727(5) 0.1940(3) 0.0344(3) 0.0364(12) Uani 1 1 d . . . . .
H16A H 0.3879 0.1513 -0.0106 0.044 Uiso 1 1 calc R U . . .
C31 C 0.1290(4) 0.5760(3) 0.5520(3) 0.0347(11) Uani 1 1 d . . . . .
H31A H 0.0775 0.5174 0.5601 0.042 Uiso 1 1 calc R U . . .
C17 C 0.2561(5) 0.2409(3) 0.0402(3) 0.0356(11) Uani 1 1 d . . . . .
H17A H 0.1919 0.2325 -0.0025 0.043 Uiso 1 1 calc R U . . .
C33 C 0.2826(4) 0.6846(4) 0.4598(3) 0.0363(11) Uani 1 1 d . . . . .
H33A H 0.3349 0.7010 0.4050 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4680(5) 0.2091(3) 0.0942(3) 0.0367(12) Uani 1 1 d . . . . .
H15A H 0.5493 0.1787 0.0888 0.044 Uiso 1 1 calc R U . . .
C21 C -0.1329(4) 0.8429(3) 0.1927(3) 0.0339(11) Uani 1 1 d . . . . .
H21A H -0.1133 0.8525 0.2575 0.041 Uiso 1 1 calc R U . . .
H21B H -0.2248 0.8532 0.1837 0.041 Uiso 1 1 calc R U . . .
C39 C -0.1581(4) 0.9213(3) 0.6912(3) 0.0369(11) Uani 1 1 d . . . . .
H39A H -0.2379 0.8974 0.7143 0.044 Uiso 1 1 calc R U . . .
C32 C 0.2061(4) 0.6010(4) 0.4715(3) 0.0380(12) Uani 1 1 d . . . . .
H32A H 0.2056 0.5598 0.4245 0.046 Uiso 1 1 calc R U . . .
C3 C 0.5523(5) 0.6082(3) 0.1713(4) 0.0439(13) Uani 1 1 d . . . . .
H3B H 0.5776 0.6506 0.1125 0.053 Uiso 1 1 calc R U . . .
C43 C 0.6506(5) 1.1519(4) 0.8193(4) 0.0439(13) Uani 1 1 d . . . . .
H43A H 0.5836 1.2011 0.8327 0.053 Uiso 1 1 calc R U . . .
H43B H 0.7189 1.1931 0.7845 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5753(4) 0.5544(3) 0.3394(4) 0.0426(13) Uani 1 1 d . . . . .
H5A H 0.6158 0.5598 0.3966 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6103(4) 0.6161(3) 0.2542(4) 0.0460(14) Uani 1 1 d . . . . .
H4B H 0.6749 0.6642 0.2525 0.055 Uiso 1 1 calc R U . . .
C44 C 0.7003(5) 1.0886(4) 0.9113(4) 0.0533(14) Uani 1 1 d . . . . .
H44A H 0.7446 1.1337 0.9452 0.080 Uiso 1 1 calc R U . . .
H44B H 0.7584 1.0337 0.8984 0.080 Uiso 1 1 calc R U . . .
H44C H 0.6304 1.0571 0.9507 0.080 Uiso 1 1 calc R U . . .
C22 C -0.0687(5) 0.9226(4) 0.1215(4) 0.0553(15) Uani 1 1 d . . . . .
H22A H -0.1054 0.9917 0.1229 0.083 Uiso 1 1 calc R U . . .
H22B H -0.0792 0.9084 0.0578 0.083 Uiso 1 1 calc R U . . .
H22C H 0.0209 0.9204 0.1366 0.083 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.622(3) . ?
P1 C13 1.795(4) . ?
P1 C7 1.805(4) . ?
P1 C1 1.810(4) . ?
P2 N3 1.635(3) . ?
P2 C29 1.797(4) . ?
P2 C35 1.803(4) . ?
P2 C23 1.813(4) . ?
O2 C20 1.350(5) . ?
O2 C21 1.451(5) . ?
O4 C42 1.352(5) . ?
O4 C43 1.454(5) . ?
O3 C42 1.211(5) . ?
N2 C19 1.295(5) . ?
N2 N1 1.364(4) . ?
N4 C41 1.295(5) . ?
N4 N3 1.368(4) . ?
O1 C20 1.207(5) . ?
C23 C24 1.397(5) . ?
C23 C28 1.404(5) . ?
C41 C42 1.461(6) . ?
C41 H41A 0.9500 . ?
C7 C8 1.391(5) . ?
C7 C12 1.406(5) . ?
C19 C20 1.462(5) . ?
C19 H19A 0.9500 . ?
C13 C14 1.393(5) . ?
C13 C18 1.407(6) . ?
C8 C9 1.383(5) . ?
C8 H8A 0.9500 . ?
C1 C2 1.391(5) . ?
C1 C6 1.394(6) . ?
C35 C40 1.392(5) . ?
C35 C36 1.392(5) . ?
C29 C30 1.397(6) . ?
C29 C34 1.399(5) . ?
C36 C37 1.386(5) . ?
C36 H36A 0.9500 . ?
C18 C17 1.377(6) . ?
C18 H18A 0.9500 . ?
C26 C25 1.390(6) . ?
C26 C27 1.390(6) . ?
C26 H26A 0.9500 . ?
C28 C27 1.373(5) . ?
C28 H28A 0.9500 . ?
C40 C39 1.377(5) . ?
C40 H40A 0.9500 . ?
C37 C38 1.383(6) . ?
C37 H37A 0.9500 . ?
C14 C15 1.392(6) . ?
C14 H14A 0.9500 . ?
C9 C10 1.388(6) . ?
C9 H9A 0.9500 . ?
C34 C33 1.376(6) . ?
C34 H34A 0.9500 . ?
C11 C10 1.381(6) . ?
C11 C12 1.381(6) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C38 C39 1.383(6) . ?
C38 H38A 0.9500 . ?
C27 H27A 0.9500 . ?
C2 C3 1.381(6) . ?
C2 H2B 0.9500 . ?
C6 C5 1.384(6) . ?
C6 H6A 0.9500 . ?
C24 C25 1.385(6) . ?
C24 H24A 0.9500 . ?
C30 C31 1.381(6) . ?
C30 H30A 0.9500 . ?
C25 H25A 0.9500 . ?
C10 H10A 0.9500 . ?
C16 C17 1.376(6) . ?
C16 C15 1.385(6) . ?
C16 H16A 0.9500 . ?
C31 C32 1.399(6) . ?
C31 H31A 0.9500 . ?
C17 H17A 0.9500 . ?
C33 C32 1.376(6) . ?
C33 H33A 0.9500 . ?
C15 H15A 0.9500 . ?
C21 C22 1.482(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C39 H39A 0.9500 . ?
C32 H32A 0.9500 . ?
C3 C4 1.373(7) . ?
C3 H3B 0.9500 . ?
C43 C44 1.495(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C5 C4 1.373(7) . ?
C5 H5A 0.9500 . ?
C4 H4B 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C13 104.10(18) . . ?
N1 P1 C7 113.45(17) . . ?
C13 P1 C7 110.17(17) . . ?
N1 P1 C1 115.82(17) . . ?
C13 P1 C1 108.30(18) . . ?
C7 P1 C1 104.95(18) . . ?
N3 P2 C29 103.60(18) . . ?
N3 P2 C35 113.95(17) . . ?
C29 P2 C35 109.01(18) . . ?
N3 P2 C23 115.76(18) . . ?
C29 P2 C23 107.85(18) . . ?
C35 P2 C23 106.39(18) . . ?
C20 O2 C21 116.7(3) . . ?
C42 O4 C43 116.9(3) . . ?
C19 N2 N1 114.7(3) . . ?
C41 N4 N3 113.8(3) . . ?
N4 N3 P2 111.9(2) . . ?
N2 N1 P1 114.9(3) . . ?
C24 C23 C28 118.6(4) . . ?
C24 C23 P2 120.8(3) . . ?
C28 C23 P2 120.5(3) . . ?
N4 C41 C42 119.6(4) . . ?
N4 C41 H41A 120.2 . . ?
C42 C41 H41A 120.2 . . ?
C8 C7 C12 118.3(3) . . ?
C8 C7 P1 118.5(3) . . ?
C12 C7 P1 123.1(3) . . ?
N2 C19 C20 119.3(4) . . ?
N2 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
C14 C13 C18 118.5(4) . . ?
C14 C13 P1 121.5(3) . . ?
C18 C13 P1 120.0(3) . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C2 C1 C6 119.2(4) . . ?
C2 C1 P1 118.6(3) . . ?
C6 C1 P1 122.2(3) . . ?
C40 C35 C36 119.1(4) . . ?
C40 C35 P2 122.1(3) . . ?
C36 C35 P2 118.8(3) . . ?
C30 C29 C34 119.7(4) . . ?
C30 C29 P2 120.7(3) . . ?
C34 C29 P2 119.5(3) . . ?
C37 C36 C35 120.1(4) . . ?
C37 C36 H36A 120.0 . . ?
C35 C36 H36A 120.0 . . ?
C17 C18 C13 120.3(4) . . ?
C17 C18 H18A 119.9 . . ?
C13 C18 H18A 119.9 . . ?
O1 C20 O2 123.1(4) . . ?
O1 C20 C19 126.7(4) . . ?
O2 C20 C19 110.1(4) . . ?
O3 C42 O4 123.3(4) . . ?
O3 C42 C41 127.3(4) . . ?
O4 C42 C41 109.4(3) . . ?
C25 C26 C27 119.6(4) . . ?
C25 C26 H26A 120.2 . . ?
C27 C26 H26A 120.2 . . ?
C27 C28 C23 120.5(4) . . ?
C27 C28 H28A 119.8 . . ?
C23 C28 H28A 119.8 . . ?
C39 C40 C35 120.5(4) . . ?
C39 C40 H40A 119.7 . . ?
C35 C40 H40A 119.7 . . ?
C38 C37 C36 120.1(4) . . ?
C38 C37 H37A 119.9 . . ?
C36 C37 H37A 119.9 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C33 C34 C29 120.4(4) . . ?
C33 C34 H34A 119.8 . . ?
C29 C34 H34A 119.8 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C7 120.6(4) . . ?
C11 C12 H12A 119.7 . . ?
C7 C12 H12A 119.7 . . ?
C39 C38 C37 120.0(4) . . ?
C39 C38 H38A 120.0 . . ?
C37 C38 H38A 120.0 . . ?
C28 C27 C26 120.6(4) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2B 120.1 . . ?
C1 C2 H2B 120.1 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C25 C24 C23 120.6(4) . . ?
C25 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C31 C30 C29 119.5(4) . . ?
C31 C30 H30A 120.3 . . ?
C29 C30 H30A 120.3 . . ?
C24 C25 C26 120.1(4) . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C11 C10 C9 119.5(4) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
C30 C31 C32 120.0(4) . . ?
C30 C31 H31A 120.0 . . ?
C32 C31 H31A 120.0 . . ?
C16 C17 C18 120.8(4) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C34 C33 C32 119.9(4) . . ?
C34 C33 H33A 120.1 . . ?
C32 C33 H33A 120.1 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
O2 C21 C22 112.7(4) . . ?
O2 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
O2 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C40 C39 C38 120.1(4) . . ?
C40 C39 H39A 119.9 . . ?
C38 C39 H39A 119.9 . . ?
C33 C32 C31 120.4(4) . . ?
C33 C32 H32A 119.8 . . ?
C31 C32 H32A 119.8 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3B 119.6 . . ?
C2 C3 H3B 119.6 . . ?
O4 C43 C44 111.6(4) . . ?
O4 C43 H43A 109.3 . . ?
C44 C43 H43A 109.3 . . ?
O4 C43 H43B 109.3 . . ?
C44 C43 H43B 109.3 . . ?
H43A C43 H43B 108.0 . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4B 120.0 . . ?
C5 C4 H4B 120.0 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.099

