# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_2-H
_database_code_depnum_ccdc_archive 'CCDC 1849551'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2019-04-07 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N2 O2 P Se'
_chemical_formula_sum            'C18 H15 N2 O2 P Se'
_chemical_formula_weight         401.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 '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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   27.298(3)
_cell_length_b                   9.3728(5)
_cell_length_c                   16.0877(15)
_cell_angle_alpha                90
_cell_angle_beta                 122.050(13)
_cell_angle_gamma                90
_cell_volume                     3488.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3147
_cell_measurement_theta_min      3.2397
_cell_measurement_theta_max      70.6517

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    3.890
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7342
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.821
_diffrn_reflns_theta_max         70.759
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3298
_reflns_number_gt                2754
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+2.0904P] 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         3298
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.14506(2) 0.56888(4) 0.43589(2) 0.06559(15) Uani 1 1 d . . . . .
P1 P 0.14570(3) 0.75702(7) 0.50673(5) 0.04780(18) Uani 1 1 d . . . . .
N1 N 0.08803(10) 0.7811(3) 0.51699(17) 0.0544(6) Uani 1 1 d . . . . .
H1 H 0.068973 0.858687 0.491719 0.065 Uiso 1 1 calc R U . . .
C4 C 0.02703(16) 0.5204(4) 0.6550(3) 0.0715(9) Uani 1 1 d . . . . .
H4 H 0.013993 0.462138 0.686149 0.086 Uiso 1 1 calc R U . . .
C13 C 0.20814(12) 0.7719(3) 0.62972(19) 0.0491(6) Uani 1 1 d . . . . .
C2 C 0.10027(13) 0.5820(3) 0.6222(2) 0.0532(7) Uani 1 1 d . . . . .
H2 H 0.136608 0.564480 0.632414 0.064 Uiso 1 1 calc R U . . .
C8 C 0.09618(18) 0.9316(4) 0.3444(2) 0.0785(10) Uani 1 1 d . . . . .
H8 H 0.071768 0.854560 0.312675 0.094 Uiso 1 1 calc R U . . .
C14 C 0.20483(14) 0.8431(3) 0.7024(2) 0.0628(8) Uani 1 1 d . . . . .
H14 H 0.170487 0.886963 0.687320 0.075 Uiso 1 1 calc R U . . .
N2 N -0.02708(11) 0.8242(3) 0.4840(2) 0.0683(7) Uani 1 1 d . . . . .
C6 C 0.01253(12) 0.7142(3) 0.5483(2) 0.0523(6) Uani 1 1 d . . . . .
C3 C 0.08045(14) 0.4976(3) 0.6681(2) 0.0617(7) Uani 1 1 d . . . . .
H3 H 0.103553 0.423903 0.708673 0.074 Uiso 1 1 calc R U . . .
C1 C 0.06690(11) 0.6936(3) 0.56048(18) 0.0478(6) Uani 1 1 d . . . . .
C5 C -0.00663(14) 0.6291(4) 0.5960(2) 0.0669(8) Uani 1 1 d . . . . .
H5 H -0.042522 0.646248 0.587744 0.080 Uiso 1 1 calc R U . . .
C9 C 0.0880(2) 1.0568(4) 0.2942(3) 0.0938(13) Uani 1 1 d . . . . .
H9 H 0.057598 1.064927 0.229304 0.113 Uiso 1 1 calc R U . . .
C12 C 0.17709(15) 1.0324(4) 0.4863(2) 0.0653(8) Uani 1 1 d . . . . .
H12 H 0.207439 1.024891 0.551278 0.078 Uiso 1 1 calc R U . . .
C18 C 0.25995(13) 0.7096(3) 0.6528(2) 0.0600(7) Uani 1 1 d . . . . .
H18 H 0.262919 0.663134 0.604575 0.072 Uiso 1 1 calc R U . . .
C17 C 0.30751(14) 0.7169(4) 0.7485(3) 0.0729(9) Uani 1 1 d . . . . .
H17 H 0.342365 0.675463 0.764150 0.087 Uiso 1 1 calc R U . . .
C16 C 0.30304(15) 0.7850(4) 0.8198(3) 0.0732(9) Uani 1 1 d . . . . .
H16 H 0.334689 0.787676 0.883852 0.088 Uiso 1 1 calc R U . . .
C15 C 0.25245(16) 0.8489(4) 0.7971(2) 0.0725(9) Uani 1 1 d . . . . .
H15 H 0.250022 0.896378 0.845589 0.087 Uiso 1 1 calc R U . . .
C7 C 0.14013(12) 0.9191(3) 0.4412(2) 0.0518(7) Uani 1 1 d . . . . .
O1 O -0.06831(12) 0.8545(4) 0.4904(3) 0.1097(10) Uani 1 1 d . . . . .
C10 C 0.12471(19) 1.1700(4) 0.3396(3) 0.0826(11) Uani 1 1 d . . . . .
H10 H 0.119339 1.254589 0.305545 0.099 Uiso 1 1 calc R U . . .
C11 C 0.16900(18) 1.1575(4) 0.4347(3) 0.0782(10) Uani 1 1 d . . . . .
H11 H 0.194071 1.233827 0.465358 0.094 Uiso 1 1 calc R U . . .
O2 O -0.01875(11) 0.8815(3) 0.4237(2) 0.0914(8) 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
Se1 P1 2.0948(8) . ?
P1 N1 1.683(2) . ?
P1 C13 1.806(3) . ?
P1 C7 1.809(3) . ?
N1 C1 1.387(3) . ?
N1 H1 0.8600 . ?
C4 C5 1.363(5) . ?
C4 C3 1.375(5) . ?
C4 H4 0.9300 . ?
C13 C18 1.386(4) . ?
C13 C14 1.391(4) . ?
C2 C3 1.374(4) . ?
C2 C1 1.396(4) . ?
C2 H2 0.9300 . ?
C8 C9 1.375(5) . ?
C8 C7 1.377(4) . ?
C8 H8 0.9300 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
N2 O1 1.217(3) . ?
N2 O2 1.231(4) . ?
N2 C6 1.454(4) . ?
C6 C5 1.388(4) . ?
C6 C1 1.403(4) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C9 C10 1.373(6) . ?
C9 H9 0.9300 . ?
C12 C7 1.376(4) . ?
C12 C11 1.386(5) . ?
C12 H12 0.9300 . ?
C18 C17 1.392(4) . ?
C18 H18 0.9300 . ?
C17 C16 1.373(5) . ?
C17 H17 0.9300 . ?
C16 C15 1.365(5) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C10 C11 1.362(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C13 105.69(12) . . ?
N1 P1 C7 98.67(12) . . ?
C13 P1 C7 108.19(13) . . ?
N1 P1 Se1 115.36(9) . . ?
C13 P1 Se1 113.06(9) . . ?
C7 P1 Se1 114.58(9) . . ?
C1 N1 P1 129.1(2) . . ?
C1 N1 H1 115.4 . . ?
P1 N1 H1 115.4 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C18 C13 C14 119.3(3) . . ?
C18 C13 P1 119.8(2) . . ?
C14 C13 P1 120.9(2) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O1 N2 O2 122.1(3) . . ?
O1 N2 C6 118.5(3) . . ?
O2 N2 C6 119.4(3) . . ?
C5 C6 C1 121.6(3) . . ?
C5 C6 N2 116.4(3) . . ?
C1 C6 N2 121.9(3) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
N1 C1 C2 120.9(2) . . ?
N1 C1 C6 122.7(3) . . ?
C2 C1 C6 116.4(3) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C7 C12 C11 119.9(3) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C13 C18 C17 119.7(3) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C12 C7 C8 119.0(3) . . ?
C12 C7 P1 122.0(2) . . ?
C8 C7 P1 119.0(2) . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?

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
C13 P1 N1 C1 -68.5(3) . . . . ?
C7 P1 N1 C1 179.8(2) . . . . ?
Se1 P1 N1 C1 57.2(3) . . . . ?
N1 P1 C13 C18 157.2(2) . . . . ?
C7 P1 C13 C18 -97.9(2) . . . . ?
Se1 P1 C13 C18 30.1(3) . . . . ?
N1 P1 C13 C14 -21.7(3) . . . . ?
C7 P1 C13 C14 83.2(3) . . . . ?
Se1 P1 C13 C14 -148.7(2) . . . . ?
C18 C13 C14 C15 -1.3(5) . . . . ?
P1 C13 C14 C15 177.5(3) . . . . ?
O1 N2 C6 C5 14.5(4) . . . . ?
O2 N2 C6 C5 -164.0(3) . . . . ?
O1 N2 C6 C1 -166.4(3) . . . . ?
O2 N2 C6 C1 15.1(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C5 C4 C3 C2 -0.4(5) . . . . ?
P1 N1 C1 C2 14.2(4) . . . . ?
P1 N1 C1 C6 -168.1(2) . . . . ?
C3 C2 C1 N1 177.9(3) . . . . ?
C3 C2 C1 C6 0.0(4) . . . . ?
C5 C6 C1 N1 -177.1(3) . . . . ?
N2 C6 C1 N1 3.9(4) . . . . ?
C5 C6 C1 C2 0.7(4) . . . . ?
N2 C6 C1 C2 -178.4(3) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C1 C6 C5 C4 -1.3(5) . . . . ?
N2 C6 C5 C4 177.8(3) . . . . ?
C7 C8 C9 C10 1.7(7) . . . . ?
C14 C13 C18 C17 1.1(5) . . . . ?
P1 C13 C18 C17 -177.7(2) . . . . ?
C13 C18 C17 C16 0.2(5) . . . . ?
C18 C17 C16 C15 -1.4(5) . . . . ?
C17 C16 C15 C14 1.2(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C11 C12 C7 C8 1.2(5) . . . . ?
C11 C12 C7 P1 -176.1(3) . . . . ?
C9 C8 C7 C12 -2.1(6) . . . . ?
C9 C8 C7 P1 175.3(3) . . . . ?
N1 P1 C7 C12 105.7(3) . . . . ?
C13 P1 C7 C12 -4.0(3) . . . . ?
Se1 P1 C7 C12 -131.2(2) . . . . ?
N1 P1 C7 C8 -71.6(3) . . . . ?
C13 P1 C7 C8 178.6(3) . . . . ?
Se1 P1 C7 C8 51.5(3) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C7 C12 C11 C10 0.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.05 2.644(3) 125.7 .
C18 H18 Se1 0.93 3.04 3.484(3) 111.2 .

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1849554'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H38 F N Na O3 P Se'
_chemical_formula_weight         612.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.9424(17)
_cell_length_b                   15.5693(7)
_cell_length_c                   10.617(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.65(4)
_cell_angle_gamma                90
_cell_volume                     1505.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3460
_cell_measurement_theta_min      3.3491
_cell_measurement_theta_max      28.9488

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.352
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6394
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.352
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_point_group_measured_fraction_full 0.826
_reflns_number_total             5152
_reflns_number_gt                4802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_max     0.570
_reflns_Friedel_fraction_full    0.640

_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.005(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5152
_refine_ls_number_parameters     436
_refine_ls_number_restraints     203
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.015
_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
Na1 Na 0.5871(2) 0.20121(11) -0.2598(2) 0.0311(4) Uani 1 1 d . . . . .
Se1 Se 0.95894(5) 0.36061(3) 0.08715(4) 0.03252(14) Uani 1 1 d . . . . .
P2 P 0.76012(12) 0.38867(7) -0.08608(11) 0.0191(2) Uani 1 1 d . . . . .
F1 F 0.5942(3) 0.25953(17) -0.4743(3) 0.0337(6) Uani 1 1 d . . . . .
O1 O 0.6512(6) 0.0825(2) -0.3551(5) 0.0589(13) Uani 1 1 d D . . . .
O2 O 0.3403(4) 0.1734(3) -0.3507(6) 0.0741(16) Uani 1 1 d D . . . .
O3 O 0.6425(4) 0.1287(2) -0.0556(4) 0.0447(9) Uani 1 1 d D . . . .
N1 N 0.7155(4) 0.3353(2) -0.2275(4) 0.0231(8) Uani 1 1 d . . . . .
C1 C 0.7835(4) 0.3462(3) -0.3179(4) 0.0219(9) Uani 1 1 d . . . . .
C2 C 0.7189(5) 0.3071(3) -0.4479(5) 0.0236(9) Uani 1 1 d . . . . .
C3 C 0.7714(6) 0.3132(3) -0.5498(5) 0.0304(11) Uani 1 1 d . . . . .
H3 H 0.724116 0.285083 -0.633293 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8962(5) 0.3623(4) -0.5253(4) 0.0348(10) Uani 1 1 d . . . . .
H4 H 0.933800 0.367597 -0.592188 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9633(5) 0.4031(4) -0.3999(5) 0.0344(12) Uani 1 1 d . . . . .
H5 H 1.045829 0.436820 -0.383675 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9105(5) 0.3949(3) -0.2975(5) 0.0288(10) Uani 1 1 d . . . . .
H6 H 0.959904 0.422178 -0.213488 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7497(5) 0.5041(3) -0.1257(5) 0.0253(10) Uani 1 1 d . . . . .
C8 C 0.6510(7) 0.5310(3) -0.2533(6) 0.0462(15) Uani 1 1 d . . . . .
H8 H 0.592978 0.490899 -0.316818 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6380(9) 0.6179(4) -0.2875(7) 0.0600(19) Uani 1 1 d . . . . .
H9 H 0.571192 0.635716 -0.373489 0.072 Uiso 1 1 calc R U . . .
C10 C 0.7244(8) 0.6778(3) -0.1934(7) 0.0514(16) Uani 1 1 d . . . . .
H10 H 0.716724 0.735728 -0.216449 0.062 Uiso 1 1 calc R U . . .
C11 C 0.8218(7) 0.6512(3) -0.0658(7) 0.0469(15) Uani 1 1 d . . . . .
H11 H 0.879431 0.691401 -0.002256 0.056 Uiso 1 1 calc R U . . .
C12 C 0.8346(5) 0.5648(3) -0.0313(6) 0.0323(11) Uani 1 1 d . . . . .
H12 H 0.900296 0.547424 0.055431 0.039 Uiso 1 1 calc R U . . .
C13 C 0.5990(4) 0.3716(3) -0.0463(4) 0.0210(9) Uani 1 1 d . . . . .
C14 C 0.4609(4) 0.3619(4) -0.1516(4) 0.0276(9) Uani 1 1 d . . . . .
H14 H 0.451075 0.361149 -0.242429 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3365(5) 0.3530(4) -0.1225(5) 0.0335(10) Uani 1 1 d . . . . .
H15 H 0.244587 0.345909 -0.193784 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3497(5) 0.3549(4) 0.0119(5) 0.0373(11) Uani 1 1 d . . . . .
H16 H 0.266808 0.349789 0.031396 0.045 Uiso 1 1 calc R U . . .
C17 C 0.4858(5) 0.3644(4) 0.1168(5) 0.0352(10) Uani 1 1 d . . . . .
H17 H 0.494788 0.365284 0.207408 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6111(5) 0.3728(3) 0.0888(4) 0.0287(10) Uani 1 1 d . . . . .
H18 H 0.702768 0.379098 0.160706 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7484(7) -0.0216(4) -0.4517(7) 0.0509(15) Uani 1 1 d D . . . .
H20A H 0.693278 -0.015021 -0.550005 0.061 Uiso 0.674(12) 1 calc R U P A 1
H20B H 0.839997 -0.051207 -0.434596 0.061 Uiso 0.674(12) 1 calc R U P A 1
H20C H 0.852244 -0.032638 -0.400146 0.061 Uiso 0.326(12) 1 calc R U P A 2
H20D H 0.721009 -0.043079 -0.544521 0.061 Uiso 0.326(12) 1 calc R U P A 2
C21 C 0.6598(7) -0.0666(3) -0.3844(7) 0.0491(15) Uani 1 1 d D . . . .
H21A H 0.724211 -0.093447 -0.299001 0.059 Uiso 0.674(12) 1 calc R U P A 1
H21B H 0.597775 -0.110464 -0.444785 0.059 Uiso 0.674(12) 1 calc R U P A 1
H21C H 0.555390 -0.068253 -0.441335 0.059 Uiso 0.326(12) 1 calc R U P A 2
H21D H 0.696326 -0.123416 -0.350087 0.059 Uiso 0.326(12) 1 calc R U P A 2
C22A C 0.5665(10) 0.0029(4) -0.3570(9) 0.039(2) Uani 0.674(12) 1 d D . P A 1
H22A H 0.468641 0.004926 -0.429638 0.047 Uiso 0.674(12) 1 calc R U P A 1
H22B H 0.559300 -0.006086 -0.269544 0.047 Uiso 0.674(12) 1 calc R U P A 1
C23 C 0.2062(17) 0.2066(17) -0.451(2) 0.039(4) Uani 0.340(11) 1 d D . P B 1
H23A H 0.191251 0.188746 -0.543646 0.047 Uiso 0.340(11) 1 calc R U P B 1
H23B H 0.202391 0.268767 -0.447768 0.047 Uiso 0.340(11) 1 calc R U P B 1
C24A C 0.096(3) 0.1645(19) -0.404(5) 0.142(5) Uani 0.340(11) 1 d D . P B 1
H24A H 0.078612 0.200492 -0.337554 0.171 Uiso 0.340(11) 1 calc R U P B 1
H24B H 0.003774 0.154032 -0.481160 0.171 Uiso 0.340(11) 1 calc R U P B 1
C25A C 0.166(2) 0.0833(13) -0.341(3) 0.069(4) Uani 0.340(11) 1 d D . P B 1
H25A H 0.103105 0.035050 -0.384566 0.083 Uiso 0.340(11) 1 calc R U P B 1
H25B H 0.186211 0.082755 -0.243487 0.083 Uiso 0.340(11) 1 calc R U P B 1
C26A C 0.3057(19) 0.0783(9) -0.361(2) 0.063(5) Uani 0.340(11) 1 d D . P B 1
H26A H 0.290875 0.055006 -0.450606 0.076 Uiso 0.340(11) 1 calc R U P B 1
H26B H 0.380459 0.045392 -0.289474 0.076 Uiso 0.340(11) 1 calc R U P B 1
C27 C 0.5986(14) 0.1314(13) 0.0606(13) 0.030(3) Uani 0.405(17) 1 d D . P C 1
H27A H 0.542844 0.080786 0.063073 0.037 Uiso 0.405(17) 1 calc R U P C 1
H27B H 0.541017 0.182337 0.057395 0.037 Uiso 0.405(17) 1 calc R U P C 1
C28 C 0.7437(14) 0.1338(12) 0.1802(13) 0.037(3) Uani 0.405(17) 1 d D . P C 1
H28A H 0.773963 0.192773 0.205608 0.044 Uiso 0.405(17) 1 calc R U P C 1
H28B H 0.737473 0.105024 0.258706 0.044 Uiso 0.405(17) 1 calc R U P C 1
C29 C 0.8477(16) 0.0905(15) 0.1388(15) 0.058(4) Uani 0.405(17) 1 d D . P C 1
H29A H 0.850197 0.029640 0.158973 0.070 Uiso 0.405(17) 1 calc R U P C 1
H29B H 0.945316 0.113993 0.187566 0.070 Uiso 0.405(17) 1 calc R U P C 1
C30 C 0.7980(14) 0.1045(18) -0.0126(15) 0.050(5) Uani 0.405(17) 1 d D . P C 1
H30A H 0.853506 0.150101 -0.031760 0.060 Uiso 0.405(17) 1 calc R U P C 1
H30B H 0.807753 0.052388 -0.058408 0.060 Uiso 0.405(17) 1 calc R U P C 1
C19A C 0.7739(10) 0.0646(6) -0.3764(11) 0.043(3) Uani 0.674(12) 1 d D . P A 1
H19A H 0.858425 0.061048 -0.289348 0.052 Uiso 0.674(12) 1 calc R U P A 1
H19B H 0.791560 0.109316 -0.431513 0.052 Uiso 0.674(12) 1 calc R U P A 1
C22B C 0.702(2) 0.0005(8) -0.2747(16) 0.053(6) Uani 0.326(12) 1 d D . P A 2
H22C H 0.807169 0.001078 -0.221270 0.064 Uiso 0.326(12) 1 calc R U P A 2
H22D H 0.652519 -0.008710 -0.213396 0.064 Uiso 0.326(12) 1 calc R U P A 2
C25B C 0.1138(13) 0.1255(14) -0.3513(14) 0.101(4) Uani 0.660(11) 1 d D . P B 2
H25C H 0.074408 0.068369 -0.352589 0.122 Uiso 0.660(11) 1 calc R U P B 2
H25D H 0.061227 0.165724 -0.317715 0.122 Uiso 0.660(11) 1 calc R U P B 2
C24B C 0.1020(13) 0.1500(9) -0.4871(14) 0.086(3) Uani 0.660(11) 1 d D . P B 2
H24C H 0.008144 0.177136 -0.539119 0.104 Uiso 0.660(11) 1 calc R U P B 2
H24D H 0.112364 0.100293 -0.537594 0.104 Uiso 0.660(11) 1 calc R U P B 2
C23A C 0.2289(12) 0.2135(11) -0.4597(18) 0.072(3) Uani 0.660(11) 1 d D . P B 2
H23C H 0.253531 0.219077 -0.538926 0.086 Uiso 0.660(11) 1 calc R U P B 2
H23D H 0.206216 0.269667 -0.433878 0.086 Uiso 0.660(11) 1 calc R U P B 2
C19 C 0.719(2) 0.0733(9) -0.455(2) 0.040(5) Uani 0.326(12) 1 d D . P A 2
H19C H 0.808994 0.106180 -0.427275 0.048 Uiso 0.326(12) 1 calc R U P A 2
H19D H 0.652046 0.091661 -0.546169 0.048 Uiso 0.326(12) 1 calc R U P A 2
C30A C 0.7949(15) 0.1085(11) 0.0231(13) 0.070(3) Uani 0.595(17) 1 d D . P C 2
H30C H 0.856559 0.144652 -0.005943 0.084 Uiso 0.595(17) 1 calc R U P C 2
H30D H 0.813690 0.049012 0.008208 0.084 Uiso 0.595(17) 1 calc R U P C 2
C28A C 0.686(2) 0.1046(11) 0.1738(14) 0.088(3) Uani 0.595(17) 1 d D . P C 2
H28C H 0.668463 0.142278 0.238634 0.106 Uiso 0.595(17) 1 calc R U P C 2
H28D H 0.683692 0.045802 0.203330 0.106 Uiso 0.595(17) 1 calc R U P C 2
C27A C 0.5631(19) 0.1174(12) 0.0295(14) 0.075(3) Uani 0.595(17) 1 d D . P C 2
H27C H 0.499490 0.067523 0.001331 0.090 Uiso 0.595(17) 1 calc R U P C 2
H27D H 0.504391 0.167691 0.026776 0.090 Uiso 0.595(17) 1 calc R U P C 2
C29A C 0.830(2) 0.1232(18) 0.1733(15) 0.128(6) Uani 0.595(17) 1 d D . P C 2
H29C H 0.904821 0.083928 0.231714 0.154 Uiso 0.595(17) 1 calc R U P C 2
H29D H 0.860525 0.181918 0.200762 0.154 Uiso 0.595(17) 1 calc R U P C 2
C22 C 0.2742(11) 0.1278(8) -0.2638(13) 0.078(3) Uani 0.660(11) 1 d D . P B 2
H22E H 0.313489 0.070112 -0.241244 0.094 Uiso 0.660(11) 1 calc R U P B 2
H22F H 0.293829 0.159008 -0.179174 0.094 Uiso 0.660(11) 1 calc R U P B 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
Na1 O2 2.289(4) . ?
Na1 O3 2.307(4) . ?
Na1 O1 2.316(4) . ?
Na1 N1 2.399(4) . ?
Na1 F1 2.479(3) . ?
Se1 P2 2.1364(16) . ?
P2 N1 1.615(4) . ?
P2 C13 1.832(4) . ?
P2 C7 1.839(4) . ?
F1 C2 1.373(5) . ?
O1 C19A 1.356(9) . ?
O1 C19 1.475(14) . ?
O1 C22A 1.493(8) . ?
O1 C22B 1.506(13) . ?
O2 C23A 1.388(12) . ?
O2 C23 1.430(15) . ?
O2 C22 1.508(11) . ?
O2 C26A 1.515(14) . ?
O3 C27A 1.429(12) . ?
O3 C30A 1.441(12) . ?
O3 C27 1.465(13) . ?
O3 C30 1.475(12) . ?
N1 C1 1.389(5) . ?
C1 C2 1.406(6) . ?
C1 C6 1.413(6) . ?
C2 C3 1.380(6) . ?
C3 C4 1.390(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.382(7) . ?
C7 C12 1.390(6) . ?
C8 C9 1.394(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.388(6) . ?
C13 C18 1.391(5) . ?
C14 C15 1.397(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.398(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C19 1.505(14) . ?
C20 C21 1.511(8) . ?
C20 C19A 1.531(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C21 C22B 1.494(14) . ?
C21 C22A 1.527(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C23 C24A 1.523(17) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24A C25A 1.469(18) . ?
C24A H24A 0.9700 . ?
C24A H24B 0.9700 . ?
C25A C26A 1.489(16) . ?
C25A H25A 0.9700 . ?
C25A H25B 0.9700 . ?
C26A H26A 0.9700 . ?
C26A H26B 0.9700 . ?
C27 C28 1.492(13) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.443(15) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.496(14) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C25B C24B 1.450(15) . ?
C25B C22 1.490(12) . ?
C25B H25C 0.9700 . ?
C25B H25D 0.9700 . ?
C24B C23A 1.536(14) . ?
C24B H24C 0.9700 . ?
C24B H24D 0.9700 . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C30A C29A 1.507(14) . ?
C30A H30C 0.9700 . ?
C30A H30D 0.9700 . ?
C28A C29A 1.468(16) . ?
C28A C27A 1.541(15) . ?
C28A H28C 0.9700 . ?
C28A H28D 0.9700 . ?
C27A H27C 0.9700 . ?
C27A H27D 0.9700 . ?
C29A H29C 0.9700 . ?
C29A H29D 0.9700 . ?
C22 H22E 0.9700 . ?
C22 H22F 0.9700 . ?

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
O2 Na1 O3 96.63(17) . . ?
O2 Na1 O1 95.8(2) . . ?
O3 Na1 O1 90.91(16) . . ?
O2 Na1 N1 130.08(17) . . ?
O3 Na1 N1 112.28(16) . . ?
O1 Na1 N1 122.22(15) . . ?
O2 Na1 F1 95.88(16) . . ?
O3 Na1 F1 163.47(14) . . ?
O1 Na1 F1 77.10(13) . . ?
N1 Na1 F1 66.59(11) . . ?
N1 P2 C13 101.55(19) . . ?
N1 P2 C7 108.74(19) . . ?
C13 P2 C7 102.69(19) . . ?
N1 P2 Se1 120.62(14) . . ?
C13 P2 Se1 111.38(14) . . ?
C7 P2 Se1 110.15(16) . . ?
C2 F1 Na1 111.5(2) . . ?
C19A O1 C22A 111.5(5) . . ?
C19 O1 C22B 100.4(10) . . ?
C19A O1 Na1 131.3(5) . . ?
C19 O1 Na1 132.6(6) . . ?
C22A O1 Na1 114.6(3) . . ?
C22B O1 Na1 121.2(6) . . ?
C23A O2 C22 108.9(8) . . ?
C23 O2 C26A 100.5(13) . . ?
C23A O2 Na1 129.0(6) . . ?
C23 O2 Na1 140.1(8) . . ?
C22 O2 Na1 119.2(5) . . ?
C26A O2 Na1 112.9(7) . . ?
C27A O3 C30A 109.0(9) . . ?
C27 O3 C30 112.1(8) . . ?
C27A O3 Na1 132.1(8) . . ?
C30A O3 Na1 116.8(6) . . ?
C27 O3 Na1 137.5(7) . . ?
C30 O3 Na1 104.0(8) . . ?
C1 N1 P2 123.5(3) . . ?
C1 N1 Na1 112.7(3) . . ?
P2 N1 Na1 120.84(18) . . ?
N1 C1 C2 117.9(4) . . ?
N1 C1 C6 127.7(4) . . ?
C2 C1 C6 114.3(4) . . ?
F1 C2 C3 118.2(4) . . ?
F1 C2 C1 117.0(4) . . ?
C3 C2 C1 124.9(4) . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C8 C7 C12 119.2(4) . . ?
C8 C7 P2 118.2(4) . . ?
C12 C7 P2 122.5(4) . . ?
C7 C8 C9 120.3(6) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.0(6) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.3(5) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 118.7(4) . . ?
C14 C13 P2 120.3(3) . . ?
C18 C13 P2 120.9(3) . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 120.2(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C19 C20 C21 108.7(7) . . ?
C21 C20 C19A 99.5(5) . . ?
C21 C20 H20A 111.9 . . ?
C19A C20 H20A 111.9 . . ?
C21 C20 H20B 111.9 . . ?
C19A C20 H20B 111.9 . . ?
H20A C20 H20B 109.6 . . ?
C19 C20 H20C 109.9 . . ?
C21 C20 H20C 109.9 . . ?
C19 C20 H20D 109.9 . . ?
C21 C20 H20D 109.9 . . ?
H20C C20 H20D 108.3 . . ?
C22B C21 C20 90.6(8) . . ?
C20 C21 C22A 106.0(5) . . ?
C20 C21 H21A 110.5 . . ?
C22A C21 H21A 110.5 . . ?
C20 C21 H21B 110.5 . . ?
C22A C21 H21B 110.5 . . ?
H21A C21 H21B 108.7 . . ?
C22B C21 H21C 113.5 . . ?
C20 C21 H21C 113.5 . . ?
C22B C21 H21D 113.5 . . ?
C20 C21 H21D 113.5 . . ?
H21C C21 H21D 110.8 . . ?
O1 C22A C21 102.0(5) . . ?
O1 C22A H22A 111.4 . . ?
C21 C22A H22A 111.4 . . ?
O1 C22A H22B 111.4 . . ?
C21 C22A H22B 111.4 . . ?
H22A C22A H22B 109.2 . . ?
O2 C23 C24A 100.0(16) . . ?
O2 C23 H23A 111.8 . . ?
C24A C23 H23A 111.8 . . ?
O2 C23 H23B 111.8 . . ?
C24A C23 H23B 111.8 . . ?
H23A C23 H23B 109.5 . . ?
C25A C24A C23 104.5(16) . . ?
C25A C24A H24A 110.8 . . ?
C23 C24A H24A 110.8 . . ?
C25A C24A H24B 110.9 . . ?
C23 C24A H24B 110.9 . . ?
H24A C24A H24B 108.9 . . ?
C24A C25A C26A 106.0(15) . . ?
C24A C25A H25A 110.5 . . ?
C26A C25A H25A 110.5 . . ?
C24A C25A H25B 110.5 . . ?
C26A C25A H25B 110.5 . . ?
H25A C25A H25B 108.7 . . ?
C25A C26A O2 97.8(13) . . ?
C25A C26A H26A 112.2 . . ?
O2 C26A H26A 112.2 . . ?
C25A C26A H26B 112.2 . . ?
O2 C26A H26B 112.2 . . ?
H26A C26A H26B 109.8 . . ?
O3 C27 C28 101.8(10) . . ?
O3 C27 H27A 111.4 . . ?
C28 C27 H27A 111.4 . . ?
O3 C27 H27B 111.4 . . ?
C28 C27 H27B 111.4 . . ?
H27A C27 H27B 109.3 . . ?
C29 C28 C27 107.2(11) . . ?
C29 C28 H28A 110.3 . . ?
C27 C28 H28A 110.3 . . ?
C29 C28 H28B 110.3 . . ?
C27 C28 H28B 110.3 . . ?
H28A C28 H28B 108.5 . . ?
C28 C29 C30 107.0(12) . . ?
C28 C29 H29A 110.3 . . ?
C30 C29 H29A 110.3 . . ?
C28 C29 H29B 110.3 . . ?
C30 C29 H29B 110.3 . . ?
H29A C29 H29B 108.6 . . ?
O3 C30 C29 102.9(10) . . ?
O3 C30 H30A 111.2 . . ?
C29 C30 H30A 111.2 . . ?
O3 C30 H30B 111.2 . . ?
C29 C30 H30B 111.2 . . ?
H30A C30 H30B 109.1 . . ?
O1 C19A C20 107.2(6) . . ?
O1 C19A H19A 110.3 . . ?
C20 C19A H19A 110.3 . . ?
O1 C19A H19B 110.3 . . ?
C20 C19A H19B 110.3 . . ?
H19A C19A H19B 108.5 . . ?
C21 C22B O1 103.0(9) . . ?
C21 C22B H22C 111.2 . . ?
O1 C22B H22C 111.2 . . ?
C21 C22B H22D 111.2 . . ?
O1 C22B H22D 111.2 . . ?
H22C C22B H22D 109.1 . . ?
C24B C25B C22 104.6(10) . . ?
C24B C25B H25C 110.8 . . ?
C22 C25B H25C 110.8 . . ?
C24B C25B H25D 110.8 . . ?
C22 C25B H25D 110.8 . . ?
H25C C25B H25D 108.9 . . ?
C25B C24B C23A 104.4(12) . . ?
C25B C24B H24C 110.9 . . ?
C23A C24B H24C 110.9 . . ?
C25B C24B H24D 110.9 . . ?
C23A C24B H24D 110.9 . . ?
H24C C24B H24D 108.9 . . ?
O2 C23A C24B 100.9(10) . . ?
O2 C23A H23C 111.6 . . ?
C24B C23A H23C 111.6 . . ?
O2 C23A H23D 111.6 . . ?
C24B C23A H23D 111.6 . . ?
H23C C23A H23D 109.4 . . ?
O1 C19 C20 102.7(9) . . ?
O1 C19 H19C 111.2 . . ?
C20 C19 H19C 111.2 . . ?
O1 C19 H19D 111.2 . . ?
C20 C19 H19D 111.2 . . ?
H19C C19 H19D 109.1 . . ?
O3 C30A C29A 108.9(12) . . ?
O3 C30A H30C 109.9 . . ?
C29A C30A H30C 109.9 . . ?
O3 C30A H30D 109.9 . . ?
C29A C30A H30D 109.9 . . ?
H30C C30A H30D 108.3 . . ?
C29A C28A C27A 110.8(12) . . ?
C29A C28A H28C 109.5 . . ?
C27A C28A H28C 109.5 . . ?
C29A C28A H28D 109.5 . . ?
C27A C28A H28D 109.5 . . ?
H28C C28A H28D 108.1 . . ?
O3 C27A C28A 103.2(11) . . ?
O3 C27A H27C 111.1 . . ?
C28A C27A H27C 111.1 . . ?
O3 C27A H27D 111.1 . . ?
C28A C27A H27D 111.1 . . ?
H27C C27A H27D 109.1 . . ?
C28A C29A C30A 99.3(13) . . ?
C28A C29A H29C 111.9 . . ?
C30A C29A H29C 111.9 . . ?
C28A C29A H29D 111.9 . . ?
C30A C29A H29D 111.9 . . ?
H29C C29A H29D 109.6 . . ?
C25B C22 O2 104.5(9) . . ?
C25B C22 H22E 110.9 . . ?
O2 C22 H22E 110.9 . . ?
C25B C22 H22F 110.9 . . ?
O2 C22 H22F 110.9 . . ?
H22E C22 H22F 108.9 . . ?

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
C13 P2 N1 C1 162.6(3) . . . . ?
C7 P2 N1 C1 54.7(4) . . . . ?
Se1 P2 N1 C1 -73.8(4) . . . . ?
C13 P2 N1 Na1 -38.3(3) . . . . ?
C7 P2 N1 Na1 -146.1(2) . . . . ?
Se1 P2 N1 Na1 85.3(2) . . . . ?
P2 N1 C1 C2 -169.3(3) . . . . ?
Na1 N1 C1 C2 30.1(5) . . . . ?
P2 N1 C1 C6 8.6(6) . . . . ?
Na1 N1 C1 C6 -152.0(4) . . . . ?
Na1 F1 C2 C3 153.1(3) . . . . ?
Na1 F1 C2 C1 -27.0(4) . . . . ?
N1 C1 C2 F1 -1.2(6) . . . . ?
C6 C1 C2 F1 -179.4(4) . . . . ?
N1 C1 C2 C3 178.7(4) . . . . ?
C6 C1 C2 C3 0.5(6) . . . . ?
F1 C2 C3 C4 179.0(4) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 1.1(8) . . . . ?
C4 C5 C6 C1 -1.6(8) . . . . ?
N1 C1 C6 C5 -177.3(5) . . . . ?
C2 C1 C6 C5 0.7(7) . . . . ?
N1 P2 C7 C8 28.9(5) . . . . ?
C13 P2 C7 C8 -78.2(4) . . . . ?
Se1 P2 C7 C8 163.1(4) . . . . ?
N1 P2 C7 C12 -152.5(4) . . . . ?
C13 P2 C7 C12 100.4(4) . . . . ?
Se1 P2 C7 C12 -18.3(4) . . . . ?
C12 C7 C8 C9 0.7(9) . . . . ?
P2 C7 C8 C9 179.3(5) . . . . ?
C7 C8 C9 C10 0.2(10) . . . . ?
C8 C9 C10 C11 -0.8(10) . . . . ?
C9 C10 C11 C12 0.5(9) . . . . ?
C10 C11 C12 C7 0.4(8) . . . . ?
C8 C7 C12 C11 -0.9(7) . . . . ?
P2 C7 C12 C11 -179.5(4) . . . . ?
N1 P2 C13 C14 -31.6(4) . . . . ?
C7 P2 C13 C14 80.8(4) . . . . ?
Se1 P2 C13 C14 -161.3(3) . . . . ?
N1 P2 C13 C18 151.8(4) . . . . ?
C7 P2 C13 C18 -95.8(4) . . . . ?
Se1 P2 C13 C18 22.1(4) . . . . ?
C18 C13 C14 C15 -0.2(7) . . . . ?
P2 C13 C14 C15 -176.8(5) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 C18 0.4(9) . . . . ?
C14 C13 C18 C17 -0.2(7) . . . . ?
P2 C13 C18 C17 176.5(4) . . . . ?
C16 C17 C18 C13 0.1(9) . . . . ?
C19 C20 C21 C22B -44.1(13) . . . . ?
C19A C20 C21 C22A 34.6(8) . . . . ?
C19A O1 C22A C21 -0.3(8) . . . . ?
Na1 O1 C22A C21 -164.4(4) . . . . ?
C20 C21 C22A O1 -22.6(7) . . . . ?
C26A O2 C23 C24A 52(3) . . . . ?
Na1 O2 C23 C24A -161.2(19) . . . . ?
O2 C23 C24A C25A -30(4) . . . . ?
C23 C24A C25A C26A -4(4) . . . . ?
C24A C25A C26A O2 34(3) . . . . ?
C23 O2 C26A C25A -53.6(19) . . . . ?
Na1 O2 C26A C25A 148.6(13) . . . . ?
C30 O3 C27 C28 16.4(18) . . . . ?
Na1 O3 C27 C28 -129.7(10) . . . . ?
O3 C27 C28 C29 -28.4(19) . . . . ?
C27 C28 C29 C30 31(2) . . . . ?
C27 O3 C30 C29 1(2) . . . . ?
Na1 O3 C30 C29 158.2(13) . . . . ?
C28 C29 C30 O3 -19(2) . . . . ?
C22A O1 C19A C20 23.0(9) . . . . ?
Na1 O1 C19A C20 -176.4(4) . . . . ?
C21 C20 C19A O1 -35.5(8) . . . . ?
C20 C21 C22B O1 56.5(11) . . . . ?
C19 O1 C22B C21 -50.9(15) . . . . ?
Na1 O1 C22B C21 152.9(7) . . . . ?
C22 C25B C24B C23A -32.7(19) . . . . ?
C22 O2 C23A C24B -33.5(15) . . . . ?
Na1 O2 C23A C24B 166.6(7) . . . . ?
C25B C24B C23A O2 41.5(18) . . . . ?
C22B O1 C19 C20 19.6(15) . . . . ?
Na1 O1 C19 C20 171.7(5) . . . . ?
C21 C20 C19 O1 16.2(16) . . . . ?
C27A O3 C30A C29A -26.1(16) . . . . ?
Na1 O3 C30A C29A 139.3(12) . . . . ?
C30A O3 C27A C28A 9.9(14) . . . . ?
Na1 O3 C27A C28A -152.5(8) . . . . ?
C29A C28A C27A O3 10(2) . . . . ?
C27A C28A C29A C30A -24(2) . . . . ?
O3 C30A C29A C28A 30(2) . . . . ?
C24B C25B C22 O2 12.6(17) . . . . ?
C23A O2 C22 C25B 14.5(15) . . . . ?
Na1 O2 C22 C25B 176.7(9) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1849555'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2019-04-07 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H38 N2 Na O5 P Se'
_chemical_formula_sum            'C30 H38 N2 Na O5 P Se'
_chemical_formula_weight         639.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Na Na 0.1353 0.1239 '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'
P P 0.2955 0.4335 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.2014(7)
_cell_length_b                   17.4404(7)
_cell_length_c                   20.4846(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6145.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10746
_cell_measurement_theta_min      3.3263
_cell_measurement_theta_max      70.4937

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             2656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    2.618
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28196
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.206
_diffrn_reflns_theta_max         70.569
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5806
_reflns_number_gt                4302
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1215P)²+2.9515P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5806
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2104
_refine_ls_wR_factor_gt          0.1807
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Na1 Na 0.34813(9) -0.14473(8) 0.60049(7) 0.0532(4) Uani 1 1 d . . . . .
Se1 Se 0.24572(2) 0.02672(2) 0.73710(2) 0.0533(2) Uani 1 1 d . . . . .
P1 P 0.19054(6) -0.04546(5) 0.66685(5) 0.0438(3) Uani 1 1 d . . . . .
O1 O 0.23716(17) -0.12356(17) 0.40512(15) 0.0663(8) Uani 1 1 d . . . . .
O2 O 0.28347(18) -0.15412(15) 0.49887(14) 0.0636(8) Uani 1 1 d . . . . .
O3 O 0.42904(17) -0.23824(15) 0.55260(13) 0.0623(7) Uani 1 1 d . . . . .
O4 O 0.44157(18) -0.04982(16) 0.58730(17) 0.0701(8) Uani 1 1 d . . . . .
O5 O 0.38639(18) -0.19108(14) 0.70097(13) 0.0628(7) Uani 1 1 d . . . . .
N1 N 0.23080(18) -0.06139(16) 0.59600(15) 0.0446(7) Uani 1 1 d . . . . .
N2 N 0.25666(17) -0.1055(2) 0.46122(17) 0.0510(8) Uani 1 1 d . . . . .
C1 C 0.2336(2) -0.0073(2) 0.5481(2) 0.0458(9) Uani 1 1 d . . . . .
C2 C 0.2479(2) -0.0268(2) 0.4811(2) 0.0499(10) Uani 1 1 d . . . . .
C3 C 0.2509(2) 0.0283(2) 0.4316(2) 0.0556(11) Uani 1 1 d . . . . .
H3 H 0.259470 0.013198 0.388679 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2413(2) 0.1042(3) 0.4459(2) 0.0614(11) Uani 1 1 d . . . . .
H4 H 0.244715 0.140944 0.413087 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2266(3) 0.1259(2) 0.5097(2) 0.0592(10) Uani 1 1 d . . . . .
H5 H 0.219787 0.177548 0.519417 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2217(2) 0.0729(2) 0.5586(2) 0.0533(9) Uani 1 1 d . . . . .
H6 H 0.210214 0.089718 0.600562 0.064 Uiso 1 1 calc R U . . .
C7 C 0.0902(2) -0.01460(18) 0.65311(18) 0.0459(8) Uani 1 1 d . . . . .
C8 C 0.0509(3) -0.0377(2) 0.5969(2) 0.0538(10) Uani 1 1 d . . . . .
H8 H 0.077074 -0.066339 0.565492 0.065 Uiso 1 1 calc R U . . .
C9 C -0.0262(3) -0.0187(2) 0.5870(2) 0.0623(11) Uani 1 1 d . . . . .
H9 H -0.051757 -0.034541 0.549267 0.075 Uiso 1 1 calc R U . . .
C10 C -0.0653(3) 0.0240(2) 0.6337(2) 0.0643(12) Uani 1 1 d . . . . .
H10 H -0.117152 0.037244 0.627445 0.077 Uiso 1 1 calc R U . . .
C11 C -0.0272(3) 0.0467(3) 0.6892(2) 0.0715(13) Uani 1 1 d . . . . .
H11 H -0.053810 0.074625 0.720786 0.086 Uiso 1 1 calc R U . . .
C12 C 0.0508(3) 0.0287(2) 0.6992(2) 0.0591(10) Uani 1 1 d . . . . .
H12 H 0.076254 0.045577 0.736524 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1786(2) -0.14186(18) 0.70001(18) 0.0463(8) Uani 1 1 d . . . . .
C14 C 0.1698(2) -0.1514(2) 0.7670(2) 0.0565(10) Uani 1 1 d . . . . .
H14 H 0.171208 -0.108966 0.794443 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1589(3) -0.2245(2) 0.7929(3) 0.0701(13) Uani 1 1 d . . . . .
H15 H 0.152932 -0.230869 0.837726 0.084 Uiso 1 1 calc R U . . .
C16 C 0.1568(3) -0.2872(2) 0.7520(3) 0.0713(13) Uani 1 1 d . . . . .
H16 H 0.150238 -0.336063 0.769380 0.086 Uiso 1 1 calc R U . . .
C17 C 0.1645(3) -0.2779(2) 0.6855(3) 0.0688(12) Uani 1 1 d . . . . .
H17 H 0.162619 -0.320415 0.658213 0.083 Uiso 1 1 calc R U . . .
C18 C 0.1750(2) -0.2059(2) 0.6592(2) 0.0562(10) Uani 1 1 d . . . . .
H18 H 0.179702 -0.199925 0.614279 0.067 Uiso 1 1 calc R U . . .
C19 C 0.4839(3) -0.2879(3) 0.5841(2) 0.0847(15) Uani 1 1 d . . . . .
H19A H 0.460434 -0.337305 0.593186 0.102 Uiso 1 1 calc R U . . .
H19B H 0.501131 -0.265571 0.625054 0.102 Uiso 1 1 calc R U . . .
C20 C 0.5515(4) -0.2970(4) 0.5382(3) 0.106(2) Uani 1 1 d . . . . .
H20A H 0.598350 -0.275505 0.557188 0.127 Uiso 1 1 calc R U . . .
H20B H 0.560578 -0.350796 0.528863 0.127 Uiso 1 1 calc R U . . .
C21 C 0.5306(3) -0.2554(3) 0.4777(3) 0.0813(15) Uani 1 1 d . . . . .
H21A H 0.542790 -0.285594 0.439306 0.098 Uiso 1 1 calc R U . . .
H21B H 0.557557 -0.206664 0.475073 0.098 Uiso 1 1 calc R U . . .
C22 C 0.4442(3) -0.2438(3) 0.4844(2) 0.0783(14) Uani 1 1 d . . . . .
H22A H 0.428222 -0.197315 0.462178 0.094 Uiso 1 1 calc R U . . .
H22B H 0.416275 -0.286826 0.465623 0.094 Uiso 1 1 calc R U . . .
C23 C 0.5238(3) -0.0556(3) 0.5985(3) 0.0852(16) Uani 1 1 d . . . . .
H23A H 0.548569 -0.083941 0.563521 0.102 Uiso 1 1 calc R U . . .
H23B H 0.534002 -0.081720 0.639456 0.102 Uiso 1 1 calc R U . . .
C24 C 0.5543(3) 0.0258(3) 0.6009(3) 0.0884(16) Uani 1 1 d . . . . .
H24A H 0.598209 0.029958 0.630405 0.106 Uiso 1 1 calc R U . . .
H24B H 0.569906 0.043204 0.557914 0.106 Uiso 1 1 calc R U . . .
C25 C 0.4864(3) 0.0709(3) 0.6256(3) 0.0752(13) Uani 1 1 d . . . . .
H25A H 0.488571 0.123679 0.610727 0.090 Uiso 1 1 calc R U . . .
H25B H 0.484033 0.070131 0.672895 0.090 Uiso 1 1 calc R U . . .
C26 C 0.4186(3) 0.0292(2) 0.5961(2) 0.0645(12) Uani 1 1 d . . . . .
H26A H 0.373847 0.032319 0.624709 0.077 Uiso 1 1 calc R U . . .
H26B H 0.404954 0.051858 0.554363 0.077 Uiso 1 1 calc R U . . .
C27 C 0.3705(4) -0.2646(3) 0.7298(2) 0.0745(14) Uani 1 1 d . . . . .
H27A H 0.314798 -0.273185 0.731799 0.089 Uiso 1 1 calc R U . . .
H27B H 0.393515 -0.305008 0.703619 0.089 Uiso 1 1 calc R U . . .
C28 C 0.4021(6) -0.2658(3) 0.7930(4) 0.153(4) Uani 1 1 d . . . . .
H28A H 0.446255 -0.300303 0.794624 0.184 Uiso 1 1 calc R U . . .
H28B H 0.363488 -0.283560 0.824042 0.184 Uiso 1 1 calc R U . . .
C29 C 0.4268(5) -0.1876(3) 0.8098(3) 0.123(3) Uani 1 1 d . . . . .
H29A H 0.395402 -0.167359 0.845143 0.147 Uiso 1 1 calc R U . . .
H29B H 0.480900 -0.187124 0.823115 0.147 Uiso 1 1 calc R U . . .
C30 C 0.4161(4) -0.1423(2) 0.7510(2) 0.0786(15) Uani 1 1 d . . . . .
H30A H 0.379898 -0.100793 0.759299 0.094 Uiso 1 1 calc R U . . .
H30B H 0.465279 -0.120354 0.737400 0.094 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
Na1 O5 2.307(3) . ?
Na1 O4 2.323(3) . ?
Na1 O3 2.358(3) . ?
Na1 O2 2.366(3) . ?
Na1 N1 2.489(3) . ?
Se1 P1 2.1345(10) . ?
P1 N1 1.632(3) . ?
P1 C13 1.825(3) . ?
P1 C7 1.830(4) . ?
O1 N2 1.238(4) . ?
O2 N2 1.236(4) . ?
O3 C22 1.425(5) . ?
O3 C19 1.435(5) . ?
O4 C23 1.436(6) . ?
O4 C26 1.445(5) . ?
O5 C30 1.426(5) . ?
O5 C27 1.439(5) . ?
N1 C1 1.362(5) . ?
N2 C2 1.441(5) . ?
C1 C6 1.430(5) . ?
C1 C2 1.434(6) . ?
C2 C3 1.398(6) . ?
C3 C4 1.365(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.385(5) . ?
C7 C8 1.395(5) . ?
C8 C9 1.383(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.390(5) . ?
C13 C18 1.396(5) . ?
C14 C15 1.394(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.505(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.480(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.505(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.515(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.495(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.502(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.405(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.468(8) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.452(7) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?

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
O5 Na1 O4 98.97(12) . . ?
O5 Na1 O3 87.73(11) . . ?
O4 Na1 O3 92.07(12) . . ?
O5 Na1 O2 153.49(12) . . ?
O4 Na1 O2 105.80(13) . . ?
O3 Na1 O2 82.16(10) . . ?
O5 Na1 N1 117.96(12) . . ?
O4 Na1 N1 98.08(11) . . ?
O3 Na1 N1 150.14(12) . . ?
O2 Na1 N1 68.08(10) . . ?
N1 P1 C13 102.82(16) . . ?
N1 P1 C7 108.28(17) . . ?
C13 P1 C7 102.83(16) . . ?
N1 P1 Se1 120.74(12) . . ?
C13 P1 Se1 110.03(12) . . ?
C7 P1 Se1 110.47(12) . . ?
N2 O2 Na1 132.6(2) . . ?
C22 O3 C19 106.2(3) . . ?
C22 O3 Na1 124.3(3) . . ?
C19 O3 Na1 128.2(3) . . ?
C23 O4 C26 108.4(3) . . ?
C23 O4 Na1 127.8(3) . . ?
C26 O4 Na1 118.4(2) . . ?
C30 O5 C27 107.7(3) . . ?
C30 O5 Na1 122.3(2) . . ?
C27 O5 Na1 128.6(3) . . ?
C1 N1 P1 122.5(3) . . ?
C1 N1 Na1 113.7(2) . . ?
P1 N1 Na1 114.25(16) . . ?
O2 N2 O1 120.4(3) . . ?
O2 N2 C2 121.1(3) . . ?
O1 N2 C2 118.5(3) . . ?
N1 C1 C6 124.4(4) . . ?
N1 C1 C2 122.1(3) . . ?
C6 C1 C2 113.5(3) . . ?
C3 C2 C1 122.5(4) . . ?
C3 C2 N2 116.5(4) . . ?
C1 C2 N2 121.0(3) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 122.9(4) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
C12 C7 C8 118.8(4) . . ?
C12 C7 P1 121.2(3) . . ?
C8 C7 P1 119.9(3) . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 119.7(4) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C18 119.4(3) . . ?
C14 C13 P1 119.3(3) . . ?
C18 C13 P1 121.3(3) . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O3 C19 C20 106.9(4) . . ?
O3 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
O3 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
C21 C20 C19 106.5(4) . . ?
C21 C20 H20A 110.4 . . ?
C19 C20 H20A 110.4 . . ?
C21 C20 H20B 110.4 . . ?
C19 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 C22 103.3(4) . . ?
C20 C21 H21A 111.1 . . ?
C22 C21 H21A 111.1 . . ?
C20 C21 H21B 111.1 . . ?
C22 C21 H21B 111.1 . . ?
H21A C21 H21B 109.1 . . ?
O3 C22 C21 106.2(4) . . ?
O3 C22 H22A 110.5 . . ?
C21 C22 H22A 110.5 . . ?
O3 C22 H22B 110.5 . . ?
C21 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
O4 C23 C24 106.3(4) . . ?
O4 C23 H23A 110.5 . . ?
C24 C23 H23A 110.5 . . ?
O4 C23 H23B 110.5 . . ?
C24 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
C25 C24 C23 103.5(4) . . ?
C25 C24 H24A 111.1 . . ?
C23 C24 H24A 111.1 . . ?
C25 C24 H24B 111.1 . . ?
C23 C24 H24B 111.1 . . ?
H24A C24 H24B 109.0 . . ?
C24 C25 C26 102.4(4) . . ?
C24 C25 H25A 111.3 . . ?
C26 C25 H25A 111.3 . . ?
C24 C25 H25B 111.3 . . ?
C26 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
O4 C26 C25 107.5(4) . . ?
O4 C26 H26A 110.2 . . ?
C25 C26 H26A 110.2 . . ?
O4 C26 H26B 110.2 . . ?
C25 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
C28 C27 O5 108.5(4) . . ?
C28 C27 H27A 110.0 . . ?
O5 C27 H27A 110.0 . . ?
C28 C27 H27B 110.0 . . ?
O5 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
C27 C28 C29 108.3(4) . . ?
C27 C28 H28A 110.0 . . ?
C29 C28 H28A 110.0 . . ?
C27 C28 H28B 110.0 . . ?
C29 C28 H28B 110.0 . . ?
H28A C28 H28B 108.4 . . ?
C30 C29 C28 105.9(5) . . ?
C30 C29 H29A 110.6 . . ?
C28 C29 H29A 110.6 . . ?
C30 C29 H29B 110.6 . . ?
C28 C29 H29B 110.6 . . ?
H29A C29 H29B 108.7 . . ?
O5 C30 C29 108.5(4) . . ?
O5 C30 H30A 110.0 . . ?
C29 C30 H30A 110.0 . . ?
O5 C30 H30B 110.0 . . ?
C29 C30 H30B 110.0 . . ?
H30A C30 H30B 108.4 . . ?

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
C13 P1 N1 C1 164.2(3) . . . . ?
C7 P1 N1 C1 55.8(3) . . . . ?
Se1 P1 N1 C1 -72.9(3) . . . . ?
C13 P1 N1 Na1 -51.64(19) . . . . ?
C7 P1 N1 Na1 -160.01(15) . . . . ?
Se1 P1 N1 Na1 71.32(16) . . . . ?
Na1 O2 N2 O1 167.3(3) . . . . ?
Na1 O2 N2 C2 -12.2(5) . . . . ?
P1 N1 C1 C6 17.4(5) . . . . ?
Na1 N1 C1 C6 -126.9(3) . . . . ?
P1 N1 C1 C2 -161.6(3) . . . . ?
Na1 N1 C1 C2 54.0(4) . . . . ?
N1 C1 C2 C3 -179.9(3) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
N1 C1 C2 N2 2.7(5) . . . . ?
C6 C1 C2 N2 -176.4(3) . . . . ?
O2 N2 C2 C3 152.6(3) . . . . ?
O1 N2 C2 C3 -27.0(5) . . . . ?
O2 N2 C2 C1 -29.9(5) . . . . ?
O1 N2 C2 C1 150.5(3) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
N2 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 -1.7(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 1.8(7) . . . . ?
N1 C1 C6 C5 178.5(4) . . . . ?
C2 C1 C6 C5 -2.3(6) . . . . ?
N1 P1 C7 C12 -156.3(3) . . . . ?
C13 P1 C7 C12 95.4(3) . . . . ?
Se1 P1 C7 C12 -22.0(3) . . . . ?
N1 P1 C7 C8 26.8(3) . . . . ?
C13 P1 C7 C8 -81.6(3) . . . . ?
Se1 P1 C7 C8 161.1(3) . . . . ?
C12 C7 C8 C9 -0.6(6) . . . . ?
P1 C7 C8 C9 176.4(3) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C10 C11 C12 1.1(7) . . . . ?
C8 C7 C12 C11 1.4(6) . . . . ?
P1 C7 C12 C11 -175.6(3) . . . . ?
C10 C11 C12 C7 -1.7(7) . . . . ?
N1 P1 C13 C14 159.2(3) . . . . ?
C7 P1 C13 C14 -88.3(3) . . . . ?
Se1 P1 C13 C14 29.4(3) . . . . ?
N1 P1 C13 C18 -23.4(3) . . . . ?
C7 P1 C13 C18 89.0(3) . . . . ?
Se1 P1 C13 C18 -153.3(3) . . . . ?
C18 C13 C14 C15 1.1(6) . . . . ?
P1 C13 C14 C15 178.5(3) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C15 C16 C17 -0.9(7) . . . . ?
C15 C16 C17 C18 0.6(7) . . . . ?
C16 C17 C18 C13 0.6(6) . . . . ?
C14 C13 C18 C17 -1.4(6) . . . . ?
P1 C13 C18 C17 -178.8(3) . . . . ?
C22 O3 C19 C20 23.3(6) . . . . ?
Na1 O3 C19 C20 -144.2(4) . . . . ?
O3 C19 C20 C21 -3.9(7) . . . . ?
C19 C20 C21 C22 -15.6(6) . . . . ?
C19 O3 C22 C21 -33.6(5) . . . . ?
Na1 O3 C22 C21 134.5(3) . . . . ?
C20 C21 C22 O3 30.3(6) . . . . ?
C26 O4 C23 C24 -11.5(6) . . . . ?
Na1 O4 C23 C24 -164.8(3) . . . . ?
O4 C23 C24 C25 28.9(6) . . . . ?
C23 C24 C25 C26 -34.1(6) . . . . ?
C23 O4 C26 C25 -10.5(5) . . . . ?
Na1 O4 C26 C25 145.7(3) . . . . ?
C24 C25 C26 O4 28.1(5) . . . . ?
C30 O5 C27 C28 -10.0(7) . . . . ?
Na1 O5 C27 C28 -176.9(5) . . . . ?
O5 C27 C28 C29 10.0(10) . . . . ?
C27 C28 C29 C30 -6.1(10) . . . . ?
C27 O5 C30 C29 6.1(6) . . . . ?
Na1 O5 C30 C29 174.0(4) . . . . ?
C28 C29 C30 O5 -0.1(8) . . . . ?

_refine_diff_density_max         0.691
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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-H
_database_code_depnum_ccdc_archive 'CCDC 1849552'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2019-04-07 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 F N P Se'
_chemical_formula_sum            'C18 H15 F N P Se'
_chemical_formula_weight         374.24

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'
F F 0.0727 0.0534 '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'
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/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                   9.9310(5)
_cell_length_b                   16.1798(5)
_cell_length_c                   13.6047(7)
_cell_angle_alpha                90
_cell_angle_beta                 130.222(3)
_cell_angle_gamma                90
_cell_volume                     1669.13(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5336
_cell_measurement_theta_min      4.2579
_cell_measurement_theta_max      70.3182

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    3.997
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7494
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.060
_diffrn_reflns_theta_max         70.258
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3126
_reflns_number_gt                2890
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+0.1707P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0096(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3126
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.31245(3) -0.06069(2) 0.67577(2) 0.05719(15) Uani 1 1 d . . . . .
P1 P 0.14491(6) -0.14900(3) 0.53212(5) 0.04124(16) Uani 1 1 d . . . . .
F1 F -0.19126(16) -0.04309(9) 0.14857(13) 0.0598(3) Uani 1 1 d . . . . .
N1 N 0.0285(2) -0.11712(11) 0.37945(17) 0.0486(4) Uani 1 1 d . . . . .
H1 H -0.083891 -0.124094 0.328569 0.058 Uiso 1 1 calc R U . . .
C14 C -0.1023(3) -0.26300(14) 0.4865(3) 0.0637(6) Uani 1 1 d . . . . .
H14 H -0.065055 -0.297659 0.453581 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2139(3) -0.28039(14) 0.4361(2) 0.0565(5) Uani 1 1 d . . . . .
H12 H 0.123842 -0.259389 0.354553 0.068 Uiso 1 1 calc R U . . .
C13 C -0.0283(2) -0.18498(12) 0.53196(19) 0.0436(4) Uani 1 1 d . . . . .
C6 C -0.0160(3) -0.04146(13) 0.2082(2) 0.0466(5) Uani 1 1 d . . . . .
C9 C 0.4804(3) -0.34457(16) 0.6770(3) 0.0724(7) Uani 1 1 d . . . . .
H9 H 0.569461 -0.366461 0.758089 0.087 Uiso 1 1 calc R U . . .
C18 C -0.0874(3) -0.13390(16) 0.5784(2) 0.0608(6) Uani 1 1 d . . . . .
H18 H -0.039499 -0.081362 0.608451 0.073 Uiso 1 1 calc R U . . .
C1 C 0.0981(3) -0.07996(12) 0.32710(19) 0.0443(4) Uani 1 1 d . . . . .
C5 C 0.0383(3) -0.00284(16) 0.1497(2) 0.0599(6) Uani 1 1 d . . . . .
H5 H -0.042667 0.022816 0.070222 0.072 Uiso 1 1 calc R U . . .
C10 C 0.4334(3) -0.38357(16) 0.5694(3) 0.0694(7) Uani 1 1 d . . . . .
H10 H 0.491163 -0.431721 0.577663 0.083 Uiso 1 1 calc R U . . .
C4 C 0.2160(4) -0.00271(17) 0.2110(2) 0.0656(6) Uani 1 1 d . . . . .
H4 H 0.255681 0.023084 0.172762 0.079 Uiso 1 1 calc R U . . .
C17 C -0.2177(4) -0.1608(2) 0.5804(3) 0.0771(8) Uani 1 1 d . . . . .
H17 H -0.257499 -0.126255 0.611589 0.092 Uiso 1 1 calc R U . . .
C7 C 0.2604(3) -0.24026(12) 0.5442(2) 0.0445(4) Uani 1 1 d . . . . .
C3 C 0.3341(3) -0.04075(16) 0.3286(2) 0.0603(6) Uani 1 1 d . . . . .
H3 H 0.453494 -0.040880 0.369202 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3015(4) -0.35178(15) 0.4493(3) 0.0673(7) Uani 1 1 d . . . . .
H11 H 0.270751 -0.378261 0.376652 0.081 Uiso 1 1 calc R U . . .
C2 C 0.2769(3) -0.07907(15) 0.3875(2) 0.0531(5) Uani 1 1 d . . . . .
H2 H 0.358214 -0.104154 0.467390 0.064 Uiso 1 1 calc R U . . .
C16 C -0.2887(3) -0.23852(19) 0.5364(3) 0.0734(8) Uani 1 1 d . . . . .
H16 H -0.375906 -0.256514 0.538377 0.088 Uiso 1 1 calc R U . . .
C15 C -0.2317(4) -0.28897(17) 0.4902(3) 0.0747(8) Uani 1 1 d . . . . .
H15 H -0.280100 -0.341500 0.460835 0.090 Uiso 1 1 calc R U . . .
C8 C 0.3951(3) -0.27233(15) 0.6652(2) 0.0610(6) Uani 1 1 d . . . . .
H8 H 0.428268 -0.245541 0.738463 0.073 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
Se1 P1 2.1047(5) . ?
P1 N1 1.6779(17) . ?
P1 C7 1.811(2) . ?
P1 C13 1.815(2) . ?
F1 C6 1.365(2) . ?
N1 C1 1.408(3) . ?
N1 H1 0.8600 . ?
C14 C15 1.385(3) . ?
C14 C13 1.389(3) . ?
C14 H14 0.9300 . ?
C12 C7 1.386(3) . ?
C12 C11 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.381(3) . ?
C6 C5 1.368(3) . ?
C6 C1 1.386(3) . ?
C9 C10 1.370(4) . ?
C9 C8 1.391(4) . ?
C9 H9 0.9300 . ?
C18 C17 1.382(4) . ?
C18 H18 0.9300 . ?
C1 C2 1.394(3) . ?
C5 C4 1.381(3) . ?
C5 H5 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C4 C3 1.375(4) . ?
C4 H4 0.9300 . ?
C17 C16 1.375(4) . ?
C17 H17 0.9300 . ?
C7 C8 1.388(3) . ?
C3 C2 1.392(3) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C2 H2 0.9300 . ?
C16 C15 1.357(4) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C7 104.64(10) . . ?
N1 P1 C13 101.66(9) . . ?
C7 P1 C13 106.45(9) . . ?
N1 P1 Se1 116.13(7) . . ?
C7 P1 Se1 113.25(7) . . ?
C13 P1 Se1 113.53(7) . . ?
C1 N1 P1 125.90(14) . . ?
C1 N1 H1 117.1 . . ?
P1 N1 H1 117.1 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C7 C12 C11 120.1(2) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C18 C13 C14 119.3(2) . . ?
C18 C13 P1 119.38(16) . . ?
C14 C13 P1 121.35(17) . . ?
F1 C6 C5 119.6(2) . . ?
F1 C6 C1 116.91(19) . . ?
C5 C6 C1 123.5(2) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C13 C18 C17 120.1(2) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C6 C1 C2 116.97(19) . . ?
C6 C1 N1 118.91(18) . . ?
C2 C1 N1 124.12(19) . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C12 C7 C8 119.3(2) . . ?
C12 C7 P1 121.90(16) . . ?
C8 C7 P1 118.75(17) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 P1 N1 C1 -71.89(19) . . . . ?
C13 P1 N1 C1 177.45(18) . . . . ?
Se1 P1 N1 C1 53.7(2) . . . . ?
C15 C14 C13 C18 -1.1(4) . . . . ?
C15 C14 C13 P1 178.7(2) . . . . ?
N1 P1 C13 C18 -98.55(19) . . . . ?
C7 P1 C13 C18 152.19(18) . . . . ?
Se1 P1 C13 C18 26.9(2) . . . . ?
N1 P1 C13 C14 81.7(2) . . . . ?
C7 P1 C13 C14 -27.6(2) . . . . ?
Se1 P1 C13 C14 -152.83(18) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
P1 C13 C18 C17 -179.2(2) . . . . ?
F1 C6 C1 C2 179.38(19) . . . . ?
C5 C6 C1 C2 -0.7(3) . . . . ?
F1 C6 C1 N1 -0.7(3) . . . . ?
C5 C6 C1 N1 179.3(2) . . . . ?
P1 N1 C1 C6 -166.60(16) . . . . ?
P1 N1 C1 C2 13.3(3) . . . . ?
F1 C6 C5 C4 -179.3(2) . . . . ?
C1 C6 C5 C4 0.8(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C6 C5 C4 C3 -0.2(4) . . . . ?
C13 C18 C17 C16 0.1(4) . . . . ?
C11 C12 C7 C8 0.0(3) . . . . ?
C11 C12 C7 P1 -177.65(19) . . . . ?
N1 P1 C7 C12 -14.8(2) . . . . ?
C13 P1 C7 C12 92.31(19) . . . . ?
Se1 P1 C7 C12 -142.25(16) . . . . ?
N1 P1 C7 C8 167.51(18) . . . . ?
C13 P1 C7 C8 -85.33(19) . . . . ?
Se1 P1 C7 C8 40.1(2) . . . . ?
C5 C4 C3 C2 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C7 C12 C11 C10 0.6(4) . . . . ?
C4 C3 C2 C1 0.6(4) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
N1 C1 C2 C3 -179.9(2) . . . . ?
C18 C17 C16 C15 -0.4(5) . . . . ?
C17 C16 C15 C14 -0.2(5) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
P1 C7 C8 C9 177.0(2) . . . . ?
C10 C9 C8 C7 0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18 Se1 0.93 3.01 3.484(2) 113.6 .

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1849553'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2019-04-07 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Li N2 O4 P Se, C4 H8 O'
_chemical_formula_sum            'C30 H38 Li N2 O5 P Se'
_chemical_formula_weight         623.49

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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   10.3315(9)
_cell_length_b                   18.068(2)
_cell_length_c                   18.204(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.795(8)
_cell_angle_gamma                90
_cell_volume                     3109.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4899
_cell_measurement_theta_min      3.0106
_cell_measurement_theta_max      29.0603

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.298
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14754
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         29.111
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7134
_reflns_number_gt                5662
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+1.7164P] 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         7134
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 1.11670(3) 0.17295(2) 0.28032(2) 0.02360(10) Uani 1 1 d . . . . .
P1 P 1.01912(7) 0.25365(4) 0.32674(4) 0.01704(15) Uani 1 1 d . . . . .
O2 O 0.5993(2) 0.33374(13) 0.20073(13) 0.0349(5) Uani 1 1 d . . . . .
O1 O 0.4549(2) 0.32498(13) 0.25826(14) 0.0386(6) Uani 1 1 d . . . . .
O4 O 0.7837(2) 0.40401(12) 0.12941(12) 0.0326(5) Uani 1 1 d . . . . .
O3 O 0.7132(2) 0.24642(12) 0.08896(12) 0.0360(5) Uani 1 1 d . . . . .
N1 N 0.5534(2) 0.29974(15) 0.24447(14) 0.0276(6) Uani 1 1 d . . . . .
N2 N 0.8459(2) 0.26121(13) 0.28517(13) 0.0194(5) Uani 1 1 d . . . . .
C1 C 0.6128(3) 0.22887(17) 0.27910(16) 0.0232(6) Uani 1 1 d . . . . .
C14 C 1.1966(3) 0.35884(16) 0.30248(16) 0.0233(6) Uani 1 1 d . . . . .
H14 H 1.250527 0.318801 0.299126 0.028 Uiso 1 1 calc R U . . .
C16 C 1.1591(3) 0.49037(18) 0.29957(18) 0.0340(7) Uani 1 1 d . . . . .
H16 H 1.186675 0.538100 0.293165 0.041 Uiso 1 1 calc R U . . .
C7 C 1.0746(3) 0.24290(16) 0.43497(15) 0.0208(6) Uani 1 1 d . . . . .
C18 C 0.9954(3) 0.40771(17) 0.32163(17) 0.0270(6) Uani 1 1 d . . . . .
H18 H 0.914051 0.400419 0.330852 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7578(3) 0.21207(16) 0.29872(15) 0.0200(6) Uani 1 1 d . . . . .
C13 C 1.0735(3) 0.34708(15) 0.31540(15) 0.0189(5) Uani 1 1 d . . . . .
C2 C 0.5207(3) 0.18129(18) 0.29526(18) 0.0313(7) Uani 1 1 d . . . . .
H2 H 0.427758 0.195632 0.282933 0.038 Uiso 1 1 calc R U . . .
C17 C 1.0385(3) 0.47898(18) 0.31410(19) 0.0343(7) Uani 1 1 d . . . . .
H17 H 0.986432 0.519323 0.318807 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7994(3) 0.14117(17) 0.33418(17) 0.0266(6) Uani 1 1 d . . . . .
H5 H 0.892614 0.126179 0.348597 0.032 Uiso 1 1 calc R U . . .
C12 C 1.1955(3) 0.20279(18) 0.47970(17) 0.0298(7) Uani 1 1 d . . . . .
H12 H 1.248597 0.181080 0.454608 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5676(3) 0.11368(19) 0.32921(19) 0.0370(8) Uani 1 1 d . . . . .
H3 H 0.506842 0.081417 0.339574 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6923(4) 0.46717(19) 0.1171(2) 0.0406(8) Uani 1 1 d . . . . .
H19A H 0.723510 0.497921 0.164789 0.049 Uiso 1 1 calc R U . . .
H19B H 0.595639 0.451670 0.103939 0.049 Uiso 1 1 calc R U . . .
C4 C 0.7074(3) 0.09379(18) 0.34804(18) 0.0334(7) Uani 1 1 d . . . . .
H4 H 0.739332 0.047547 0.370451 0.040 Uiso 1 1 calc R U . . .
C15 C 1.2377(3) 0.43025(18) 0.29471(18) 0.0318(7) Uani 1 1 d . . . . .
H15 H 1.319497 0.437859 0.286092 0.038 Uiso 1 1 calc R U . . .
C8 C 0.9966(3) 0.27537(19) 0.47331(17) 0.0311(7) Uani 1 1 d . . . . .
H8 H 0.915786 0.302571 0.443798 0.037 Uiso 1 1 calc R U . . .
C9 C 1.0392(3) 0.2672(2) 0.55560(18) 0.0401(9) Uani 1 1 d . . . . .
H9 H 0.986800 0.288878 0.581105 0.048 Uiso 1 1 calc R U . . .
C11 C 1.2374(4) 0.1951(2) 0.56271(18) 0.0403(8) Uani 1 1 d . . . . .
H11 H 1.318484 0.168386 0.592824 0.048 Uiso 1 1 calc R U . . .
C26 C 0.6248(4) 0.2661(2) 0.0074(2) 0.0525(10) Uani 1 1 d . . . . .
H26A H 0.681899 0.282806 -0.020530 0.063 Uiso 1 1 calc R U . . .
H26B H 0.559695 0.305228 0.006067 0.063 Uiso 1 1 calc R U . . .
C22 C 0.8872(3) 0.4199(2) 0.0966(2) 0.0371(8) Uani 1 1 d . . . . .
H22A H 0.876503 0.386133 0.053093 0.045 Uiso 1 1 calc R U . . .
H22B H 0.982409 0.415227 0.137723 0.045 Uiso 1 1 calc R U . . .
C20 C 0.7034(4) 0.5083(2) 0.0482(2) 0.0459(9) Uani 1 1 d . . . . .
H20A H 0.679016 0.560094 0.048402 0.055 Uiso 1 1 calc R U . . .
H20B H 0.643773 0.486371 -0.002952 0.055 Uiso 1 1 calc R U . . .
C10 C 1.1589(4) 0.2270(2) 0.59957(18) 0.0412(9) Uani 1 1 d . . . . .
H10 H 1.186634 0.221475 0.654626 0.049 Uiso 1 1 calc R U . . .
C23 C 0.7109(4) 0.16777(19) 0.0994(2) 0.0475(9) Uani 1 1 d . . . . .
H23A H 0.655475 0.155137 0.129765 0.057 Uiso 1 1 calc R U . . .
H23B H 0.806036 0.148723 0.127431 0.057 Uiso 1 1 calc R U . . .
C25 C 0.5459(5) 0.1973(3) -0.0304(3) 0.0736(14) Uani 1 1 d . . . . .
H25A H 0.528293 0.194873 -0.086916 0.088 Uiso 1 1 calc R U . . .
H25B H 0.456443 0.194517 -0.024986 0.088 Uiso 1 1 calc R U . . .
C21 C 0.8586(4) 0.4983(2) 0.0663(2) 0.0443(9) Uani 1 1 d . . . . .
H21A H 0.876575 0.504748 0.018373 0.053 Uiso 1 1 calc R U . . .
H21B H 0.916306 0.533105 0.106960 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6444(6) 0.1367(3) 0.0162(3) 0.0753(15) Uani 1 1 d . . . . .
H24A H 0.592890 0.091531 0.015067 0.090 Uiso 1 1 calc R U . . .
H24B H 0.715064 0.126546 -0.004933 0.090 Uiso 1 1 calc R U . . .
Li1 Li 0.7657(5) 0.3132(3) 0.1790(3) 0.0274(11) Uani 1 1 d . . . . .
O5 O 0.2113(4) -0.0227(2) 0.0932(2) 0.0858(11) Uani 1 1 d . . . . .
C30 C 0.1713(6) 0.0404(5) 0.0455(5) 0.188(5) Uani 1 1 d . . . . .
H30A H 0.120634 0.073848 0.066194 0.226 Uiso 1 1 calc R U . . .
H30B H 0.108829 0.026875 -0.008922 0.226 Uiso 1 1 calc R U . . .
C29 C 0.2959(5) 0.0768(3) 0.0452(4) 0.102(2) Uani 1 1 d . . . . .
H29A H 0.290168 0.130011 0.050630 0.122 Uiso 1 1 calc R U . . .
H29B H 0.308287 0.066147 -0.003745 0.122 Uiso 1 1 calc R U . . .
C28 C 0.4129(5) 0.0448(3) 0.1163(3) 0.0705(13) Uani 1 1 d . . . . .
H28A H 0.466841 0.083225 0.153057 0.085 Uiso 1 1 calc R U . . .
H28B H 0.476072 0.015620 0.100313 0.085 Uiso 1 1 calc R U . . .
C27 C 0.3369(5) -0.0031(4) 0.1535(3) 0.097(2) Uani 1 1 d . . . . .
H27A H 0.392487 -0.046803 0.177467 0.116 Uiso 1 1 calc R U . . .
H27B H 0.320418 0.023959 0.194988 0.116 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
Se1 P1 2.1316(7) . ?
P1 N2 1.643(2) . ?
P1 C13 1.817(3) . ?
P1 C7 1.827(3) . ?
P1 Li1 3.093(5) . ?
O2 N1 1.241(3) . ?
O2 Li1 1.950(5) . ?
O1 N1 1.230(3) . ?
O4 C19 1.439(4) . ?
O4 C22 1.449(4) . ?
O4 Li1 1.917(5) . ?
O3 C23 1.435(4) . ?
O3 C26 1.438(4) . ?
O3 Li1 1.928(6) . ?
N1 C1 1.450(4) . ?
N2 C6 1.364(3) . ?
N2 Li1 2.004(5) . ?
C1 C2 1.400(4) . ?
C1 C6 1.425(4) . ?
C14 C15 1.383(4) . ?
C14 C13 1.400(4) . ?
C14 H14 0.9300 . ?
C16 C15 1.380(4) . ?
C16 C17 1.390(4) . ?
C16 H16 0.9300 . ?
C7 C12 1.389(4) . ?
C7 C8 1.391(4) . ?
C18 C17 1.387(4) . ?
C18 C13 1.392(4) . ?
C18 H18 0.9300 . ?
C6 C5 1.421(4) . ?
C2 C3 1.366(5) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C5 C4 1.377(4) . ?
C5 H5 0.9300 . ?
C12 C11 1.401(4) . ?
C12 H12 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C19 C20 1.500(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C8 C9 1.388(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C11 C10 1.371(5) . ?
C11 H11 0.9300 . ?
C26 C25 1.493(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C22 C21 1.506(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C20 C21 1.512(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C10 H10 0.9300 . ?
C23 C24 1.497(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C25 C24 1.502(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O5 C27 1.366(5) . ?
O5 C30 1.392(7) . ?
C30 C29 1.447(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C29 C28 1.486(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C28 C27 1.502(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?

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 C13 101.51(12) . . ?
N2 P1 C7 108.35(12) . . ?
C13 P1 C7 104.15(12) . . ?
N2 P1 Se1 118.40(9) . . ?
C13 P1 Se1 111.91(9) . . ?
C7 P1 Se1 111.23(9) . . ?
N2 P1 Li1 35.73(12) . . ?
C13 P1 Li1 76.70(13) . . ?
C7 P1 Li1 139.66(13) . . ?
Se1 P1 Li1 105.25(10) . . ?
N1 O2 Li1 129.2(2) . . ?
C19 O4 C22 109.0(2) . . ?
C19 O4 Li1 124.8(2) . . ?
C22 O4 Li1 126.2(2) . . ?
C23 O3 C26 110.1(3) . . ?
C23 O3 Li1 121.4(2) . . ?
C26 O3 Li1 124.5(3) . . ?
O1 N1 O2 120.6(3) . . ?
O1 N1 C1 118.6(2) . . ?
O2 N1 C1 120.8(2) . . ?
C6 N2 P1 123.03(19) . . ?
C6 N2 Li1 115.7(2) . . ?
P1 N2 Li1 115.65(18) . . ?
C2 C1 C6 123.5(3) . . ?
C2 C1 N1 115.4(2) . . ?
C6 C1 N1 121.0(2) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C12 C7 C8 119.5(3) . . ?
C12 C7 P1 120.3(2) . . ?
C8 C7 P1 120.2(2) . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N2 C6 C5 124.5(2) . . ?
N2 C6 C1 121.8(3) . . ?
C5 C6 C1 113.6(2) . . ?
C18 C13 C14 119.4(3) . . ?
C18 C13 P1 120.4(2) . . ?
C14 C13 P1 120.2(2) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C7 C12 C11 119.8(3) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
O4 C19 C20 104.9(3) . . ?
O4 C19 H19A 110.8 . . ?
C20 C19 H19A 110.8 . . ?
O4 C19 H19B 110.8 . . ?
C20 C19 H19B 110.8 . . ?
H19A C19 H19B 108.8 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
O3 C26 C25 105.8(3) . . ?
O3 C26 H26A 110.6 . . ?
C25 C26 H26A 110.6 . . ?
O3 C26 H26B 110.6 . . ?
C25 C26 H26B 110.6 . . ?
H26A C26 H26B 108.7 . . ?
O4 C22 C21 105.6(3) . . ?
O4 C22 H22A 110.6 . . ?
C21 C22 H22A 110.6 . . ?
O4 C22 H22B 110.6 . . ?
C21 C22 H22B 110.6 . . ?
H22A C22 H22B 108.8 . . ?
C19 C20 C21 101.0(3) . . ?
C19 C20 H20A 111.6 . . ?
C21 C20 H20A 111.6 . . ?
C19 C20 H20B 111.6 . . ?
C21 C20 H20B 111.6 . . ?
H20A C20 H20B 109.4 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
O3 C23 C24 105.2(3) . . ?
O3 C23 H23A 110.7 . . ?
C24 C23 H23A 110.7 . . ?
O3 C23 H23B 110.7 . . ?
C24 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
C26 C25 C24 103.1(3) . . ?
C26 C25 H25A 111.1 . . ?
C24 C25 H25A 111.1 . . ?
C26 C25 H25B 111.1 . . ?
C24 C25 H25B 111.1 . . ?
H25A C25 H25B 109.1 . . ?
C22 C21 C20 103.0(3) . . ?
C22 C21 H21A 111.2 . . ?
C20 C21 H21A 111.2 . . ?
C22 C21 H21B 111.2 . . ?
C20 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
C23 C24 C25 103.2(4) . . ?
C23 C24 H24A 111.1 . . ?
C25 C24 H24A 111.1 . . ?
C23 C24 H24B 111.1 . . ?
C25 C24 H24B 111.1 . . ?
H24A C24 H24B 109.1 . . ?
O4 Li1 O3 100.6(2) . . ?
O4 Li1 O2 101.2(2) . . ?
O3 Li1 O2 108.8(3) . . ?
O4 Li1 N2 140.8(3) . . ?
O3 Li1 N2 113.1(3) . . ?
O2 Li1 N2 87.0(2) . . ?
O4 Li1 P1 119.9(2) . . ?
O3 Li1 P1 111.8(2) . . ?
O2 Li1 P1 113.3(2) . . ?
N2 Li1 P1 28.62(9) . . ?
C27 O5 C30 103.6(5) . . ?
O5 C30 C29 109.5(5) . . ?
O5 C30 H30A 109.8 . . ?
C29 C30 H30A 109.8 . . ?
O5 C30 H30B 109.8 . . ?
C29 C30 H30B 109.8 . . ?
H30A C30 H30B 108.2 . . ?
C30 C29 C28 103.4(4) . . ?
C30 C29 H29A 111.1 . . ?
C28 C29 H29A 111.1 . . ?
C30 C29 H29B 111.1 . . ?
C28 C29 H29B 111.1 . . ?
H29A C29 H29B 109.0 . . ?
C29 C28 C27 103.2(4) . . ?
C29 C28 H28A 111.1 . . ?
C27 C28 H28A 111.1 . . ?
C29 C28 H28B 111.1 . . ?
C27 C28 H28B 111.1 . . ?
H28A C28 H28B 109.1 . . ?
O5 C27 C28 106.6(4) . . ?
O5 C27 H27A 110.4 . . ?
C28 C27 H27A 110.4 . . ?
O5 C27 H27B 110.4 . . ?
C28 C27 H27B 110.4 . . ?
H27A C27 H27B 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
Li1 O2 N1 O1 172.1(3) . . . . ?
Li1 O2 N1 C1 -9.2(4) . . . . ?
C13 P1 N2 C6 -160.9(2) . . . . ?
C7 P1 N2 C6 -51.6(2) . . . . ?
Se1 P1 N2 C6 76.2(2) . . . . ?
Li1 P1 N2 C6 152.3(3) . . . . ?
C13 P1 N2 Li1 46.8(2) . . . . ?
C7 P1 N2 Li1 156.1(2) . . . . ?
Se1 P1 N2 Li1 -76.1(2) . . . . ?
O1 N1 C1 C2 26.4(4) . . . . ?
O2 N1 C1 C2 -152.4(3) . . . . ?
O1 N1 C1 C6 -150.3(3) . . . . ?
O2 N1 C1 C6 30.9(4) . . . . ?
N2 P1 C7 C12 150.0(2) . . . . ?
C13 P1 C7 C12 -102.5(3) . . . . ?
Se1 P1 C7 C12 18.2(3) . . . . ?
Li1 P1 C7 C12 171.4(2) . . . . ?
N2 P1 C7 C8 -30.6(3) . . . . ?
C13 P1 C7 C8 76.9(3) . . . . ?
Se1 P1 C7 C8 -162.4(2) . . . . ?
Li1 P1 C7 C8 -9.1(4) . . . . ?
P1 N2 C6 C5 -14.9(4) . . . . ?
Li1 N2 C6 C5 137.5(3) . . . . ?
P1 N2 C6 C1 164.0(2) . . . . ?
Li1 N2 C6 C1 -43.7(4) . . . . ?
C2 C1 C6 N2 -177.1(3) . . . . ?
N1 C1 C6 N2 -0.7(4) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
N1 C1 C6 C5 178.3(2) . . . . ?
C17 C18 C13 C14 0.8(4) . . . . ?
C17 C18 C13 P1 179.0(2) . . . . ?
C15 C14 C13 C18 -1.1(4) . . . . ?
C15 C14 C13 P1 -179.4(2) . . . . ?
N2 P1 C13 C18 35.5(2) . . . . ?
C7 P1 C13 C18 -77.0(2) . . . . ?
Se1 P1 C13 C18 162.7(2) . . . . ?
Li1 P1 C13 C18 61.4(2) . . . . ?
N2 P1 C13 C14 -146.2(2) . . . . ?
C7 P1 C13 C14 101.3(2) . . . . ?
Se1 P1 C13 C14 -19.0(2) . . . . ?
Li1 P1 C13 C14 -120.3(2) . . . . ?
C6 C1 C2 C3 -2.3(4) . . . . ?
N1 C1 C2 C3 -178.9(3) . . . . ?
C13 C18 C17 C16 0.6(5) . . . . ?
C15 C16 C17 C18 -1.6(5) . . . . ?
N2 C6 C5 C4 178.8(3) . . . . ?
C1 C6 C5 C4 -0.1(4) . . . . ?
C8 C7 C12 C11 0.3(5) . . . . ?
P1 C7 C12 C11 179.8(2) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C22 O4 C19 C20 22.6(4) . . . . ?
Li1 O4 C19 C20 -155.9(3) . . . . ?
C6 C5 C4 C3 -1.3(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C17 C16 C15 C14 1.3(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C12 C7 C8 C9 -0.4(5) . . . . ?
P1 C7 C8 C9 -179.9(3) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C7 C12 C11 C10 0.2(5) . . . . ?
C23 O3 C26 C25 9.5(5) . . . . ?
Li1 O3 C26 C25 -148.1(3) . . . . ?
C19 O4 C22 C21 2.5(3) . . . . ?
Li1 O4 C22 C21 -179.0(3) . . . . ?
O4 C19 C20 C21 -38.0(4) . . . . ?
C12 C11 C10 C9 -0.5(6) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C26 O3 C23 C24 13.1(4) . . . . ?
Li1 O3 C23 C24 171.5(3) . . . . ?
O3 C26 C25 C24 -28.0(5) . . . . ?
O4 C22 C21 C20 -26.2(3) . . . . ?
C19 C20 C21 C22 38.9(4) . . . . ?
O3 C23 C24 C25 -30.1(5) . . . . ?
C26 C25 C24 C23 35.4(5) . . . . ?
C27 O5 C30 C29 34.8(9) . . . . ?
O5 C30 C29 C28 -17.8(9) . . . . ?
C30 C29 C28 C27 -4.6(8) . . . . ?
C30 O5 C27 C28 -36.9(7) . . . . ?
C29 C28 C27 O5 25.9(6) . . . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.075

