# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1042262'
_audit_update_record             
;
2015-01-06 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 N3 O2, F6 P, 2(C2 H3 N)'
_chemical_formula_sum            'C36 H28 F6 N5 O2 P'
_chemical_formula_weight         707.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.895(3)
_cell_length_b                   11.505(5)
_cell_length_c                   14.869(4)
_cell_angle_alpha                71.806(5)
_cell_angle_beta                 80.889(2)
_cell_angle_gamma                82.139(5)
_cell_volume                     1580.9(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8857
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.75

_exptl_crystal_description       needles
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction  
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27399
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.90
_reflns_number_total             7472
_reflns_number_gt                5725
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0632P)²+1.5462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7472
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5809(2) 0.47555(18) 0.11586(14) 0.0172(4) Uani 1 1 d . . .
C2 C 0.4434(2) 0.51890(19) 0.12148(14) 0.0183(4) Uani 1 1 d . . .
H2 H 0.3752 0.4704 0.1179 0.022 Uiso 1 1 calc R . .
C3 C 0.4075(2) 0.63477(19) 0.13251(14) 0.0176(4) Uani 1 1 d . . .
H3 H 0.3141 0.6679 0.1355 0.021 Uiso 1 1 calc R . .
C4 C 0.5105(2) 0.70220(18) 0.13914(14) 0.0152(4) Uani 1 1 d . . .
C5 C 0.6475(2) 0.65696(18) 0.13454(14) 0.0176(4) Uani 1 1 d . . .
H5 H 0.7156 0.7044 0.1398 0.021 Uiso 1 1 calc R . .
C6 C 0.6846(2) 0.54181(19) 0.12219(15) 0.0192(4) Uani 1 1 d . . .
H6 H 0.7781 0.5091 0.1182 0.023 Uiso 1 1 calc R . .
C7 C 0.3789(2) 0.91510(18) 0.10598(14) 0.0148(4) Uani 1 1 d . . .
C8 C 0.3133(2) 0.92870(19) 0.02790(14) 0.0172(4) Uani 1 1 d . . .
H8 H 0.3301 0.8701 -0.0066 0.021 Uiso 1 1 calc R . .
C9 C 0.2194(2) 1.03447(19) 0.00149(14) 0.0166(4) Uani 1 1 d . . .
C10 C 0.1428(2) 1.0540(2) -0.07663(15) 0.0213(4) Uani 1 1 d . . .
H10 H 0.1587 0.9978 -0.1131 0.026 Uiso 1 1 calc R . .
C11 C 0.0470(2) 1.1524(2) -0.09948(15) 0.0243(5) Uani 1 1 d . . .
H11 H -0.0025 1.1640 -0.1519 0.029 Uiso 1 1 calc R . .
C12 C 0.0205(2) 1.2372(2) -0.04610(16) 0.0234(5) Uani 1 1 d . . .
H12 H -0.0475 1.3045 -0.0622 0.028 Uiso 1 1 calc R . .
C13 C 0.0923(2) 1.22277(19) 0.02850(15) 0.0200(4) Uani 1 1 d . . .
H13 H 0.0738 1.2805 0.0638 0.024 Uiso 1 1 calc R . .
C14 C 0.1947(2) 1.12217(18) 0.05423(14) 0.0164(4) Uani 1 1 d . . .
C15 C 0.2696(2) 1.10747(18) 0.13134(14) 0.0166(4) Uani 1 1 d . . .
H15 H 0.2581 1.1665 0.1652 0.020 Uiso 1 1 calc R . .
C16 C 0.3596(2) 1.00413(18) 0.15482(13) 0.0149(4) Uani 1 1 d . . .
C17 C 0.5046(2) 0.85188(18) 0.22693(14) 0.0159(4) Uani 1 1 d . . .
H17 H 0.5643 0.8026 0.2712 0.019 Uiso 1 1 calc R . .
C18 C 0.4461(2) 1.02370(18) 0.30147(14) 0.0168(4) Uani 1 1 d . . .
H18A H 0.3512 1.0378 0.3317 0.020 Uiso 1 1 calc R . .
H18B H 0.4812 1.1049 0.2693 0.020 Uiso 1 1 calc R . .
C19 C 0.5348(2) 0.95204(18) 0.37816(14) 0.0155(4) Uani 1 1 d . . .
C20 C 0.4760(2) 0.86804(18) 0.46148(14) 0.0168(4) Uani 1 1 d . . .
C21 C 0.3361(2) 0.8397(2) 0.47569(16) 0.0209(4) Uani 1 1 d . . .
H21 H 0.2790 0.8782 0.4269 0.025 Uiso 1 1 calc R . .
C22 C 0.2833(2) 0.7585(2) 0.55785(17) 0.0273(5) Uani 1 1 d . . .
H22 H 0.1900 0.7420 0.5657 0.033 Uiso 1 1 calc R . .
C23 C 0.3658(3) 0.6984(2) 0.63185(17) 0.0297(5) Uani 1 1 d . . .
H23 H 0.3277 0.6416 0.6886 0.036 Uiso 1 1 calc R . .
C24 C 0.4993(3) 0.7216(2) 0.62188(15) 0.0259(5) Uani 1 1 d . . .
H24 H 0.5537 0.6808 0.6719 0.031 Uiso 1 1 calc R . .
C25 C 0.5589(2) 0.80682(18) 0.53709(14) 0.0192(4) Uani 1 1 d . . .
C26 C 0.6951(2) 0.83164(19) 0.52678(15) 0.0210(4) Uani 1 1 d . . .
H26 H 0.7488 0.7917 0.5773 0.025 Uiso 1 1 calc R . .
C27 C 0.7548(2) 0.91340(19) 0.44439(15) 0.0198(4) Uani 1 1 d . . .
C28 C 0.8948(2) 0.9392(2) 0.43460(18) 0.0271(5) Uani 1 1 d . . .
H28 H 0.9477 0.9013 0.4859 0.033 Uiso 1 1 calc R . .
C29 C 0.9529(2) 1.0168(2) 0.35353(19) 0.0304(5) Uani 1 1 d . . .
H29 H 1.0458 1.0331 0.3484 0.037 Uiso 1 1 calc R . .
C30 C 0.8755(2) 1.0740(2) 0.27607(17) 0.0283(5) Uani 1 1 d . . .
H30 H 0.9177 1.1269 0.2188 0.034 Uiso 1 1 calc R . .
C31 C 0.7409(2) 1.0539(2) 0.28302(15) 0.0221(4) Uani 1 1 d . . .
H31 H 0.6905 1.0939 0.2307 0.027 Uiso 1 1 calc R . .
C32 C 0.6744(2) 0.97373(18) 0.36740(14) 0.0172(4) Uani 1 1 d . . .
C33 C 0.7047(4) 0.4879(3) 0.5408(2) 0.0499(8) Uani 1 1 d . . .
H33A H 0.7649 0.4171 0.5304 0.075 Uiso 1 1 calc R . .
H33B H 0.6236 0.4592 0.5854 0.075 Uiso 1 1 calc R . .
H33C H 0.7545 0.5348 0.5675 0.075 Uiso 1 1 calc R . .
C34 C 0.6617(3) 0.5660(2) 0.45039(19) 0.0324(6) Uani 1 1 d . . .
C35 C -0.0262(3) 0.6835(3) 0.3754(2) 0.0470(8) Uani 1 1 d . . .
H35A H -0.0379 0.6792 0.4430 0.070 Uiso 1 1 calc R . .
H35B H -0.0214 0.6005 0.3695 0.070 Uiso 1 1 calc R . .
H35C H -0.1044 0.7339 0.3453 0.070 Uiso 1 1 calc R . .
C36 C 0.1007(2) 0.7388(2) 0.32837(17) 0.0275(5) Uani 1 1 d . . .
N1 N 0.61891(19) 0.35177(16) 0.10502(12) 0.0212(4) Uani 1 1 d . . .
N2 N 0.47173(17) 0.82081(15) 0.15397(12) 0.0151(3) Uani 1 1 d . . .
N3 N 0.44260(17) 0.96068(15) 0.22882(11) 0.0147(3) Uani 1 1 d . . .
N4 N 0.6313(3) 0.6271(2) 0.37934(17) 0.0423(6) Uani 1 1 d . . .
N5 N 0.2007(2) 0.78088(19) 0.29254(14) 0.0299(4) Uani 1 1 d . . .
O1 O 0.52620(17) 0.28544(14) 0.11552(12) 0.0281(4) Uani 1 1 d . . .
O2 O 0.74065(17) 0.32001(15) 0.08591(13) 0.0323(4) Uani 1 1 d . . .
F1 F -0.0410(3) 0.3336(2) 0.23845(15) 0.0874(8) Uani 1 1 d . . .
F2 F -0.0432(3) 0.5224(2) 0.24105(15) 0.0880(8) Uani 1 1 d . . .
F3 F 0.02275(18) 0.37222(15) 0.36644(10) 0.0450(4) Uani 1 1 d . . .
F4 F 0.11677(19) 0.44747(17) 0.14177(11) 0.0515(5) Uani 1 1 d . . .
F5 F 0.1791(3) 0.2964(2) 0.26592(15) 0.1085(12) Uani 1 1 d . . .
F6 F 0.1751(2) 0.4891(3) 0.26847(15) 0.0941(10) Uani 1 1 d . . .
P1 P 0.06876(6) 0.40915(5) 0.25389(4) 0.02143(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(3) . ?
C1 C6 1.390(3) . ?
C1 N1 1.474(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 N2 1.441(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.375(3) . ?
C7 C16 1.407(3) . ?
C7 N2 1.407(2) . ?
C8 C9 1.416(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.430(3) . ?
C9 C14 1.435(3) . ?
C10 C11 1.365(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.414(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.365(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.427(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(3) . ?
C15 C16 1.370(3) . ?
C15 H15 0.9500 . ?
C16 N3 1.402(2) . ?
C17 N3 1.323(3) . ?
C17 N2 1.340(2) . ?
C17 H17 0.9500 . ?
C18 N3 1.484(2) . ?
C18 C19 1.511(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.409(3) . ?
C19 C32 1.413(3) . ?
C20 C21 1.434(3) . ?
C20 C25 1.439(3) . ?
C21 C22 1.362(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.418(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.359(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.432(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C26 C27 1.392(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.432(3) . ?
C27 C32 1.437(3) . ?
C28 C29 1.353(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.419(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.365(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.428(3) . ?
C31 H31 0.9500 . ?
C33 C34 1.455(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 N4 1.131(3) . ?
C35 C36 1.459(4) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N5 1.141(3) . ?
N1 O2 1.225(2) . ?
N1 O1 1.233(2) . ?
F1 P1 1.5648(18) . ?
F2 P1 1.574(2) . ?
F3 P1 1.5989(16) . ?
F4 P1 1.5958(17) . ?
F5 P1 1.5607(19) . ?
F6 P1 1.5688(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 123.19(19) . . ?
C2 C1 N1 118.31(18) . . ?
C6 C1 N1 118.48(18) . . ?
C1 C2 C3 118.33(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.08(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.90(18) . . ?
C5 C4 N2 119.39(17) . . ?
C3 C4 N2 118.68(17) . . ?
C4 C5 C6 119.44(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 118.04(19) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
C8 C7 C16 122.11(18) . . ?
C8 C7 N2 131.90(18) . . ?
C16 C7 N2 105.99(16) . . ?
C7 C8 C9 116.61(18) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 H8 121.7 . . ?
C8 C9 C10 120.54(19) . . ?
C8 C9 C14 121.19(17) . . ?
C10 C9 C14 118.23(19) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.77(19) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.93(19) . . ?
C15 C14 C9 120.19(18) . . ?
C13 C14 C9 118.87(18) . . ?
C16 C15 C14 116.92(18) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C15 C16 N3 130.69(18) . . ?
C15 C16 C7 122.83(17) . . ?
N3 C16 C7 106.42(17) . . ?
N3 C17 N2 110.71(17) . . ?
N3 C17 H17 124.6 . . ?
N2 C17 H17 124.6 . . ?
N3 C18 C19 113.23(16) . . ?
N3 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
N3 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C32 120.64(18) . . ?
C20 C19 C18 119.66(18) . . ?
C32 C19 C18 119.65(18) . . ?
C19 C20 C21 123.33(18) . . ?
C19 C20 C25 119.23(18) . . ?
C21 C20 C25 117.44(19) . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 120.9(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.9(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 121.14(19) . . ?
C26 C25 C20 119.57(19) . . ?
C24 C25 C20 119.3(2) . . ?
C25 C26 C27 121.77(18) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C28 121.46(19) . . ?
C26 C27 C32 119.47(19) . . ?
C28 C27 C32 119.1(2) . . ?
C29 C28 C27 121.1(2) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 120.2(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 120.7(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 121.3(2) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C19 C32 C31 123.09(18) . . ?
C19 C32 C27 119.27(19) . . ?
C31 C32 C27 117.65(19) . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N4 C34 C33 178.5(3) . . ?
C36 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C36 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N5 C36 C35 179.1(3) . . ?
O2 N1 O1 123.31(18) . . ?
O2 N1 C1 118.52(18) . . ?
O1 N1 C1 118.17(18) . . ?
C17 N2 C7 108.18(16) . . ?
C17 N2 C4 123.88(16) . . ?
C7 N2 C4 127.29(16) . . ?
C17 N3 C16 108.67(15) . . ?
C17 N3 C18 127.15(16) . . ?
C16 N3 C18 123.91(16) . . ?
F5 P1 F1 91.47(17) . . ?
F5 P1 F6 90.58(17) . . ?
F1 P1 F6 177.93(17) . . ?
F5 P1 F2 179.40(13) . . ?
F1 P1 F2 88.00(16) . . ?
F6 P1 F2 89.95(16) . . ?
F5 P1 F4 88.73(12) . . ?
F1 P1 F4 88.82(10) . . ?
F6 P1 F4 90.99(10) . . ?
F2 P1 F4 90.97(11) . . ?
F5 P1 F3 91.24(11) . . ?
F1 P1 F3 92.25(10) . . ?
F6 P1 F3 87.95(10) . . ?
F2 P1 F3 89.06(11) . . ?
F4 P1 F3 178.94(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(3) . . . . ?
N1 C1 C2 C3 179.44(18) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 N2 -177.84(18) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
N2 C4 C5 C6 178.71(18) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 C5 -178.56(18) . . . . ?
C16 C7 C8 C9 -3.0(3) . . . . ?
N2 C7 C8 C9 176.7(2) . . . . ?
C7 C8 C9 C10 -177.75(19) . . . . ?
C7 C8 C9 C14 -0.1(3) . . . . ?
C8 C9 C10 C11 176.6(2) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 179.7(2) . . . . ?
C12 C13 C14 C9 -1.2(3) . . . . ?
C8 C9 C14 C15 3.2(3) . . . . ?
C10 C9 C14 C15 -179.08(19) . . . . ?
C8 C9 C14 C13 -175.84(19) . . . . ?
C10 C9 C14 C13 1.8(3) . . . . ?
C13 C14 C15 C16 175.95(19) . . . . ?
C9 C14 C15 C16 -3.1(3) . . . . ?
C14 C15 C16 N3 -176.68(19) . . . . ?
C14 C15 C16 C7 0.0(3) . . . . ?
C8 C7 C16 C15 3.2(3) . . . . ?
N2 C7 C16 C15 -176.58(18) . . . . ?
C8 C7 C16 N3 -179.41(18) . . . . ?
N2 C7 C16 N3 0.8(2) . . . . ?
N3 C18 C19 C20 -90.3(2) . . . . ?
N3 C18 C19 C32 92.3(2) . . . . ?
C32 C19 C20 C21 -178.36(18) . . . . ?
C18 C19 C20 C21 4.3(3) . . . . ?
C32 C19 C20 C25 1.8(3) . . . . ?
C18 C19 C20 C25 -175.54(17) . . . . ?
C19 C20 C21 C22 -179.4(2) . . . . ?
C25 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C26 179.5(2) . . . . ?
C23 C24 C25 C20 -0.2(3) . . . . ?
C19 C20 C25 C26 0.1(3) . . . . ?
C21 C20 C25 C26 -179.77(18) . . . . ?
C19 C20 C25 C24 179.87(18) . . . . ?
C21 C20 C25 C24 0.0(3) . . . . ?
C24 C25 C26 C27 179.4(2) . . . . ?
C20 C25 C26 C27 -0.8(3) . . . . ?
C25 C26 C27 C28 179.50(19) . . . . ?
C25 C26 C27 C32 -0.3(3) . . . . ?
C26 C27 C28 C29 178.6(2) . . . . ?
C32 C27 C28 C29 -1.6(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C31 1.5(3) . . . . ?
C29 C30 C31 C32 -0.9(3) . . . . ?
C20 C19 C32 C31 177.31(18) . . . . ?
C18 C19 C32 C31 -5.4(3) . . . . ?
C20 C19 C32 C27 -2.9(3) . . . . ?
C18 C19 C32 C27 174.42(17) . . . . ?
C30 C31 C32 C19 178.8(2) . . . . ?
C30 C31 C32 C27 -1.0(3) . . . . ?
C26 C27 C32 C19 2.2(3) . . . . ?
C28 C27 C32 C19 -177.64(18) . . . . ?
C26 C27 C32 C31 -178.04(19) . . . . ?
C28 C27 C32 C31 2.2(3) . . . . ?
C2 C1 N1 O2 169.36(19) . . . . ?
C6 C1 N1 O2 -12.1(3) . . . . ?
C2 C1 N1 O1 -10.5(3) . . . . ?
C6 C1 N1 O1 167.99(18) . . . . ?
N3 C17 N2 C7 -1.4(2) . . . . ?
N3 C17 N2 C4 -172.80(17) . . . . ?
C8 C7 N2 C17 -179.4(2) . . . . ?
C16 C7 N2 C17 0.3(2) . . . . ?
C8 C7 N2 C4 -8.4(3) . . . . ?
C16 C7 N2 C4 171.32(18) . . . . ?
C5 C4 N2 C17 -54.6(3) . . . . ?
C3 C4 N2 C17 123.6(2) . . . . ?
C5 C4 N2 C7 135.7(2) . . . . ?
C3 C4 N2 C7 -46.1(3) . . . . ?
N2 C17 N3 C16 1.9(2) . . . . ?
N2 C17 N3 C18 176.15(18) . . . . ?
C15 C16 N3 C17 175.4(2) . . . . ?
C7 C16 N3 C17 -1.7(2) . . . . ?
C15 C16 N3 C18 1.0(3) . . . . ?
C7 C16 N3 C18 -176.13(17) . . . . ?
C19 C18 N3 C17 1.6(3) . . . . ?
C19 C18 N3 C16 174.97(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.90
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042263'
_audit_update_record             
;
2015-01-06 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H23 N3 O3'
_chemical_formula_sum            'C32 H23 N3 O3'
_chemical_formula_weight         497.53

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.816(4)
_cell_length_b                   11.381(4)
_cell_length_c                   13.411(6)
_cell_angle_alpha                99.225(19)
_cell_angle_beta                 92.06(2)
_cell_angle_gamma                100.585(19)
_cell_volume                     1450.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5036
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.36

_exptl_crystal_description       needles
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   
;
SADABS from Bruker
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21829
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5099
_reflns_number_gt                3749
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 The refinement showed lot of very diffuse electro density with the
highest peak of 3.4 eA3 which looked like some unidentified solvent molecules
but it could not be modelled despite our efforts therefore this electron
density was removed using SQUEEZE from PLATON software. The remaining
structure refined and converged nicely and there was a huge decline in the
R index. This leaves SAV of 342 A3 in the crystal structure. 
  
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5099
_refine_ls_number_parameters     346
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.089
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.95782(16) 0.64807(13) 0.70456(12) 0.0211(4) Uani 1 1 d . . .
C2 C 1.07038(16) 0.59240(14) 0.68312(12) 0.0217(4) Uani 1 1 d . . .
H2 H 1.0791 0.5512 0.6169 0.026 Uiso 1 1 calc R . .
C3 C 1.16892(17) 0.59852(13) 0.76022(12) 0.0207(4) Uani 1 1 d . . .
H3 H 1.2467 0.5608 0.7474 0.025 Uiso 1 1 calc R . .
C4 C 1.15571(16) 0.65982(13) 0.85750(12) 0.0190(4) Uani 1 1 d . . .
C5 C 1.03869(16) 0.71294(13) 0.87665(12) 0.0213(4) Uani 1 1 d . . .
H5 H 1.0282 0.7534 0.9428 0.026 Uiso 1 1 calc R . .
C6 C 0.94064(17) 0.70651(13) 0.80086(12) 0.0214(4) Uani 1 1 d . . .
H6 H 0.8611 0.7417 0.8137 0.026 Uiso 1 1 calc R . .
C7 C 1.30674(15) 0.76804(13) 1.00622(12) 0.0189(4) Uani 1 1 d . . .
C8 C 1.38446(16) 0.75522(13) 1.09363(12) 0.0182(4) Uani 1 1 d . . .
C9 C 1.44467(16) 0.85430(14) 1.16243(12) 0.0221(4) Uani 1 1 d . . .
H9 H 1.4962 0.8434 1.2204 0.027 Uiso 1 1 calc R . .
C10 C 1.43242(17) 0.97334(14) 1.14976(13) 0.0250(4) Uani 1 1 d . . .
C11 C 1.49702(18) 1.07867(15) 1.21837(14) 0.0330(5) Uani 1 1 d . . .
H11 H 1.5510 1.0707 1.2763 0.040 Uiso 1 1 calc R . .
C12 C 1.4826(2) 1.19178(16) 1.20233(16) 0.0407(5) Uani 1 1 d . . .
H12 H 1.5269 1.2614 1.2490 0.049 Uiso 1 1 calc R . .
C13 C 1.4034(2) 1.20555(15) 1.11795(16) 0.0394(5) Uani 1 1 d . . .
H13 H 1.3937 1.2844 1.1077 0.047 Uiso 1 1 calc R . .
C14 C 1.33986(18) 1.10657(15) 1.05013(15) 0.0315(4) Uani 1 1 d . . .
H14 H 1.2864 1.1171 0.9929 0.038 Uiso 1 1 calc R . .
C15 C 1.35264(16) 0.98712(14) 1.06402(13) 0.0252(4) Uani 1 1 d . . .
C16 C 1.29228(16) 0.88350(14) 0.99379(13) 0.0232(4) Uani 1 1 d . . .
H16 H 1.2397 0.8931 0.9358 0.028 Uiso 1 1 calc R . .
C17 C 1.52489(16) 0.60248(14) 1.09744(11) 0.0206(4) Uani 1 1 d . . .
H17 H 1.5971 0.6588 1.0760 0.025 Uiso 1 1 calc R . .
C18 C 1.28500(16) 0.55367(13) 1.14237(12) 0.0201(4) Uani 1 1 d . . .
H18A H 1.3165 0.4799 1.1567 0.024 Uiso 1 1 calc R . .
H18B H 1.2102 0.5284 1.0874 0.024 Uiso 1 1 calc R . .
C19 C 1.22771(16) 0.61390(13) 1.23650(12) 0.0187(4) Uani 1 1 d . . .
C20 C 1.09886(16) 0.65150(13) 1.23195(12) 0.0198(4) Uani 1 1 d . . .
C21 C 1.01741(16) 0.64189(14) 1.13998(13) 0.0222(4) Uani 1 1 d . . .
H21 H 1.0512 0.6109 1.0776 0.027 Uiso 1 1 calc R . .
C22 C 0.89184(17) 0.67639(15) 1.14004(13) 0.0266(4) Uani 1 1 d . . .
H22 H 0.8395 0.6689 1.0776 0.032 Uiso 1 1 calc R . .
C23 C 0.83737(18) 0.72341(15) 1.23153(14) 0.0297(4) Uani 1 1 d . . .
H23 H 0.7489 0.7459 1.2301 0.036 Uiso 1 1 calc R . .
C24 C 0.91143(17) 0.73601(14) 1.32008(13) 0.0267(4) Uani 1 1 d . . .
H24 H 0.8745 0.7673 1.3811 0.032 Uiso 1 1 calc R . .
C25 C 1.04425(17) 0.70332(14) 1.32395(12) 0.0218(4) Uani 1 1 d . . .
C26 C 1.12224(17) 0.72078(14) 1.41516(13) 0.0234(4) Uani 1 1 d . . .
H26 H 1.0865 0.7556 1.4754 0.028 Uiso 1 1 calc R . .
C27 C 1.25183(17) 0.68838(13) 1.42009(12) 0.0224(4) Uani 1 1 d . . .
C28 C 1.33234(18) 0.70900(15) 1.51336(13) 0.0276(4) Uani 1 1 d . . .
H28 H 1.2979 0.7462 1.5733 0.033 Uiso 1 1 calc R . .
C29 C 1.45728(19) 0.67627(16) 1.51782(13) 0.0313(4) Uani 1 1 d . . .
H29 H 1.5107 0.6919 1.5807 0.038 Uiso 1 1 calc R . .
C30 C 1.50995(19) 0.61868(15) 1.42979(13) 0.0294(4) Uani 1 1 d . . .
H30 H 1.5977 0.5953 1.4345 0.035 Uiso 1 1 calc R . .
C31 C 1.43663(17) 0.59678(14) 1.33929(13) 0.0239(4) Uani 1 1 d . . .
H31 H 1.4732 0.5575 1.2812 0.029 Uiso 1 1 calc R . .
C32 C 1.30489(16) 0.63184(13) 1.32981(12) 0.0198(4) Uani 1 1 d . . .
N1 N 0.85411(15) 0.64560(12) 0.62428(11) 0.0264(3) Uani 1 1 d . . .
N2 N 1.40194(13) 0.63536(11) 1.10842(9) 0.0176(3) Uani 1 1 d . . .
N3 N 1.25454(14) 0.66325(11) 0.93472(10) 0.0199(3) Uani 1 1 d D . .
H3A H 1.3128(16) 0.6133(14) 0.9234(12) 0.024 Uiso 1 1 d D . .
O1 O 0.75744(14) 0.69887(12) 0.64544(10) 0.0444(4) Uani 1 1 d . . .
O2 O 0.86748(13) 0.59247(11) 0.53895(9) 0.0348(3) Uani 1 1 d . . .
O3 O 1.55315(11) 0.50496(9) 1.11279(8) 0.0235(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(2) . ?
C1 C2 1.388(2) . ?
C1 N1 1.448(2) . ?
C2 C3 1.375(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C4 N3 1.384(2) . ?
C4 C5 1.406(2) . ?
C5 C6 1.358(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C16 1.383(2) . ?
C7 N3 1.406(2) . ?
C7 C8 1.417(2) . ?
C8 C9 1.362(2) . ?
C8 N2 1.449(2) . ?
C9 C10 1.418(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.414(2) . ?
C10 C11 1.418(2) . ?
C11 C12 1.370(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.429(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.406(2) . ?
C16 H16 0.9500 . ?
C17 O3 1.2383(19) . ?
C17 N2 1.334(2) . ?
C17 H17 0.9500 . ?
C18 N2 1.4732(19) . ?
C18 C19 1.515(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C32 1.405(2) . ?
C19 C20 1.410(2) . ?
C20 C21 1.423(2) . ?
C20 C25 1.445(2) . ?
C21 C22 1.361(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.421(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.343(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.421(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(2) . ?
C26 C27 1.390(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.418(2) . ?
C27 C32 1.439(2) . ?
C28 C29 1.348(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.418(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.352(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.429(2) . ?
C31 H31 0.9500 . ?
N1 O2 1.2290(18) . ?
N1 O1 1.2346(19) . ?
N3 H3A 0.878(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.20(15) . . ?
C6 C1 N1 118.34(15) . . ?
C2 C1 N1 119.46(15) . . ?
C3 C2 C1 118.24(15) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.58(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N3 C4 C3 119.85(15) . . ?
N3 C4 C5 120.65(14) . . ?
C3 C4 C5 119.44(14) . . ?
C6 C5 C4 120.18(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.32(16) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C16 C7 N3 123.74(15) . . ?
C16 C7 C8 118.12(14) . . ?
N3 C7 C8 118.06(13) . . ?
C9 C8 C7 120.69(14) . . ?
C9 C8 N2 119.95(14) . . ?
C7 C8 N2 119.35(13) . . ?
C8 C9 C10 121.73(16) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C15 C10 C9 118.12(14) . . ?
C15 C10 C11 118.69(15) . . ?
C9 C10 C11 123.19(17) . . ?
C12 C11 C10 120.91(19) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.49(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.39(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.82(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C10 119.04(14) . . ?
C16 C15 C14 122.22(17) . . ?
C10 C15 C14 118.70(15) . . ?
C7 C16 C15 122.28(16) . . ?
C7 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
O3 C17 N2 125.69(15) . . ?
O3 C17 H17 117.2 . . ?
N2 C17 H17 117.2 . . ?
N2 C18 C19 111.86(12) . . ?
N2 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N2 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C32 C19 C20 119.80(15) . . ?
C32 C19 C18 118.98(14) . . ?
C20 C19 C18 121.22(14) . . ?
C19 C20 C21 123.33(15) . . ?
C19 C20 C25 119.73(14) . . ?
C21 C20 C25 116.94(14) . . ?
C22 C21 C20 121.00(16) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 121.39(16) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 119.79(16) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 121.03(16) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 120.68(15) . . ?
C26 C25 C20 119.54(15) . . ?
C24 C25 C20 119.78(15) . . ?
C25 C26 C27 121.25(16) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C28 120.90(16) . . ?
C26 C27 C32 119.83(15) . . ?
C28 C27 C32 119.26(15) . . ?
C29 C28 C27 120.62(17) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.76(16) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C31 C30 C29 120.69(17) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.91(16) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C19 C32 C31 122.50(15) . . ?
C19 C32 C27 119.76(14) . . ?
C31 C32 C27 117.74(14) . . ?
O2 N1 O1 123.50(14) . . ?
O2 N1 C1 118.78(15) . . ?
O1 N1 C1 117.72(15) . . ?
C17 N2 C8 120.27(13) . . ?
C17 N2 C18 120.52(13) . . ?
C8 N2 C18 119.08(12) . . ?
C4 N3 C7 123.12(13) . . ?
C4 N3 H3A 117.0(11) . . ?
C7 N3 H3A 114.0(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.5(2) . . . . ?
N1 C1 C2 C3 178.53(13) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 N3 178.82(13) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
N3 C4 C5 C6 -178.40(13) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
N1 C1 C6 C5 -178.12(13) . . . . ?
C16 C7 C8 C9 -0.9(2) . . . . ?
N3 C7 C8 C9 176.01(14) . . . . ?
C16 C7 C8 N2 -179.70(14) . . . . ?
N3 C7 C8 N2 -2.8(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
N2 C8 C9 C10 178.73(14) . . . . ?
C8 C9 C10 C15 1.4(2) . . . . ?
C8 C9 C10 C11 -178.14(15) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
C9 C10 C11 C12 179.58(16) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C9 C10 C15 C16 -1.7(2) . . . . ?
C11 C10 C15 C16 177.80(15) . . . . ?
C9 C10 C15 C14 -179.77(15) . . . . ?
C11 C10 C15 C14 -0.2(2) . . . . ?
C13 C14 C15 C16 -177.84(15) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
N3 C7 C16 C15 -176.23(14) . . . . ?
C8 C7 C16 C15 0.5(2) . . . . ?
C10 C15 C16 C7 0.8(2) . . . . ?
C14 C15 C16 C7 178.78(15) . . . . ?
N2 C18 C19 C32 -73.41(17) . . . . ?
N2 C18 C19 C20 106.84(15) . . . . ?
C32 C19 C20 C21 176.96(14) . . . . ?
C18 C19 C20 C21 -3.3(2) . . . . ?
C32 C19 C20 C25 -2.7(2) . . . . ?
C18 C19 C20 C25 177.03(13) . . . . ?
C19 C20 C21 C22 178.13(14) . . . . ?
C25 C20 C21 C22 -2.2(2) . . . . ?
C20 C21 C22 C23 0.1(2) . . . . ?
C21 C22 C23 C24 0.9(2) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
C23 C24 C25 C26 177.59(15) . . . . ?
C23 C24 C25 C20 -2.3(2) . . . . ?
C19 C20 C25 C26 3.0(2) . . . . ?
C21 C20 C25 C26 -176.67(13) . . . . ?
C19 C20 C25 C24 -177.06(13) . . . . ?
C21 C20 C25 C24 3.2(2) . . . . ?
C24 C25 C26 C27 179.52(14) . . . . ?
C20 C25 C26 C27 -0.6(2) . . . . ?
C25 C26 C27 C28 178.60(15) . . . . ?
C25 C26 C27 C32 -2.1(2) . . . . ?
C26 C27 C28 C29 179.32(15) . . . . ?
C32 C27 C28 C29 0.1(2) . . . . ?
C27 C28 C29 C30 -1.1(2) . . . . ?
C28 C29 C30 C31 0.8(3) . . . . ?
C29 C30 C31 C32 0.5(2) . . . . ?
C20 C19 C32 C31 -179.42(13) . . . . ?
C18 C19 C32 C31 0.8(2) . . . . ?
C20 C19 C32 C27 0.0(2) . . . . ?
C18 C19 C32 C27 -179.72(13) . . . . ?
C30 C31 C32 C19 178.02(15) . . . . ?
C30 C31 C32 C27 -1.5(2) . . . . ?
C26 C27 C32 C19 2.4(2) . . . . ?
C28 C27 C32 C19 -178.30(14) . . . . ?
C26 C27 C32 C31 -178.09(13) . . . . ?
C28 C27 C32 C31 1.2(2) . . . . ?
C6 C1 N1 O2 -178.97(14) . . . . ?
C2 C1 N1 O2 1.0(2) . . . . ?
C6 C1 N1 O1 2.0(2) . . . . ?
C2 C1 N1 O1 -178.05(14) . . . . ?
O3 C17 N2 C8 176.42(14) . . . . ?
O3 C17 N2 C18 0.6(2) . . . . ?
C9 C8 N2 C17 -70.7(2) . . . . ?
C7 C8 N2 C17 108.02(17) . . . . ?
C9 C8 N2 C18 105.17(17) . . . . ?
C7 C8 N2 C18 -76.06(18) . . . . ?
C19 C18 N2 C17 123.66(15) . . . . ?
C19 C18 N2 C8 -52.25(18) . . . . ?
C3 C4 N3 C7 138.30(15) . . . . ?
C5 C4 N3 C7 -44.4(2) . . . . ?
C16 C7 N3 C4 -16.3(2) . . . . ?
C8 C7 N3 C4 166.90(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.005 0.000 0.002 345 92 ' '
_platon_squeeze_details          
;
;


