# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_7a
_database_code_depnum_ccdc_archive 'CCDC 1877993'
_audit_update_record             
;
2018-11-09 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Br N4 O'
_chemical_formula_sum            'C17 H17 Br N4 O'
_chemical_formula_weight         373.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -2.6470 0.5500 '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                   5.2572(10)
_cell_length_b                   12.458(3)
_cell_length_c                   13.205(3)
_cell_angle_alpha                69.94(3)
_cell_angle_beta                 83.57(3)
_cell_angle_gamma                89.74(3)
_cell_volume                     806.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      32.0

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.947
_shelx_estimated_absorpt_T_min   0.783
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96260
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13207
_diffrn_reflns_av_unetI/netI     0.1348
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         38.307
_diffrn_reflns_theta_full        35.279
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             3237
_reflns_number_gt                2399
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  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)+(0.0278P)²+0.55P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Br1 Br 1.45350(9) 0.03570(4) 0.11965(3) 0.0287(3) Uani 1 1 d . . . . .
O1 O 0.6157(5) 0.1317(2) 0.5233(2) 0.0221(6) Uani 1 1 d . . . . .
N1 N 0.5602(6) 0.3637(3) 0.6210(2) 0.0181(7) Uani 1 1 d . . . . .
N2 N 0.7089(6) 0.4646(3) 0.5846(2) 0.0204(7) Uani 1 1 d . . . . .
N3 N 0.6009(6) 0.5305(3) 0.6359(2) 0.0208(7) Uani 1 1 d . . . . .
N4 N 0.4863(6) 0.1869(3) 0.5919(2) 0.0225(8) Uani 1 1 d . . . . .
C3A C 0.3842(7) 0.4740(3) 0.7043(3) 0.0184(8) Uani 1 1 d . . . . .
C4 C 0.2345(7) 0.5304(3) 0.7756(3) 0.0211(9) Uani 1 1 d . . . . .
H4A H 0.0490 0.5199 0.7731 0.025 Uiso 1 1 calc R U . . .
H4B H 0.2772 0.6136 0.7469 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2931(8) 0.4803(3) 0.8954(3) 0.0270(10) Uani 1 1 d . . . . .
H5A H 0.4682 0.5064 0.8993 0.032 Uiso 1 1 calc R U . . .
H5B H 0.1723 0.5118 0.9402 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2745(8) 0.3491(3) 0.9451(3) 0.0271(10) Uani 1 1 d . . . . .
H6A H 0.3083 0.3272 1.0217 0.032 Uiso 1 1 calc R U . . .
H6B H 0.4142 0.3189 0.9069 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0210(8) 0.2875(3) 0.9432(3) 0.0248(9) Uani 1 1 d . . . . .
H7A H -0.1203 0.3212 0.9770 0.030 Uiso 1 1 calc R U . . .
H7B H 0.0283 0.2064 0.9899 0.030 Uiso 1 1 calc R U . . .
C8 C -0.0514(8) 0.2902(3) 0.8303(3) 0.0250(9) Uani 1 1 d . . . . .
H8A H -0.1918 0.2327 0.8434 0.030 Uiso 1 1 calc R U . . .
H8B H -0.1192 0.3662 0.7933 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1655(7) 0.2674(3) 0.7524(3) 0.0203(9) Uani 1 1 d . . . . .
H9A H 0.2598 0.2008 0.7938 0.024 Uiso 1 1 calc R U . . .
H9B H 0.0880 0.2467 0.6963 0.024 Uiso 1 1 calc R U . . .
C9A C 0.3556(7) 0.3671(3) 0.6960(3) 0.0189(9) Uani 1 1 d . . . . .
C10 C 0.6315(7) 0.2806(3) 0.5714(3) 0.0185(9) Uani 1 1 d . . . . .
C11 C 0.8530(7) 0.2922(3) 0.4937(3) 0.0185(8) Uani 1 1 d . . . . .
H11 H 0.9822 0.3515 0.4676 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8305(7) 0.1956(3) 0.4665(3) 0.0189(9) Uani 1 1 d . . . . .
C13 C 0.9818(7) 0.1545(3) 0.3862(3) 0.0191(9) Uani 1 1 d . . . . .
C14 C 1.2125(7) 0.2138(3) 0.3296(3) 0.0201(9) Uani 1 1 d . . . . .
H14 H 1.2721 0.2776 0.3452 0.024 Uiso 1 1 calc R U . . .
C15 C 1.3540(7) 0.1786(3) 0.2503(3) 0.0218(9) Uani 1 1 d . . . . .
H15 H 1.5090 0.2180 0.2120 0.026 Uiso 1 1 calc R U . . .
C16 C 1.2603(8) 0.0833(3) 0.2292(3) 0.0214(9) Uani 1 1 d . . . . .
C17 C 1.0345(8) 0.0235(3) 0.2845(3) 0.0246(10) Uani 1 1 d . . . . .
H17 H 0.9757 -0.0406 0.2690 0.029 Uiso 1 1 calc R U . . .
C18 C 0.8950(7) 0.0592(3) 0.3634(3) 0.0207(9) Uani 1 1 d . . . . .
H18 H 0.7409 0.0189 0.4019 0.025 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
Br1 C16 1.931(4) . ?
O1 C12 1.371(5) . ?
O1 N4 1.429(4) . ?
N1 N2 1.389(4) . ?
N1 C9A 1.390(5) . ?
N1 C10 1.430(4) . ?
N2 N3 1.322(4) . ?
N3 C3A 1.396(5) . ?
N4 C10 1.328(5) . ?
C3A C9A 1.383(5) . ?
C3A C4 1.511(5) . ?
C4 C5 1.556(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.537(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.548(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.568(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.541(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9A 1.518(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.436(5) . ?
C11 C12 1.378(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.483(5) . ?
C13 C18 1.410(5) . ?
C13 C14 1.415(6) . ?
C14 C15 1.407(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.412(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(6) . ?
C17 C18 1.401(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 N4 109.6(3) . . ?
N2 N1 C9A 111.4(3) . . ?
N2 N1 C10 116.4(3) . . ?
C9A N1 C10 132.0(3) . . ?
N3 N2 N1 106.1(3) . . ?
N2 N3 C3A 109.8(3) . . ?
C10 N4 O1 103.2(3) . . ?
C9A C3A N3 109.0(3) . . ?
C9A C3A C4 131.3(4) . . ?
N3 C3A C4 119.6(3) . . ?
C3A C4 C5 112.1(3) . . ?
C3A C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3A C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 114.8(3) . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 C7 118.2(3) . . ?
C5 C6 H6A 107.8 . . ?
C7 C6 H6A 107.8 . . ?
C5 C6 H6B 107.8 . . ?
C7 C6 H6B 107.8 . . ?
H6A C6 H6B 107.1 . . ?
C6 C7 C8 117.9(3) . . ?
C6 C7 H7A 107.8 . . ?
C8 C7 H7A 107.8 . . ?
C6 C7 H7B 107.8 . . ?
C8 C7 H7B 107.8 . . ?
H7A C7 H7B 107.2 . . ?
C9 C8 C7 116.5(3) . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C9A C9 C8 114.8(3) . . ?
C9A C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C9A C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C3A C9A N1 103.7(3) . . ?
C3A C9A C9 133.1(3) . . ?
N1 C9A C9 123.2(3) . . ?
N4 C10 N1 121.1(3) . . ?
N4 C10 C11 114.6(3) . . ?
N1 C10 C11 124.3(3) . . ?
C12 C11 C10 102.4(3) . . ?
C12 C11 H11 128.8 . . ?
C10 C11 H11 128.8 . . ?
O1 C12 C11 110.2(3) . . ?
O1 C12 C13 117.2(3) . . ?
C11 C12 C13 132.6(4) . . ?
C18 C13 C14 119.7(3) . . ?
C18 C13 C12 120.9(4) . . ?
C14 C13 C12 119.4(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 118.5(4) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 122.0(3) . . ?
C17 C16 Br1 119.6(3) . . ?
C15 C16 Br1 118.4(3) . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 120.5(4) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?

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
C9A N1 N2 N3 0.2(3) . . . . ?
C10 N1 N2 N3 176.4(3) . . . . ?
N1 N2 N3 C3A -0.3(3) . . . . ?
C12 O1 N4 C10 0.2(3) . . . . ?
N2 N3 C3A C9A 0.4(4) . . . . ?
N2 N3 C3A C4 177.3(3) . . . . ?
C9A C3A C4 C5 74.0(5) . . . . ?
N3 C3A C4 C5 -102.2(4) . . . . ?
C3A C4 C5 C6 -50.1(5) . . . . ?
C4 C5 C6 C7 -55.4(5) . . . . ?
C5 C6 C7 C8 68.3(5) . . . . ?
C6 C7 C8 C9 44.3(5) . . . . ?
C7 C8 C9 C9A -76.4(4) . . . . ?
N3 C3A C9A N1 -0.2(3) . . . . ?
C4 C3A C9A N1 -176.7(3) . . . . ?
N3 C3A C9A C9 177.5(3) . . . . ?
C4 C3A C9A C9 1.0(6) . . . . ?
N2 N1 C9A C3A 0.0(3) . . . . ?
C10 N1 C9A C3A -175.4(3) . . . . ?
N2 N1 C9A C9 -178.0(3) . . . . ?
C10 N1 C9A C9 6.6(5) . . . . ?
C8 C9 C9A C3A 4.3(5) . . . . ?
C8 C9 C9A N1 -178.4(3) . . . . ?
O1 N4 C10 N1 177.0(3) . . . . ?
O1 N4 C10 C11 -0.4(4) . . . . ?
N2 N1 C10 N4 -172.7(3) . . . . ?
C9A N1 C10 N4 2.5(5) . . . . ?
N2 N1 C10 C11 4.4(4) . . . . ?
C9A N1 C10 C11 179.6(3) . . . . ?
N4 C10 C11 C12 0.5(4) . . . . ?
N1 C10 C11 C12 -176.8(3) . . . . ?
N4 O1 C12 C11 0.1(4) . . . . ?
N4 O1 C12 C13 -176.7(3) . . . . ?
C10 C11 C12 O1 -0.3(4) . . . . ?
C10 C11 C12 C13 175.8(3) . . . . ?
O1 C12 C13 C18 5.2(5) . . . . ?
C11 C12 C13 C18 -170.7(3) . . . . ?
O1 C12 C13 C14 -176.6(3) . . . . ?
C11 C12 C13 C14 7.5(5) . . . . ?
C18 C13 C14 C15 0.5(5) . . . . ?
C12 C13 C14 C15 -177.7(3) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C14 C15 C16 Br1 179.6(2) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
Br1 C16 C17 C18 -179.6(2) . . . . ?
C16 C17 C18 C13 0.2(5) . . . . ?
C14 C13 C18 C17 -0.6(5) . . . . ?
C12 C13 C18 C17 177.6(3) . . . . ?

_refine_diff_density_max         0.809
_refine_diff_density_min         -1.391
_refine_diff_density_rms         0.149

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_11c
_database_code_depnum_ccdc_archive 'CCDC 1877998'
_audit_update_record             
;
2018-11-09 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N2 O P'
_chemical_formula_sum            'C27 H21 N2 O P'
_chemical_formula_weight         420.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1650 0.1760 '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                   12.429(3)
_cell_length_b                   10.415(2)
_cell_length_c                   37.841(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.13(3)
_cell_angle_gamma                90
_cell_volume                     4898.4(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      35.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96260
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46720
_diffrn_reflns_av_unetI/netI     0.0866
_diffrn_reflns_av_R_equivalents  0.1035
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         3.436
_diffrn_reflns_theta_max         38.468
_diffrn_reflns_theta_full        35.279
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             10579
_reflns_number_gt                8072
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  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)+(0.0756P)²+P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0062(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10579
_refine_ls_number_parameters     560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1369
_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_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 0.76517(4) 0.73176(5) 0.10849(2) 0.01761(13) Uani 1 1 d . . . . .
O1 O 0.51421(10) 0.86010(12) 0.03338(3) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.67566(12) 0.65408(15) 0.08666(4) 0.0213(3) Uani 1 1 d . . . . .
N2 N 0.60275(12) 0.84003(15) 0.05756(4) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.60486(14) 0.71377(18) 0.06372(4) 0.0182(4) Uani 1 1 d . . . . .
C4 C 0.52141(14) 0.64878(18) 0.04375(4) 0.0189(4) Uani 1 1 d . . . . .
H4 H 0.5068 0.5593 0.0432 0.023 Uiso 1 1 calc R U . . .
C5 C 0.46867(14) 0.74330(17) 0.02606(4) 0.0176(4) Uani 1 1 d . . . . .
C6 C 0.83624(14) 0.61184(18) 0.13426(4) 0.0205(4) Uani 1 1 d . . . . .
C7 C 0.82560(15) 0.48091(18) 0.12583(5) 0.0235(4) Uani 1 1 d . . . . .
H7 H 0.7757 0.4545 0.1082 0.028 Uiso 1 1 calc R U . . .
C8 C 0.88884(16) 0.3895(2) 0.14346(5) 0.0291(5) Uani 1 1 d . . . . .
H8 H 0.8823 0.3011 0.1376 0.035 Uiso 1 1 calc R U . . .
C9 C 0.96155(16) 0.4279(2) 0.16969(5) 0.0292(5) Uani 1 1 d . . . . .
H9 H 1.0043 0.3658 0.1816 0.035 Uiso 1 1 calc R U . . .
C10 C 0.97120(15) 0.55805(19) 0.17841(5) 0.0265(4) Uani 1 1 d . . . . .
H10 H 1.0203 0.5840 0.1963 0.032 Uiso 1 1 calc R U . . .
C11 C 0.90922(15) 0.64969(19) 0.16094(5) 0.0234(4) Uani 1 1 d . . . . .
H11 H 0.9161 0.7378 0.1670 0.028 Uiso 1 1 calc R U . . .
C12 C 0.86928(14) 0.80578(18) 0.08092(4) 0.0194(4) Uani 1 1 d . . . . .
C13 C 0.94581(15) 0.89229(19) 0.09456(5) 0.0246(4) Uani 1 1 d . . . . .
H13 H 0.9422 0.9178 0.1186 0.030 Uiso 1 1 calc R U . . .
C14 C 1.02719(16) 0.9410(2) 0.07283(5) 0.0285(5) Uani 1 1 d . . . . .
H14 H 1.0777 1.0007 0.0820 0.034 Uiso 1 1 calc R U . . .
C15 C 1.03417(15) 0.9018(2) 0.03759(5) 0.0294(5) Uani 1 1 d . . . . .
H15 H 1.0900 0.9340 0.0229 0.035 Uiso 1 1 calc R U . . .
C16 C 0.95877(16) 0.8150(2) 0.02390(5) 0.0280(4) Uani 1 1 d . . . . .
H16 H 0.9636 0.7884 -0.0001 0.034 Uiso 1 1 calc R U . . .
C17 C 0.87666(15) 0.76727(18) 0.04524(5) 0.0227(4) Uani 1 1 d . . . . .
H17 H 0.8256 0.7087 0.0358 0.027 Uiso 1 1 calc R U . . .
C18 C 0.72141(13) 0.85576(18) 0.13956(4) 0.0187(4) Uani 1 1 d . . . . .
C19 C 0.72697(16) 0.9867(2) 0.13124(5) 0.0275(4) Uani 1 1 d . . . . .
H19 H 0.7526 1.0129 0.1087 0.033 Uiso 1 1 calc R U . . .
C20 C 0.69476(17) 1.0794(2) 0.15610(5) 0.0303(5) Uani 1 1 d . . . . .
H20 H 0.7001 1.1681 0.1505 0.036 Uiso 1 1 calc R U . . .
C21 C 0.65516(15) 1.0417(2) 0.18880(5) 0.0263(4) Uani 1 1 d . . . . .
H21 H 0.6344 1.1046 0.2056 0.032 Uiso 1 1 calc R U . . .
C22 C 0.64581(15) 0.9113(2) 0.19695(5) 0.0258(4) Uani 1 1 d . . . . .
H22 H 0.6163 0.8858 0.2190 0.031 Uiso 1 1 calc R U . . .
C23 C 0.67977(14) 0.81777(19) 0.17273(4) 0.0224(4) Uani 1 1 d . . . . .
H23 H 0.6748 0.7293 0.1786 0.027 Uiso 1 1 calc R U . . .
C24 C 0.37335(14) 0.74525(18) 0.00247(4) 0.0183(4) Uani 1 1 d . . . . .
C25 C 0.33827(14) 0.86066(19) -0.01336(4) 0.0203(4) Uani 1 1 d . . . . .
H25 H 0.3773 0.9378 -0.0095 0.024 Uiso 1 1 calc R U . . .
C26 C 0.24615(14) 0.8618(2) -0.03474(4) 0.0231(4) Uani 1 1 d . . . . .
H26 H 0.2220 0.9402 -0.0448 0.028 Uiso 1 1 calc R U . . .
C27 C 0.18986(15) 0.7489(2) -0.04128(5) 0.0258(4) Uani 1 1 d . . . . .
H27 H 0.1277 0.7500 -0.0559 0.031 Uiso 1 1 calc R U . . .
C28 C 0.22510(15) 0.6335(2) -0.02615(5) 0.0281(4) Uani 1 1 d . . . . .
H28 H 0.1872 0.5561 -0.0309 0.034 Uiso 1 1 calc R U . . .
C29 C 0.31563(15) 0.63159(19) -0.00419(5) 0.0237(4) Uani 1 1 d . . . . .
H29 H 0.3383 0.5532 0.0063 0.028 Uiso 1 1 calc R U . . .
P2 P 0.61325(4) -0.04575(5) 0.32378(2) 0.01802(13) Uani 1 1 d . . . . .
O2 O 0.85237(10) 0.09087(12) 0.24525(3) 0.0205(3) Uani 1 1 d . . . . .
N3 N 0.70702(12) -0.11717(15) 0.30251(4) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.76877(12) 0.06950(15) 0.27107(4) 0.0215(3) Uani 1 1 d . . . . .
C30 C 0.77309(14) -0.05612(18) 0.27856(4) 0.0188(4) Uani 1 1 d . . . . .
C31 C 0.85707(14) -0.11935(18) 0.25852(4) 0.0185(4) Uani 1 1 d . . . . .
H31 H 0.8762 -0.2076 0.2591 0.022 Uiso 1 1 calc R U . . .
C32 C 0.90259(14) -0.02431(18) 0.23869(4) 0.0183(4) Uani 1 1 d . . . . .
C33 C 0.56210(14) -0.16304(18) 0.35504(4) 0.0200(4) Uani 1 1 d . . . . .
C34 C 0.59900(16) -0.2906(2) 0.35315(5) 0.0285(5) Uani 1 1 d . . . . .
H34 H 0.6497 -0.3147 0.3356 0.034 Uiso 1 1 calc R U . . .
C35 C 0.56091(17) -0.3817(2) 0.37717(6) 0.0364(5) Uani 1 1 d . . . . .
H35 H 0.5850 -0.4681 0.3757 0.044 Uiso 1 1 calc R U . . .
C36 C 0.48732(16) -0.3463(2) 0.40348(5) 0.0327(5) Uani 1 1 d . . . . .
H36 H 0.4625 -0.4084 0.4200 0.039 Uiso 1 1 calc R U . . .
C37 C 0.45056(15) -0.2200(2) 0.40545(5) 0.0276(5) Uani 1 1 d . . . . .
H37 H 0.4006 -0.1964 0.4233 0.033 Uiso 1 1 calc R U . . .
C38 C 0.48685(15) -0.1278(2) 0.38130(5) 0.0237(4) Uani 1 1 d . . . . .
H38 H 0.4611 -0.0420 0.3826 0.028 Uiso 1 1 calc R U . . .
C39 C 0.49852(14) 0.00600(18) 0.29692(4) 0.0203(4) Uani 1 1 d . . . . .
C40 C 0.40402(16) -0.0693(2) 0.29539(5) 0.0298(5) Uani 1 1 d . . . . .
H40 H 0.3967 -0.1420 0.3104 0.036 Uiso 1 1 calc R U . . .
C41 C 0.32124(17) -0.0371(2) 0.27186(6) 0.0374(5) Uani 1 1 d . . . . .
H41 H 0.2574 -0.0872 0.2711 0.045 Uiso 1 1 calc R U . . .
C42 C 0.33237(17) 0.0686(2) 0.24939(5) 0.0323(5) Uani 1 1 d . . . . .
H42 H 0.2766 0.0895 0.2332 0.039 Uiso 1 1 calc R U . . .
C43 C 0.42478(16) 0.1429(2) 0.25078(5) 0.0267(4) Uani 1 1 d . . . . .
H43 H 0.4318 0.2147 0.2354 0.032 Uiso 1 1 calc R U . . .
C44 C 0.50823(15) 0.11370(19) 0.27454(4) 0.0230(4) Uani 1 1 d . . . . .
H44 H 0.5707 0.1661 0.2755 0.028 Uiso 1 1 calc R U . . .
C45 C 0.65596(14) 0.08979(19) 0.35078(4) 0.0215(4) Uani 1 1 d . . . . .
C46 C 0.76308(16) 0.0914(2) 0.36270(5) 0.0337(5) Uani 1 1 d . . . . .
H46 H 0.8124 0.0285 0.3545 0.040 Uiso 1 1 calc R U . . .
C47 C 0.79732(18) 0.1849(2) 0.38654(6) 0.0421(6) Uani 1 1 d . . . . .
H47 H 0.8705 0.1875 0.3938 0.051 Uiso 1 1 calc R U . . .
C48 C 0.72434(19) 0.2748(2) 0.39978(5) 0.0384(6) Uani 1 1 d . . . . .
H48 H 0.7473 0.3368 0.4166 0.046 Uiso 1 1 calc R U . . .
C49 C 0.61779(18) 0.2732(2) 0.38821(5) 0.0313(5) Uani 1 1 d . . . . .
H49 H 0.5681 0.3343 0.3972 0.038 Uiso 1 1 calc R U . . .
C50 C 0.58360(16) 0.18217(19) 0.36338(5) 0.0262(4) Uani 1 1 d . . . . .
H50 H 0.5114 0.1830 0.3551 0.031 Uiso 1 1 calc R U . . .
C51 C 0.99257(14) -0.02062(18) 0.21322(4) 0.0189(4) Uani 1 1 d . . . . .
C52 C 1.00165(15) 0.08104(19) 0.18887(5) 0.0241(4) Uani 1 1 d . . . . .
H52 H 0.9493 0.1475 0.1887 0.029 Uiso 1 1 calc R U . . .
C53 C 1.08763(16) 0.0846(2) 0.16494(5) 0.0279(4) Uani 1 1 d . . . . .
H53 H 1.0939 0.1539 0.1488 0.033 Uiso 1 1 calc R U . . .
C54 C 1.16377(16) -0.0136(2) 0.16488(5) 0.0293(5) Uani 1 1 d . . . . .
H54 H 1.2215 -0.0114 0.1485 0.035 Uiso 1 1 calc R U . . .
C55 C 1.15549(15) -0.1158(2) 0.18894(5) 0.0290(5) Uani 1 1 d . . . . .
H55 H 1.2074 -0.1827 0.1887 0.035 Uiso 1 1 calc R U . . .
C56 C 1.07064(14) -0.11910(19) 0.21323(5) 0.0230(4) Uani 1 1 d . . . . .
H56 H 1.0656 -0.1876 0.2297 0.028 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 1.6034(15) . ?
P1 C6 1.8132(19) . ?
P1 C18 1.8299(18) . ?
P1 C12 1.8338(19) . ?
O1 C5 1.370(2) . ?
O1 N2 1.4448(18) . ?
N1 C3 1.382(2) . ?
N2 C3 1.336(2) . ?
C3 C4 1.450(2) . ?
C4 C5 1.358(2) . ?
C4 H4 0.9500 . ?
C5 C24 1.482(2) . ?
C6 C7 1.407(3) . ?
C6 C11 1.412(2) . ?
C7 C8 1.403(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.407(3) . ?
C12 C17 1.412(2) . ?
C13 C14 1.400(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.401(3) . ?
C18 C23 1.415(2) . ?
C19 C20 1.407(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.403(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.407(3) . ?
C24 C25 1.412(3) . ?
C25 C26 1.400(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.401(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.398(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
P2 N3 1.6012(16) . ?
P2 C33 1.8163(18) . ?
P2 C45 1.821(2) . ?
P2 C39 1.8305(19) . ?
O2 C32 1.375(2) . ?
O2 N4 1.4450(18) . ?
N3 C30 1.379(2) . ?
N4 C30 1.340(2) . ?
C30 C31 1.450(2) . ?
C31 C32 1.366(3) . ?
C31 H31 0.9500 . ?
C32 C51 1.478(2) . ?
C33 C34 1.407(3) . ?
C33 C38 1.415(2) . ?
C34 C35 1.397(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.403(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.394(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.401(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C44 1.411(3) . ?
C39 C40 1.413(3) . ?
C40 C41 1.400(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.398(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.386(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.405(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C50 1.401(3) . ?
C45 C46 1.405(3) . ?
C46 C47 1.393(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.397(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.394(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.401(3) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.408(3) . ?
C51 C56 1.412(3) . ?
C52 C53 1.403(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.393(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.405(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.401(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C6 105.44(8) . . ?
N1 P1 C18 118.70(8) . . ?
C6 P1 C18 106.61(8) . . ?
N1 P1 C12 114.12(8) . . ?
C6 P1 C12 104.60(8) . . ?
C18 P1 C12 106.25(9) . . ?
C5 O1 N2 108.26(13) . . ?
C3 N1 P1 122.45(13) . . ?
C3 N2 O1 105.52(13) . . ?
N2 C3 N1 124.37(16) . . ?
N2 C3 C4 110.80(15) . . ?
N1 C3 C4 124.82(17) . . ?
C5 C4 C3 105.21(16) . . ?
C5 C4 H4 127.4 . . ?
C3 C4 H4 127.4 . . ?
C4 C5 O1 110.20(15) . . ?
C4 C5 C24 133.71(17) . . ?
O1 C5 C24 116.05(15) . . ?
C7 C6 C11 119.53(17) . . ?
C7 C6 P1 120.02(13) . . ?
C11 C6 P1 120.25(15) . . ?
C8 C7 C6 119.87(17) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 120.23(19) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.93(18) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.31(17) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 120.13(18) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C12 C17 119.17(16) . . ?
C13 C12 P1 122.52(13) . . ?
C17 C12 P1 118.17(14) . . ?
C14 C13 C12 120.33(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.07(19) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.91(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.37(17) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 120.14(18) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C19 C18 C23 119.32(17) . . ?
C19 C18 P1 121.84(13) . . ?
C23 C18 P1 118.84(14) . . ?
C18 C19 C20 120.22(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.24(19) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.06(18) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120.33(17) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 119.77(18) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
C29 C24 C25 118.93(16) . . ?
C29 C24 C5 120.20(16) . . ?
C25 C24 C5 120.87(16) . . ?
C26 C25 C24 120.23(18) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C25 120.42(18) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 119.74(17) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 120.37(19) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C24 120.28(18) . . ?
C28 C29 H29 119.9 . . ?
C24 C29 H29 119.9 . . ?
N3 P2 C33 105.73(8) . . ?
N3 P2 C45 115.50(8) . . ?
C33 P2 C45 104.95(8) . . ?
N3 P2 C39 115.13(8) . . ?
C33 P2 C39 106.64(8) . . ?
C45 P2 C39 108.01(9) . . ?
C32 O2 N4 108.36(13) . . ?
C30 N3 P2 123.44(14) . . ?
C30 N4 O2 105.37(13) . . ?
N4 C30 N3 124.44(16) . . ?
N4 C30 C31 111.18(15) . . ?
N3 C30 C31 124.37(17) . . ?
C32 C31 C30 104.94(16) . . ?
C32 C31 H31 127.5 . . ?
C30 C31 H31 127.5 . . ?
C31 C32 O2 110.15(15) . . ?
C31 C32 C51 133.78(17) . . ?
O2 C32 C51 116.06(15) . . ?
C34 C33 C38 119.79(17) . . ?
C34 C33 P2 119.16(13) . . ?
C38 C33 P2 121.05(15) . . ?
C35 C34 C33 119.79(18) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.4(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 120.00(18) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.40(18) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C33 119.62(18) . . ?
C37 C38 H38 120.2 . . ?
C33 C38 H38 120.2 . . ?
C44 C39 C40 119.26(17) . . ?
C44 C39 P2 119.99(14) . . ?
C40 C39 P2 120.37(14) . . ?
C41 C40 C39 120.18(19) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C42 C41 C40 120.1(2) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C43 C42 C41 120.01(18) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.90(19) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
C43 C44 C39 119.51(18) . . ?
C43 C44 H44 120.2 . . ?
C39 C44 H44 120.2 . . ?
C50 C45 C46 119.40(18) . . ?
C50 C45 P2 122.45(14) . . ?
C46 C45 P2 117.68(15) . . ?
C47 C46 C45 120.3(2) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C46 C47 C48 120.2(2) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C49 C48 C47 119.76(19) . . ?
C49 C48 H48 120.1 . . ?
C47 C48 H48 120.1 . . ?
C48 C49 C50 120.4(2) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C49 C50 C45 119.95(19) . . ?
C49 C50 H50 120.0 . . ?
C45 C50 H50 120.0 . . ?
C52 C51 C56 119.35(16) . . ?
C52 C51 C32 120.52(16) . . ?
C56 C51 C32 120.13(16) . . ?
C53 C52 C51 120.30(18) . . ?
C53 C52 H52 119.9 . . ?
C51 C52 H52 119.9 . . ?
C54 C53 C52 120.00(19) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C53 C54 C55 120.29(18) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 H54 119.9 . . ?
C56 C55 C54 120.02(19) . . ?
C56 C55 H55 120.0 . . ?
C54 C55 H55 120.0 . . ?
C55 C56 C51 120.03(18) . . ?
C55 C56 H56 120.0 . . ?
C51 C56 H56 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 P1 N1 C3 -179.94(13) . . . . ?
C18 P1 N1 C3 60.76(16) . . . . ?
C12 P1 N1 C3 -65.73(16) . . . . ?
C5 O1 N2 C3 -0.69(17) . . . . ?
O1 N2 C3 N1 -177.54(15) . . . . ?
O1 N2 C3 C4 1.13(18) . . . . ?
P1 N1 C3 N2 -0.5(2) . . . . ?
P1 N1 C3 C4 -178.99(13) . . . . ?
N2 C3 C4 C5 -1.17(19) . . . . ?
N1 C3 C4 C5 177.49(16) . . . . ?
C3 C4 C5 O1 0.70(18) . . . . ?
C3 C4 C5 C24 -176.79(17) . . . . ?
N2 O1 C5 C4 -0.04(18) . . . . ?
N2 O1 C5 C24 177.94(13) . . . . ?
N1 P1 C6 C7 15.54(16) . . . . ?
C18 P1 C6 C7 142.58(14) . . . . ?
C12 P1 C6 C7 -105.12(15) . . . . ?
N1 P1 C6 C11 -169.67(14) . . . . ?
C18 P1 C6 C11 -42.64(16) . . . . ?
C12 P1 C6 C11 69.66(16) . . . . ?
C11 C6 C7 C8 -1.2(3) . . . . ?
P1 C6 C7 C8 173.60(15) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
C7 C6 C11 C10 0.9(3) . . . . ?
P1 C6 C11 C10 -173.93(14) . . . . ?
N1 P1 C12 C13 170.92(15) . . . . ?
C6 P1 C12 C13 -74.37(17) . . . . ?
C18 P1 C12 C13 38.18(17) . . . . ?
N1 P1 C12 C17 -13.41(17) . . . . ?
C6 P1 C12 C17 101.29(15) . . . . ?
C18 P1 C12 C17 -146.15(14) . . . . ?
C17 C12 C13 C14 1.0(3) . . . . ?
P1 C12 C13 C14 176.61(15) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C13 C12 C17 C16 -0.2(3) . . . . ?
P1 C12 C17 C16 -175.98(14) . . . . ?
N1 P1 C18 C19 -102.12(16) . . . . ?
C6 P1 C18 C19 139.20(15) . . . . ?
C12 P1 C18 C19 28.04(17) . . . . ?
N1 P1 C18 C23 77.20(16) . . . . ?
C6 P1 C18 C23 -41.49(16) . . . . ?
C12 P1 C18 C23 -152.65(14) . . . . ?
C23 C18 C19 C20 2.1(3) . . . . ?
P1 C18 C19 C20 -178.61(15) . . . . ?
C18 C19 C20 C21 -1.3(3) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 2.2(3) . . . . ?
C21 C22 C23 C18 -1.4(3) . . . . ?
C19 C18 C23 C22 -0.7(3) . . . . ?
P1 C18 C23 C22 179.96(13) . . . . ?
C4 C5 C24 C29 2.8(3) . . . . ?
O1 C5 C24 C29 -174.62(15) . . . . ?
C4 C5 C24 C25 -177.93(18) . . . . ?
O1 C5 C24 C25 4.7(2) . . . . ?
C29 C24 C25 C26 1.3(2) . . . . ?
C5 C24 C25 C26 -178.05(15) . . . . ?
C24 C25 C26 C27 -1.5(3) . . . . ?
C25 C26 C27 C28 0.5(3) . . . . ?
C26 C27 C28 C29 0.8(3) . . . . ?
C27 C28 C29 C24 -1.1(3) . . . . ?
C25 C24 C29 C28 0.0(3) . . . . ?
C5 C24 C29 C28 179.37(16) . . . . ?
C33 P2 N3 C30 -173.54(13) . . . . ?
C45 P2 N3 C30 -57.99(16) . . . . ?
C39 P2 N3 C30 69.03(16) . . . . ?
C32 O2 N4 C30 -0.04(16) . . . . ?
O2 N4 C30 N3 179.35(15) . . . . ?
O2 N4 C30 C31 -0.02(18) . . . . ?
P2 N3 C30 N4 2.0(2) . . . . ?
P2 N3 C30 C31 -178.75(13) . . . . ?
N4 C30 C31 C32 0.06(19) . . . . ?
N3 C30 C31 C32 -179.30(15) . . . . ?
C30 C31 C32 O2 -0.08(18) . . . . ?
C30 C31 C32 C51 178.57(17) . . . . ?
N4 O2 C32 C31 0.08(17) . . . . ?
N4 O2 C32 C51 -178.84(13) . . . . ?
N3 P2 C33 C34 -7.22(17) . . . . ?
C45 P2 C33 C34 -129.78(16) . . . . ?
C39 P2 C33 C34 115.78(16) . . . . ?
N3 P2 C33 C38 172.20(14) . . . . ?
C45 P2 C33 C38 49.64(16) . . . . ?
C39 P2 C33 C38 -64.80(16) . . . . ?
C38 C33 C34 C35 0.1(3) . . . . ?
P2 C33 C34 C35 179.57(16) . . . . ?
C33 C34 C35 C36 -0.9(3) . . . . ?
C34 C35 C36 C37 0.9(3) . . . . ?
C35 C36 C37 C38 -0.1(3) . . . . ?
C36 C37 C38 C33 -0.7(3) . . . . ?
C34 C33 C38 C37 0.7(3) . . . . ?
P2 C33 C38 C37 -178.76(14) . . . . ?
N3 P2 C39 C44 -74.62(17) . . . . ?
C33 P2 C39 C44 168.46(14) . . . . ?
C45 P2 C39 C44 56.11(16) . . . . ?
N3 P2 C39 C40 98.29(16) . . . . ?
C33 P2 C39 C40 -18.63(18) . . . . ?
C45 P2 C39 C40 -130.98(16) . . . . ?
C44 C39 C40 C41 0.1(3) . . . . ?
P2 C39 C40 C41 -172.88(16) . . . . ?
C39 C40 C41 C42 0.9(3) . . . . ?
C40 C41 C42 C43 -1.0(3) . . . . ?
C41 C42 C43 C44 0.0(3) . . . . ?
C42 C43 C44 C39 1.0(3) . . . . ?
C40 C39 C44 C43 -1.0(3) . . . . ?
P2 C39 C44 C43 171.96(14) . . . . ?
N3 P2 C45 C50 162.75(14) . . . . ?
C33 P2 C45 C50 -81.25(17) . . . . ?
C39 P2 C45 C50 32.23(17) . . . . ?
N3 P2 C45 C46 -25.19(18) . . . . ?
C33 P2 C45 C46 90.81(16) . . . . ?
C39 P2 C45 C46 -155.71(15) . . . . ?
C50 C45 C46 C47 -0.7(3) . . . . ?
P2 C45 C46 C47 -173.00(17) . . . . ?
C45 C46 C47 C48 2.4(3) . . . . ?
C46 C47 C48 C49 -2.0(3) . . . . ?
C47 C48 C49 C50 -0.1(3) . . . . ?
C48 C49 C50 C45 1.8(3) . . . . ?
C46 C45 C50 C49 -1.4(3) . . . . ?
P2 C45 C50 C49 170.54(14) . . . . ?
C31 C32 C51 C52 160.70(19) . . . . ?
O2 C32 C51 C52 -20.7(2) . . . . ?
C31 C32 C51 C56 -19.6(3) . . . . ?
O2 C32 C51 C56 159.01(16) . . . . ?
C56 C51 C52 C53 -0.2(3) . . . . ?
C32 C51 C52 C53 179.52(16) . . . . ?
C51 C52 C53 C54 0.8(3) . . . . ?
C52 C53 C54 C55 -0.6(3) . . . . ?
C53 C54 C55 C56 -0.2(3) . . . . ?
C54 C55 C56 C51 0.9(3) . . . . ?
C52 C51 C56 C55 -0.6(3) . . . . ?
C32 C51 C56 C55 179.64(16) . . . . ?

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 1.000 0.000 0.500 317 75 ' '
2 0.000 0.500 0.000 317 75 ' '
3 0.596 0.102 0.811 11 1 ' '
4 0.596 0.398 0.311 11 1 ' '
5 0.404 0.602 0.689 11 1 ' '
6 0.404 0.898 0.189 11 1 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.071

_shelxl_version_number           2014/6



