# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_comp_4
_database_code_depnum_ccdc_archive 'CCDC 2189643'
loop_
_audit_author_name
_audit_author_address
'Harish S. Kunchur '
;IITBombay
India
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N2 O P Se'
_chemical_formula_sum            'C17 H17 N2 O P Se'
_chemical_formula_weight         375.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   10.9392(3)
_cell_length_b                   8.0482(3)
_cell_length_c                   37.8833(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3335.28(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8045
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.3330
_cell_measurement_theta_min      2.1390
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            55566
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.660
_diffrn_reflns_theta_min         2.150
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     67.17 201.67   0.50    2.00  13.96 -12.24 -31.50    --   269
  2  φ   -121.38  29.12   0.50    2.00  78.62 -12.24  31.50    --   301
  3  ω   -110.52  18.48   0.50    2.00    --  -12.24 -59.25  20.08  258
  4  ω   -110.52  18.48   0.50    2.00    --  -12.24 -59.25  71.08  258
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3181
_reflns_number_total             5557
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         5557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+1.2104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1419
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C12(H12), C3(H3), C6(H6), C15(H15), C13(H13), C14(H14),
 C9(H9), C8(H8), C7(H7), C2(H2)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.44329(3) 0.17993(5) 0.45092(2) 0.06098(15) Uani 1 1 d . . . . .
P1 P 0.60376(6) 0.37252(8) 0.34353(2) 0.03228(16) Uani 1 1 d . . . . .
O1 O 0.72616(16) 0.4212(2) 0.33052(5) 0.0439(4) Uani 1 1 d . . . . .
N2 N 0.6589(2) 0.2685(3) 0.41183(5) 0.0378(5) Uani 1 1 d . . . . .
N1 N 0.6775(2) 0.3153(3) 0.46768(6) 0.0518(6) Uani 1 1 d . . . . .
C5 C 0.5125(2) 0.2644(3) 0.31091(6) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.5146(2) 0.5466(3) 0.35803(6) 0.0342(5) Uani 1 1 d . . . . .
C1 C 0.5980(3) 0.2594(4) 0.44312(7) 0.0413(6) Uani 1 1 d . . . . .
C4 C 0.6086(2) 0.2151(3) 0.37841(6) 0.0361(5) Uani 1 1 d . . . . .
H4A H 0.524277 0.174744 0.382525 0.043 Uiso 1 1 calc R U . . .
H4B H 0.657312 0.119736 0.369792 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3859(3) 0.2694(3) 0.31093(7) 0.0430(6) Uani 1 1 d . . . . .
H10 H 0.344036 0.335692 0.327810 0.052 Uiso 1 1 calc R U . . .
C16 C 0.5281(3) 0.6930(3) 0.33892(7) 0.0411(6) Uani 1 1 d . . . . .
H16 H 0.584533 0.697442 0.319890 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4320(2) 0.5417(4) 0.38607(7) 0.0445(6) Uani 1 1 d . . . . .
H12 H 0.421554 0.442467 0.399318 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7767(3) 0.3266(4) 0.41749(8) 0.0470(7) Uani 1 1 d . . . . .
H3 H 0.838148 0.342432 0.400089 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5734(3) 0.1657(4) 0.28629(7) 0.0448(7) Uani 1 1 d . . . . .
H6 H 0.660178 0.161105 0.286146 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4602(3) 0.8316(4) 0.34735(9) 0.0528(8) Uani 1 1 d . . . . .
H15 H 0.469342 0.930903 0.334046 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3653(3) 0.6829(4) 0.39446(9) 0.0569(8) Uani 1 1 d . . . . .
H13 H 0.309827 0.680250 0.413739 0.068 Uiso 1 1 calc R U . . .
C14 C 0.3784(3) 0.8260(4) 0.37532(9) 0.0548(8) Uani 1 1 d . . . . .
H14 H 0.331545 0.921399 0.381184 0.066 Uiso 1 1 calc R U . . .
C9 C 0.3197(3) 0.1778(4) 0.28632(8) 0.0539(8) Uani 1 1 d . . . . .
H9 H 0.232915 0.182127 0.286228 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3807(3) 0.0806(4) 0.26209(8) 0.0551(8) Uani 1 1 d . . . . .
H8 H 0.335877 0.017484 0.245314 0.066 Uiso 1 1 calc R U . . .
C7 C 0.5068(3) 0.0748(4) 0.26214(7) 0.0540(8) Uani 1 1 d . . . . .
H7 H 0.548165 0.007491 0.245365 0.065 Uiso 1 1 calc R U . . .
C2 C 0.7873(3) 0.3562(4) 0.45208(8) 0.0557(8) Uani 1 1 d . . . . .
H2 H 0.857767 0.397755 0.463787 0.067 Uiso 1 1 calc R U . . .
C17 C 0.6493(3) 0.3298(5) 0.50545(8) 0.0766(12) Uani 1 1 d . . . . .
H17A H 0.596926 0.426933 0.509347 0.115 Uiso 1 1 calc R U . . .
H17B H 0.725375 0.342858 0.518820 0.115 Uiso 1 1 calc R U . . .
H17C H 0.606695 0.229446 0.513384 0.115 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 C1 1.833(3) . ?
P1 O1 1.4796(18) . ?
P1 C5 1.811(3) . ?
P1 C11 1.793(3) . ?
P1 C4 1.831(2) . ?
N2 C1 1.362(3) . ?
N2 C4 1.446(3) . ?
N2 C3 1.388(4) . ?
N1 C1 1.351(4) . ?
N1 C2 1.378(4) . ?
N1 C17 1.468(4) . ?
C5 C10 1.386(4) . ?
C5 C6 1.395(4) . ?
C11 C16 1.391(4) . ?
C11 C12 1.395(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C9 1.392(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.378(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.337(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(4) . ?
C14 H14 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.378(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(5) . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C5 113.51(11) . . ?
O1 P1 C11 112.79(11) . . ?
O1 P1 C4 113.43(12) . . ?
C5 P1 C4 100.12(11) . . ?
C11 P1 C5 106.52(12) . . ?
C11 P1 C4 109.57(12) . . ?
C1 N2 C4 124.1(2) . . ?
C1 N2 C3 109.7(2) . . ?
C3 N2 C4 126.1(2) . . ?
C1 N1 C2 110.2(2) . . ?
C1 N1 C17 124.2(3) . . ?
C2 N1 C17 125.6(3) . . ?
C10 C5 P1 122.46(19) . . ?
C10 C5 C6 119.6(2) . . ?
C6 C5 P1 117.8(2) . . ?
C16 C11 P1 116.4(2) . . ?
C16 C11 C12 119.3(2) . . ?
C12 C11 P1 124.3(2) . . ?
N2 C1 Se1 127.6(2) . . ?
N1 C1 Se1 126.9(2) . . ?
N1 C1 N2 105.5(2) . . ?
P1 C4 H4A 108.3 . . ?
P1 C4 H4B 108.3 . . ?
N2 C4 P1 115.92(17) . . ?
N2 C4 H4A 108.3 . . ?
N2 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C5 C10 H10 119.9 . . ?
C5 C10 C9 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 107.0(3) . . ?
C2 C3 H3 126.5 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.9(3) . . ?
C14 C15 H15 120.1 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.1(3) . . ?
C7 C8 H8 119.9 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N1 C2 H2 126.2 . . ?
C3 C2 N1 107.6(3) . . ?
C3 C2 H2 126.2 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C5 C10 C9 -176.9(2) . . . . ?
P1 C5 C6 C7 176.8(2) . . . . ?
P1 C11 C16 C15 177.8(2) . . . . ?
P1 C11 C12 C13 -178.3(2) . . . . ?
O1 P1 C5 C10 -152.0(2) . . . . ?
O1 P1 C5 C6 31.7(2) . . . . ?
O1 P1 C11 C16 36.2(2) . . . . ?
O1 P1 C11 C12 -145.6(2) . . . . ?
O1 P1 C4 N2 68.3(2) . . . . ?
N2 C3 C2 N1 0.5(4) . . . . ?
C5 P1 C11 C16 -88.9(2) . . . . ?
C5 P1 C11 C12 89.2(2) . . . . ?
C5 P1 C4 N2 -170.45(19) . . . . ?
C5 C10 C9 C8 0.6(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C11 P1 C5 C10 -27.2(2) . . . . ?
C11 P1 C5 C6 156.4(2) . . . . ?
C11 P1 C4 N2 -58.7(2) . . . . ?
C11 C16 C15 C14 0.6(4) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C1 N2 C4 P1 123.1(2) . . . . ?
C1 N2 C3 C2 -1.2(3) . . . . ?
C1 N1 C2 C3 0.3(4) . . . . ?
C4 P1 C5 C10 86.8(2) . . . . ?
C4 P1 C5 C6 -89.5(2) . . . . ?
C4 P1 C11 C16 163.6(2) . . . . ?
C4 P1 C11 C12 -18.3(3) . . . . ?
C4 N2 C1 Se1 0.2(4) . . . . ?
C4 N2 C1 N1 177.9(2) . . . . ?
C4 N2 C3 C2 -177.6(3) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
C10 C9 C8 C7 -0.3(5) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C16 C15 C14 C13 0.0(5) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C3 N2 C1 Se1 -176.3(2) . . . . ?
C3 N2 C1 N1 1.4(3) . . . . ?
C3 N2 C4 P1 -61.0(3) . . . . ?
C6 C5 C10 C9 -0.6(4) . . . . ?
C9 C8 C7 C6 0.0(5) . . . . ?
C2 N1 C1 Se1 176.6(2) . . . . ?
C2 N1 C1 N2 -1.0(3) . . . . ?
C17 N1 C1 Se1 -3.4(5) . . . . ?
C17 N1 C1 N2 178.9(3) . . . . ?
C17 N1 C2 C3 -179.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_comp_5
_database_code_depnum_ccdc_archive 'CCDC 2189644'
loop_
_audit_author_name
_audit_author_address
'Harish S. Kunchur '
;IITBombay
India
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N2 O P S'
_chemical_formula_sum            'C20 H23 N2 O P S'
_chemical_formula_weight         370.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.6482(15)
_cell_length_b                   21.1068(17)
_cell_length_c                   9.3551(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.860(14)
_cell_angle_gamma                90
_cell_volume                     1937.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.9340
_cell_measurement_theta_min      2.2720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.1188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12285
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.076
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  70.00   1.00    8.00    --  -20.00  72.00 -36.00  129
  2  ω    -59.00  44.00   1.00    8.00    --  -20.00  72.00-108.00  103
  3  ω    -69.00 -21.00   1.00    8.00    --  -20.00 -72.00  36.00   48
  4  ω   -110.00 -45.00   1.00    8.00    --  -20.00 -72.00-108.00   65
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0536122000
_diffrn_orient_matrix_UB_12      -0.0005067000
_diffrn_orient_matrix_UB_13      0.0745991000
_diffrn_orient_matrix_UB_21      0.0055308000
_diffrn_orient_matrix_UB_22      0.0334498000
_diffrn_orient_matrix_UB_23      -0.0022546000
_diffrn_orient_matrix_UB_31      -0.0481381000
_diffrn_orient_matrix_UB_32      0.0032383000
_diffrn_orient_matrix_UB_33      0.0347369000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1921
_reflns_number_total             3409
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+1.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C17A \\sim N1-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.02
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.02
 C20A-C19A \\sim C20B-C19B
 with sigma of 0.02
 C18A-C20A \\sim C18B-C20B
 with sigma of 0.04
 N1-C18A \\sim N1-C18B
 with sigma of 0.04
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C18B) \\sim Ueq, Uanis(C19B) \\sim Ueq, Uanis(C20B) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C17A, C18A, C20A, C19A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17B, C18B, C20B, C19B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C17A(0.575) H17A(0.575) H17B(0.575) C18A(0.575) H18A(0.575)
 H18B(0.575) C20A(0.575) H20A(0.575) H20B(0.575) H20C(0.575) C19A(0.575)
 H19A(0.575) H19B(0.575) C17B(0.425) H17C(0.425) H17D(0.425) C18B(0.425)
 H18C(0.425) H18D(0.425) C19B(0.425) H19C(0.425) H19D(0.425) C20B(0.425)
 H20D(0.425) H20E(0.425) H20F(0.425)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,H19B), C17B(H17C,
 H17D), C18B(H18C,H18D), C19B(H19C,H19D)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C14(H14), C16(H16), C7(H7), C3(H3), C2(H2), C12(H12),
 C8(H8), C15(H15), C13(H13), C9(H9)
6.c Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.08631(15) 0.40347(6) 0.64101(14) 0.0417(4) Uani 1 1 d . . . . .
S1 S 0.46304(15) 0.37701(6) 0.52312(15) 0.0544(4) Uani 1 1 d . . . . .
O1 O 0.0159(4) 0.45645(14) 0.6838(4) 0.0500(10) Uani 1 1 d . . . . .
N2 N 0.3076(4) 0.45890(17) 0.6101(4) 0.0409(10) Uani 1 1 d . . . . .
N1 N 0.5229(5) 0.48211(18) 0.7091(5) 0.0459(11) Uani 1 1 d D . . . .
C5 C -0.0304(5) 0.3448(2) 0.5244(5) 0.0356(11) Uani 1 1 d . . . . .
C11 C 0.2085(5) 0.3642(2) 0.8092(5) 0.0396(12) Uani 1 1 d . . . . .
C6 C 0.0090(5) 0.2931(2) 0.4569(5) 0.0437(12) Uani 1 1 d . . . . .
H6 H 0.100549 0.287187 0.475507 0.052 Uiso 1 1 calc R U . . .
C1 C 0.4313(6) 0.4401(2) 0.6148(5) 0.0440(13) Uani 1 1 d . . . . .
C10 C -0.1674(6) 0.3508(2) 0.4982(5) 0.0494(14) Uani 1 1 d . . . . .
H10 H -0.195449 0.384069 0.543877 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3844(6) 0.3021(3) 1.0727(6) 0.0591(16) Uani 1 1 d . . . . .
H14 H 0.442606 0.280836 1.160459 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1921(5) 0.3698(2) 0.9476(5) 0.0452(13) Uani 1 1 d . . . . .
H16 H 0.121948 0.394742 0.952622 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1789(5) 0.4278(2) 0.5215(5) 0.0446(13) Uani 1 1 d . . . . .
H4A H 0.196390 0.390698 0.470781 0.054 Uiso 1 1 calc R U . . .
H4B H 0.122064 0.456403 0.441387 0.054 Uiso 1 1 calc R U . . .
C7 C -0.0865(5) 0.2511(2) 0.3634(6) 0.0514(14) Uani 1 1 d . . . . .
H7 H -0.059533 0.217685 0.317005 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3231(6) 0.5119(2) 0.7034(6) 0.0524(15) Uani 1 1 d . . . . .
H3 H 0.254162 0.533296 0.721007 0.063 Uiso 1 1 calc R U . . .
C2 C 0.4545(7) 0.5262(2) 0.7626(6) 0.0557(15) Uani 1 1 d . . . . .
H2 H 0.494185 0.559889 0.828685 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3153(6) 0.3275(2) 0.8055(6) 0.0585(16) Uani 1 1 d . . . . .
H12 H 0.327901 0.323415 0.712970 0.070 Uiso 1 1 calc R U . . .
C8 C -0.2228(6) 0.2585(3) 0.3382(6) 0.0571(15) Uani 1 1 d . . . . .
H8 H -0.287181 0.229825 0.275872 0.068 Uiso 1 1 calc R U . . .
C15 C 0.2797(6) 0.3386(3) 1.0804(6) 0.0605(17) Uani 1 1 d . . . . .
H15 H 0.267604 0.342277 1.173269 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4029(6) 0.2971(2) 0.9366(6) 0.0597(16) Uani 1 1 d . . . . .
H13 H 0.474678 0.273128 0.932430 0.072 Uiso 1 1 calc R U . . .
C9 C -0.2626(6) 0.3083(3) 0.4059(6) 0.0578(15) Uani 1 1 d . . . . .
H9 H -0.353982 0.313338 0.389254 0.069 Uiso 1 1 calc R U . . .
C17A C 0.6696(11) 0.4784(11) 0.7607(19) 0.050(5) Uani 0.575 1 d D . P A 1
H17A H 0.709207 0.520485 0.777464 0.059 Uiso 0.575 1 calc R U P A 1
H17B H 0.694557 0.456966 0.683785 0.059 Uiso 0.575 1 calc R U P A 1
C18A C 0.7210(10) 0.4401(6) 0.9158(13) 0.057(3) Uani 0.575 1 d D . P A 1
H18A H 0.702265 0.463319 0.994804 0.069 Uiso 0.575 1 calc R U P A 1
H18B H 0.675038 0.399497 0.900494 0.069 Uiso 0.575 1 calc R U P A 1
C20A C 0.9330(11) 0.3948(7) 1.1161(13) 0.056(4) Uani 0.575 1 d D . P A 1
H20A H 0.894858 0.352996 1.105093 0.084 Uiso 0.575 1 calc R U P A 1
H20B H 0.916948 0.416887 1.197113 0.084 Uiso 0.575 1 calc R U P A 1
H20C H 1.029312 0.391845 1.141917 0.084 Uiso 0.575 1 calc R U P A 1
C19A C 0.8658(10) 0.4310(5) 0.9633(12) 0.063(3) Uani 0.575 1 d D . P A 1
H19A H 0.909119 0.472092 0.973711 0.075 Uiso 0.575 1 calc R U P A 1
H19B H 0.882110 0.408042 0.882232 0.075 Uiso 0.575 1 calc R U P A 1
C17B C 0.6661(14) 0.4836(19) 0.732(3) 0.066(9) Uani 0.425 1 d D . P A 2
H17C H 0.686671 0.525952 0.707726 0.079 Uiso 0.425 1 calc R U P A 2
H17D H 0.678158 0.455077 0.657345 0.079 Uiso 0.425 1 calc R U P A 2
C18B C 0.7735(18) 0.4660(8) 0.894(2) 0.099(7) Uani 0.425 1 d D U P A 2
H18C H 0.863637 0.472196 0.893690 0.118 Uiso 0.425 1 calc R U P A 2
H18D H 0.764106 0.494719 0.970276 0.118 Uiso 0.425 1 calc R U P A 2
C19B C 0.763(2) 0.4039(8) 0.939(2) 0.106(7) Uani 0.425 1 d D U P A 2
H19C H 0.771746 0.375944 0.861170 0.127 Uiso 0.425 1 calc R U P A 2
H19D H 0.671922 0.398324 0.936648 0.127 Uiso 0.425 1 calc R U P A 2
C20B C 0.8647(17) 0.3813(11) 1.099(2) 0.075(7) Uani 0.425 1 d D U P A 2
H20D H 0.947120 0.367223 1.089975 0.113 Uiso 0.425 1 calc R U P A 2
H20E H 0.825240 0.346899 1.134254 0.113 Uiso 0.425 1 calc R U P A 2
H20F H 0.884953 0.415619 1.171605 0.113 Uiso 0.425 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.485(3) . ?
P1 C5 1.793(5) . ?
P1 C11 1.807(5) . ?
P1 C4 1.827(5) . ?
S1 C1 1.688(5) . ?
N2 C1 1.360(6) . ?
N2 C4 1.454(6) . ?
N2 C3 1.388(6) . ?
N1 C1 1.359(6) . ?
N1 C2 1.389(6) . ?
N1 C17A 1.447(11) . ?
N1 C17B 1.454(14) . ?
C5 C6 1.404(6) . ?
C5 C10 1.388(7) . ?
C11 C16 1.377(6) . ?
C11 C12 1.387(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.377(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(7) . ?
C14 C13 1.366(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.396(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.386(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.324(7) . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.378(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(7) . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A C18A 1.562(13) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A C19A 1.442(11) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C20A C19A 1.531(12) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C17B C18B 1.545(15) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C18B C19B 1.394(15) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C19B C20B 1.541(15) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?

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
O1 P1 C5 112.4(2) . . ?
O1 P1 C11 112.3(2) . . ?
O1 P1 C4 113.7(2) . . ?
C5 P1 C11 107.9(2) . . ?
C5 P1 C4 103.4(2) . . ?
C11 P1 C4 106.5(2) . . ?
C1 N2 C4 125.0(4) . . ?
C1 N2 C3 109.7(4) . . ?
C3 N2 C4 125.3(4) . . ?
C1 N1 C2 109.0(5) . . ?
C1 N1 C17A 126.2(10) . . ?
C1 N1 C17B 123.9(18) . . ?
C2 N1 C17A 124.4(11) . . ?
C2 N1 C17B 126.7(18) . . ?
C6 C5 P1 123.6(4) . . ?
C10 C5 P1 118.5(3) . . ?
C10 C5 C6 117.9(5) . . ?
C16 C11 P1 117.9(4) . . ?
C16 C11 C12 118.5(4) . . ?
C12 C11 P1 123.6(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 H6 119.6 . . ?
N2 C1 S1 126.6(4) . . ?
N1 C1 S1 127.6(4) . . ?
N1 C1 N2 105.8(4) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.3(5) . . ?
C9 C10 H10 119.4 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(5) . . ?
C11 C16 H16 119.6 . . ?
C11 C16 C15 120.7(5) . . ?
C15 C16 H16 119.6 . . ?
P1 C4 H4A 109.0 . . ?
P1 C4 H4B 109.0 . . ?
N2 C4 P1 113.0(3) . . ?
N2 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(5) . . ?
C8 C7 H7 119.9 . . ?
N2 C3 H3 126.4 . . ?
C2 C3 N2 107.2(5) . . ?
C2 C3 H3 126.4 . . ?
N1 C2 H2 125.9 . . ?
C3 C2 N1 108.3(5) . . ?
C3 C2 H2 125.9 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C14 C15 C16 119.4(5) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C14 C13 C12 120.0(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N1 C17A H17A 110.5 . . ?
N1 C17A H17B 110.5 . . ?
N1 C17A C18A 106.3(9) . . ?
H17A C17A H17B 108.7 . . ?
C18A C17A H17A 110.5 . . ?
C18A C17A H17B 110.5 . . ?
C17A C18A H18A 110.2 . . ?
C17A C18A H18B 110.2 . . ?
H18A C18A H18B 108.5 . . ?
C19A C18A C17A 107.6(9) . . ?
C19A C18A H18A 110.2 . . ?
C19A C18A H18B 110.2 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
C18A C19A C20A 114.2(9) . . ?
C18A C19A H19A 108.7 . . ?
C18A C19A H19B 108.7 . . ?
C20A C19A H19A 108.7 . . ?
C20A C19A H19B 108.7 . . ?
H19A C19A H19B 107.6 . . ?
N1 C17B H17C 107.7 . . ?
N1 C17B H17D 107.7 . . ?
N1 C17B C18B 118.4(16) . . ?
H17C C17B H17D 107.1 . . ?
C18B C17B H17C 107.7 . . ?
C18B C17B H17D 107.7 . . ?
C17B C18B H18C 108.8 . . ?
C17B C18B H18D 108.8 . . ?
H18C C18B H18D 107.7 . . ?
C19B C18B C17B 113.9(19) . . ?
C19B C18B H18C 108.8 . . ?
C19B C18B H18D 108.8 . . ?
C18B C19B H19C 107.7 . . ?
C18B C19B H19D 107.7 . . ?
C18B C19B C20B 118.5(16) . . ?
H19C C19B H19D 107.1 . . ?
C20B C19B H19C 107.7 . . ?
C20B C19B H19D 107.7 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C5 C6 C7 -177.4(4) . . . . ?
P1 C5 C10 C9 178.0(4) . . . . ?
P1 C11 C16 C15 177.4(4) . . . . ?
P1 C11 C12 C13 -178.0(4) . . . . ?
O1 P1 C5 C6 173.9(3) . . . . ?
O1 P1 C5 C10 -5.7(4) . . . . ?
O1 P1 C11 C16 22.2(4) . . . . ?
O1 P1 C11 C12 -159.5(4) . . . . ?
O1 P1 C4 N2 77.1(4) . . . . ?
N2 C3 C2 N1 -0.7(6) . . . . ?
N1 C17A C18A C19A 175.2(12) . . . . ?
N1 C17B C18B C19B 63(4) . . . . ?
C5 P1 C11 C16 -102.2(4) . . . . ?
C5 P1 C11 C12 76.1(5) . . . . ?
C5 P1 C4 N2 -160.7(3) . . . . ?
C5 C6 C7 C8 -1.8(7) . . . . ?
C5 C10 C9 C8 0.5(8) . . . . ?
C11 P1 C5 C6 -61.8(4) . . . . ?
C11 P1 C5 C10 118.6(4) . . . . ?
C11 P1 C4 N2 -47.1(4) . . . . ?
C11 C16 C15 C14 0.6(8) . . . . ?
C11 C12 C13 C14 0.8(9) . . . . ?
C6 C5 C10 C9 -1.5(7) . . . . ?
C6 C7 C8 C9 0.6(8) . . . . ?
C1 N2 C4 P1 123.8(4) . . . . ?
C1 N2 C3 C2 1.1(5) . . . . ?
C1 N1 C2 C3 0.2(6) . . . . ?
C1 N1 C17A C18A -90.3(14) . . . . ?
C1 N1 C17B C18B -113(3) . . . . ?
C10 C5 C6 C7 2.2(7) . . . . ?
C16 C11 C12 C13 0.3(8) . . . . ?
C4 P1 C5 C6 50.8(4) . . . . ?
C4 P1 C5 C10 -128.8(4) . . . . ?
C4 P1 C11 C16 147.3(4) . . . . ?
C4 P1 C11 C12 -34.4(5) . . . . ?
C4 N2 C1 S1 -1.0(6) . . . . ?
C4 N2 C1 N1 179.5(4) . . . . ?
C4 N2 C3 C2 -179.4(4) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C3 N2 C1 S1 178.5(4) . . . . ?
C3 N2 C1 N1 -1.0(5) . . . . ?
C3 N2 C4 P1 -55.6(5) . . . . ?
C2 N1 C1 S1 -179.0(4) . . . . ?
C2 N1 C1 N2 0.5(5) . . . . ?
C2 N1 C17A C18A 82.4(15) . . . . ?
C2 N1 C17B C18B 75(3) . . . . ?
C12 C11 C16 C15 -1.0(7) . . . . ?
C15 C14 C13 C12 -1.3(8) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C17A N1 C1 S1 -5.3(9) . . . . ?
C17A N1 C1 N2 174.1(8) . . . . ?
C17A N1 C2 C3 -173.6(8) . . . . ?
C17A C18A C19A C20A 179.1(13) . . . . ?
C17B N1 C1 S1 7.7(11) . . . . ?
C17B N1 C1 N2 -172.9(10) . . . . ?
C17B N1 C2 C3 173.3(10) . . . . ?
C17B C18B C19B C20B -179.7(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.420
_oxdiff_exptl_absorpt_empirical_full_min 0.685
####################################################################### 
# 
# 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_comp_6
_database_code_depnum_ccdc_archive 'CCDC 2189645'
loop_
_audit_author_name
_audit_author_address
'Harish S. Kunchur '
;IITBombay
India
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N2 O P Se'
_chemical_formula_sum            'C20 H23 N2 O P Se'
_chemical_formula_weight         417.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.6448(7)
_cell_length_b                   21.0365(8)
_cell_length_c                   9.5229(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.495(7)
_cell_angle_gamma                90
_cell_volume                     1955.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8320
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0810
_cell_measurement_theta_min      2.1680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16625
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.173
_diffrn_reflns_theta_min         1.936
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   1.00    8.00    --  -20.00   0.00  36.00  180
  2  ω    -69.00  11.00   1.00    8.00    --  -20.00 -72.00-108.00   80
  3  ω    -20.00  10.00   1.00    8.00    --  -20.00  72.00 -36.00   30
  4  ω   -110.00 -71.00   1.00    8.00    --  -20.00   0.00 -36.00   39
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4263
_reflns_number_total             5747
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.575
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5747
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+1.3908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C17A \\sim N1-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.02
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.02
 C18A-C20A \\sim C18B-C20B
 with sigma of 0.04
 C20A-C19A \\sim C20B-C19B
 with sigma of 0.02
 N1-C18A \\sim N1-C18B
 with sigma of 0.04
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C17A) \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(C20A) \\sim Ueq,
Uanis(C19A) \\sim Ueq, Uanis(C17B) \\sim Ueq, Uanis(C18B) \\sim Ueq,
Uanis(C19B) \\sim Ueq, Uanis(C20B) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C17A, C18A, C20A, C19A, C17B, C18B, C19B, C20B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C17B)=Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=Sof(C19B)=
 Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(C20A)=
 Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C19A)=Sof(H19A)=Sof(H19B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,H19B), C17B(H17C,
 H17D), C18B(H18C,H18D), C19B(H19C,H19D)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C14(H14), C10(H10), C2(H2), C9(H9), C12(H12), C7(H7), C8(H8),
 C13(H13), C16(H16), C15(H15)
6.c Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.47058(3) 0.62354(2) 0.51773(3) 0.04052(11) Uani 1 1 d . . . . .
P1 P 0.08961(7) 0.59583(3) 0.64062(7) 0.02877(15) Uani 1 1 d . . . . .
O1 O 0.0176(2) 0.54378(9) 0.6833(2) 0.0379(4) Uani 1 1 d . . . . .
N2 N 0.3119(2) 0.53828(10) 0.6169(3) 0.0313(5) Uani 1 1 d . . . . .
N1 N 0.5278(3) 0.51610(11) 0.7203(3) 0.0369(5) Uani 1 1 d D . . . .
C4 C 0.1829(3) 0.56916(12) 0.5265(3) 0.0315(5) Uani 1 1 d . . . . .
H4A H 0.124505 0.539151 0.447267 0.038 Uiso 1 1 calc R U . . .
H4B H 0.201025 0.606275 0.473435 0.038 Uiso 1 1 calc R U . . .
C6 C -0.1644(3) 0.64924(14) 0.4920(3) 0.0368(6) Uani 1 1 d . . . . .
H6 H -0.194472 0.615609 0.537684 0.044 Uiso 1 1 calc R U . . .
C5 C -0.0265(3) 0.65497(12) 0.5207(3) 0.0295(5) Uani 1 1 d . . . . .
C3 C 0.3271(4) 0.48689(13) 0.7138(3) 0.0408(7) Uani 1 1 d . . . . .
H3 H 0.256107 0.465389 0.731137 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2129(3) 0.63581(11) 0.8062(3) 0.0300(5) Uani 1 1 d . . . . .
C1 C 0.4358(3) 0.55653(12) 0.6216(3) 0.0313(5) Uani 1 1 d . . . . .
C14 C 0.3883(3) 0.69875(14) 1.0657(3) 0.0447(7) Uani 1 1 d . . . . .
H14 H 0.447765 0.720823 1.154350 0.054 Uiso 1 1 calc R U . . .
C10 C 0.0169(3) 0.70525(13) 0.4549(3) 0.0358(6) Uani 1 1 d . . . . .
H10 H 0.111319 0.710155 0.475266 0.043 Uiso 1 1 calc R U . . .
C2 C 0.4613(4) 0.47347(13) 0.7781(4) 0.0446(7) Uani 1 1 d . . . . .
H2 H 0.503210 0.440664 0.850172 0.054 Uiso 1 1 calc R U . . .
C9 C -0.0780(3) 0.74771(15) 0.3603(4) 0.0450(7) Uani 1 1 d . . . . .
H9 H -0.048395 0.781719 0.315301 0.054 Uiso 1 1 calc R U . . .
C12 C 0.3210(3) 0.67111(13) 0.8021(3) 0.0394(6) Uani 1 1 d . . . . .
H12 H 0.334779 0.673926 0.709638 0.047 Uiso 1 1 calc R U . . .
C7 C -0.2587(3) 0.69235(17) 0.3971(4) 0.0482(7) Uani 1 1 d . . . . .
H7 H -0.353041 0.688197 0.377909 0.058 Uiso 1 1 calc R U . . .
C8 C -0.2156(3) 0.74140(16) 0.3302(4) 0.0478(7) Uani 1 1 d . . . . .
H8 H -0.280216 0.770590 0.263873 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4096(4) 0.70248(14) 0.9324(3) 0.0456(7) Uani 1 1 d . . . . .
H13 H 0.484286 0.726347 0.929547 0.055 Uiso 1 1 calc R U . . .
C16 C 0.1945(3) 0.63102(13) 0.9429(3) 0.0379(6) Uani 1 1 d . . . . .
H16 H 0.122411 0.605719 0.947837 0.045 Uiso 1 1 calc R U . . .
C15 C 0.2821(4) 0.66344(16) 1.0718(3) 0.0454(7) Uani 1 1 d . . . . .
H15 H 0.268503 0.661182 1.164402 0.055 Uiso 1 1 calc R U . . .
C17A C 0.6712(6) 0.5184(3) 0.7732(6) 0.0492(13) Uani 0.671(7) 1 d D U P A 1
H17A H 0.697917 0.537047 0.693656 0.059 Uiso 0.671(7) 1 calc R U P A 1
H17B H 0.709635 0.474912 0.796042 0.059 Uiso 0.671(7) 1 calc R U P A 1
C18A C 0.7293(6) 0.5609(3) 0.9243(6) 0.0541(12) Uani 0.671(7) 1 d D U P A 1
H18A H 0.686267 0.603487 0.902938 0.065 Uiso 0.671(7) 1 calc R U P A 1
H18B H 0.707485 0.540771 1.005891 0.065 Uiso 0.671(7) 1 calc R U P A 1
C20A C 0.9386(7) 0.6065(3) 1.1177(7) 0.0593(14) Uani 0.671(7) 1 d D U P A 1
H20A H 0.896691 0.648818 1.097948 0.089 Uiso 0.671(7) 1 calc R U P A 1
H20B H 1.037669 0.610435 1.147926 0.089 Uiso 0.671(7) 1 calc R U P A 1
H20C H 0.920543 0.586014 1.200202 0.089 Uiso 0.671(7) 1 calc R U P A 1
C19A C 0.8784(6) 0.5669(3) 0.9748(7) 0.0607(13) Uani 0.671(7) 1 d D U P A 1
H19A H 0.899423 0.586795 0.892476 0.073 Uiso 0.671(7) 1 calc R U P A 1
H19B H 0.920587 0.524074 0.994857 0.073 Uiso 0.671(7) 1 calc R U P A 1
C17B C 0.6800(10) 0.5147(6) 0.7348(13) 0.045(2) Uani 0.329(7) 1 d D U P A 2
H17C H 0.692040 0.546059 0.663618 0.054 Uiso 0.329(7) 1 calc R U P A 2
H17D H 0.702051 0.472039 0.707335 0.054 Uiso 0.329(7) 1 calc R U P A 2
C18B C 0.7800(12) 0.5314(5) 0.9060(11) 0.055(2) Uani 0.329(7) 1 d D U P A 2
H18C H 0.753551 0.506387 0.977977 0.066 Uiso 0.329(7) 1 calc R U P A 2
H18D H 0.874960 0.519703 0.922710 0.066 Uiso 0.329(7) 1 calc R U P A 2
C19B C 0.7739(13) 0.5996(5) 0.9368(13) 0.060(2) Uani 0.329(7) 1 d D U P A 2
H19C H 0.679379 0.610687 0.923228 0.072 Uiso 0.329(7) 1 calc R U P A 2
H19D H 0.796027 0.624384 0.861146 0.072 Uiso 0.329(7) 1 calc R U P A 2
C20B C 0.8734(13) 0.6187(6) 1.0991(12) 0.053(2) Uani 0.329(7) 1 d D U P A 2
H20D H 0.961570 0.597419 1.123958 0.079 Uiso 0.329(7) 1 calc R U P A 2
H20E H 0.835121 0.605877 1.172910 0.079 Uiso 0.329(7) 1 calc R U P A 2
H20F H 0.886717 0.664835 1.103810 0.079 Uiso 0.329(7) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.842(3) . ?
P1 O1 1.4832(19) . ?
P1 C4 1.828(3) . ?
P1 C5 1.804(3) . ?
P1 C11 1.807(3) . ?
N2 C4 1.452(4) . ?
N2 C3 1.388(3) . ?
N2 C1 1.357(3) . ?
N1 C1 1.354(4) . ?
N1 C2 1.385(4) . ?
N1 C17A 1.405(6) . ?
N1 C17B 1.570(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.387(4) . ?
C6 C7 1.387(4) . ?
C5 C10 1.399(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.341(5) . ?
C11 C12 1.384(4) . ?
C11 C16 1.396(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.378(5) . ?
C14 C15 1.373(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.380(4) . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.382(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(5) . ?
C8 H8 0.9500 . ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.389(4) . ?
C15 H15 0.9500 . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C17A C18A 1.595(7) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18A C19A 1.469(7) . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C20A C19A 1.503(7) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C17B C18B 1.590(12) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C18B C19B 1.471(13) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C19B C20B 1.538(13) . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C4 113.50(12) . . ?
O1 P1 C5 112.58(13) . . ?
O1 P1 C11 112.29(12) . . ?
C5 P1 C4 103.46(12) . . ?
C5 P1 C11 107.89(11) . . ?
C11 P1 C4 106.50(13) . . ?
C3 N2 C4 125.1(2) . . ?
C1 N2 C4 124.8(2) . . ?
C1 N2 C3 110.2(2) . . ?
C1 N1 C2 109.9(3) . . ?
C1 N1 C17A 127.5(3) . . ?
C1 N1 C17B 120.5(5) . . ?
C2 N1 C17A 122.3(3) . . ?
C2 N1 C17B 128.7(5) . . ?
P1 C4 H4A 108.9 . . ?
P1 C4 H4B 108.9 . . ?
N2 C4 P1 113.25(17) . . ?
N2 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.4(3) . . ?
C6 C5 P1 118.0(2) . . ?
C6 C5 C10 119.4(3) . . ?
C10 C5 P1 122.7(2) . . ?
N2 C3 H3 126.6 . . ?
C2 C3 N2 106.7(3) . . ?
C2 C3 H3 126.6 . . ?
C12 C11 P1 123.2(2) . . ?
C12 C11 C16 119.5(3) . . ?
C16 C11 P1 117.2(2) . . ?
N2 C1 Se1 126.8(2) . . ?
N1 C1 Se1 127.5(2) . . ?
N1 C1 N2 105.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C15 C14 C13 120.7(3) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
N1 C2 H2 126.2 . . ?
C3 C2 N1 107.6(3) . . ?
C3 C2 H2 126.2 . . ?
C10 C9 H9 119.6 . . ?
C10 C9 C8 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N1 C17A H17A 110.0 . . ?
N1 C17A H17B 110.0 . . ?
N1 C17A C18A 108.5(4) . . ?
H17A C17A H17B 108.4 . . ?
C18A C17A H17A 110.0 . . ?
C18A C17A H17B 110.0 . . ?
C17A C18A H18A 109.9 . . ?
C17A C18A H18B 109.9 . . ?
H18A C18A H18B 108.3 . . ?
C19A C18A C17A 108.8(5) . . ?
C19A C18A H18A 109.9 . . ?
C19A C18A H18B 109.9 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
C18A C19A C20A 111.0(5) . . ?
C18A C19A H19A 109.4 . . ?
C18A C19A H19B 109.4 . . ?
C20A C19A H19A 109.4 . . ?
C20A C19A H19B 109.4 . . ?
H19A C19A H19B 108.0 . . ?
N1 C17B H17C 109.8 . . ?
N1 C17B H17D 109.8 . . ?
N1 C17B C18B 109.4(8) . . ?
H17C C17B H17D 108.2 . . ?
C18B C17B H17C 109.8 . . ?
C18B C17B H17D 109.8 . . ?
C17B C18B H18C 109.5 . . ?
C17B C18B H18D 109.5 . . ?
H18C C18B H18D 108.1 . . ?
C19B C18B C17B 110.8(9) . . ?
C19B C18B H18C 109.5 . . ?
C19B C18B H18D 109.5 . . ?
C18B C19B H19C 109.0 . . ?
C18B C19B H19D 109.0 . . ?
C18B C19B C20B 112.8(9) . . ?
H19C C19B H19D 107.8 . . ?
C20B C19B H19C 109.0 . . ?
C20B C19B H19D 109.0 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C5 C10 C9 177.9(2) . . . . ?
P1 C11 C12 C13 177.8(2) . . . . ?
P1 C11 C16 C15 -176.8(2) . . . . ?
O1 P1 C4 N2 -77.7(2) . . . . ?
O1 P1 C5 C6 5.2(2) . . . . ?
O1 P1 C5 C10 -174.0(2) . . . . ?
O1 P1 C11 C12 159.1(2) . . . . ?
O1 P1 C11 C16 -22.1(2) . . . . ?
N2 C3 C2 N1 -0.3(3) . . . . ?
N1 C17A C18A C19A -176.4(5) . . . . ?
N1 C17B C18B C19B -74.0(12) . . . . ?
C4 P1 C5 C6 128.1(2) . . . . ?
C4 P1 C5 C10 -51.0(2) . . . . ?
C4 P1 C11 C12 34.2(3) . . . . ?
C4 P1 C11 C16 -146.9(2) . . . . ?
C4 N2 C3 C2 -178.7(2) . . . . ?
C4 N2 C1 Se1 0.2(3) . . . . ?
C4 N2 C1 N1 179.1(2) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
C6 C7 C8 C9 -0.9(5) . . . . ?
C5 P1 C4 N2 160.02(18) . . . . ?
C5 P1 C11 C12 -76.3(3) . . . . ?
C5 P1 C11 C16 102.6(2) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C5 C10 C9 C8 0.3(5) . . . . ?
C3 N2 C4 P1 54.6(3) . . . . ?
C3 N2 C1 Se1 -178.30(19) . . . . ?
C3 N2 C1 N1 0.5(3) . . . . ?
C11 P1 C4 N2 46.4(2) . . . . ?
C11 P1 C5 C6 -119.3(2) . . . . ?
C11 P1 C5 C10 61.6(2) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C11 C16 C15 C14 -1.6(4) . . . . ?
C1 N2 C4 P1 -123.8(2) . . . . ?
C1 N2 C3 C2 -0.1(3) . . . . ?
C1 N1 C2 C3 0.7(3) . . . . ?
C1 N1 C17A C18A 89.5(5) . . . . ?
C1 N1 C17B C18B 120.1(7) . . . . ?
C10 C9 C8 C7 0.8(5) . . . . ?
C2 N1 C1 Se1 178.08(19) . . . . ?
C2 N1 C1 N2 -0.8(3) . . . . ?
C2 N1 C17A C18A -83.6(5) . . . . ?
C2 N1 C17B C18B -71.6(10) . . . . ?
C12 C11 C16 C15 2.1(4) . . . . ?
C7 C6 C5 P1 -178.1(2) . . . . ?
C7 C6 C5 C10 1.0(4) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C16 C11 C12 C13 -1.0(4) . . . . ?
C15 C14 C13 C12 1.2(5) . . . . ?
C17A N1 C1 Se1 4.2(5) . . . . ?
C17A N1 C1 N2 -174.6(4) . . . . ?
C17A N1 C2 C3 174.9(4) . . . . ?
C17A C18A C19A C20A -179.8(5) . . . . ?
C17B N1 C1 Se1 -11.6(6) . . . . ?
C17B N1 C1 N2 169.5(5) . . . . ?
C17B N1 C2 C3 -168.6(6) . . . . ?
C17B C18B C19B C20B -177.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
