# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1813440'
_audit_update_record             
;
2017-12-27 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N P Se'
_chemical_formula_weight         430.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.689(3)
_cell_length_b                   9.904(3)
_cell_length_c                   11.312(4)
_cell_angle_alpha                95.848(7)
_cell_angle_beta                 101.924(7)
_cell_angle_gamma                111.026(6)
_cell_volume                     972.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4679
_cell_measurement_theta_min      0.794
_cell_measurement_theta_max      0.823

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7936
_exptl_absorpt_correction_T_max  0.8235
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8102
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         28.33
_reflns_number_total             4679
_reflns_number_gt                4046
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0299P)²+0.6153P] 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         4679
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.7545(2) 0.3830(2) 0.17068(17) 0.0309(4) Uani 1 1 d . . .
C2 C 0.8974(2) 0.4481(2) 0.1488(2) 0.0387(4) Uani 1 1 d . . .
H2 H 0.9465 0.5501 0.1607 0.046 Uiso 1 1 calc R . .
C3 C 0.9643(3) 0.3561(3) 0.1087(2) 0.0459(5) Uani 1 1 d . . .
H3 H 1.0597 0.3974 0.0929 0.055 Uiso 1 1 calc R . .
C4 C 0.8926(3) 0.2040(3) 0.0914(2) 0.0496(6) Uani 1 1 d . . .
H4 H 0.9403 0.1449 0.0643 0.060 Uiso 1 1 calc R . .
C5 C 0.7517(3) 0.1398(3) 0.1138(2) 0.0460(5) Uani 1 1 d . . .
H5 H 0.7040 0.0378 0.1025 0.055 Uiso 1 1 calc R . .
C6 C 0.6811(2) 0.2299(2) 0.15397(18) 0.0338(4) Uani 1 1 d . . .
C7 C 0.5385(2) 0.1991(2) 0.18664(18) 0.0352(4) Uani 1 1 d . . .
C8 C 0.4220(3) 0.0670(3) 0.1863(2) 0.0516(6) Uani 1 1 d . . .
H8 H 0.4303 -0.0221 0.1635 0.062 Uiso 1 1 calc R . .
C9 C 0.2951(3) 0.0687(3) 0.2197(3) 0.0570(7) Uani 1 1 d . . .
H9 H 0.2161 -0.0195 0.2188 0.068 Uiso 1 1 calc R . .
C10 C 0.2834(3) 0.2020(3) 0.2551(2) 0.0476(5) Uani 1 1 d . . .
H10 H 0.1962 0.2013 0.2777 0.057 Uiso 1 1 calc R . .
C11 C 0.3984(2) 0.3357(2) 0.2576(2) 0.0385(4) Uani 1 1 d . . .
H11 H 0.3900 0.4243 0.2824 0.046 Uiso 1 1 calc R . .
C12 C 0.5265(2) 0.3337(2) 0.22184(16) 0.0300(4) Uani 1 1 d . . .
C13 C 0.4333(2) 0.6673(2) 0.1806(2) 0.0374(4) Uani 1 1 d . . .
H13 H 0.4330 0.6509 0.0981 0.045 Uiso 1 1 calc R . .
C14 C 0.3116(3) 0.6876(3) 0.2133(3) 0.0482(6) Uani 1 1 d . . .
H14 H 0.2290 0.6844 0.1524 0.058 Uiso 1 1 calc R . .
C15 C 0.3112(3) 0.7125(3) 0.3349(3) 0.0580(7) Uani 1 1 d . . .
H15 H 0.2273 0.7233 0.3558 0.070 Uiso 1 1 calc R . .
C16 C 0.4350(3) 0.7215(3) 0.4261(3) 0.0583(7) Uani 1 1 d . . .
H16 H 0.4361 0.7418 0.5084 0.070 Uiso 1 1 calc R . .
C17 C 0.5573(3) 0.7002(3) 0.3948(2) 0.0429(5) Uani 1 1 d . . .
H17 H 0.6402 0.7053 0.4563 0.051 Uiso 1 1 calc R . .
C18 C 0.5568(2) 0.6714(2) 0.27193(18) 0.0307(4) Uani 1 1 d . . .
C19 C 0.8918(3) 0.6384(3) 0.4522(2) 0.0456(5) Uani 1 1 d . . .
H19 H 0.8191 0.5453 0.4491 0.055 Uiso 1 1 calc R . .
C20 C 1.0190(3) 0.7054(4) 0.5542(2) 0.0601(7) Uani 1 1 d . . .
H20 H 1.0305 0.6574 0.6198 0.072 Uiso 1 1 calc R . .
C21 C 1.1268(3) 0.8424(3) 0.5573(2) 0.0590(7) Uani 1 1 d . . .
H21 H 1.2114 0.8864 0.6251 0.071 Uiso 1 1 calc R . .
C22 C 1.1111(3) 0.9137(3) 0.4626(2) 0.0539(6) Uani 1 1 d . . .
H22 H 1.1853 1.0060 0.4657 0.065 Uiso 1 1 calc R . .
C23 C 0.9854(2) 0.8503(2) 0.3610(2) 0.0389(4) Uani 1 1 d . . .
H23 H 0.9750 0.9004 0.2967 0.047 Uiso 1 1 calc R . .
C24 C 0.8752(2) 0.7123(2) 0.35553(17) 0.0308(4) Uani 1 1 d . . .
N1 N 0.66108(18) 0.44984(17) 0.21244(16) 0.0315(3) Uani 1 1 d . . .
P1 P 0.70870(5) 0.63536(5) 0.22424(4) 0.02645(11) Uani 1 1 d . . .
Se1 Se 0.74568(3) 0.71441(3) 0.064571(19) 0.04301(9) 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 1.389(3) . ?
C1 C6 1.397(3) . ?
C1 N1 1.422(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(3) . ?
C7 C8 1.387(3) . ?
C7 C12 1.404(3) . ?
C8 C9 1.364(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 N1 1.428(2) . ?
C13 C14 1.379(3) . ?
C13 C18 1.395(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 P1 1.803(2) . ?
C19 C24 1.390(3) . ?
C19 C20 1.400(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.355(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 P1 1.812(2) . ?
N1 P1 1.7096(17) . ?
P1 Se1 2.0876(8) . ?

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 121.23(18) . . ?
C2 C1 N1 129.59(18) . . ?
C6 C1 N1 109.18(17) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 C7 107.32(17) . . ?
C5 C6 C7 132.9(2) . . ?
C8 C7 C12 120.3(2) . . ?
C8 C7 C6 131.4(2) . . ?
C12 C7 C6 108.23(17) . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 C7 120.24(18) . . ?
C11 C12 N1 131.67(18) . . ?
C7 C12 N1 108.09(17) . . ?
C14 C13 C18 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C18 C13 H13 120.2 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 119.35(19) . . ?
C17 C18 P1 122.64(15) . . ?
C13 C18 P1 118.00(16) . . ?
C24 C19 C20 119.4(2) . . ?
C24 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 119.54(19) . . ?
C23 C24 P1 118.89(16) . . ?
C19 C24 P1 121.53(16) . . ?
C1 N1 C12 107.18(15) . . ?
C1 N1 P1 120.42(13) . . ?
C12 N1 P1 131.86(13) . . ?
N1 P1 C18 105.89(8) . . ?
N1 P1 C24 102.66(9) . . ?
C18 P1 C24 106.50(9) . . ?
N1 P1 Se1 114.62(6) . . ?
C18 P1 Se1 112.18(7) . . ?
C24 P1 Se1 114.10(7) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1813444'
_audit_update_record             
;
2017-12-27 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H25 N2 P Se'
_chemical_formula_weight         523.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '

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

_cell_length_a                   11.612(3)
_cell_length_b                   17.433(5)
_cell_length_c                   12.594(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.247(6)
_cell_angle_gamma                90.00
_cell_volume                     2481.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9797
_cell_measurement_theta_min      0.831
_cell_measurement_theta_max      0.857

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    1.599
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8313
_exptl_absorpt_correction_T_max  0.8565
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30981
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         33.67
_reflns_number_total             9797
_reflns_number_gt                6889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0460P)²+0.7614P] 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         9797
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_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 0.78643(13) 0.66130(8) 1.01733(12) 0.0303(3) Uani 1 1 d . . .
C2 C 0.68126(16) 0.63711(12) 0.95003(17) 0.0487(4) Uani 1 1 d . . .
H2 H 0.6682 0.6437 0.8749 0.058 Uiso 1 1 calc R . .
C3 C 0.59576(19) 0.60322(14) 0.9947(2) 0.0642(6) Uani 1 1 d . . .
H3 H 0.5256 0.5860 0.9495 0.077 Uiso 1 1 calc R . .
C4 C 0.6142(2) 0.59481(12) 1.1065(2) 0.0597(6) Uani 1 1 d . . .
H4 H 0.5565 0.5720 1.1365 0.072 Uiso 1 1 calc R . .
C5 C 0.7170(2) 0.62010(12) 1.17258(18) 0.0558(5) Uani 1 1 d . . .
H5 H 0.7285 0.6154 1.2478 0.067 Uiso 1 1 calc R . .
C6 C 0.80433(17) 0.65269(10) 1.12881(14) 0.0433(4) Uani 1 1 d . . .
H6 H 0.8750 0.6688 1.1744 0.052 Uiso 1 1 calc R . .
C7 C 0.93128(13) 0.63713(8) 0.91008(11) 0.0275(3) Uani 1 1 d . . .
C8 C 0.87995(15) 0.62194(9) 0.80141(13) 0.0362(3) Uani 1 1 d . . .
H8 H 0.8129 0.6487 0.7657 0.043 Uiso 1 1 calc R . .
C9 C 0.92913(18) 0.56685(11) 0.74666(14) 0.0468(4) Uani 1 1 d . . .
H9 H 0.8942 0.5558 0.6742 0.056 Uiso 1 1 calc R . .
C10 C 1.02913(19) 0.52830(10) 0.79843(16) 0.0483(4) Uani 1 1 d . . .
H10 H 1.0624 0.4917 0.7608 0.058 Uiso 1 1 calc R . .
C11 C 1.08041(17) 0.54364(10) 0.90618(16) 0.0456(4) Uani 1 1 d . . .
H11 H 1.1486 0.5177 0.9409 0.055 Uiso 1 1 calc R . .
C12 C 1.03070(15) 0.59754(9) 0.96286(13) 0.0365(3) Uani 1 1 d . . .
H12 H 1.0642 0.6070 1.0361 0.044 Uiso 1 1 calc R . .
C13 C 0.95304(13) 0.85411(8) 0.83946(12) 0.0292(3) Uani 1 1 d . . .
C14 C 0.95107(16) 0.93192(10) 0.85812(14) 0.0405(3) Uani 1 1 d . . .
H14 H 0.9942 0.9524 0.9234 0.049 Uiso 1 1 calc R . .
C15 C 0.88475(18) 0.97931(11) 0.77938(18) 0.0521(5) Uani 1 1 d . . .
H15 H 0.8825 1.0318 0.7921 0.063 Uiso 1 1 calc R . .
C16 C 0.82211(17) 0.94925(12) 0.68238(17) 0.0518(5) Uani 1 1 d . . .
H16 H 0.7763 0.9813 0.6303 0.062 Uiso 1 1 calc R . .
C17 C 0.82696(16) 0.87246(12) 0.66232(14) 0.0468(4) Uani 1 1 d . . .
H17 H 0.7863 0.8524 0.5958 0.056 Uiso 1 1 calc R . .
C18 C 0.89240(15) 0.82448(10) 0.74105(13) 0.0377(3) Uani 1 1 d . . .
H18 H 0.8955 0.7722 0.7275 0.045 Uiso 1 1 calc R . .
C19 C 1.13948(13) 0.79089(9) 0.92432(12) 0.0306(3) Uani 1 1 d . . .
C20 C 1.16788(17) 0.73479(10) 0.85751(15) 0.0413(4) Uani 1 1 d . . .
H20 H 1.1086 0.7053 0.8140 0.050 Uiso 1 1 calc R . .
C21 C 1.28522(19) 0.72265(12) 0.85555(19) 0.0549(5) Uani 1 1 d . . .
H21 H 1.3046 0.6847 0.8107 0.066 Uiso 1 1 calc R . .
C22 C 1.37296(19) 0.76600(14) 0.9191(2) 0.0588(5) Uani 1 1 d . . .
H22 H 1.4516 0.7572 0.9178 0.071 Uiso 1 1 calc R . .
C23 C 1.34483(16) 0.82217(14) 0.98430(18) 0.0573(5) Uani 1 1 d . . .
H23 H 1.4045 0.8517 1.0273 0.069 Uiso 1 1 calc R . .
C24 C 1.22786(15) 0.83546(11) 0.98678(15) 0.0445(4) Uani 1 1 d . . .
H24 H 1.2089 0.8743 1.0304 0.053 Uiso 1 1 calc R . .
C25 C 0.83748(13) 0.83721(8) 1.02897(12) 0.0293(3) Uani 1 1 d . . .
C26 C 0.73334(14) 0.83947(10) 0.94834(14) 0.0387(3) Uani 1 1 d . . .
H26 H 0.7211 0.8046 0.8909 0.046 Uiso 1 1 calc R . .
C27 C 0.64793(17) 0.89370(12) 0.95370(19) 0.0540(5) Uani 1 1 d . . .
H27 H 0.5780 0.8952 0.9001 0.065 Uiso 1 1 calc R . .
C28 C 0.6663(2) 0.94515(13) 1.0378(2) 0.0685(7) Uani 1 1 d . . .
H28 H 0.6091 0.9819 1.0406 0.082 Uiso 1 1 calc R . .
C29 C 0.7685(2) 0.94305(13) 1.1181(2) 0.0672(6) Uani 1 1 d . . .
H29 H 0.7800 0.9780 1.1753 0.081 Uiso 1 1 calc R . .
C30 C 0.85413(17) 0.88913(10) 1.11399(15) 0.0443(4) Uani 1 1 d . . .
H30 H 0.9233 0.8877 1.1686 0.053 Uiso 1 1 calc R . .
N1 N 0.87663(10) 0.69320(6) 0.96738(9) 0.0269(2) Uani 1 1 d . . .
N2 N 1.01731(10) 0.80477(7) 0.92514(10) 0.0287(2) Uani 1 1 d . . .
P1 P 0.95427(3) 0.77080(2) 1.02134(3) 0.02491(7) Uani 1 1 d . . .
Se1 Se 1.079179(15) 0.757006(11) 1.169572(13) 0.04175(6) 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 1.379(2) . ?
C1 C2 1.383(2) . ?
C1 N1 1.4505(18) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.378(2) . ?
C7 C8 1.387(2) . ?
C7 N1 1.4453(17) . ?
C8 C9 1.380(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.378(2) . ?
C13 C14 1.378(2) . ?
C13 N2 1.4465(19) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.378(2) . ?
C19 C24 1.380(2) . ?
C19 N2 1.4416(19) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.381(2) . ?
C25 C26 1.390(2) . ?
C25 P1 1.8023(15) . ?
C26 C27 1.383(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.367(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.372(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
N1 P1 1.6805(12) . ?
N2 P1 1.6614(12) . ?
P1 Se1 2.0989(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
C6 C1 C2 119.77(15) . . ?
C6 C1 N1 121.85(14) . . ?
C2 C1 N1 118.36(14) . . ?
C3 C2 C1 119.79(19) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.80(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.82(18) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C12 C7 C8 120.22(14) . . ?
C12 C7 N1 120.86(13) . . ?
C8 C7 N1 118.89(13) . . ?
C9 C8 C7 119.49(16) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.41(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.09(16) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.18(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.58(15) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C18 C13 C14 119.84(15) . . ?
C18 C13 N2 121.19(14) . . ?
C14 C13 N2 118.96(14) . . ?
C13 C14 C15 119.65(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.28(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.15(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.94(17) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.09(16) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C24 119.77(15) . . ?
C20 C19 N2 119.80(14) . . ?
C24 C19 N2 120.38(14) . . ?
C19 C20 C21 119.56(18) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.57(19) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 119.93(19) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.30(19) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 119.85(17) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C30 C25 C26 119.44(15) . . ?
C30 C25 P1 119.27(12) . . ?
C26 C25 P1 121.23(12) . . ?
C27 C26 C25 119.81(17) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.58(19) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C30 120.0(2) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 120.14(19) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
C7 N1 C1 113.61(11) . . ?
C7 N1 P1 119.35(9) . . ?
C1 N1 P1 120.47(9) . . ?
C19 N2 C13 115.77(11) . . ?
C19 N2 P1 122.97(10) . . ?
C13 N2 P1 121.18(9) . . ?
N2 P1 N1 106.09(6) . . ?
N2 P1 C25 105.82(7) . . ?
N1 P1 C25 101.43(7) . . ?
N2 P1 Se1 111.05(5) . . ?
N1 P1 Se1 117.69(5) . . ?
C25 P1 Se1 113.65(5) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        33.67
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1813443'
_audit_update_record             
;
2017-12-27 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H21 N2 P Se'
_chemical_formula_weight         519.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'

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

_cell_length_a                   9.5713(14)
_cell_length_b                   11.6043(17)
_cell_length_c                   12.0406(17)
_cell_angle_alpha                72.019(3)
_cell_angle_beta                 68.768(3)
_cell_angle_gamma                73.861(3)
_cell_volume                     1164.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5584
_cell_measurement_theta_min      0.882
_cell_measurement_theta_max      0.848

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8217
_exptl_absorpt_correction_T_max  0.8482
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9746
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.25
_reflns_number_total             5584
_reflns_number_gt                4745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0579P)²+0.9624P] 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         5584
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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 0.2144(3) 0.1976(2) 0.1925(2) 0.0270(5) Uani 1 1 d . . .
C2 C 0.0744(3) 0.1625(3) 0.2264(3) 0.0362(6) Uani 1 1 d . . .
H2 H -0.0026 0.1787 0.2968 0.043 Uiso 1 1 calc R . .
C3 C 0.0531(4) 0.1025(3) 0.1519(3) 0.0415(7) Uani 1 1 d . . .
H3 H -0.0405 0.0796 0.1726 0.050 Uiso 1 1 calc R . .
C4 C 0.1673(4) 0.0754(3) 0.0475(3) 0.0427(7) Uani 1 1 d . . .
H4 H 0.1492 0.0356 -0.0008 0.051 Uiso 1 1 calc R . .
C5 C 0.3070(4) 0.1075(3) 0.0156(3) 0.0373(6) Uani 1 1 d . . .
H5 H 0.3846 0.0879 -0.0531 0.045 Uiso 1 1 calc R . .
C6 C 0.3309(3) 0.1699(2) 0.0874(2) 0.0281(5) Uani 1 1 d . . .
C7 C 0.4625(3) 0.2134(2) 0.0779(2) 0.0295(5) Uani 1 1 d . . .
C8 C 0.6067(3) 0.2128(3) -0.0082(3) 0.0423(7) Uani 1 1 d . . .
H8 H 0.6311 0.1822 -0.0771 0.051 Uiso 1 1 calc R . .
C9 C 0.7132(4) 0.2585(3) 0.0110(3) 0.0521(9) Uani 1 1 d . . .
H9 H 0.8095 0.2595 -0.0461 0.063 Uiso 1 1 calc R . .
C10 C 0.6773(3) 0.3024(3) 0.1139(4) 0.0528(9) Uani 1 1 d . . .
H10 H 0.7515 0.3305 0.1260 0.063 Uiso 1 1 calc R . .
C11 C 0.5344(3) 0.3061(3) 0.1996(3) 0.0420(7) Uani 1 1 d . . .
H11 H 0.5119 0.3354 0.2691 0.050 Uiso 1 1 calc R . .
C12 C 0.4253(3) 0.2644(2) 0.1784(2) 0.0298(5) Uani 1 1 d . . .
C13 C -0.0776(3) 0.4278(2) 0.2975(3) 0.0302(5) Uani 1 1 d . . .
C14 C -0.0099(4) 0.5011(3) 0.1857(3) 0.0401(6) Uani 1 1 d . . .
H14 H 0.0951 0.4971 0.1561 0.048 Uiso 1 1 calc R . .
C15 C -0.1057(4) 0.5803(3) 0.1203(3) 0.0487(8) Uani 1 1 d . . .
H15 H -0.0637 0.6306 0.0449 0.058 Uiso 1 1 calc R . .
C16 C -0.2630(4) 0.5871(3) 0.1639(4) 0.0501(8) Uani 1 1 d . . .
H16 H -0.3240 0.6423 0.1179 0.060 Uiso 1 1 calc R . .
C17 C -0.3288(3) 0.5137(3) 0.2735(3) 0.0415(7) Uani 1 1 d . . .
H17 H -0.4340 0.5182 0.3023 0.050 Uiso 1 1 calc R . .
C18 C -0.2353(3) 0.4316(2) 0.3414(3) 0.0309(5) Uani 1 1 d . . .
C19 C -0.2662(3) 0.3395(2) 0.4547(3) 0.0292(5) Uani 1 1 d . . .
C20 C -0.4022(3) 0.3025(3) 0.5344(3) 0.0394(7) Uani 1 1 d . . .
H20 H -0.4945 0.3407 0.5186 0.047 Uiso 1 1 calc R . .
C21 C -0.3969(3) 0.2087(3) 0.6364(3) 0.0443(7) Uani 1 1 d . . .
H21 H -0.4867 0.1839 0.6911 0.053 Uiso 1 1 calc R . .
C22 C -0.2586(3) 0.1506(3) 0.6586(3) 0.0389(6) Uani 1 1 d . . .
H22 H -0.2575 0.0870 0.7280 0.047 Uiso 1 1 calc R . .
C23 C -0.1222(3) 0.1848(3) 0.5801(3) 0.0335(6) Uani 1 1 d . . .
H23 H -0.0301 0.1441 0.5952 0.040 Uiso 1 1 calc R . .
C24 C -0.1267(3) 0.2813(2) 0.4787(2) 0.0267(5) Uani 1 1 d . . .
C25 C 0.2174(3) 0.2119(2) 0.4989(2) 0.0292(5) Uani 1 1 d . . .
C26 C 0.1898(3) 0.2472(3) 0.6070(3) 0.0398(6) Uani 1 1 d . . .
H26 H 0.1504 0.3290 0.6116 0.048 Uiso 1 1 calc R . .
C27 C 0.2213(4) 0.1606(4) 0.7061(3) 0.0488(8) Uani 1 1 d . . .
H27 H 0.2011 0.1836 0.7787 0.059 Uiso 1 1 calc R . .
C28 C 0.2828(4) 0.0392(4) 0.6993(3) 0.0499(8) Uani 1 1 d . . .
H28 H 0.3060 -0.0186 0.7664 0.060 Uiso 1 1 calc R . .
C29 C 0.3097(4) 0.0040(3) 0.5934(3) 0.0480(8) Uani 1 1 d . . .
H29 H 0.3498 -0.0780 0.5895 0.058 Uiso 1 1 calc R . .
C30 C 0.2775(3) 0.0899(3) 0.4921(3) 0.0394(6) Uani 1 1 d . . .
H30 H 0.2960 0.0659 0.4204 0.047 Uiso 1 1 calc R . .
N1 N 0.2703(2) 0.2594(2) 0.2486(2) 0.0283(4) Uani 1 1 d . . .
N2 N -0.0085(2) 0.3369(2) 0.38258(19) 0.0266(4) Uani 1 1 d . . .
P1 P 0.17601(7) 0.32688(6) 0.36981(6) 0.02621(15) Uani 1 1 d . . .
Se1 Se 0.22665(3) 0.49568(3) 0.35172(3) 0.04175(12) 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 1.390(4) . ?
C1 C6 1.406(3) . ?
C1 N1 1.425(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.437(4) . ?
C7 C8 1.394(4) . ?
C7 C12 1.398(3) . ?
C8 C9 1.385(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.425(3) . ?
C13 C14 1.386(4) . ?
C13 C18 1.400(4) . ?
C13 N2 1.426(3) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.441(4) . ?
C19 C20 1.397(4) . ?
C19 C24 1.407(3) . ?
C20 C21 1.373(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9300 . ?
C24 N2 1.425(3) . ?
C25 C30 1.389(4) . ?
C25 C26 1.397(4) . ?
C25 P1 1.795(3) . ?
C26 C27 1.370(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.372(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.388(5) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
N1 P1 1.708(2) . ?
N2 P1 1.690(2) . ?
P1 Se1 2.0754(7) . ?

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 120.4(2) . . ?
C2 C1 N1 131.1(2) . . ?
C6 C1 N1 108.4(2) . . ?
C3 C2 C1 117.9(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 131.7(2) . . ?
C1 C6 C7 107.9(2) . . ?
C8 C7 C12 120.0(3) . . ?
C8 C7 C6 132.5(2) . . ?
C12 C7 C6 107.5(2) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 N1 129.9(2) . . ?
C7 C12 N1 109.1(2) . . ?
C14 C13 C18 121.7(3) . . ?
C14 C13 N2 129.4(2) . . ?
C18 C13 N2 108.8(2) . . ?
C15 C14 C13 117.0(3) . . ?
C15 C14 H14 121.5 . . ?
C13 C14 H14 121.5 . . ?
C14 C15 C16 122.0(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C13 119.8(3) . . ?
C17 C18 C19 132.7(3) . . ?
C13 C18 C19 107.5(2) . . ?
C20 C19 C24 120.5(3) . . ?
C20 C19 C18 131.4(2) . . ?
C24 C19 C18 108.1(2) . . ?
C21 C20 C19 118.7(3) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 121.8(3) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C24 C23 C22 118.2(3) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C23 C24 C19 120.4(2) . . ?
C23 C24 N2 131.5(2) . . ?
C19 C24 N2 108.1(2) . . ?
C30 C25 C26 119.9(3) . . ?
C30 C25 P1 121.1(2) . . ?
C26 C25 P1 118.9(2) . . ?
C27 C26 C25 119.6(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 119.4(3) . . ?
C29 C30 H30 120.3 . . ?
C25 C30 H30 120.3 . . ?
C12 N1 C1 106.9(2) . . ?
C12 N1 P1 123.34(17) . . ?
C1 N1 P1 129.58(17) . . ?
C24 N2 C13 107.4(2) . . ?
C24 N2 P1 131.24(18) . . ?
C13 N2 P1 120.53(18) . . ?
N2 P1 N1 102.02(10) . . ?
N2 P1 C25 107.79(11) . . ?
N1 P1 C25 104.41(12) . . ?
N2 P1 Se1 112.75(8) . . ?
N1 P1 Se1 115.94(8) . . ?
C25 P1 Se1 112.95(9) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.984
_refine_diff_density_rms         0.110
