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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1557385'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C26 H55 N3 Na2 O3.5 P2 S Se), 0.5(C4 H8 O)'
_chemical_formula_sum            'C28 H59 N3 Na2 O4 P2 S Se'
_chemical_formula_weight         720.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.6757(4)
_cell_length_b                   16.6222(5)
_cell_length_c                   16.4866(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.2240(10)
_cell_angle_gamma                90
_cell_volume                     3797.52(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9794
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      66.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.139
_shelx_estimated_absorpt_T_min   0.532
_shelx_estimated_absorpt_T_max   0.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5855
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47113
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.503
_diffrn_reflns_theta_max         66.789
_diffrn_reflns_theta_full        66.789
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6707
_reflns_number_gt                5521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
'Multiple THF molecules displayed a significant ammount of thermal motion. Atoms with Uij > 0.4 were refined to approximate isotropic behaviour (ISOR). One THF molecule was disordered over two sites - one of these was coordinated to a Na ion, the other was not (FVAR 0.5). On the disordered, coordinated THF very high thermal motion was observed, necessitating EADP restraints.'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0846P)²+10.3219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6707
_refine_ls_number_parameters     404
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1807
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.068
_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
Se1 Se 0.40198(4) 0.67761(3) 0.58350(3) 0.04691(18) Uani 1 1 d . . . . .
P1 P 0.45647(8) 0.80297(7) 0.81587(6) 0.0390(3) Uani 1 1 d . . . . .
P2 P 0.34501(7) 0.73188(6) 0.67778(6) 0.0328(2) Uani 1 1 d . . . . .
S1 S 0.10125(8) 0.69412(9) 0.32804(8) 0.0560(3) Uani 1 1 d . . . . .
Na1 Na 0.59840(16) 0.7064(2) 0.69311(14) 0.0900(9) Uani 1 1 d . . . . .
Na2 Na 0.19323(14) 0.66181(11) 0.50195(11) 0.0505(5) Uani 1 1 d . . . . .
N1 N 0.4098(3) 0.7075(2) 0.7803(2) 0.0390(8) Uani 1 1 d . . . . .
N3 N 0.2325(2) 0.7196(2) 0.6409(2) 0.0377(8) Uani 1 1 d . . . . .
N2 N 0.3891(2) 0.8242(2) 0.7092(2) 0.0349(7) Uani 1 1 d . . . . .
C1 C 0.4199(3) 0.6326(3) 0.8307(3) 0.0480(11) Uani 1 1 d . . . . .
C2 C 0.5260(4) 0.6097(3) 0.8684(4) 0.0613(14) Uani 1 1 d . . . . .
H2A H 0.5321 0.5600 0.9017 0.092 Uiso 1 1 calc R U . . .
H2B H 0.5526 0.6013 0.8217 0.092 Uiso 1 1 calc R U . . .
H2C H 0.5615 0.6530 0.9059 0.092 Uiso 1 1 calc R U . . .
C3 C 0.3654(4) 0.5651(3) 0.7728(4) 0.0656(15) Uani 1 1 d . . . . .
H3A H 0.3722 0.5155 0.8064 0.098 Uiso 1 1 calc R U . . .
H3B H 0.2970 0.5794 0.7487 0.098 Uiso 1 1 calc R U . . .
H3C H 0.3919 0.5569 0.7261 0.098 Uiso 1 1 calc R U . . .
C4 C 0.3793(4) 0.6464(4) 0.9042(3) 0.0620(14) Uani 1 1 d . . . . .
H4A H 0.3857 0.5969 0.9379 0.093 Uiso 1 1 calc R U . . .
H4B H 0.4151 0.6898 0.9412 0.093 Uiso 1 1 calc R U . . .
H4C H 0.3109 0.6612 0.8803 0.093 Uiso 1 1 calc R U . . .
C5 C 0.3874(3) 0.8984(2) 0.6599(3) 0.0391(9) Uani 1 1 d . . . . .
C6 C 0.4735(4) 0.9013(3) 0.6262(3) 0.0554(12) Uani 1 1 d . . . . .
H6A H 0.4707 0.9511 0.5936 0.083 Uiso 1 1 calc R U . . .
H6B H 0.5339 0.8997 0.6747 0.083 Uiso 1 1 calc R U . . .
H6C H 0.4706 0.8550 0.5887 0.083 Uiso 1 1 calc R U . . .
C7 C 0.2933(4) 0.9033(3) 0.5841(3) 0.0533(12) Uani 1 1 d . . . . .
H7A H 0.2928 0.9527 0.5517 0.080 Uiso 1 1 calc R U . . .
H7B H 0.2883 0.8566 0.5465 0.080 Uiso 1 1 calc R U . . .
H7C H 0.2384 0.9035 0.6056 0.080 Uiso 1 1 calc R U . . .
C8 C 0.3933(4) 0.9703(3) 0.7186(3) 0.0520(12) Uani 1 1 d . . . . .
H8A H 0.3923 1.0202 0.6866 0.078 Uiso 1 1 calc R U . . .
H8B H 0.3382 0.9695 0.7396 0.078 Uiso 1 1 calc R U . . .
H8C H 0.4534 0.9676 0.7675 0.078 Uiso 1 1 calc R U . . .
C9 C 0.1574(3) 0.7451(3) 0.6768(3) 0.0442(10) Uani 1 1 d . . . . .
C10 C 0.1898(4) 0.8060(3) 0.7512(3) 0.0565(13) Uani 1 1 d . . . . .
H10A H 0.1352 0.8191 0.7705 0.085 Uiso 1 1 calc R U . . .
H10B H 0.2419 0.7826 0.7990 0.085 Uiso 1 1 calc R U . . .
H10C H 0.2131 0.8551 0.7315 0.085 Uiso 1 1 calc R U . . .
C11 C 0.0753(3) 0.7823(3) 0.6041(3) 0.0566(13) Uani 1 1 d . . . . .
H11A H 0.0242 0.7999 0.6261 0.085 Uiso 1 1 calc R U . . .
H11B H 0.0996 0.8286 0.5806 0.085 Uiso 1 1 calc R U . . .
H11C H 0.0494 0.7422 0.5587 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1182(4) 0.6711(3) 0.7088(4) 0.0600(13) Uani 1 1 d . . . . .
H12A H 0.0682 0.6875 0.7328 0.090 Uiso 1 1 calc R U . . .
H12B H 0.0904 0.6340 0.6608 0.090 Uiso 1 1 calc R U . . .
H12C H 0.1707 0.6442 0.7533 0.090 Uiso 1 1 calc R U . . .
O1 O 0.1486(3) 0.5294(2) 0.5098(2) 0.0696(11) Uani 1 1 d . . . . .
C13 C 0.0896(4) 0.4832(3) 0.4397(3) 0.0622(14) Uani 1 1 d . . . . .
H13A H 0.1062 0.4941 0.3872 0.075 Uiso 1 1 calc R U . . .
H13B H 0.0206 0.4960 0.4281 0.075 Uiso 1 1 calc R U . . .
C14 C 0.1096(5) 0.3970(4) 0.4663(4) 0.0735(17) Uani 1 1 d . . . . .
H14A H 0.0654 0.3775 0.4963 0.088 Uiso 1 1 calc R U . . .
H14B H 0.1033 0.3620 0.4162 0.088 Uiso 1 1 calc R U . . .
C15 C 0.2104(5) 0.3997(4) 0.5250(4) 0.0746(17) Uani 1 1 d . . . . .
H15A H 0.2566 0.4000 0.4928 0.090 Uiso 1 1 calc R U . . .
H15B H 0.2249 0.3535 0.5652 0.090 Uiso 1 1 calc R U . . .
C16 C 0.2129(5) 0.4773(4) 0.5713(4) 0.0734(17) Uani 1 1 d . . . . .
H16A H 0.1911 0.4694 0.6215 0.088 Uiso 1 1 calc R U . . .
H16B H 0.2791 0.4998 0.5913 0.088 Uiso 1 1 calc R U . . .
O2 O 0.7388(4) 0.6430(3) 0.7655(3) 0.0930(14) Uani 1 1 d . U . . .
C17 C 0.8109(7) 0.6198(8) 0.7303(6) 0.135(4) Uani 1 1 d . . . . .
H17A H 0.7934 0.5678 0.6997 0.162 Uiso 1 1 calc R U . . .
H17B H 0.8169 0.6608 0.6889 0.162 Uiso 1 1 calc R U . . .
C18 C 0.8937(10) 0.6127(9) 0.7943(8) 0.153(4) Uani 1 1 d . U . . .
H18A H 0.9356 0.6594 0.7946 0.184 Uiso 1 1 calc R U . . .
H18B H 0.9276 0.5633 0.7866 0.184 Uiso 1 1 calc R U . . .
C19 C 0.8743(7) 0.6087(6) 0.8773(6) 0.113(3) Uani 1 1 d . U . . .
H19A H 0.8846 0.5535 0.9011 0.136 Uiso 1 1 calc R U . . .
H19B H 0.9169 0.6461 0.9198 0.136 Uiso 1 1 calc R U . . .
C20 C 0.7779(6) 0.6312(6) 0.8570(4) 0.108(3) Uani 1 1 d . . . . .
H20A H 0.7730 0.6817 0.8872 0.130 Uiso 1 1 calc R U . . .
H20B H 0.7414 0.5888 0.8750 0.130 Uiso 1 1 calc R U . . .
O3 O 0.6655(3) 0.7576(3) 0.5930(3) 0.0827(13) Uani 1 1 d . . . . .
C21 C 0.7397(10) 0.8136(8) 0.6171(8) 0.168(6) Uani 1 1 d . . . . .
H21A H 0.7434 0.8363 0.6736 0.201 Uiso 1 1 calc R U . . .
H21B H 0.8014 0.7856 0.6243 0.201 Uiso 1 1 calc R U . . .
C22 C 0.7299(11) 0.8751(7) 0.5604(9) 0.168(5) Uani 1 1 d . . . . .
H22A H 0.7885 0.8802 0.5436 0.201 Uiso 1 1 calc R U . . .
H22B H 0.7191 0.9266 0.5860 0.201 Uiso 1 1 calc R U . . .
C23 C 0.6506(8) 0.8557(7) 0.4899(8) 0.130(3) Uani 1 1 d . U . . .
H23A H 0.6684 0.8565 0.4369 0.156 Uiso 1 1 calc R U . . .
H23B H 0.5982 0.8953 0.4834 0.156 Uiso 1 1 calc R U . . .
C24 C 0.6160(6) 0.7699(5) 0.5046(4) 0.090(2) Uani 1 1 d . . . . .
H24A H 0.5452 0.7683 0.4917 0.108 Uiso 1 1 calc R U . . .
H24B H 0.6347 0.7293 0.4690 0.108 Uiso 1 1 calc R U . . .
O4B O 0.6161(11) 0.5401(8) 0.6396(12) 0.147(6) Uani 0.493(8) 1 d D . P A 1
C25B C 0.565(2) 0.5089(18) 0.5598(16) 0.194(10) Uani 0.493(8) 1 d D U P A 1
H25C H 0.6097 0.4860 0.5323 0.233 Uiso 0.493(8) 1 calc R U P A 1
H25D H 0.5263 0.5517 0.5222 0.233 Uiso 0.493(8) 1 calc R U P A 1
C26B C 0.5031(18) 0.4475(16) 0.5732(16) 0.164(7) Uani 0.493(8) 1 d D U P A 1
H26C H 0.4835 0.4095 0.5243 0.197 Uiso 0.493(8) 1 calc R U P A 1
H26D H 0.4446 0.4711 0.5809 0.197 Uiso 0.493(8) 1 calc R U P A 1
C27B C 0.562(2) 0.4080(16) 0.6509(18) 0.164(7) Uani 0.493(8) 1 d D U P A 1
H27C H 0.5915 0.3584 0.6369 0.197 Uiso 0.493(8) 1 calc R U P A 1
H27D H 0.5235 0.3936 0.6877 0.197 Uiso 0.493(8) 1 calc R U P A 1
C28B C 0.638(2) 0.4669(18) 0.6951(19) 0.194(10) Uani 0.493(8) 1 d D U P A 1
H28C H 0.7032 0.4458 0.7003 0.233 Uiso 0.493(8) 1 calc R U P A 1
H28D H 0.6363 0.4792 0.7532 0.233 Uiso 0.493(8) 1 calc R U P A 1
O4A O 0.5684(10) 0.3370(7) 0.7038(9) 0.117(4) Uani 0.507(8) 1 d D . P A 2
C25A C 0.5319(13) 0.4122(10) 0.7085(13) 0.111(6) Uani 0.507(8) 1 d D U P A 2
H25A H 0.5304 0.4216 0.7673 0.133 Uiso 0.507(8) 1 calc R U P A 2
H25B H 0.4650 0.4156 0.6681 0.133 Uiso 0.507(8) 1 calc R U P A 2
C26A C 0.5889(18) 0.4715(13) 0.6877(16) 0.134(8) Uani 0.507(8) 1 d D U P A 2
H26A H 0.6274 0.5010 0.7399 0.160 Uiso 0.507(8) 1 calc R U P A 2
H26B H 0.5477 0.5104 0.6462 0.160 Uiso 0.507(8) 1 calc R U P A 2
C27A C 0.6541(13) 0.4280(10) 0.6486(12) 0.105(5) Uani 0.507(8) 1 d D U P A 2
H27A H 0.6434 0.4469 0.5893 0.126 Uiso 0.507(8) 1 calc R U P A 2
H27B H 0.7227 0.4365 0.6832 0.126 Uiso 0.507(8) 1 calc R U P A 2
C28A C 0.6284(14) 0.3442(11) 0.6489(12) 0.112(6) Uani 0.507(8) 1 d D U P A 2
H28A H 0.6872 0.3108 0.6717 0.134 Uiso 0.507(8) 1 calc R U P A 2
H28B H 0.5923 0.3260 0.5899 0.134 Uiso 0.507(8) 1 calc R U P A 2


_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
Se1 P2 2.1873(11) . ?
Se1 Na1 2.894(2) . ?
Se1 Na2 2.9240(19) . ?
P1 N2 1.746(3) . ?
P1 N1 1.751(4) . ?
P1 S1 2.0681(17) 4_676 ?
P1 P2 2.6082(14) . ?
P2 N3 1.574(4) . ?
P2 N2 1.680(3) . ?
P2 N1 1.693(3) . ?
P2 Na2 3.2356(19) . ?
S1 P1 2.0681(17) 4_575 ?
S1 Na1 2.761(3) 4_575 ?
S1 Na2 2.790(2) . ?
Na1 O2 2.271(6) . ?
Na1 O3 2.343(5) . ?
Na1 S1 2.761(3) 4_676 ?
Na1 O4B 2.938(14) . ?
Na2 O1 2.311(4) . ?
Na2 N3 2.374(4) . ?
N1 C1 1.476(6) . ?
N3 C9 1.473(6) . ?
N2 C5 1.473(5) . ?
C1 C3 1.519(7) . ?
C1 C2 1.522(7) . ?
C1 C4 1.534(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C8 1.523(6) . ?
C5 C7 1.529(6) . ?
C5 C6 1.539(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.523(6) . ?
C9 C12 1.525(7) . ?
C9 C10 1.539(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 C13 1.421(6) . ?
O1 C16 1.428(7) . ?
C13 C14 1.499(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.478(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.493(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
O2 C17 1.417(9) . ?
O2 C20 1.439(8) . ?
C17 C18 1.327(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.488(14) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.393(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
O3 C21 1.387(11) . ?
O3 C24 1.414(8) . ?
C21 C22 1.361(14) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.386(15) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.559(13) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
O4B C25B 1.38(2) . ?
O4B C28B 1.49(2) . ?
C25B C26B 1.43(3) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B C27B 1.45(2) . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C27B C28B 1.48(2) . ?
C27B H27C 0.9900 . ?
C27B H27D 0.9900 . ?
C28B H28C 0.9900 . ?
C28B H28D 0.9900 . ?
O4A C25A 1.372(18) . ?
O4A C28A 1.461(19) . ?
C25A C26A 1.41(2) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A C27A 1.50(2) . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C27A C28A 1.44(2) . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?

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
P2 Se1 Na1 91.34(6) . . ?
P2 Se1 Na2 77.06(5) . . ?
Na1 Se1 Na2 168.37(7) . . ?
N2 P1 N1 79.44(16) . . ?
N2 P1 S1 108.42(13) . 4_676 ?
N1 P1 S1 109.24(14) . 4_676 ?
N2 P1 P2 39.48(11) . . ?
N1 P1 P2 39.96(11) . . ?
S1 P1 P2 115.11(6) 4_676 . ?
N3 P2 N2 119.10(18) . . ?
N3 P2 N1 121.83(19) . . ?
N2 P2 N1 82.97(17) . . ?
N3 P2 Se1 105.69(13) . . ?
N2 P2 Se1 113.43(13) . . ?
N1 P2 Se1 112.96(14) . . ?
N3 P2 P1 132.25(14) . . ?
N2 P2 P1 41.36(11) . . ?
N1 P2 P1 41.62(12) . . ?
Se1 P2 P1 122.04(5) . . ?
N3 P2 Na2 44.14(13) . . ?
N2 P2 Na2 133.40(12) . . ?
N1 P2 Na2 143.41(13) . . ?
Se1 P2 Na2 61.73(4) . . ?
P1 P2 Na2 173.71(6) . . ?
P1 S1 Na1 99.51(7) 4_575 4_575 ?
P1 S1 Na2 103.78(7) 4_575 . ?
Na1 S1 Na2 144.80(9) 4_575 . ?
O2 Na1 O3 91.14(19) . . ?
O2 Na1 S1 94.82(15) . 4_676 ?
O3 Na1 S1 116.81(18) . 4_676 ?
O2 Na1 Se1 142.8(2) . . ?
O3 Na1 Se1 100.58(13) . . ?
S1 Na1 Se1 110.47(10) 4_676 . ?
O2 Na1 O4B 64.3(3) . . ?
O3 Na1 O4B 91.8(4) . . ?
S1 Na1 O4B 145.7(4) 4_676 . ?
Se1 Na1 O4B 79.9(3) . . ?
O1 Na2 N3 108.30(15) . . ?
O1 Na2 S1 101.00(11) . . ?
N3 Na2 S1 142.71(12) . . ?
O1 Na2 Se1 109.45(12) . . ?
N3 Na2 Se1 68.62(9) . . ?
S1 Na2 Se1 122.30(8) . . ?
O1 Na2 P2 114.61(11) . . ?
N3 Na2 P2 27.50(9) . . ?
S1 Na2 P2 143.99(8) . . ?
Se1 Na2 P2 41.21(3) . . ?
C1 N1 P2 133.0(3) . . ?
C1 N1 P1 128.3(3) . . ?
P2 N1 P1 98.42(18) . . ?
C9 N3 P2 129.5(3) . . ?
C9 N3 Na2 121.9(3) . . ?
P2 N3 Na2 108.36(19) . . ?
C5 N2 P2 131.2(3) . . ?
C5 N2 P1 128.8(3) . . ?
P2 N2 P1 99.16(18) . . ?
N1 C1 C3 109.6(4) . . ?
N1 C1 C2 109.9(4) . . ?
C3 C1 C2 109.1(5) . . ?
N1 C1 C4 109.0(4) . . ?
C3 C1 C4 110.1(5) . . ?
C2 C1 C4 109.0(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C8 108.6(3) . . ?
N2 C5 C7 110.0(4) . . ?
C8 C5 C7 109.0(4) . . ?
N2 C5 C6 111.1(4) . . ?
C8 C5 C6 108.8(4) . . ?
C7 C5 C6 109.3(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C11 107.6(4) . . ?
N3 C9 C12 108.9(4) . . ?
C11 C9 C12 107.9(4) . . ?
N3 C9 C10 115.7(4) . . ?
C11 C9 C10 108.5(4) . . ?
C12 C9 C10 108.0(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 O1 C16 109.4(4) . . ?
C13 O1 Na2 125.3(3) . . ?
C16 O1 Na2 119.0(3) . . ?
O1 C13 C14 105.7(4) . . ?
O1 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
O1 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C15 C14 C13 102.7(5) . . ?
C15 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
C14 C15 C16 102.2(5) . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
O1 C16 C15 105.2(4) . . ?
O1 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
O1 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C17 O2 C20 107.3(6) . . ?
C17 O2 Na1 125.6(5) . . ?
C20 O2 Na1 126.4(4) . . ?
C18 C17 O2 108.1(8) . . ?
C18 C17 H17A 110.1 . . ?
O2 C17 H17A 110.1 . . ?
C18 C17 H17B 110.1 . . ?
O2 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 C19 109.4(10) . . ?
C17 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 C18 104.7(8) . . ?
C20 C19 H19A 110.8 . . ?
C18 C19 H19A 110.8 . . ?
C20 C19 H19B 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.9 . . ?
C19 C20 O2 108.2(6) . . ?
C19 C20 H20A 110.1 . . ?
O2 C20 H20A 110.1 . . ?
C19 C20 H20B 110.1 . . ?
O2 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C21 O3 C24 106.6(7) . . ?
C21 O3 Na1 121.0(6) . . ?
C24 O3 Na1 125.9(4) . . ?
C22 C21 O3 114.3(11) . . ?
C22 C21 H21A 108.7 . . ?
O3 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
O3 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 C23 105.7(11) . . ?
C21 C22 H22A 110.6 . . ?
C23 C22 H22A 110.6 . . ?
C21 C22 H22B 110.6 . . ?
C23 C22 H22B 110.6 . . ?
H22A C22 H22B 108.7 . . ?
C22 C23 C24 108.0(9) . . ?
C22 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
C22 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
O3 C24 C23 102.1(7) . . ?
O3 C24 H24A 111.3 . . ?
C23 C24 H24A 111.3 . . ?
O3 C24 H24B 111.3 . . ?
C23 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
C25B O4B C28B 102.6(17) . . ?
C25B O4B Na1 124.4(15) . . ?
C28B O4B Na1 127.3(18) . . ?
O4B C25B C26B 107(2) . . ?
O4B C25B H25C 110.3 . . ?
C26B C25B H25C 110.3 . . ?
O4B C25B H25D 110.3 . . ?
C26B C25B H25D 110.3 . . ?
H25C C25B H25D 108.5 . . ?
C25B C26B C27B 103(2) . . ?
C25B C26B H26C 111.1 . . ?
C27B C26B H26C 111.1 . . ?
C25B C26B H26D 111.1 . . ?
C27B C26B H26D 111.1 . . ?
H26C C26B H26D 109.0 . . ?
C26B C27B C28B 105.7(19) . . ?
C26B C27B H27C 110.6 . . ?
C28B C27B H27C 110.6 . . ?
C26B C27B H27D 110.6 . . ?
C28B C27B H27D 110.6 . . ?
H27C C27B H27D 108.7 . . ?
C27B C28B O4B 105.1(18) . . ?
C27B C28B H28C 110.7 . . ?
O4B C28B H28C 110.7 . . ?
C27B C28B H28D 110.7 . . ?
O4B C28B H28D 110.7 . . ?
H28C C28B H28D 108.8 . . ?
C25A O4A C28A 106.6(13) . . ?
O4A C25A C26A 110.5(16) . . ?
O4A C25A H25A 109.6 . . ?
C26A C25A H25A 109.6 . . ?
O4A C25A H25B 109.6 . . ?
C26A C25A H25B 109.6 . . ?
H25A C25A H25B 108.1 . . ?
C25A C26A C27A 106.3(17) . . ?
C25A C26A H26A 110.5 . . ?
C27A C26A H26A 110.5 . . ?
C25A C26A H26B 110.5 . . ?
C27A C26A H26B 110.5 . . ?
H26A C26A H26B 108.7 . . ?
C28A C27A C26A 105.0(15) . . ?
C28A C27A H27A 110.7 . . ?
C26A C27A H27A 110.7 . . ?
C28A C27A H27B 110.7 . . ?
C26A C27A H27B 110.7 . . ?
H27A C27A H27B 108.8 . . ?
C27A C28A O4A 107.0(14) . . ?
C27A C28A H28A 110.3 . . ?
O4A C28A H28A 110.3 . . ?
C27A C28A H28B 110.3 . . ?
O4A C28A H28B 110.3 . . ?
H28A C28A H28B 108.6 . . ?

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
N3 P2 N1 C1 55.2(5) . . . . ?
N2 P2 N1 C1 175.2(5) . . . . ?
Se1 P2 N1 C1 -72.2(4) . . . . ?
P1 P2 N1 C1 174.8(6) . . . . ?
Na2 P2 N1 C1 0.8(6) . . . . ?
N3 P2 N1 P1 -119.5(2) . . . . ?
N2 P2 N1 P1 0.49(18) . . . . ?
Se1 P2 N1 P1 113.00(15) . . . . ?
Na2 P2 N1 P1 -174.00(11) . . . . ?
N2 P1 N1 C1 -175.6(4) . . . . ?
S1 P1 N1 C1 78.4(4) 4_676 . . . ?
P2 P1 N1 C1 -175.1(5) . . . . ?
N2 P1 N1 P2 -0.47(18) . . . . ?
S1 P1 N1 P2 -106.46(15) 4_676 . . . ?
N2 P2 N3 C9 -50.0(4) . . . . ?
N1 P2 N3 C9 50.4(4) . . . . ?
Se1 P2 N3 C9 -179.0(3) . . . . ?
P1 P2 N3 C9 -0.9(5) . . . . ?
Na2 P2 N3 C9 -173.8(5) . . . . ?
N2 P2 N3 Na2 123.76(18) . . . . ?
N1 P2 N3 Na2 -135.84(18) . . . . ?
Se1 P2 N3 Na2 -5.21(18) . . . . ?
P1 P2 N3 Na2 172.84(8) . . . . ?
N3 P2 N2 C5 -67.6(4) . . . . ?
N1 P2 N2 C5 169.7(4) . . . . ?
Se1 P2 N2 C5 57.7(4) . . . . ?
P1 P2 N2 C5 170.2(5) . . . . ?
Na2 P2 N2 C5 -14.8(5) . . . . ?
N3 P2 N2 P1 122.16(19) . . . . ?
N1 P2 N2 P1 -0.49(18) . . . . ?
Se1 P2 N2 P1 -112.50(13) . . . . ?
Na2 P2 N2 P1 174.99(9) . . . . ?
N1 P1 N2 C5 -170.1(4) . . . . ?
S1 P1 N2 C5 -63.2(4) 4_676 . . . ?
P2 P1 N2 C5 -170.6(5) . . . . ?
N1 P1 N2 P2 0.48(18) . . . . ?
S1 P1 N2 P2 107.40(15) 4_676 . . . ?
P2 N1 C1 C3 5.5(7) . . . . ?
P1 N1 C1 C3 178.8(4) . . . . ?
P2 N1 C1 C2 125.4(4) . . . . ?
P1 N1 C1 C2 -61.2(6) . . . . ?
P2 N1 C1 C4 -115.1(4) . . . . ?
P1 N1 C1 C4 58.2(5) . . . . ?
P2 N2 C5 C8 153.7(3) . . . . ?
P1 N2 C5 C8 -38.7(5) . . . . ?
P2 N2 C5 C7 34.5(5) . . . . ?
P1 N2 C5 C7 -157.9(3) . . . . ?
P2 N2 C5 C6 -86.7(5) . . . . ?
P1 N2 C5 C6 80.9(4) . . . . ?
P2 N3 C9 C11 134.6(4) . . . . ?
Na2 N3 C9 C11 -38.5(5) . . . . ?
P2 N3 C9 C12 -108.7(4) . . . . ?
Na2 N3 C9 C12 78.3(4) . . . . ?
P2 N3 C9 C10 13.1(6) . . . . ?
Na2 N3 C9 C10 -160.0(3) . . . . ?
C16 O1 C13 C14 8.5(7) . . . . ?
Na2 O1 C13 C14 159.9(4) . . . . ?
O1 C13 C14 C15 -29.3(6) . . . . ?
C13 C14 C15 C16 37.8(6) . . . . ?
C13 O1 C16 C15 15.6(7) . . . . ?
Na2 O1 C16 C15 -137.9(4) . . . . ?
C14 C15 C16 O1 -33.4(7) . . . . ?
C20 O2 C17 C18 -13.4(14) . . . . ?
Na1 O2 C17 C18 157.3(8) . . . . ?
O2 C17 C18 C19 15.9(15) . . . . ?
C17 C18 C19 C20 -12.4(15) . . . . ?
C18 C19 C20 O2 3.7(12) . . . . ?
C17 O2 C20 C19 5.4(12) . . . . ?
Na1 O2 C20 C19 -165.2(6) . . . . ?
C24 O3 C21 C22 16.4(16) . . . . ?
Na1 O3 C21 C22 -137.0(11) . . . . ?
O3 C21 C22 C23 -6.5(19) . . . . ?
C21 C22 C23 C24 -5.2(16) . . . . ?
C21 O3 C24 C23 -17.4(10) . . . . ?
Na1 O3 C24 C23 134.3(6) . . . . ?
C22 C23 C24 O3 14.3(12) . . . . ?
C28B O4B C25B C26B 40(3) . . . . ?
Na1 O4B C25B C26B -115(2) . . . . ?
O4B C25B C26B C27B -39(3) . . . . ?
C25B C26B C27B C28B 21(4) . . . . ?
C26B C27B C28B O4B 2(4) . . . . ?
C25B O4B C28B C27B -25(4) . . . . ?
Na1 O4B C28B C27B 129(2) . . . . ?
C28A O4A C25A C26A -21(2) . . . . ?
O4A C25A C26A C27A 13(3) . . . . ?
C25A C26A C27A C28A 1(3) . . . . ?
C26A C27A C28A O4A -13(2) . . . . ?
C25A O4A C28A C27A 21(2) . . . . ?

_refine_diff_density_max         1.170
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1557386'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H29 N3 P2 S'
_chemical_formula_sum            'C12 H29 N3 P2 S'
_chemical_formula_weight         309.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   20.1254(14)
_cell_length_b                   9.8130(6)
_cell_length_c                   20.1672(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.388(4)
_cell_angle_gamma                90
_cell_volume                     3598.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9670
_cell_measurement_theta_min      8.798
_cell_measurement_theta_max      133.844

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.190
_shelx_estimated_absorpt_T_min   0.503
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.481848
_exptl_absorpt_correction_T_max  0.752817
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a

_diffrn_detector_area_resol_mean 0
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            6102
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.399
_diffrn_reflns_theta_max         66.816
_diffrn_reflns_theta_full        66.816
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             6102
_reflns_number_gt                5119
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+15.7765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6102
_refine_ls_number_parameters     381
_refine_ls_number_restraints     302
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.1644
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.094
_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
C1 C 0.4255(5) -0.1364(6) 0.1652(4) 0.0447(19) Uani 1 1 d . U . . .
C2 C 0.4050(6) -0.2512(8) 0.2030(5) 0.076(3) Uani 1 1 d . U . . .
H2A H 0.4082 -0.2193 0.2503 0.113 Uiso 1 1 calc R U . . .
H2B H 0.4388 -0.3278 0.2110 0.113 Uiso 1 1 calc R U . . .
H2C H 0.3546 -0.2810 0.1720 0.113 Uiso 1 1 calc R U . . .
C3 C 0.4120(6) -0.1831(9) 0.0880(5) 0.071(3) Uani 1 1 d . U . . .
H3A H 0.3592 -0.1972 0.0585 0.106 Uiso 1 1 calc R U . . .
H3B H 0.4383 -0.2686 0.0912 0.106 Uiso 1 1 calc R U . . .
H3C H 0.4298 -0.1132 0.0648 0.106 Uiso 1 1 calc R U . . .
C4 C 0.5034(5) -0.0945(9) 0.2108(5) 0.071(3) Uani 1 1 d . U . . .
H4A H 0.5165 -0.0197 0.1864 0.106 Uiso 1 1 calc R U . . .
H4B H 0.5361 -0.1721 0.2168 0.106 Uiso 1 1 calc R U . . .
H4C H 0.5087 -0.0640 0.2591 0.106 Uiso 1 1 calc R U . . .
C5 C 0.2556(4) 0.2702(7) 0.1434(4) 0.0423(18) Uani 1 1 d D U . . .
C6 C 0.2614(7) 0.3285(12) 0.2163(6) 0.064(4) Uani 0.707(10) 1 d D U P A 1
H6A H 0.2218 0.3948 0.2066 0.096 Uiso 0.707(10) 1 calc R U P A 1
H6B H 0.2569 0.2544 0.2467 0.096 Uiso 0.707(10) 1 calc R U P A 1
H6C H 0.3091 0.3735 0.2423 0.096 Uiso 0.707(10) 1 calc R U P A 1
C7 C 0.2622(7) 0.3938(10) 0.0970(6) 0.068(4) Uani 0.707(10) 1 d D U P A 1
H7A H 0.2233 0.4601 0.0899 0.102 Uiso 0.707(10) 1 calc R U P A 1
H7B H 0.3103 0.4373 0.1230 0.102 Uiso 0.707(10) 1 calc R U P A 1
H7C H 0.2570 0.3611 0.0491 0.102 Uiso 0.707(10) 1 calc R U P A 1
C8 C 0.1811(6) 0.2052(13) 0.1004(7) 0.079(4) Uani 0.707(10) 1 d D U P A 1
H8A H 0.1424 0.2721 0.0930 0.118 Uiso 0.707(10) 1 calc R U P A 1
H8B H 0.1772 0.1745 0.0527 0.118 Uiso 0.707(10) 1 calc R U P A 1
H8C H 0.1754 0.1271 0.1278 0.118 Uiso 0.707(10) 1 calc R U P A 1
C6' C 0.2106(14) 0.212(3) 0.1826(14) 0.080(7) Uani 0.293(10) 1 d D U P A 2
H6'1 H 0.1709 0.2760 0.1768 0.120 Uiso 0.293(10) 1 calc R U P A 2
H6'2 H 0.1895 0.1243 0.1610 0.120 Uiso 0.293(10) 1 calc R U P A 2
H6'3 H 0.2428 0.2005 0.2349 0.120 Uiso 0.293(10) 1 calc R U P A 2
C7' C 0.2974(15) 0.395(2) 0.1811(14) 0.083(8) Uani 0.293(10) 1 d D U P A 2
H7'1 H 0.2628 0.4683 0.1766 0.125 Uiso 0.293(10) 1 calc R U P A 2
H7'2 H 0.3272 0.3746 0.2331 0.125 Uiso 0.293(10) 1 calc R U P A 2
H7'3 H 0.3295 0.4230 0.1584 0.125 Uiso 0.293(10) 1 calc R U P A 2
C8' C 0.2075(13) 0.287(3) 0.0629(8) 0.058(6) Uani 0.293(10) 1 d D U P A 2
H8'1 H 0.1690 0.3536 0.0558 0.087 Uiso 0.293(10) 1 calc R U P A 2
H8'2 H 0.2373 0.3181 0.0382 0.087 Uiso 0.293(10) 1 calc R U P A 2
H8'3 H 0.1849 0.1988 0.0422 0.087 Uiso 0.293(10) 1 calc R U P A 2
C9 C 0.4225(4) 0.2548(8) 0.0316(4) 0.0418(19) Uani 1 1 d . U . . .
C10 C 0.3784(5) 0.1768(9) -0.0396(4) 0.053(2) Uani 1 1 d . U . . .
H10A H 0.3890 0.0792 -0.0314 0.080 Uiso 1 1 calc R U . . .
H10B H 0.3922 0.2090 -0.0780 0.080 Uiso 1 1 calc R U . . .
H10C H 0.3258 0.1924 -0.0551 0.080 Uiso 1 1 calc R U . . .
C11 C 0.5035(5) 0.2366(11) 0.0535(5) 0.069(3) Uani 1 1 d . U . . .
H11A H 0.5317 0.2799 0.1012 0.103 Uiso 1 1 calc R U . . .
H11B H 0.5164 0.2788 0.0165 0.103 Uiso 1 1 calc R U . . .
H11C H 0.5152 0.1391 0.0569 0.103 Uiso 1 1 calc R U . . .
C12 C 0.4037(6) 0.4058(9) 0.0212(5) 0.065(3) Uani 1 1 d . U . . .
H12A H 0.3511 0.4181 0.0079 0.098 Uiso 1 1 calc R U . . .
H12B H 0.4152 0.4421 -0.0179 0.098 Uiso 1 1 calc R U . . .
H12C H 0.4326 0.4546 0.0671 0.098 Uiso 1 1 calc R U . . .
C13 C 0.8904(4) 0.2086(7) 0.0018(4) 0.0335(16) Uani 1 1 d . U . . .
C14 C 0.9222(5) 0.0860(8) 0.0503(4) 0.052(2) Uani 1 1 d . U . . .
H14A H 0.9721 0.1070 0.0869 0.079 Uiso 1 1 calc R U . . .
H14B H 0.9239 0.0088 0.0202 0.079 Uiso 1 1 calc R U . . .
H14C H 0.8913 0.0626 0.0752 0.079 Uiso 1 1 calc R U . . .
C15 C 0.8122(5) 0.1837(9) -0.0521(4) 0.059(2) Uani 1 1 d . U . . .
H15A H 0.7832 0.1575 -0.0256 0.089 Uiso 1 1 calc R U . . .
H15B H 0.8106 0.1103 -0.0857 0.089 Uiso 1 1 calc R U . . .
H15C H 0.7917 0.2671 -0.0802 0.089 Uiso 1 1 calc R U . . .
C16 C 0.9358(5) 0.2417(8) -0.0407(5) 0.056(2) Uani 1 1 d . U . . .
H16A H 0.9149 0.3216 -0.0718 0.084 Uiso 1 1 calc R U . . .
H16B H 0.9348 0.1636 -0.0714 0.084 Uiso 1 1 calc R U . . .
H16C H 0.9867 0.2609 -0.0060 0.084 Uiso 1 1 calc R U . . .
C17 C 0.9005(4) 0.6240(6) 0.1658(4) 0.0354(17) Uani 1 1 d . U . . .
C18 C 0.9400(5) 0.7432(7) 0.1497(5) 0.062(2) Uani 1 1 d . U . . .
H18A H 0.9909 0.7173 0.1617 0.093 Uiso 1 1 calc R U . . .
H18B H 0.9398 0.8219 0.1795 0.093 Uiso 1 1 calc R U . . .
H18C H 0.9148 0.7671 0.0975 0.093 Uiso 1 1 calc R U . . .
C19 C 0.9416(6) 0.5799(9) 0.2451(4) 0.068(3) Uani 1 1 d . U . . .
H19A H 0.9150 0.5050 0.2551 0.102 Uiso 1 1 calc R U . . .
H19B H 0.9453 0.6569 0.2774 0.102 Uiso 1 1 calc R U . . .
H19C H 0.9911 0.5492 0.2540 0.102 Uiso 1 1 calc R U . . .
C20 C 0.8237(5) 0.6712(9) 0.1506(6) 0.067(3) Uani 1 1 d . U . . .
H20A H 0.7974 0.6973 0.0988 0.101 Uiso 1 1 calc R U . . .
H20B H 0.8267 0.7499 0.1817 0.101 Uiso 1 1 calc R U . . .
H20C H 0.7972 0.5971 0.1613 0.101 Uiso 1 1 calc R U . . .
C21 C 0.7844(4) 0.2175(7) 0.1691(4) 0.0379(17) Uani 1 1 d . U . . .
C22 C 0.7825(6) 0.0646(9) 0.1526(5) 0.070(3) Uani 1 1 d . U . . .
H22A H 0.7699 0.0514 0.1004 0.104 Uiso 1 1 calc R U . . .
H22B H 0.7456 0.0201 0.1647 0.104 Uiso 1 1 calc R U . . .
H22C H 0.8310 0.0247 0.1822 0.104 Uiso 1 1 calc R U . . .
C23 C 0.7102(4) 0.2797(11) 0.1251(5) 0.066(3) Uani 1 1 d . U . . .
H23A H 0.7124 0.3779 0.1346 0.099 Uiso 1 1 calc R U . . .
H23B H 0.6740 0.2379 0.1394 0.099 Uiso 1 1 calc R U . . .
H23C H 0.6956 0.2638 0.0727 0.099 Uiso 1 1 calc R U . . .
C24 C 0.8069(5) 0.2378(9) 0.2512(4) 0.053(2) Uani 1 1 d . U . . .
H24A H 0.8541 0.1924 0.2795 0.079 Uiso 1 1 calc R U . . .
H24B H 0.7692 0.1987 0.2641 0.079 Uiso 1 1 calc R U . . .
H24C H 0.8118 0.3355 0.2625 0.079 Uiso 1 1 calc R U . . .
N1 N 0.3769(3) -0.0181(5) 0.1576(3) 0.0379(14) Uani 1 1 d . U . . .
N2 N 0.3131(3) 0.1707(6) 0.1544(3) 0.0332(13) Uani 1 1 d . U . . .
N3 N 0.4073(3) 0.2002(6) 0.0931(3) 0.0321(13) Uani 1 1 d D U . . .
H3N H 0.440(3) 0.232(7) 0.1355(19) 0.039 Uiso 1 1 d D U . . .
N4 N 0.8929(3) 0.3279(6) 0.0486(3) 0.0351(14) Uani 1 1 d . U . . .
N5 N 0.8943(3) 0.5100(5) 0.1157(3) 0.0341(13) Uani 1 1 d . U . . .
N6 N 0.8403(3) 0.2826(6) 0.1505(3) 0.0356(13) Uani 1 1 d D U . . .
H6N H 0.8842(17) 0.248(7) 0.177(3) 0.043 Uiso 1 1 d D U . . .
P1 P 0.34462(10) 0.04357(18) 0.21446(9) 0.0343(4) Uani 1 1 d . U . . .
H1P H 0.296(4) -0.047(7) 0.216(3) 0.041 Uiso 1 1 d . U . . .
P2 P 0.33884(9) 0.10337(15) 0.08757(8) 0.0286(3) Uani 1 1 d . U . . .
P3 P 0.82821(10) 0.38254(15) 0.07948(9) 0.0306(4) Uani 1 1 d . U . . .
P4 P 0.95178(10) 0.45368(17) 0.08320(9) 0.0317(4) Uani 1 1 d . U . . .
H4P H 0.945(3) 0.533(7) 0.020(3) 0.038 Uiso 1 1 d . U . . .
S1 S 0.40500(12) 0.0707(2) 0.31819(9) 0.0456(5) Uani 1 1 d . U . . .
S2 S 1.05371(10) 0.4235(2) 0.14651(11) 0.0465(5) Uani 1 1 d . 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
C1 N1 1.483(8) . ?
C1 C4 1.495(11) . ?
C1 C2 1.513(11) . ?
C1 C3 1.533(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N2 1.457(9) . ?
C5 C7' 1.493(13) . ?
C5 C8' 1.500(13) . ?
C5 C8 1.514(11) . ?
C5 C6 1.536(10) . ?
C5 C6' 1.543(14) . ?
C5 C7 1.572(10) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6' H6'1 0.9800 . ?
C6' H6'2 0.9800 . ?
C6' H6'3 0.9800 . ?
C7' H7'1 0.9800 . ?
C7' H7'2 0.9800 . ?
C7' H7'3 0.9800 . ?
C8' H8'1 0.9800 . ?
C8' H8'2 0.9800 . ?
C8' H8'3 0.9800 . ?
C9 N3 1.497(8) . ?
C9 C11 1.506(12) . ?
C9 C12 1.522(11) . ?
C9 C10 1.531(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N4 1.492(8) . ?
C13 C15 1.501(11) . ?
C13 C14 1.509(10) . ?
C13 C16 1.530(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N5 1.477(7) . ?
C17 C20 1.514(11) . ?
C17 C19 1.514(10) . ?
C17 C18 1.526(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N6 1.474(9) . ?
C21 C23 1.502(11) . ?
C21 C24 1.531(10) . ?
C21 C22 1.533(11) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 P1 1.657(6) . ?
N1 P2 1.753(5) . ?
N2 P1 1.664(6) . ?
N2 P2 1.765(5) . ?
N3 P2 1.638(6) . ?
N3 H3N 0.880(10) . ?
N4 P4 1.645(6) . ?
N4 P3 1.751(6) . ?
N5 P4 1.650(5) . ?
N5 P3 1.742(5) . ?
N6 P3 1.666(6) . ?
N6 H6N 0.881(10) . ?
P1 S1 1.935(2) . ?
P1 P2 2.579(2) . ?
P1 H1P 1.34(7) . ?
P3 P4 2.553(3) . ?
P4 S2 1.918(3) . ?
P4 H4P 1.46(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C4 108.6(6) . . ?
N1 C1 C2 109.0(7) . . ?
C4 C1 C2 109.7(7) . . ?
N1 C1 C3 107.8(6) . . ?
C4 C1 C3 112.9(8) . . ?
C2 C1 C3 108.7(7) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C7' 103.5(13) . . ?
N2 C5 C8' 109.8(12) . . ?
C7' C5 C8' 115.1(11) . . ?
N2 C5 C8 109.4(7) . . ?
N2 C5 C6 112.0(7) . . ?
C8 C5 C6 110.7(7) . . ?
N2 C5 C6' 106.2(12) . . ?
C7' C5 C6' 111.4(11) . . ?
C8' C5 C6' 110.2(10) . . ?
N2 C5 C7 110.1(6) . . ?
C8 C5 C7 107.5(7) . . ?
C6 C5 C7 107.0(7) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6' H6'1 109.5 . . ?
C5 C6' H6'2 109.5 . . ?
H6'1 C6' H6'2 109.5 . . ?
C5 C6' H6'3 109.5 . . ?
H6'1 C6' H6'3 109.5 . . ?
H6'2 C6' H6'3 109.5 . . ?
C5 C7' H7'1 109.5 . . ?
C5 C7' H7'2 109.5 . . ?
H7'1 C7' H7'2 109.5 . . ?
C5 C7' H7'3 109.5 . . ?
H7'1 C7' H7'3 109.5 . . ?
H7'2 C7' H7'3 109.5 . . ?
C5 C8' H8'1 109.5 . . ?
C5 C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C5 C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
N3 C9 C11 107.2(6) . . ?
N3 C9 C12 109.5(6) . . ?
C11 C9 C12 109.3(7) . . ?
N3 C9 C10 110.8(6) . . ?
C11 C9 C10 109.6(7) . . ?
C12 C9 C10 110.3(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C15 109.0(6) . . ?
N4 C13 C14 109.0(5) . . ?
C15 C13 C14 111.2(6) . . ?
N4 C13 C16 108.8(5) . . ?
C15 C13 C16 108.8(6) . . ?
C14 C13 C16 110.0(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 C20 108.3(6) . . ?
N5 C17 C19 110.7(5) . . ?
C20 C17 C19 110.5(7) . . ?
N5 C17 C18 109.5(5) . . ?
C20 C17 C18 107.6(6) . . ?
C19 C17 C18 110.2(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 C23 110.4(6) . . ?
N6 C21 C24 108.3(6) . . ?
C23 C21 C24 110.1(7) . . ?
N6 C21 C22 108.6(6) . . ?
C23 C21 C22 110.1(8) . . ?
C24 C21 C22 109.3(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 P1 130.6(5) . . ?
C1 N1 P2 131.1(5) . . ?
P1 N1 P2 98.2(3) . . ?
C5 N2 P1 130.0(4) . . ?
C5 N2 P2 127.5(4) . . ?
P1 N2 P2 97.5(3) . . ?
C9 N3 P2 128.0(5) . . ?
C9 N3 H3N 110(4) . . ?
P2 N3 H3N 121(4) . . ?
C13 N4 P4 132.8(5) . . ?
C13 N4 P3 129.6(4) . . ?
P4 N4 P3 97.5(3) . . ?
C17 N5 P4 131.1(4) . . ?
C17 N5 P3 131.0(4) . . ?
P4 N5 P3 97.6(3) . . ?
C21 N6 P3 128.9(5) . . ?
C21 N6 H6N 111(5) . . ?
P3 N6 H6N 119(5) . . ?
N1 P1 N2 84.8(3) . . ?
N1 P1 S1 123.2(2) . . ?
N2 P1 S1 123.4(2) . . ?
N1 P1 P2 42.28(19) . . ?
N2 P1 P2 42.74(18) . . ?
S1 P1 P2 141.42(11) . . ?
N1 P1 H1P 107(3) . . ?
N2 P1 H1P 117(3) . . ?
S1 P1 H1P 101(3) . . ?
P2 P1 H1P 117(3) . . ?
N3 P2 N1 106.0(3) . . ?
N3 P2 N2 104.1(3) . . ?
N1 P2 N2 79.0(3) . . ?
N3 P2 P1 112.71(19) . . ?
N1 P2 P1 39.47(18) . . ?
N2 P2 P1 39.76(18) . . ?
N6 P3 N5 105.0(3) . . ?
N6 P3 N4 105.6(3) . . ?
N5 P3 N4 79.5(3) . . ?
N6 P3 P4 110.8(2) . . ?
N5 P3 P4 39.84(17) . . ?
N4 P3 P4 39.70(18) . . ?
N4 P4 N5 85.4(3) . . ?
N4 P4 S2 122.4(2) . . ?
N5 P4 S2 121.3(2) . . ?
N4 P4 P3 42.85(19) . . ?
N5 P4 P3 42.55(18) . . ?
S2 P4 P3 136.68(10) . . ?
N4 P4 H4P 105(3) . . ?
N5 P4 H4P 111(2) . . ?
S2 P4 H4P 109(2) . . ?
P3 P4 H4P 114(2) . . ?

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
C4 C1 N1 P1 -80.8(9) . . . . ?
C2 C1 N1 P1 38.6(9) . . . . ?
C3 C1 N1 P1 156.5(6) . . . . ?
C4 C1 N1 P2 96.3(8) . . . . ?
C2 C1 N1 P2 -144.2(6) . . . . ?
C3 C1 N1 P2 -26.4(10) . . . . ?
C7' C5 N2 P1 100.6(13) . . . . ?
C8' C5 N2 P1 -136.0(11) . . . . ?
C8 C5 N2 P1 -78.9(9) . . . . ?
C6 C5 N2 P1 44.3(9) . . . . ?
C6' C5 N2 P1 -16.9(13) . . . . ?
C7 C5 N2 P1 163.2(6) . . . . ?
C7' C5 N2 P2 -110.3(12) . . . . ?
C8' C5 N2 P2 13.1(13) . . . . ?
C8 C5 N2 P2 70.2(9) . . . . ?
C6 C5 N2 P2 -166.6(6) . . . . ?
C6' C5 N2 P2 132.3(12) . . . . ?
C7 C5 N2 P2 -47.7(9) . . . . ?
C11 C9 N3 P2 -136.1(6) . . . . ?
C12 C9 N3 P2 105.4(7) . . . . ?
C10 C9 N3 P2 -16.6(9) . . . . ?
C15 C13 N4 P4 -142.3(6) . . . . ?
C14 C13 N4 P4 96.2(7) . . . . ?
C16 C13 N4 P4 -23.8(9) . . . . ?
C15 C13 N4 P3 33.1(8) . . . . ?
C14 C13 N4 P3 -88.4(7) . . . . ?
C16 C13 N4 P3 151.6(6) . . . . ?
C20 C17 N5 P4 154.3(6) . . . . ?
C19 C17 N5 P4 -84.5(8) . . . . ?
C18 C17 N5 P4 37.2(9) . . . . ?
C20 C17 N5 P3 -32.9(9) . . . . ?
C19 C17 N5 P3 88.3(8) . . . . ?
C18 C17 N5 P3 -150.0(6) . . . . ?
C23 C21 N6 P3 -14.4(9) . . . . ?
C24 C21 N6 P3 -135.0(6) . . . . ?
C22 C21 N6 P3 106.4(7) . . . . ?
C1 N1 P1 N2 172.9(7) . . . . ?
P2 N1 P1 N2 -5.0(3) . . . . ?
C1 N1 P1 S1 45.9(7) . . . . ?
P2 N1 P1 S1 -132.0(2) . . . . ?
C1 N1 P1 P2 177.8(8) . . . . ?
C5 N2 P1 N1 160.7(6) . . . . ?
P2 N2 P1 N1 4.9(3) . . . . ?
C5 N2 P1 S1 -72.5(7) . . . . ?
P2 N2 P1 S1 131.8(2) . . . . ?
C5 N2 P1 P2 155.7(8) . . . . ?
C9 N3 P2 N1 138.4(6) . . . . ?
C9 N3 P2 N2 -139.2(6) . . . . ?
C9 N3 P2 P1 179.7(5) . . . . ?
C1 N1 P2 N3 -71.3(7) . . . . ?
P1 N1 P2 N3 106.5(3) . . . . ?
C1 N1 P2 N2 -173.1(7) . . . . ?
P1 N1 P2 N2 4.8(3) . . . . ?
C1 N1 P2 P1 -177.8(8) . . . . ?
C5 N2 P2 N3 94.7(6) . . . . ?
P1 N2 P2 N3 -108.6(3) . . . . ?
C5 N2 P2 N1 -161.4(6) . . . . ?
P1 N2 P2 N1 -4.7(3) . . . . ?
C5 N2 P2 P1 -156.6(7) . . . . ?
C21 N6 P3 N5 139.4(6) . . . . ?
C21 N6 P3 N4 -137.6(6) . . . . ?
C21 N6 P3 P4 -179.1(5) . . . . ?
C17 N5 P3 N6 -69.9(6) . . . . ?
P4 N5 P3 N6 104.6(3) . . . . ?
C17 N5 P3 N4 -173.4(6) . . . . ?
P4 N5 P3 N4 1.1(3) . . . . ?
C17 N5 P3 P4 -174.5(8) . . . . ?
C13 N4 P3 N6 79.5(6) . . . . ?
P4 N4 P3 N6 -103.9(3) . . . . ?
C13 N4 P3 N5 -177.7(6) . . . . ?
P4 N4 P3 N5 -1.1(3) . . . . ?
C13 N4 P3 P4 -176.6(8) . . . . ?
C13 N4 P4 N5 177.6(7) . . . . ?
P3 N4 P4 N5 1.2(3) . . . . ?
C13 N4 P4 S2 -58.0(7) . . . . ?
P3 N4 P4 S2 125.6(2) . . . . ?
C13 N4 P4 P3 176.4(8) . . . . ?
C17 N5 P4 N4 173.3(6) . . . . ?
P3 N5 P4 N4 -1.2(3) . . . . ?
C17 N5 P4 S2 47.8(6) . . . . ?
P3 N5 P4 S2 -126.7(2) . . . . ?
C17 N5 P4 P3 174.5(8) . . . . ?

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1557383'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C12 H29 N3 P2 S)'
_chemical_formula_sum            'C12 H29 N3 P2 S'
_chemical_formula_weight         309.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.958(2)
_cell_length_b                   11.381(2)
_cell_length_c                   15.909(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1803.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6562
_cell_measurement_theta_min      5.24
_cell_measurement_theta_max      66.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.183
_shelx_estimated_absorpt_T_min   0.420
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5972
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11288
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.240
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_full        66.591
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3164
_reflns_number_gt                2811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
'PH and NH hydrogens were identified from the fourier map and were allowed to refine freely. Bond lengths correspond well to literature values.'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.4462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1093 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3164
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.49464(8) 0.72302(8) 0.42604(5) 0.0229(2) Uani 1 1 d . . . . .
H1 H 0.437(3) 0.800(3) 0.479(2) 0.017(9) Uiso 1 1 d . . . . .
P2 P 0.35985(8) 0.54749(7) 0.37003(5) 0.0207(2) Uani 1 1 d . . . . .
S1 S 0.67959(9) 0.77281(9) 0.41087(6) 0.0358(2) Uani 1 1 d . . . . .
N1 N 0.3937(3) 0.6955(2) 0.34584(17) 0.0231(7) Uani 1 1 d . . . . .
N2 N 0.4574(3) 0.5888(2) 0.45718(17) 0.0238(7) Uani 1 1 d . . . . .
N3 N 0.2057(3) 0.5463(3) 0.40788(19) 0.0241(6) Uani 1 1 d . . . . .
H2 H 0.183(4) 0.599(3) 0.446(3) 0.035(11) Uiso 1 1 d . . . . .
C1 C 0.3847(3) 0.7548(3) 0.2628(2) 0.0249(8) Uani 1 1 d . . . . .
C2 C 0.3916(4) 0.8875(3) 0.2772(2) 0.0336(9) Uani 1 1 d . . . . .
H2A H 0.3858 0.9283 0.2231 0.050 Uiso 1 1 calc R U . . .
H2B H 0.3167 0.9119 0.3132 0.050 Uiso 1 1 calc R U . . .
H2C H 0.4767 0.9073 0.3047 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4996(4) 0.7150(3) 0.2060(2) 0.0367(9) Uani 1 1 d . . . . .
H3A H 0.4925 0.7547 0.1515 0.055 Uiso 1 1 calc R U . . .
H3B H 0.5856 0.7351 0.2323 0.055 Uiso 1 1 calc R U . . .
H3C H 0.4944 0.6298 0.1977 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2500(4) 0.7226(4) 0.2240(2) 0.0379(9) Uani 1 1 d . . . . .
H4A H 0.2413 0.7607 0.1690 0.057 Uiso 1 1 calc R U . . .
H4B H 0.2445 0.6372 0.2171 0.057 Uiso 1 1 calc R U . . .
H4C H 0.1773 0.7493 0.2610 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5164(4) 0.5158(3) 0.5245(2) 0.0275(8) Uani 1 1 d . . . . .
C6 C 0.5416(4) 0.5944(4) 0.6011(2) 0.0405(10) Uani 1 1 d . . . . .
H6A H 0.5808 0.5474 0.6465 0.061 Uiso 1 1 calc R U . . .
H6B H 0.6037 0.6576 0.5857 0.061 Uiso 1 1 calc R U . . .
H6C H 0.4564 0.6284 0.6200 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6477(4) 0.4597(4) 0.4950(3) 0.0431(10) Uani 1 1 d . . . . .
H7A H 0.6853 0.4117 0.5404 0.065 Uiso 1 1 calc R U . . .
H7B H 0.6301 0.4099 0.4459 0.065 Uiso 1 1 calc R U . . .
H7C H 0.7118 0.5214 0.4797 0.065 Uiso 1 1 calc R U . . .
C8 C 0.4159(4) 0.4203(4) 0.5482(3) 0.0436(11) Uani 1 1 d . . . . .
H8A H 0.4538 0.3711 0.5929 0.065 Uiso 1 1 calc R U . . .
H8B H 0.3326 0.4567 0.5681 0.065 Uiso 1 1 calc R U . . .
H8C H 0.3967 0.3715 0.4988 0.065 Uiso 1 1 calc R U . . .
C9 C 0.0939(3) 0.4654(3) 0.3869(2) 0.0277(8) Uani 1 1 d . . . . .
C10 C -0.0172(4) 0.5356(4) 0.3438(3) 0.0404(10) Uani 1 1 d . . . . .
H10A H -0.0917 0.4830 0.3296 0.061 Uiso 1 1 calc R U . . .
H10B H -0.0492 0.5972 0.3818 0.061 Uiso 1 1 calc R U . . .
H10C H 0.0181 0.5715 0.2924 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0399(4) 0.4144(4) 0.4691(3) 0.0425(11) Uani 1 1 d . . . . .
H11A H -0.0343 0.3605 0.4570 0.064 Uiso 1 1 calc R U . . .
H11B H 0.1118 0.3718 0.4981 0.064 Uiso 1 1 calc R U . . .
H11C H 0.0076 0.4784 0.5051 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1413(4) 0.3674(3) 0.3297(3) 0.0444(11) Uani 1 1 d . . . . .
H12A H 0.0657 0.3152 0.3167 0.067 Uiso 1 1 calc R U . . .
H12B H 0.1765 0.4010 0.2774 0.067 Uiso 1 1 calc R U . . .
H12C H 0.2122 0.3225 0.3578 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N2 1.648(3) . ?
P1 N1 1.654(3) . ?
P1 S1 1.9420(13) . ?
P1 P2 2.5664(12) . ?
P1 H1 1.35(3) . ?
P2 N3 1.649(3) . ?
P2 N2 1.757(3) . ?
P2 N1 1.761(3) . ?
N1 C1 1.486(4) . ?
N2 C5 1.477(4) . ?
N3 C9 1.483(4) . ?
N3 H2 0.88(4) . ?
C1 C4 1.521(5) . ?
C1 C3 1.527(5) . ?
C1 C2 1.529(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C8 1.526(5) . ?
C5 C7 1.529(5) . ?
C5 C6 1.532(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C12 1.515(5) . ?
C9 C10 1.526(5) . ?
C9 C11 1.529(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 P1 N1 85.39(14) . . ?
N2 P1 S1 121.42(11) . . ?
N1 P1 S1 122.39(11) . . ?
S1 P1 P2 132.85(6) . . ?
N2 P1 H1 108.6(13) . . ?
N1 P1 H1 110.5(13) . . ?
S1 P1 H1 106.9(13) . . ?
P2 P1 H1 120.2(13) . . ?
N3 P2 N2 103.21(14) . . ?
N3 P2 N1 105.40(14) . . ?
N2 P2 N1 79.08(13) . . ?
N3 P2 P1 111.49(11) . . ?
C1 N1 P1 129.5(2) . . ?
C1 N1 P2 128.1(2) . . ?
P1 N1 P2 97.40(14) . . ?
C5 N2 P1 130.5(2) . . ?
C5 N2 P2 129.9(2) . . ?
P1 N2 P2 97.77(14) . . ?
C9 N3 P2 128.4(2) . . ?
C9 N3 H2 113(3) . . ?
P2 N3 H2 119(3) . . ?
N1 C1 C4 107.7(3) . . ?
N1 C1 C3 110.3(3) . . ?
C4 C1 C3 110.5(3) . . ?
N1 C1 C2 108.2(3) . . ?
C4 C1 C2 109.8(3) . . ?
C3 C1 C2 110.4(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C8 108.6(3) . . ?
N2 C5 C7 110.6(3) . . ?
C8 C5 C7 109.8(3) . . ?
N2 C5 C6 108.3(3) . . ?
C8 C5 C6 109.1(3) . . ?
C7 C5 C6 110.4(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C12 111.1(3) . . ?
N3 C9 C10 108.7(3) . . ?
C12 C9 C10 109.9(3) . . ?
N3 C9 C11 107.9(3) . . ?
C12 C9 C11 110.1(3) . . ?
C10 C9 C11 109.1(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
N2 P1 N1 C1 -160.7(3) . . . . ?
S1 P1 N1 C1 -36.1(3) . . . . ?
P2 P1 N1 C1 -156.1(4) . . . . ?
N2 P1 N1 P2 -4.62(15) . . . . ?
S1 P1 N1 P2 120.02(11) . . . . ?
N3 P2 N1 C1 -98.2(3) . . . . ?
N2 P2 N1 C1 161.0(3) . . . . ?
P1 P2 N1 C1 156.6(3) . . . . ?
N3 P2 N1 P1 105.25(15) . . . . ?
N2 P2 N1 P1 4.39(14) . . . . ?
N1 P1 N2 C5 170.1(3) . . . . ?
S1 P1 N2 C5 44.6(3) . . . . ?
P2 P1 N2 C5 165.5(4) . . . . ?
N1 P1 N2 P2 4.63(15) . . . . ?
S1 P1 N2 P2 -120.87(11) . . . . ?
N3 P2 N2 C5 86.5(3) . . . . ?
N1 P2 N2 C5 -170.0(3) . . . . ?
P1 P2 N2 C5 -165.6(4) . . . . ?
N3 P2 N2 P1 -107.86(16) . . . . ?
N1 P2 N2 P1 -4.41(14) . . . . ?
N2 P2 N3 C9 -144.0(3) . . . . ?
N1 P2 N3 C9 133.9(3) . . . . ?
P1 P2 N3 C9 175.4(3) . . . . ?
P1 N1 C1 C4 -162.4(3) . . . . ?
P2 N1 C1 C4 48.3(4) . . . . ?
P1 N1 C1 C3 77.0(4) . . . . ?
P2 N1 C1 C3 -72.3(3) . . . . ?
P1 N1 C1 C2 -43.8(4) . . . . ?
P2 N1 C1 C2 166.9(2) . . . . ?
P1 N2 C5 C8 159.7(3) . . . . ?
P2 N2 C5 C8 -39.2(4) . . . . ?
P1 N2 C5 C7 -79.8(4) . . . . ?
P2 N2 C5 C7 81.4(4) . . . . ?
P1 N2 C5 C6 41.3(4) . . . . ?
P2 N2 C5 C6 -157.6(3) . . . . ?
P2 N3 C9 C12 6.6(5) . . . . ?
P2 N3 C9 C10 -114.5(3) . . . . ?
P2 N3 C9 C11 127.3(3) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1557384'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C12 H29 N3 P2 S Se)'
_chemical_formula_sum            'C12 H29 N3 P2 S Se'
_chemical_formula_weight         388.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   16.9527(4)
_cell_length_b                   14.5736(4)
_cell_length_c                   16.9848(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.4630(10)
_cell_angle_gamma                90
_cell_volume                     3819.59(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      69.79

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    5.204
_shelx_estimated_absorpt_T_min   0.271
_shelx_estimated_absorpt_T_max   0.490
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.4558
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28431
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.858
_diffrn_reflns_theta_max         70.014
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7208
_reflns_number_gt                6084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin. The crystals contains two isostructural molecules per assymetric unit. Both PH and NH atoms were identified in the electron density map and both heteroatomic pairs were restrained to be equal using SADI. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+6.2211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7208
_refine_ls_number_parameters     360
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Se1 Se 0.73791(3) 0.75994(6) 0.18906(3) 0.03134(16) Uani 1 1 d . . . . .
Se2 Se 0.18469(4) 0.27978(4) 0.23107(3) 0.03157(15) Uani 1 1 d . . . . .
P1 P 0.61173(7) 0.74984(9) 0.18219(7) 0.0194(2) Uani 1 1 d . . . . .
P2 P 0.57103(8) 0.75342(10) 0.30769(8) 0.0248(3) Uani 1 1 d D . . . .
P3 P 0.30034(8) 0.22499(9) 0.06614(8) 0.0255(3) Uani 1 1 d D . . . .
P4 P 0.17677(7) 0.25984(8) 0.10614(7) 0.0195(2) Uani 1 1 d . . . . .
C1 C 0.5861(4) 0.9303(4) 0.2412(4) 0.0351(12) Uani 1 1 d . . . . .
C2 C 0.5698(4) 0.9680(4) 0.1526(4) 0.0528(17) Uani 1 1 d . . . . .
H2A H 0.5743 1.0351 0.1554 0.079 Uiso 1 1 calc R U . . .
H2B H 0.6130 0.9431 0.1339 0.079 Uiso 1 1 calc R U . . .
H2C H 0.5117 0.9502 0.1111 0.079 Uiso 1 1 calc R U . . .
C3 C 0.6756(4) 0.9585(4) 0.3068(4) 0.0468(15) Uani 1 1 d . . . . .
H3A H 0.6796 1.0256 0.3097 0.070 Uiso 1 1 calc R U . . .
H3B H 0.6853 0.9340 0.3638 0.070 Uiso 1 1 calc R U . . .
H3C H 0.7197 0.9340 0.2891 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5161(5) 0.9641(5) 0.2691(5) 0.065(2) Uani 1 1 d . . . . .
H4A H 0.5183 1.0312 0.2734 0.097 Uiso 1 1 calc R U . . .
H4B H 0.4590 0.9450 0.2263 0.097 Uiso 1 1 calc R U . . .
H4C H 0.5262 0.9377 0.3256 0.097 Uiso 1 1 calc R U . . .
C6 C 0.6147(3) 0.5751(3) 0.2671(3) 0.0282(11) Uani 1 1 d . . . . .
C7 C 0.5579(4) 0.5372(4) 0.3095(4) 0.0414(14) Uani 1 1 d . . . . .
H7A H 0.5710 0.4720 0.3228 0.062 Uiso 1 1 calc R U . . .
H7B H 0.5695 0.5710 0.3631 0.062 Uiso 1 1 calc R U . . .
H7C H 0.4967 0.5442 0.2699 0.062 Uiso 1 1 calc R U . . .
C8 C 0.7107(3) 0.5654(4) 0.3287(3) 0.0374(13) Uani 1 1 d . . . . .
H8A H 0.7248 0.5003 0.3412 0.056 Uiso 1 1 calc R U . . .
H8B H 0.7466 0.5915 0.3016 0.056 Uiso 1 1 calc R U . . .
H8C H 0.7219 0.5981 0.3827 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5968(4) 0.5253(4) 0.1831(3) 0.0423(14) Uani 1 1 d . . . . .
H9A H 0.6110 0.4601 0.1950 0.063 Uiso 1 1 calc R U . . .
H9B H 0.5354 0.5317 0.1440 0.063 Uiso 1 1 calc R U . . .
H9C H 0.6325 0.5517 0.1558 0.063 Uiso 1 1 calc R U . . .
C10 C 0.4105(4) 0.8139(4) -0.0191(4) 0.0507(16) Uani 1 1 d . . . . .
H10A H 0.3476 0.8074 -0.0506 0.076 Uiso 1 1 calc R U . . .
H10B H 0.4234 0.8671 0.0195 0.076 Uiso 1 1 calc R U . . .
H10C H 0.4366 0.8226 -0.0604 0.076 Uiso 1 1 calc R U . . .
C11 C 0.4033(3) 0.7089(5) 0.0936(4) 0.0465(16) Uani 1 1 d . . . . .
H11A H 0.3408 0.7020 0.0591 0.070 Uiso 1 1 calc R U . . .
H11B H 0.4265 0.6524 0.1262 0.070 Uiso 1 1 calc R U . . .
H11C H 0.4137 0.7603 0.1338 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4326(4) 0.6477(4) -0.0282(4) 0.0414(14) Uani 1 1 d . . . . .
H12A H 0.3702 0.6380 -0.0606 0.062 Uiso 1 1 calc R U . . .
H12B H 0.4587 0.6617 -0.0685 0.062 Uiso 1 1 calc R U . . .
H12C H 0.4591 0.5920 0.0044 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4478(3) 0.7274(4) 0.0343(3) 0.0309(12) Uani 1 1 d . . . . .
C14 C 0.2711(3) 0.4160(3) 0.0815(3) 0.0300(11) Uani 1 1 d . . . . .
C15 C 0.3111(4) 0.4326(4) 0.0168(4) 0.0444(14) Uani 1 1 d . . . . .
H15A H 0.3284 0.4971 0.0193 0.067 Uiso 1 1 calc R U . . .
H15B H 0.3621 0.3933 0.0314 0.067 Uiso 1 1 calc R U . . .
H15C H 0.2684 0.4181 -0.0417 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3361(4) 0.4388(4) 0.1728(4) 0.0406(14) Uani 1 1 d . . . . .
H16A H 0.3520 0.5038 0.1759 0.061 Uiso 1 1 calc R U . . .
H16B H 0.3101 0.4264 0.2136 0.061 Uiso 1 1 calc R U . . .
H16C H 0.3880 0.4009 0.1876 0.061 Uiso 1 1 calc R U . . .
C17 C 0.1898(3) 0.4745(4) 0.0577(4) 0.0423(14) Uani 1 1 d . . . . .
H17A H 0.2055 0.5396 0.0615 0.063 Uiso 1 1 calc R U . . .
H17B H 0.1487 0.4601 -0.0015 0.063 Uiso 1 1 calc R U . . .
H17C H 0.1631 0.4613 0.0977 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2271(3) 0.0686(4) 0.1144(3) 0.0327(12) Uani 1 1 d . . . . .
C19 C 0.1372(4) 0.0422(4) 0.1053(4) 0.0547(18) Uani 1 1 d . . . . .
H19A H 0.1376 -0.0218 0.1233 0.082 Uiso 1 1 calc R U . . .
H19B H 0.1201 0.0821 0.1419 0.082 Uiso 1 1 calc R U . . .
H19C H 0.0958 0.0490 0.0448 0.082 Uiso 1 1 calc R U . . .
C20 C 0.2529(5) 0.0108(4) 0.0541(4) 0.065(2) Uani 1 1 d . . . . .
H20A H 0.2546 -0.0541 0.0699 0.097 Uiso 1 1 calc R U . . .
H20B H 0.2105 0.0195 -0.0057 0.097 Uiso 1 1 calc R U . . .
H20C H 0.3104 0.0299 0.0593 0.097 Uiso 1 1 calc R U . . .
C21 C 0.2928(4) 0.0565(4) 0.2077(3) 0.0393(13) Uani 1 1 d . . . . .
H21A H 0.2930 -0.0077 0.2250 0.059 Uiso 1 1 calc R U . . .
H21B H 0.3506 0.0732 0.2126 0.059 Uiso 1 1 calc R U . . .
H21C H 0.2770 0.0960 0.2455 0.059 Uiso 1 1 calc R U . . .
C22 C 0.0276(3) 0.2668(4) -0.0596(3) 0.0309(12) Uani 1 1 d . . . . .
C23 C 0.0891(3) 0.2653(5) -0.1039(3) 0.0430(16) Uani 1 1 d . . . . .
H23A H 0.0556 0.2627 -0.1667 0.064 Uiso 1 1 calc R U . . .
H23B H 0.1247 0.3210 -0.0887 0.064 Uiso 1 1 calc R U . . .
H23C H 0.1266 0.2113 -0.0848 0.064 Uiso 1 1 calc R U . . .
C24 C -0.0304(4) 0.3515(4) -0.0863(4) 0.0489(15) Uani 1 1 d . . . . .
H24A H -0.0633 0.3516 -0.1493 0.073 Uiso 1 1 calc R U . . .
H24B H -0.0705 0.3503 -0.0583 0.073 Uiso 1 1 calc R U . . .
H24C H 0.0055 0.4069 -0.0687 0.073 Uiso 1 1 calc R U . . .
C25 C -0.0279(4) 0.1811(4) -0.0835(3) 0.0416(13) Uani 1 1 d . . . . .
H25A H -0.0598 0.1778 -0.1465 0.062 Uiso 1 1 calc R U . . .
H25B H 0.0092 0.1268 -0.0630 0.062 Uiso 1 1 calc R U . . .
H25C H -0.0691 0.1831 -0.0566 0.062 Uiso 1 1 calc R U . . .
N1 N 0.5792(2) 0.8278(3) 0.2361(2) 0.0237(8) Uani 1 1 d . . . . .
N2 N 0.5928(2) 0.6746(3) 0.2477(2) 0.0209(8) Uani 1 1 d . . . . .
N3 N 0.5435(3) 0.7389(3) 0.0816(3) 0.0258(9) Uani 1 1 d D . . . .
N4 N 0.2459(2) 0.3173(3) 0.0752(2) 0.0220(8) Uani 1 1 d . . . . .
N5 N 0.2258(2) 0.1664(3) 0.0868(2) 0.0230(8) Uani 1 1 d . . . . .
N6 N 0.0761(3) 0.2708(3) 0.0371(3) 0.0256(9) Uani 1 1 d D . . . .
S1 S 0.63982(10) 0.76514(12) 0.43023(9) 0.0403(4) Uani 1 1 d . . . . .
S2 S 0.42340(9) 0.21175(11) 0.13386(10) 0.0429(4) Uani 1 1 d . . . . .
H3N H 0.571(3) 0.740(3) 0.050(3) 0.016(12) Uiso 1 1 d D . . . .
H2P H 0.4892(18) 0.747(3) 0.289(2) 0.004(10) Uiso 1 1 d D . . . .
H3P H 0.283(3) 0.207(3) -0.015(2) 0.026(13) Uiso 1 1 d D . . . .
H6N H 0.043(3) 0.282(4) 0.062(4) 0.05(2) Uiso 1 1 d 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
Se1 P1 2.0987(12) . ?
Se2 P4 2.0902(12) . ?
P1 N3 1.627(4) . ?
P1 N2 1.685(4) . ?
P1 N1 1.690(4) . ?
P1 P2 2.4981(16) . ?
P2 N2 1.675(4) . ?
P2 N1 1.677(4) . ?
P2 S1 1.9263(19) . ?
P2 H2P 1.29(3) . ?
P3 N4 1.674(4) . ?
P3 N5 1.678(4) . ?
P3 S2 1.9301(19) . ?
P3 P4 2.5072(16) . ?
P3 H3P 1.31(3) . ?
P4 N6 1.630(4) . ?
P4 N4 1.692(4) . ?
P4 N5 1.698(4) . ?
C1 N1 1.498(6) . ?
C1 C2 1.517(8) . ?
C1 C3 1.521(8) . ?
C1 C4 1.530(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 N2 1.499(6) . ?
C6 C9 1.515(7) . ?
C6 C7 1.526(7) . ?
C6 C8 1.533(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C13 1.528(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.512(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.522(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N3 1.492(6) . ?
C14 N4 1.492(6) . ?
C14 C16 1.521(7) . ?
C14 C17 1.525(7) . ?
C14 C15 1.531(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N5 1.497(6) . ?
C18 C19 1.517(7) . ?
C18 C21 1.524(7) . ?
C18 C20 1.524(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N6 1.503(6) . ?
C22 C25 1.516(7) . ?
C22 C23 1.517(7) . ?
C22 C24 1.525(8) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N3 H3N 0.84(3) . ?
N6 H6N 0.84(4) . ?

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
N3 P1 N2 112.5(2) . . ?
N3 P1 N1 112.7(2) . . ?
N2 P1 N1 83.42(19) . . ?
N3 P1 Se1 109.29(15) . . ?
N2 P1 Se1 118.50(14) . . ?
N1 P1 Se1 118.50(15) . . ?
N3 P1 P2 124.80(15) . . ?
N2 P1 P2 41.81(13) . . ?
N1 P1 P2 41.89(14) . . ?
Se1 P1 P2 125.91(6) . . ?
N2 P2 N1 84.14(19) . . ?
N2 P2 S1 122.03(16) . . ?
N1 P2 S1 122.09(16) . . ?
N2 P2 P1 42.14(13) . . ?
N1 P2 P1 42.29(13) . . ?
S1 P2 P1 131.77(8) . . ?
N2 P2 H2P 106.9(17) . . ?
N1 P2 H2P 105.7(17) . . ?
S1 P2 H2P 112.2(16) . . ?
P1 P2 H2P 116.1(16) . . ?
N4 P3 N5 84.2(2) . . ?
N4 P3 S2 121.76(16) . . ?
N5 P3 S2 123.10(16) . . ?
N4 P3 P4 42.12(13) . . ?
N5 P3 P4 42.33(14) . . ?
S2 P3 P4 132.61(8) . . ?
N4 P3 H3P 112(2) . . ?
N5 P3 H3P 105(2) . . ?
S2 P3 H3P 109(2) . . ?
P4 P3 H3P 119(2) . . ?
N6 P4 N4 112.5(2) . . ?
N6 P4 N5 113.0(2) . . ?
N4 P4 N5 83.05(19) . . ?
N6 P4 Se2 108.93(16) . . ?
N4 P4 Se2 119.01(14) . . ?
N5 P4 Se2 118.52(14) . . ?
N6 P4 P3 124.66(16) . . ?
N4 P4 P3 41.58(14) . . ?
N5 P4 P3 41.73(13) . . ?
Se2 P4 P3 126.41(6) . . ?
N1 C1 C2 109.0(4) . . ?
N1 C1 C3 110.0(4) . . ?
C2 C1 C3 110.2(5) . . ?
N1 C1 C4 106.6(5) . . ?
C2 C1 C4 110.2(5) . . ?
C3 C1 C4 110.7(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C6 C9 108.8(4) . . ?
N2 C6 C7 107.8(4) . . ?
C9 C6 C7 110.6(4) . . ?
N2 C6 C8 109.6(4) . . ?
C9 C6 C8 109.9(4) . . ?
C7 C6 C8 110.0(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C10 H10A 109.5 . . ?
C13 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C13 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 H11A 109.5 . . ?
C13 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C13 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C11 113.1(4) . . ?
N3 C13 C12 107.1(4) . . ?
C11 C13 C12 109.9(5) . . ?
N3 C13 C10 108.5(4) . . ?
C11 C13 C10 110.1(5) . . ?
C12 C13 C10 107.9(5) . . ?
N4 C14 C16 110.4(4) . . ?
N4 C14 C17 108.6(4) . . ?
C16 C14 C17 110.0(5) . . ?
N4 C14 C15 107.4(4) . . ?
C16 C14 C15 110.3(4) . . ?
C17 C14 C15 110.0(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N5 C18 C19 109.1(4) . . ?
N5 C18 C21 110.3(4) . . ?
C19 C18 C21 110.3(5) . . ?
N5 C18 C20 106.7(4) . . ?
C19 C18 C20 110.3(5) . . ?
C21 C18 C20 110.2(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C25 108.9(4) . . ?
N6 C22 C23 111.5(4) . . ?
C25 C22 C23 109.4(5) . . ?
N6 C22 C24 106.7(4) . . ?
C25 C22 C24 109.6(5) . . ?
C23 C22 C24 110.8(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 P2 129.1(3) . . ?
C1 N1 P1 131.8(3) . . ?
P2 N1 P1 95.8(2) . . ?
C6 N2 P2 128.9(3) . . ?
C6 N2 P1 132.6(3) . . ?
P2 N2 P1 96.0(2) . . ?
C13 N3 P1 135.9(3) . . ?
C13 N3 H3N 115(3) . . ?
P1 N3 H3N 109(3) . . ?
C14 N4 P3 129.0(3) . . ?
C14 N4 P4 132.0(3) . . ?
P3 N4 P4 96.3(2) . . ?
C18 N5 P3 129.4(3) . . ?
C18 N5 P4 130.4(3) . . ?
P3 N5 P4 95.9(2) . . ?
C22 N6 P4 135.9(3) . . ?
C22 N6 H6N 112(4) . . ?
P4 N6 H6N 112(4) . . ?

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
C2 C1 N1 P2 -166.2(4) . . . . ?
C3 C1 N1 P2 72.8(6) . . . . ?
C4 C1 N1 P2 -47.3(6) . . . . ?
C2 C1 N1 P1 39.2(7) . . . . ?
C3 C1 N1 P1 -81.7(6) . . . . ?
C4 C1 N1 P1 158.2(4) . . . . ?
N2 P2 N1 C1 -166.9(4) . . . . ?
S1 P2 N1 C1 -42.5(5) . . . . ?
P1 P2 N1 C1 -161.2(5) . . . . ?
N2 P2 N1 P1 -5.8(2) . . . . ?
S1 P2 N1 P1 118.64(16) . . . . ?
N3 P1 N1 C1 -82.2(5) . . . . ?
N2 P1 N1 C1 166.1(5) . . . . ?
Se1 P1 N1 C1 47.2(5) . . . . ?
P2 P1 N1 C1 160.4(6) . . . . ?
N3 P1 N1 P2 117.4(2) . . . . ?
N2 P1 N1 P2 5.7(2) . . . . ?
Se1 P1 N1 P2 -113.21(15) . . . . ?
C9 C6 N2 P2 159.5(4) . . . . ?
C7 C6 N2 P2 39.5(6) . . . . ?
C8 C6 N2 P2 -80.3(5) . . . . ?
C9 C6 N2 P1 -43.0(6) . . . . ?
C7 C6 N2 P1 -163.0(4) . . . . ?
C8 C6 N2 P1 77.2(5) . . . . ?
N1 P2 N2 C6 169.3(4) . . . . ?
S1 P2 N2 C6 44.9(4) . . . . ?
P1 P2 N2 C6 163.5(5) . . . . ?
N1 P2 N2 P1 5.8(2) . . . . ?
S1 P2 N2 P1 -118.67(16) . . . . ?
N3 P1 N2 C6 79.8(5) . . . . ?
N1 P1 N2 C6 -168.3(4) . . . . ?
Se1 P1 N2 C6 -49.4(5) . . . . ?
P2 P1 N2 C6 -162.6(5) . . . . ?
N3 P1 N2 P2 -117.6(2) . . . . ?
N1 P1 N2 P2 -5.7(2) . . . . ?
Se1 P1 N2 P2 113.20(15) . . . . ?
C11 C13 N3 P1 -9.9(8) . . . . ?
C12 C13 N3 P1 -131.2(5) . . . . ?
C10 C13 N3 P1 112.6(5) . . . . ?
N2 P1 N3 C13 45.0(6) . . . . ?
N1 P1 N3 C13 -47.2(6) . . . . ?
Se1 P1 N3 C13 178.9(5) . . . . ?
P2 P1 N3 C13 -1.0(6) . . . . ?
C16 C14 N4 P3 -78.6(5) . . . . ?
C17 C14 N4 P3 160.8(4) . . . . ?
C15 C14 N4 P3 41.8(6) . . . . ?
C16 C14 N4 P4 78.5(5) . . . . ?
C17 C14 N4 P4 -42.2(6) . . . . ?
C15 C14 N4 P4 -161.2(4) . . . . ?
N5 P3 N4 C14 168.5(4) . . . . ?
S2 P3 N4 C14 42.9(4) . . . . ?
P4 P3 N4 C14 163.1(5) . . . . ?
N5 P3 N4 P4 5.47(19) . . . . ?
S2 P3 N4 P4 -120.17(15) . . . . ?
N6 P4 N4 C14 80.3(4) . . . . ?
N5 P4 N4 C14 -167.7(4) . . . . ?
Se2 P4 N4 C14 -48.8(5) . . . . ?
P3 P4 N4 C14 -162.3(5) . . . . ?
N6 P4 N4 P3 -117.5(2) . . . . ?
N5 P4 N4 P3 -5.42(19) . . . . ?
Se2 P4 N4 P3 113.43(15) . . . . ?
C19 C18 N5 P3 -167.5(4) . . . . ?
C21 C18 N5 P3 71.3(5) . . . . ?
C20 C18 N5 P3 -48.3(6) . . . . ?
C19 C18 N5 P4 41.4(6) . . . . ?
C21 C18 N5 P4 -79.8(5) . . . . ?
C20 C18 N5 P4 160.6(4) . . . . ?
N4 P3 N5 C18 -163.7(4) . . . . ?
S2 P3 N5 C18 -39.3(5) . . . . ?
P4 P3 N5 C18 -158.3(5) . . . . ?
N4 P3 N5 P4 -5.45(19) . . . . ?
S2 P3 N5 P4 118.97(16) . . . . ?
N6 P4 N5 C18 -85.1(4) . . . . ?
N4 P4 N5 C18 163.4(4) . . . . ?
Se2 P4 N5 C18 44.0(5) . . . . ?
P3 P4 N5 C18 158.0(5) . . . . ?
N6 P4 N5 P3 116.9(2) . . . . ?
N4 P4 N5 P3 5.40(19) . . . . ?
Se2 P4 N5 P3 -113.93(14) . . . . ?
C25 C22 N6 P4 110.4(5) . . . . ?
C23 C22 N6 P4 -10.4(8) . . . . ?
C24 C22 N6 P4 -131.4(5) . . . . ?
N4 P4 N6 C22 44.5(6) . . . . ?
N5 P4 N6 C22 -47.5(6) . . . . ?
Se2 P4 N6 C22 178.6(5) . . . . ?
P3 P4 N6 C22 -1.3(6) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.086

