# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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. 
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data_llah001_0m
_database_code_depnum_ccdc_archive 'CCDC 1912321'
loop_
_audit_author_name
_audit_author_address
'Myongwon Lucia Lee'
;McMaster University
Canada
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H18 N4 Se2, 2(Cl), H2 O'
_chemical_formula_sum            'C18 H20 Cl2 N4 O Se2'
_chemical_formula_weight         537.20
_chemical_absolute_configuration .
_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'
Cl Cl 0.1484 0.1585 '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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9756(3)
_cell_length_b                   12.4952(4)
_cell_length_c                   9.3428(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.347(2)
_cell_angle_gamma                90
_cell_volume                     994.55(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    670
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   0.710
_shelx_estimated_absorpt_T_min   0.235
_exptl_absorpt_coefficient_mu    4.003
_exptl_absorpt_correction_T_max  0.8082
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0418 before and 0.0350 after correction.
The Ratio of minimum to maximum transmission is 0.7971.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.092
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35869
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.326
_diffrn_reflns_theta_min         2.297
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                8074
_reflns_number_total             10311
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.328
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 
;
 Flack x determined using 3156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         10311
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      0.995
_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)+(0.0193P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0635
_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 O(H,H) groups
2. Restrained distances
 O1S-H1SA = O1S-H1SB
 0.85 with sigma of 0.01
 H1SA-H1SB
 1.287 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C16(H16), C15(H15), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.53998(3) -0.07362(2) 0.89139(3) 0.01412(6) Uani 1 1 d . . . . .
Se2 Se -0.06255(3) 0.08008(2) 1.01456(3) 0.01810(6) Uani 1 1 d . . . . .
Cl3 Cl -0.29557(9) 0.18599(5) 1.07797(9) 0.02199(15) Uani 1 1 d . . . . .
Cl4 Cl 0.75317(9) -0.19141(6) 0.80482(9) 0.02403(16) Uani 1 1 d . . . . .
O1S O -0.4224(4) 0.2089(2) 1.3566(3) 0.0415(7) Uani 1 1 d D . . . .
H1SA H -0.404(5) 0.198(4) 1.273(3) 0.062 Uiso 1 1 d DR . . . .
H1SB H -0.508(3) 0.245(4) 1.320(5) 0.062 Uiso 1 1 d DR . . . .
N2 N 0.4008(3) 0.01794(18) 0.9479(2) 0.0112(4) Uani 1 1 d . . . . .
N1 N 0.5063(3) 0.00267(18) 0.7248(3) 0.0151(4) Uani 1 1 d . . . . .
N4 N 0.0736(3) -0.01065(19) 0.9514(3) 0.0149(4) Uani 1 1 d . . . . .
N3 N -0.1618(3) 0.1083(2) 0.8226(3) 0.0198(5) Uani 1 1 d . . . . .
C6 C 0.3517(3) 0.0965(2) 0.8477(3) 0.0115(5) Uani 1 1 d . . . . .
C1 C 0.4097(3) 0.0839(2) 0.7219(3) 0.0138(4) Uani 1 1 d . . . . .
C2 C 0.3589(3) 0.1560(2) 0.5966(3) 0.0176(5) Uani 1 1 d . . . . .
H2 H 0.3967 0.1491 0.5129 0.021 Uiso 1 1 calc R . . . .
C3 C 0.2558(4) 0.2341(2) 0.6003(3) 0.0187(5) Uani 1 1 d . . . . .
H3 H 0.2158 0.2796 0.5153 0.022 Uiso 1 1 calc R . . . .
C4 C 0.2061(4) 0.2494(2) 0.7302(3) 0.0179(5) Uani 1 1 d . . . . .
H4 H 0.1382 0.3076 0.7310 0.021 Uiso 1 1 calc R . . . .
C5 C 0.2518(3) 0.1841(2) 0.8522(3) 0.0150(5) Uani 1 1 d . . . . .
H5 H 0.2184 0.1964 0.9377 0.018 Uiso 1 1 calc R . . . .
C7 C 0.3596(3) 0.0042(2) 1.0882(3) 0.0132(5) Uani 1 1 d . . . . .
H7 H 0.3406 0.0760 1.1266 0.016 Uiso 1 1 calc R . . . .
C12 C 0.2095(3) -0.0653(2) 1.0575(3) 0.0148(5) Uani 1 1 d . . . . .
H12 H 0.2269 -0.1345 1.0115 0.018 Uiso 1 1 calc R . . . .
C13 C -0.1004(3) 0.0533(2) 0.7326(3) 0.0172(5) Uani 1 1 d . . . . .
C18 C 0.0291(3) -0.0173(2) 0.8014(3) 0.0153(5) Uani 1 1 d . . . . .
C17 C 0.0951(3) -0.0814(2) 0.7108(3) 0.0179(5) Uani 1 1 d . . . . .
H17 H 0.1755 -0.1321 0.7547 0.021 Uiso 1 1 calc R . . . .
C16 C 0.0385(3) -0.0671(3) 0.5588(3) 0.0218(5) Uani 1 1 d . . . . .
H16 H 0.0831 -0.1077 0.4964 0.026 Uiso 1 1 calc R . . . .
C15 C -0.0851(4) 0.0062(3) 0.4892(3) 0.0255(6) Uani 1 1 d . . . . .
H15 H -0.1177 0.0152 0.3828 0.031 Uiso 1 1 calc R . . . .
C14 C -0.1567(3) 0.0634(2) 0.5723(3) 0.0230(6) Uani 1 1 d . . . . .
H14 H -0.2425 0.1092 0.5247 0.028 Uiso 1 1 calc R . . . .
C11 C 0.1758(4) -0.0894(3) 1.2051(3) 0.0257(7) Uani 1 1 d . . . . .
H11A H 0.1495 -0.0219 1.2473 0.031 Uiso 1 1 calc R . . . .
H11B H 0.0839 -0.1376 1.1841 0.031 Uiso 1 1 calc R . . . .
C10 C 0.3156(4) -0.1416(3) 1.3205(4) 0.0271(7) Uani 1 1 d . . . . .
H10A H 0.2909 -0.1543 1.4152 0.033 Uiso 1 1 calc R . . . .
H10B H 0.3379 -0.2115 1.2818 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4581(4) -0.0700(3) 1.3517(3) 0.0224(5) Uani 1 1 d . . . . .
H9A H 0.5487 -0.1044 1.4270 0.027 Uiso 1 1 calc R . . . .
H9B H 0.4371 -0.0010 1.3936 0.027 Uiso 1 1 calc R . . . .
C8 C 0.4965(3) -0.0505(2) 1.2061(3) 0.0171(5) Uani 1 1 d . . . . .
H8A H 0.5197 -0.1196 1.1658 0.020 Uiso 1 1 calc R . . . .
H8B H 0.5912 -0.0049 1.2276 0.020 Uiso 1 1 calc R . . . .


_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 N2 1.888(2) . ?
Se1 N1 1.768(2) . ?
Se2 N4 1.893(2) . ?
Se2 N3 1.769(3) . ?
O1S H1SA 0.859(13) . ?
O1S H1SB 0.862(14) . ?
N2 C6 1.332(3) . ?
N2 C7 1.480(3) . ?
N1 C1 1.330(4) . ?
N4 C12 1.475(4) . ?
N4 C18 1.333(4) . ?
N3 C13 1.332(4) . ?
C6 C1 1.436(3) . ?
C6 C5 1.424(4) . ?
C1 C2 1.433(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.352(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.432(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.356(4) . ?
C5 H5 0.9500 . ?
C7 H7 1.0000 . ?
C7 C12 1.552(4) . ?
C7 C8 1.529(4) . ?
C12 H12 1.0000 . ?
C12 C11 1.532(4) . ?
C13 C18 1.440(4) . ?
C13 C14 1.428(4) . ?
C18 C17 1.423(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.362(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.428(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.356(4) . ?
C14 H14 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.520(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.512(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.525(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 N2 88.55(10) . . ?
N3 Se2 N4 88.38(11) . . ?
H1SA O1S H1SB 97(3) . . ?
C6 N2 Se1 110.59(16) . . ?
C6 N2 C7 126.0(2) . . ?
C7 N2 Se1 123.34(17) . . ?
C1 N1 Se1 111.06(17) . . ?
C12 N4 Se2 123.08(17) . . ?
C18 N4 Se2 110.84(18) . . ?
C18 N4 C12 126.1(2) . . ?
C13 N3 Se2 111.2(2) . . ?
N2 C6 C1 111.7(2) . . ?
N2 C6 C5 128.2(2) . . ?
C5 C6 C1 120.1(2) . . ?
N1 C1 C6 117.9(2) . . ?
N1 C1 C2 122.3(2) . . ?
C2 C1 C6 119.7(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.7(3) . . ?
C5 C4 H4 118.7 . . ?
C6 C5 H5 121.2 . . ?
C4 C5 C6 117.7(2) . . ?
C4 C5 H5 121.2 . . ?
N2 C7 H7 109.4 . . ?
N2 C7 C12 110.2(2) . . ?
N2 C7 C8 108.7(2) . . ?
C12 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C8 C7 C12 109.7(2) . . ?
N4 C12 C7 110.6(2) . . ?
N4 C12 H12 108.6 . . ?
N4 C12 C11 109.9(2) . . ?
C7 C12 H12 108.6 . . ?
C11 C12 C7 110.5(2) . . ?
C11 C12 H12 108.6 . . ?
N3 C13 C18 118.1(3) . . ?
N3 C13 C14 122.5(3) . . ?
C14 C13 C18 119.5(2) . . ?
N4 C18 C13 111.3(2) . . ?
N4 C18 C17 128.1(3) . . ?
C17 C18 C13 120.5(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 C18 117.3(3) . . ?
C16 C17 H17 121.3 . . ?
C17 C16 H16 118.7 . . ?
C17 C16 C15 122.7(3) . . ?
C15 C16 H16 118.7 . . ?
C16 C15 H15 119.4 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C10 C11 C12 111.7(2) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
C9 C10 C11 110.1(3) . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C10 C9 C8 109.8(2) . . ?
H9A C9 H9B 108.2 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 C7 111.0(2) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?

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
O1S H1SA Cl3 0.859(13) 2.323(17) 3.166(3) 167(4) .
O1S H1SB Se1 0.862(14) 2.97(4) 3.511(3) 123(4) 2_557
O1S H1SB Cl4 0.862(14) 2.286(17) 3.134(3) 168(5) 2_557
C2 H2 O1S 0.95 2.61 3.477(4) 151.8 1_654
C5 H5 Cl4 0.95 2.73 3.575(3) 149.2 2_657
C12 H12 Cl3 1.00 2.54 3.532(3) 173.6 2_547
C17 H17 Cl3 0.95 2.78 3.653(3) 153.6 2_547
C14 H14 O1S 0.95 2.24 3.166(4) 163.9 1_554

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
Se1 N2 C6 C1 4.1(3) . . . . ?
Se1 N2 C6 C5 -177.1(2) . . . . ?
Se1 N2 C7 C12 -92.3(2) . . . . ?
Se1 N2 C7 C8 28.0(3) . . . . ?
Se1 N1 C1 C6 0.2(3) . . . . ?
Se1 N1 C1 C2 -177.8(2) . . . . ?
Se2 N4 C12 C7 -91.7(2) . . . . ?
Se2 N4 C12 C11 30.5(3) . . . . ?
Se2 N4 C18 C13 5.0(3) . . . . ?
Se2 N4 C18 C17 -176.4(2) . . . . ?
Se2 N3 C13 C18 0.5(3) . . . . ?
Se2 N3 C13 C14 -178.5(2) . . . . ?
N2 Se1 N1 C1 1.76(19) . . . . ?
N2 C6 C1 N1 -3.0(3) . . . . ?
N2 C6 C1 C2 175.0(2) . . . . ?
N2 C6 C5 C4 -174.2(3) . . . . ?
N2 C7 C12 N4 -63.9(3) . . . . ?
N2 C7 C12 C11 174.2(2) . . . . ?
N2 C7 C8 C9 -178.1(2) . . . . ?
N1 Se1 N2 C6 -3.47(19) . . . . ?
N1 Se1 N2 C7 178.7(2) . . . . ?
N1 C1 C2 C3 177.5(3) . . . . ?
N4 Se2 N3 C13 1.9(2) . . . . ?
N4 C12 C11 C10 -177.6(3) . . . . ?
N4 C18 C17 C16 -174.0(3) . . . . ?
N3 Se2 N4 C12 176.0(2) . . . . ?
N3 Se2 N4 C18 -4.09(19) . . . . ?
N3 C13 C18 N4 -3.8(3) . . . . ?
N3 C13 C18 C17 177.4(3) . . . . ?
N3 C13 C14 C15 178.5(3) . . . . ?
C6 N2 C7 C12 90.2(3) . . . . ?
C6 N2 C7 C8 -149.5(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C1 C6 C5 C4 4.5(4) . . . . ?
C1 C2 C3 C4 4.1(4) . . . . ?
C2 C3 C4 C5 -3.5(5) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C5 C6 C1 N1 178.1(2) . . . . ?
C5 C6 C1 C2 -3.9(4) . . . . ?
C7 N2 C6 C1 -178.1(2) . . . . ?
C7 N2 C6 C5 0.7(4) . . . . ?
C7 C12 C11 C10 -55.3(3) . . . . ?
C12 N4 C18 C13 -175.1(2) . . . . ?
C12 N4 C18 C17 3.5(4) . . . . ?
C12 C7 C8 C9 -57.5(3) . . . . ?
C12 C11 C10 C9 57.9(4) . . . . ?
C13 C18 C17 C16 4.6(4) . . . . ?
C18 N4 C12 C7 88.4(3) . . . . ?
C18 N4 C12 C11 -149.4(3) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
C18 C17 C16 C15 -1.8(4) . . . . ?
C17 C16 C15 C14 -2.3(5) . . . . ?
C16 C15 C14 C13 3.4(5) . . . . ?
C14 C13 C18 N4 175.2(2) . . . . ?
C14 C13 C18 C17 -3.6(4) . . . . ?
C11 C10 C9 C8 -59.4(3) . . . . ?
C10 C9 C8 C7 60.3(3) . . . . ?
C8 C7 C12 N4 176.4(2) . . . . ?
C8 C7 C12 C11 54.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


####################################################################### 
# 
# 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_test_a
_database_code_depnum_ccdc_archive 'CCDC 1914922'
loop_
_audit_author_name
_audit_author_address
'Myongwon Lucia Lee'
;McMaster University
Canada
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N4 Se2, C2 H3 N, 2(B F4)'
_chemical_formula_sum            'C22 H19 B2 F8 N5 Se2'
_chemical_formula_weight         684.96
_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'
B B 0.0013 0.0007 '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'
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                   10.353(2)
_cell_length_b                   7.3989(17)
_cell_length_c                   33.631(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.402(5)
_cell_angle_gamma                90
_cell_volume                     2571.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1022
_cell_measurement_temperature    446(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.957
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0381 before and 0.0285 after correction.
The Ratio of minimum to maximum transmission is 0.8789.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.832
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            7007
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         2.819
_diffrn_ambient_temperature      446.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.832
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3372
_reflns_number_total             5027
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1058
_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:
 C14(H14A,H14B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C12(H12), C2(H2), C16(H16), C10(H10), C5(H5), C3(H3),
 C4(H4), C19(H19), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Se01 Se 0.01679(4) 0.73557(6) 0.47784(2) 0.01800(13) Uani 1 1 d . . . . .
Se02 Se 0.21568(4) 0.72715(6) 0.61233(2) 0.01916(14) Uani 1 1 d . . . . .
N4 N 0.3809(3) 0.7990(5) 0.62751(11) 0.0165(9) Uani 1 1 d . . . . .
N2 N 0.1123(3) 0.7687(4) 0.43468(11) 0.0133(8) Uani 1 1 d . . . . .
N1 N -0.1264(3) 0.7381(5) 0.44709(12) 0.0194(9) Uani 1 1 d . . . . .
N3 N 0.1795(4) 0.7063(5) 0.66248(13) 0.0248(10) Uani 1 1 d . . . . .
N5 N 0.8951(5) 0.8871(7) 0.73944(15) 0.0497(14) Uani 1 1 d . . . . .
B2 B 0.5409(5) 0.3563(7) 0.63839(17) 0.0170(12) Uani 1 1 d . . . . .
B1 B -0.1021(4) 0.7383(6) 0.57410(16) 0.0142(11) Uani 1 1 d . . . . .
C11 C 0.4188(4) 0.8296(6) 0.55684(14) 0.0148(10) Uani 1 1 d . . . . .
C13 C 0.3177(4) 0.9624(6) 0.49724(14) 0.0160(10) Uani 1 1 d . . . . .
H13 H 0.2873 1.0636 0.4832 0.019 Uiso 1 1 calc R . . . .
C9 C 0.3549(4) 0.6409(6) 0.50082(14) 0.0197(11) Uani 1 1 d . . . . .
H9 H 0.3483 0.5267 0.4894 0.024 Uiso 1 1 calc R . . . .
C12 C 0.3710(4) 0.9814(6) 0.53552(14) 0.0165(10) Uani 1 1 d . . . . .
H12 H 0.3755 1.0951 0.5473 0.020 Uiso 1 1 calc R . . . .
C8 C 0.3091(4) 0.7924(6) 0.47936(14) 0.0158(10) Uani 1 1 d . . . . .
C14 C 0.4764(4) 0.8493(6) 0.59870(13) 0.0177(10) Uani 1 1 d . . . . .
H14A H 0.5520 0.7723 0.6024 0.021 Uiso 1 1 calc R . . . .
H14B H 0.5037 0.9734 0.6033 0.021 Uiso 1 1 calc R . . . .
C2 C 0.0754(4) 0.8139(6) 0.36270(14) 0.0174(11) Uani 1 1 d . . . . .
H2 H 0.1621 0.8286 0.3577 0.021 Uiso 1 1 calc R . . . .
C1 C 0.0370(4) 0.7830(5) 0.40138(14) 0.0128(10) Uani 1 1 d . . . . .
C16 C 0.5129(4) 0.8476(6) 0.69039(14) 0.0207(11) Uani 1 1 d . . . . .
H16 H 0.5879 0.8820 0.6785 0.025 Uiso 1 1 calc R . . . .
C10 C 0.4097(4) 0.6610(6) 0.53876(14) 0.0194(11) Uani 1 1 d . . . . .
H10 H 0.4412 0.5599 0.5526 0.023 Uiso 1 1 calc R . . . .
C7 C 0.2549(4) 0.7704(6) 0.43710(14) 0.0171(10) Uani 1 1 d . . . . .
H7A H 0.2851 0.8690 0.4210 0.021 Uiso 1 1 calc R . . . .
H7B H 0.2865 0.6583 0.4263 0.021 Uiso 1 1 calc R . . . .
C5 C -0.1928(4) 0.7725(6) 0.37675(16) 0.0226(11) Uani 1 1 d . . . . .
H5 H -0.2802 0.7582 0.3810 0.027 Uiso 1 1 calc R . . . .
C15 C 0.3987(4) 0.8011(6) 0.66709(14) 0.0181(11) Uani 1 1 d . . . . .
C6 C -0.0982(4) 0.7645(5) 0.40909(14) 0.0167(10) Uani 1 1 d . . . . .
C20 C 0.2821(5) 0.7498(6) 0.68645(15) 0.0223(11) Uani 1 1 d . . . . .
C3 C -0.0187(4) 0.8216(6) 0.33281(15) 0.0201(11) Uani 1 1 d . . . . .
H3 H 0.0049 0.8407 0.3069 0.024 Uiso 1 1 calc R . . . .
C21 C 0.8849(5) 0.7664(8) 0.71902(17) 0.0328(13) Uani 1 1 d . . . . .
C22 C 0.8703(5) 0.6080(8) 0.69363(16) 0.0375(14) Uani 1 1 d . . . . .
H22A H 0.8775 0.6429 0.6664 0.056 Uiso 1 1 calc GR . . . .
H22B H 0.7870 0.5545 0.6967 0.056 Uiso 1 1 calc GR . . . .
H22C H 0.9368 0.5220 0.7011 0.056 Uiso 1 1 calc GR . . . .
C4 C -0.1530(4) 0.8014(6) 0.33983(15) 0.0234(12) Uani 1 1 d . . . . .
H4 H -0.2141 0.8083 0.3185 0.028 Uiso 1 1 calc R . . . .
C19 C 0.2838(5) 0.7457(6) 0.72826(15) 0.0288(12) Uani 1 1 d . . . . .
H19 H 0.2104 0.7126 0.7412 0.035 Uiso 1 1 calc R . . . .
C17 C 0.5087(5) 0.8401(6) 0.73032(15) 0.0270(12) Uani 1 1 d . . . . .
H17 H 0.5831 0.8679 0.7460 0.032 Uiso 1 1 calc R . . . .
C18 C 0.3950(5) 0.7911(7) 0.74941(17) 0.0338(13) Uani 1 1 d . . . . .
H18 H 0.3967 0.7902 0.7771 0.041 Uiso 1 1 calc R . . . .
F5 F 0.4849(2) 0.3166(4) 0.60065(8) 0.0242(6) Uani 1 1 d . . . . .
F1 F -0.0365(2) 0.6121(3) 0.59850(8) 0.0218(6) Uani 1 1 d . . . . .
F6 F 0.6130(2) 0.2066(3) 0.65203(8) 0.0242(6) Uani 1 1 d . . . . .
F7 F 0.4471(2) 0.3954(4) 0.66439(8) 0.0258(7) Uani 1 1 d . . . . .
F2 F -0.0173(2) 0.8632(3) 0.56127(8) 0.0255(7) Uani 1 1 d . . . . .
F3 F -0.1996(3) 0.8188(3) 0.59457(9) 0.0307(7) Uani 1 1 d . . . . .
F8 F 0.6241(2) 0.5019(3) 0.63515(8) 0.0303(7) Uani 1 1 d . . . . .
F4 F -0.1579(3) 0.6486(4) 0.53998(9) 0.0319(7) 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
Se01 N2 1.821(4) . ?
Se01 N1 1.757(4) . ?
Se02 N4 1.835(3) . ?
Se02 N3 1.756(4) . ?
N4 C14 1.473(5) . ?
N4 C15 1.333(6) . ?
N2 C1 1.330(5) . ?
N2 C7 1.474(5) . ?
N1 C6 1.342(6) . ?
N3 C20 1.334(6) . ?
N5 C21 1.127(7) . ?
B2 F5 1.395(6) . ?
B2 F6 1.398(5) . ?
B2 F7 1.375(6) . ?
B2 F8 1.388(5) . ?
B1 F1 1.393(5) . ?
B1 F2 1.363(6) . ?
B1 F3 1.389(6) . ?
B1 F4 1.418(6) . ?
C11 C12 1.407(6) . ?
C11 C14 1.503(6) . ?
C11 C10 1.388(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.377(6) . ?
C13 C8 1.395(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.400(6) . ?
C9 C10 1.373(6) . ?
C12 H12 0.9300 . ?
C8 C7 1.506(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C1 1.402(6) . ?
C2 C3 1.359(6) . ?
C1 C6 1.445(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.422(6) . ?
C16 C17 1.347(7) . ?
C10 H10 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.422(6) . ?
C5 C4 1.348(7) . ?
C15 C20 1.455(7) . ?
C20 C19 1.405(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.432(6) . ?
C21 C22 1.453(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C4 H4 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.359(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.421(7) . ?
C18 H18 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 Se01 N2 90.49(17) . . ?
N3 Se02 N4 90.39(17) . . ?
C14 N4 Se02 122.8(3) . . ?
C15 N4 Se02 110.6(3) . . ?
C15 N4 C14 126.6(3) . . ?
C1 N2 Se01 111.3(3) . . ?
C1 N2 C7 125.5(4) . . ?
C7 N2 Se01 123.2(3) . . ?
C6 N1 Se01 109.8(3) . . ?
C20 N3 Se02 110.6(3) . . ?
F5 B2 F6 108.4(4) . . ?
F7 B2 F5 110.6(4) . . ?
F7 B2 F6 110.0(4) . . ?
F7 B2 F8 110.6(4) . . ?
F8 B2 F5 108.6(4) . . ?
F8 B2 F6 108.6(3) . . ?
F1 B1 F4 108.9(3) . . ?
F2 B1 F1 109.9(3) . . ?
F2 B1 F3 111.5(4) . . ?
F2 B1 F4 107.4(4) . . ?
F3 B1 F1 109.8(4) . . ?
F3 B1 F4 109.2(4) . . ?
C12 C11 C14 120.5(4) . . ?
C10 C11 C12 118.8(4) . . ?
C10 C11 C14 120.7(4) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C8 120.5(4) . . ?
C8 C13 H13 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C8 120.1(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.9 . . ?
C13 C8 C9 119.2(4) . . ?
C13 C8 C7 121.0(4) . . ?
C9 C8 C7 119.7(4) . . ?
N4 C14 C11 110.3(3) . . ?
N4 C14 H14A 109.6 . . ?
N4 C14 H14B 109.6 . . ?
C11 C14 H14A 109.6 . . ?
C11 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C3 C2 C1 117.6(4) . . ?
N2 C1 C2 127.6(4) . . ?
N2 C1 C6 111.5(4) . . ?
C2 C1 C6 120.9(4) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
C17 C16 C15 117.7(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 C11 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
N2 C7 C8 111.7(3) . . ?
N2 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.5(4) . . ?
N4 C15 C16 127.9(4) . . ?
N4 C15 C20 112.0(4) . . ?
C16 C15 C20 120.1(5) . . ?
N1 C6 C1 116.9(4) . . ?
N1 C6 C5 123.7(4) . . ?
C5 C6 C1 119.3(4) . . ?
N3 C20 C15 116.4(4) . . ?
N3 C20 C19 124.2(5) . . ?
C19 C20 C15 119.5(4) . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.3(5) . . ?
C4 C3 H3 118.8 . . ?
N5 C21 C22 178.3(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C20 C19 H19 120.7 . . ?
C18 C19 C20 118.6(5) . . ?
C18 C19 H19 120.7 . . ?
C16 C17 H17 118.7 . . ?
C16 C17 C18 122.5(5) . . ?
C18 C17 H17 118.7 . . ?
C19 C18 C17 121.7(5) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 N2 C1 C2 178.2(3) . . . . ?
Se01 N2 C1 C6 -1.2(4) . . . . ?
Se01 N2 C7 C8 -15.4(5) . . . . ?
Se01 N1 C6 C1 0.5(5) . . . . ?
Se01 N1 C6 C5 179.6(3) . . . . ?
Se02 N4 C14 C11 -0.9(5) . . . . ?
Se02 N4 C15 C16 179.5(4) . . . . ?
Se02 N4 C15 C20 -1.2(4) . . . . ?
Se02 N3 C20 C15 -0.8(5) . . . . ?
Se02 N3 C20 C19 -179.7(4) . . . . ?
N4 Se02 N3 C20 0.1(3) . . . . ?
N4 C15 C20 N3 1.3(6) . . . . ?
N4 C15 C20 C19 -179.7(4) . . . . ?
N2 Se01 N1 C6 -0.9(3) . . . . ?
N2 C1 C6 N1 0.5(5) . . . . ?
N2 C1 C6 C5 -178.7(4) . . . . ?
N1 Se01 N2 C1 1.2(3) . . . . ?
N1 Se01 N2 C7 -176.2(3) . . . . ?
N3 Se02 N4 C14 -178.3(3) . . . . ?
N3 Se02 N4 C15 0.7(3) . . . . ?
N3 C20 C19 C18 179.2(5) . . . . ?
C13 C8 C7 N2 -81.3(5) . . . . ?
C9 C8 C7 N2 100.4(4) . . . . ?
C12 C11 C14 N4 99.4(5) . . . . ?
C12 C11 C10 C9 -0.2(7) . . . . ?
C12 C13 C8 C9 0.2(6) . . . . ?
C12 C13 C8 C7 -178.1(4) . . . . ?
C8 C13 C12 C11 0.7(6) . . . . ?
C8 C9 C10 C11 1.1(7) . . . . ?
C14 N4 C15 C16 -1.5(7) . . . . ?
C14 N4 C15 C20 177.8(4) . . . . ?
C14 C11 C12 C13 -179.7(4) . . . . ?
C14 C11 C10 C9 178.8(4) . . . . ?
C2 C1 C6 N1 -178.9(4) . . . . ?
C2 C1 C6 C5 1.8(6) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C1 N2 C7 C8 167.6(4) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C16 C15 C20 N3 -179.3(4) . . . . ?
C16 C15 C20 C19 -0.4(6) . . . . ?
C16 C17 C18 C19 1.2(8) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C10 C11 C14 N4 -79.5(5) . . . . ?
C10 C9 C8 C13 -1.1(7) . . . . ?
C10 C9 C8 C7 177.2(4) . . . . ?
C7 N2 C1 C2 -4.4(6) . . . . ?
C7 N2 C1 C6 176.2(4) . . . . ?
C15 N4 C14 C11 -179.7(4) . . . . ?
C15 C16 C17 C18 -1.2(7) . . . . ?
C15 C20 C19 C18 0.4(7) . . . . ?
C6 C5 C4 C3 0.7(7) . . . . ?
C20 C19 C18 C17 -0.8(7) . . . . ?
C3 C2 C1 N2 179.2(4) . . . . ?
C3 C2 C1 C6 -1.4(6) . . . . ?
C4 C5 C6 N1 179.4(4) . . . . ?
C4 C5 C6 C1 -1.5(6) . . . . ?
C17 C16 C15 N4 180.0(4) . . . . ?
C17 C16 C15 C20 0.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_test_a              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.832 Why?  
RESPONSE: The data collection is 85% complete due to the loss of solvent molecules.
;
_vrf_PLAT911_test_a              
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        714 Report
RESPONSE: The data collection is 85% complete due to the loss of solvent molecules.
;
# end Validation Reply Form




####################################################################### 
# 
# 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_hl042_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1912325'
loop_
_audit_author_name
_audit_author_address
'Myongwon Lucia Lee'
;McMaster University
Canada
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N4 Se2, 2(B F4)'
_chemical_formula_sum            'C20 H16 B2 F8 N4 Se2'
_chemical_formula_weight         643.91
_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'
B B 0.0013 0.0007 '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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.4979(3)
_cell_length_b                   11.9131(6)
_cell_length_c                   14.6745(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.399(3)
_cell_angle_gamma                90
_cell_volume                     1126.50(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    670
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   0.725
_shelx_estimated_absorpt_T_min   0.427
_exptl_absorpt_coefficient_mu    3.367
_exptl_absorpt_correction_T_max  0.8296
_exptl_absorpt_correction_T_min  0.5293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.6380.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         33.254
_diffrn_reflns_theta_min         3.281
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                3495
_reflns_number_total             4295
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.0990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C4(H4), C5(H5), C2(H2), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.48974(2) 0.65298(2) 0.72770(2) 0.01568(5) Uani 1 1 d . . . . .
F1 F 0.21228(16) 0.82924(9) 0.72875(7) 0.0242(2) Uani 1 1 d . . . . .
F4 F -0.14093(16) 0.81822(9) 0.71471(8) 0.0254(2) Uani 1 1 d . . . . .
F3 F 0.01403(16) 0.91489(9) 0.60922(8) 0.0272(2) Uani 1 1 d . . . . .
F2 F 0.03806(17) 0.72331(9) 0.61540(8) 0.0286(2) Uani 1 1 d . . . . .
N2 N 0.73232(19) 0.57280(11) 0.73817(9) 0.0137(2) Uani 1 1 d . . . . .
N1 N 0.5578(2) 0.70830(12) 0.83927(9) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.8462(2) 0.59327(12) 0.81930(10) 0.0132(3) Uani 1 1 d . . . . .
C1 C 0.7423(2) 0.66892(12) 0.87533(11) 0.0141(3) Uani 1 1 d . . . . .
C7 C 0.8030(2) 0.50288(13) 0.66442(11) 0.0163(3) Uani 1 1 d . . . . .
H7A H 0.8268 0.4250 0.6870 0.020 Uiso 1 1 calc R . . . .
H7B H 0.9364 0.5326 0.6487 0.020 Uiso 1 1 calc R . . . .
C3 C 1.0365(3) 0.65952(13) 0.99184(12) 0.0192(3) Uani 1 1 d . . . . .
H3 H 1.1062 0.6805 1.0503 0.023 Uiso 1 1 calc R . . . .
C10 C 0.5454(3) 0.55272(13) 0.42004(11) 0.0180(3) Uani 1 1 d . . . . .
H10 H 0.5762 0.5891 0.3658 0.022 Uiso 1 1 calc R . . . .
C4 C 1.1380(2) 0.58575(14) 0.93479(11) 0.0185(3) Uani 1 1 d . . . . .
H4 H 1.2738 0.5600 0.9565 0.022 Uiso 1 1 calc R . . . .
C8 C 0.6452(2) 0.50224(12) 0.57936(11) 0.0159(3) Uani 1 1 d . . . . .
C5 C 1.0469(2) 0.55095(13) 0.85027(11) 0.0161(3) Uani 1 1 d . . . . .
H5 H 1.1152 0.5006 0.8139 0.019 Uiso 1 1 calc R . . . .
C2 C 0.8426(2) 0.70037(13) 0.96448(11) 0.0176(3) Uani 1 1 d . . . . .
H2 H 0.7757 0.7483 1.0033 0.021 Uiso 1 1 calc R . . . .
C9 C 0.6898(2) 0.55406(13) 0.49912(11) 0.0170(3) Uani 1 1 d . . . . .
H9 H 0.8195 0.5906 0.4982 0.020 Uiso 1 1 calc R . . . .
B1 B 0.0297(3) 0.82174(15) 0.66589(13) 0.0161(3) 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 N2 1.8326(12) . ?
Se1 N1 1.7674(14) . ?
F1 B1 1.409(2) . ?
F4 B1 1.396(2) . ?
F3 B1 1.383(2) . ?
F2 B1 1.392(2) . ?
N2 C6 1.3409(19) . ?
N2 C7 1.485(2) . ?
N1 C1 1.332(2) . ?
C6 C1 1.445(2) . ?
C6 C5 1.417(2) . ?
C1 C2 1.434(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.510(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.432(2) . ?
C3 C2 1.362(2) . ?
C10 H10 0.9500 . ?
C10 C8 1.402(2) 3_666 ?
C10 C9 1.395(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(2) . ?
C8 C10 1.402(2) 3_666 ?
C8 C9 1.393(2) . ?
C5 H5 0.9500 . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 N2 90.39(6) . . ?
C6 N2 Se1 110.49(10) . . ?
C6 N2 C7 124.20(12) . . ?
C7 N2 Se1 125.10(10) . . ?
C1 N1 Se1 109.98(11) . . ?
N2 C6 C1 111.94(13) . . ?
N2 C6 C5 126.86(14) . . ?
C5 C6 C1 121.19(14) . . ?
N1 C1 C6 117.16(14) . . ?
N1 C1 C2 123.40(14) . . ?
C2 C1 C6 119.42(14) . . ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
N2 C7 C8 111.36(12) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.67(15) . . ?
C8 C10 H10 120.0 3_666 . ?
C9 C10 H10 120.0 . . ?
C9 C10 C8 120.02(15) . 3_666 ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.57(15) . . ?
C5 C4 H4 118.7 . . ?
C10 C8 C7 120.25(14) 3_666 . ?
C9 C8 C7 120.20(14) . . ?
C9 C8 C10 119.53(14) . 3_666 ?
C6 C5 H5 121.5 . . ?
C4 C5 C6 117.10(14) . . ?
C4 C5 H5 121.5 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.03(15) . . ?
C3 C2 H2 121.0 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.45(14) . . ?
C8 C9 H9 119.8 . . ?
F4 B1 F1 108.87(14) . . ?
F3 B1 F1 109.47(13) . . ?
F3 B1 F4 109.33(14) . . ?
F3 B1 F2 111.15(14) . . ?
F2 B1 F1 108.33(14) . . ?
F2 B1 F4 109.64(13) . . ?

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
Se1 N2 C6 C1 1.88(15) . . . . ?
Se1 N2 C6 C5 -176.80(12) . . . . ?
Se1 N2 C7 C8 -2.08(18) . . . . ?
Se1 N1 C1 C6 0.33(17) . . . . ?
Se1 N1 C1 C2 178.48(12) . . . . ?
N2 Se1 N1 C1 0.62(11) . . . . ?
N2 C6 C1 N1 -1.52(19) . . . . ?
N2 C6 C1 C2 -179.75(13) . . . . ?
N2 C6 C5 C4 177.92(15) . . . . ?
N2 C7 C8 C10 -69.43(18) . . . 3_666 ?
N2 C7 C8 C9 112.04(16) . . . . ?
N1 Se1 N2 C6 -1.48(11) . . . . ?
N1 Se1 N2 C7 -176.34(12) . . . . ?
N1 C1 C2 C3 -176.30(15) . . . . ?
C6 N2 C7 C8 -176.26(14) . . . . ?
C6 C1 C2 C3 1.8(2) . . . . ?
C1 C6 C5 C4 -0.7(2) . . . . ?
C7 N2 C6 C1 176.80(13) . . . . ?
C7 N2 C6 C5 -1.9(2) . . . . ?
C7 C8 C9 C10 179.33(14) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C10 C8 C9 C10 0.8(3) 3_666 . . . ?
C4 C3 C2 C1 -1.1(2) . . . . ?
C8 C10 C9 C8 -0.8(3) 3_666 . . . ?
C5 C6 C1 N1 177.25(14) . . . . ?
C5 C6 C1 C2 -1.0(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_ll025_0m_a_1
_database_code_depnum_ccdc_archive 'CCDC 1912322'
loop_
_audit_author_name
_audit_author_address
'Myongwon Lucia Lee'
;McMaster University
Canada
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT417_ll025_0m_a_1        
;
PROBLEM: Short Inter D-H..H-D       H00D     ..H00F     .       1.19 Ang.
RESPONSE: This distance is consistent with similar compounds that contain H2O molecules
;
_vrf_PLAT417_ll025_0m_a_1_2      
;
PROBLEM: Short Inter D-H..H-D       H00C     ..H00F     .       1.93 Ang.
RESPONSE: This distance is consistent with similar compounds that contain H2O molecules
;
_vrf_PLAT417_ll025_0m_a_1_3      
;
PROBLEM: Short Inter D-H..H-D       H00E     ..H00H     .       2.14 Ang.
RESPONSE: This distance is consistent with similar compounds that contain H2O mo
;
# Added during the CSD deposition process: Monday 22 April 2019 07:31 PM
# end Validation Reply Form

_audit_creation_date             2019-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N4 Se2, 2.5(Cl), 4(H2 O)'
_chemical_formula_sum            'C14 H20 Cl2.50 N4 O4 Se2'
_chemical_formula_weight         554.88
_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'
Cl Cl 0.1484 0.1585 '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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.624(2)
_cell_length_b                   7.942(2)
_cell_length_c                   18.270(5)
_cell_angle_alpha                77.649(5)
_cell_angle_beta                 83.560(5)
_cell_angle_gamma                71.357(4)
_cell_volume                     1022.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4346
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.008
_cell_measurement_theta_min      2.756
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    3.969
_exptl_absorpt_correction_T_max  0.8452
_exptl_absorpt_correction_T_min  0.5094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.6027.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             549
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15656
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.285
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3364
_reflns_number_total             4016
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.637
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.068
_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)+(0.0631P)²+9.0032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1459
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9722(8)
 0.0278(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Free rotating group:
 O009(H00A,H00B), O00N(H00C,H00D), O00P(H00E,H00F), O00Q(H00G,H00H)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C4(H4), C13(H13), C10(H10), C12(H12), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Se01 Se 0.00572(9) 0.73617(8) 0.51850(4) 0.01828(19) Uani 1 1 d . . . . .
Se02 Se 0.71260(9) 0.47511(8) 0.65226(4) 0.01899(19) Uani 1 1 d . . . . .
Cl03 Cl -0.0624(2) 0.7657(2) 0.37468(10) 0.0264(4) Uani 1 1 d . . . . .
Cl04 Cl 0.5000 0.5000 0.5000 0.0390(7) Uani 1 2 d S T P . .
N2 N 0.0348(7) 0.7377(7) 0.6191(3) 0.0174(11) Uani 1 1 d . . . . .
N1 N -0.2194(7) 0.8976(7) 0.5251(3) 0.0195(12) Uani 1 1 d . . . . .
N4 N 0.5059(7) 0.6482(7) 0.6850(3) 0.0189(12) Uani 1 1 d . . . . .
N3 N 0.8064(8) 0.4385(8) 0.7412(3) 0.0249(13) Uani 1 1 d . . . . .
C1 C -0.2540(9) 0.9379(8) 0.5933(4) 0.0163(13) Uani 1 1 d . . . . .
C6 C -0.1130(9) 0.8523(8) 0.6481(4) 0.0181(13) Uani 1 1 d . . . . .
C14 C 0.5196(9) 0.6617(9) 0.7556(4) 0.0212(14) Uani 1 1 d . . . . .
C7 C 0.2044(9) 0.6343(9) 0.6577(4) 0.0216(14) Uani 1 1 d . . . . .
H7A H 0.2588 0.5204 0.6405 0.026 Uiso 1 1 calc R . . . .
H7B H 0.1767 0.6081 0.7113 0.026 Uiso 1 1 calc R . . . .
C8 C 0.3415(9) 0.7458(8) 0.6412(4) 0.0189(14) Uani 1 1 d . . . . .
H8A H 0.3770 0.7636 0.5881 0.023 Uiso 1 1 calc R . . . .
H8B H 0.2835 0.8636 0.6547 0.023 Uiso 1 1 calc R . . . .
C9 C 0.6908(10) 0.5414(10) 0.7863(4) 0.0269(16) Uani 1 1 d . . . . .
C2 C -0.4253(9) 1.0643(8) 0.6146(4) 0.0211(14) Uani 1 1 d . . . . .
H2 H -0.5177 1.1229 0.5806 0.025 Uiso 1 1 calc R . . . .
C3 C -0.4476(10) 1.0952(9) 0.6855(4) 0.0268(16) Uani 1 1 d . . . . .
H3 H -0.5591 1.1736 0.7002 0.032 Uiso 1 1 calc R . . . .
C5 C -0.1423(10) 0.8916(10) 0.7217(4) 0.0253(15) Uani 1 1 d . . . . .
H5 H -0.0528 0.8374 0.7572 0.030 Uiso 1 1 calc R . . . .
C4 C -0.3089(10) 1.0135(10) 0.7379(4) 0.0279(16) Uani 1 1 d . . . . .
H4 H -0.3308 1.0431 0.7854 0.033 Uiso 1 1 calc R . . . .
C13 C 0.3921(10) 0.7818(9) 0.7989(4) 0.0262(16) Uani 1 1 d . . . . .
H13 H 0.2825 0.8635 0.7796 0.031 Uiso 1 1 calc R . . . .
C10 C 0.7300(12) 0.5356(12) 0.8626(5) 0.041(2) Uani 1 1 d . . . . .
H10 H 0.8385 0.4564 0.8838 0.049 Uiso 1 1 calc R . . . .
C12 C 0.4394(12) 0.7706(13) 0.8701(5) 0.039(2) Uani 1 1 d . . . . .
H12 H 0.3586 0.8475 0.8994 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6046(14) 0.6485(14) 0.9017(5) 0.047(2) Uani 1 1 d . . . . .
H11 H 0.6268 0.6464 0.9509 0.056 Uiso 1 1 calc R . . . .
Cl05 Cl 0.6612(4) 0.6540(3) 1.15930(15) 0.0539(6) Uani 1 1 d . . . . .
O009 O -0.0803(9) 0.8644(9) 0.1801(4) 0.0482(16) Uani 1 1 d . . . . .
H00A H -0.0029 0.8015 0.2131 0.072 Uiso 1 1 d G . . . .
H00B H -0.1587 0.8102 0.1780 0.072 Uiso 1 1 d G . . . .
O00N O 0.4192(13) 0.9001(15) 1.0385(5) 0.085(3) Uani 1 1 d . . . . .
H00C H 0.4215 0.8351 1.0820 0.127 Uiso 1 1 d G . . . .
H00D H 0.3076 0.9484 1.0257 0.127 Uiso 1 1 d G . . . .
O00P O 0.0627(12) 1.0405(14) 1.0654(6) 0.093(3) Uani 1 1 d . . . . .
H00E H 0.0178 1.0106 1.1092 0.140 Uiso 1 1 d G . . . .
H00F H 0.1801 1.0096 1.0662 0.140 Uiso 1 1 d G . . . .
O00Q O -0.0941(15) 1.4059(14) 1.0468(6) 0.085(3) Uani 1 1 d . . . . .
H00G H -0.1684 1.4715 1.0753 0.127 Uiso 1 1 d G . . . .
H00H H -0.0588 1.2969 1.0701 0.127 Uiso 1 1 d G . . . .


_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
Se01 N2 1.879(6) . ?
Se01 N1 1.793(6) . ?
Se02 N4 1.867(5) . ?
Se02 N3 1.778(6) . ?
N2 C6 1.340(8) . ?
N2 C7 1.456(8) . ?
N1 C1 1.330(9) . ?
N4 C14 1.337(9) . ?
N4 C8 1.466(8) . ?
N3 C9 1.338(9) . ?
C1 C6 1.450(9) . ?
C1 C2 1.442(9) . ?
C6 C5 1.422(10) . ?
C14 C9 1.438(10) . ?
C14 C13 1.427(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.541(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.445(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.350(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.407(11) . ?
C5 H5 0.9300 . ?
C5 C4 1.375(10) . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.366(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.342(13) . ?
C12 H12 0.9300 . ?
C12 C11 1.415(13) . ?
C11 H11 0.9300 . ?
O009 H00A 0.8500 . ?
O009 H00B 0.8493 . ?
O00N H00C 0.8498 . ?
O00N H00D 0.8498 . ?
O00P H00E 0.8493 . ?
O00P H00F 0.8501 . ?
O00Q H00G 0.8505 . ?
O00Q H00H 0.8501 . ?

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 Se01 N2 88.4(2) . . ?
N3 Se02 N4 88.2(3) . . ?
C6 N2 Se01 111.8(4) . . ?
C6 N2 C7 125.2(6) . . ?
C7 N2 Se01 122.8(5) . . ?
C1 N1 Se01 110.5(4) . . ?
C14 N4 Se02 111.6(4) . . ?
C14 N4 C8 123.9(6) . . ?
C8 N4 Se02 124.3(4) . . ?
C9 N3 Se02 111.7(5) . . ?
N1 C1 C6 118.6(6) . . ?
N1 C1 C2 122.6(6) . . ?
C2 C1 C6 118.8(6) . . ?
N2 C6 C1 110.7(6) . . ?
N2 C6 C5 128.4(6) . . ?
C5 C6 C1 120.9(6) . . ?
N4 C14 C9 111.9(6) . . ?
N4 C14 C13 127.8(6) . . ?
C13 C14 C9 120.3(6) . . ?
N2 C7 H7A 109.9 . . ?
N2 C7 H7B 109.9 . . ?
N2 C7 C8 109.0(5) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
N4 C8 C7 108.9(5) . . ?
N4 C8 H8A 109.9 . . ?
N4 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N3 C9 C14 116.7(7) . . ?
N3 C9 C10 123.4(7) . . ?
C14 C9 C10 120.0(7) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.1(7) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 118.7 . . ?
C2 C3 C4 122.6(7) . . ?
C4 C3 H3 118.7 . . ?
C6 C5 H5 121.5 . . ?
C4 C5 C6 117.0(7) . . ?
C4 C5 H5 121.5 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.5(7) . . ?
C5 C4 H4 118.7 . . ?
C14 C13 H13 121.7 . . ?
C12 C13 C14 116.5(7) . . ?
C12 C13 H13 121.7 . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.7(8) . . ?
C11 C10 H10 121.2 . . ?
C13 C12 H12 118.2 . . ?
C13 C12 C11 123.6(8) . . ?
C11 C12 H12 118.2 . . ?
C10 C11 C12 121.9(8) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
H00A O009 H00B 109.5 . . ?
H00C O00N H00D 109.5 . . ?
H00E O00P H00F 109.5 . . ?
H00G O00Q H00H 109.4 . . ?

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
Se01 N2 C6 C1 1.5(6) . . . . ?
Se01 N2 C6 C5 -179.6(6) . . . . ?
Se01 N2 C7 C8 85.0(6) . . . . ?
Se01 N1 C1 C6 0.6(7) . . . . ?
Se01 N1 C1 C2 -180.0(5) . . . . ?
Se02 N4 C14 C9 0.9(7) . . . . ?
Se02 N4 C14 C13 178.2(6) . . . . ?
Se02 N4 C8 C7 88.1(6) . . . . ?
Se02 N3 C9 C14 -1.3(8) . . . . ?
Se02 N3 C9 C10 178.4(7) . . . . ?
N2 Se01 N1 C1 0.2(5) . . . . ?
N2 C6 C5 C4 -178.9(7) . . . . ?
N2 C7 C8 N4 175.4(5) . . . . ?
N1 Se01 N2 C6 -1.0(5) . . . . ?
N1 Se01 N2 C7 -177.2(5) . . . . ?
N1 C1 C6 N2 -1.5(8) . . . . ?
N1 C1 C6 C5 179.5(6) . . . . ?
N1 C1 C2 C3 179.6(6) . . . . ?
N4 Se02 N3 C9 1.5(5) . . . . ?
N4 C14 C9 N3 0.3(9) . . . . ?
N4 C14 C9 C10 -179.5(7) . . . . ?
N4 C14 C13 C12 -179.2(7) . . . . ?
N3 Se02 N4 C14 -1.4(5) . . . . ?
N3 Se02 N4 C8 -176.3(5) . . . . ?
N3 C9 C10 C11 178.6(9) . . . . ?
C1 C6 C5 C4 -0.1(10) . . . . ?
C1 C2 C3 C4 2.0(10) . . . . ?
C6 N2 C7 C8 -90.6(8) . . . . ?
C6 C1 C2 C3 -1.0(9) . . . . ?
C6 C5 C4 C3 1.0(11) . . . . ?
C14 N4 C8 C7 -86.2(7) . . . . ?
C14 C9 C10 C11 -1.7(13) . . . . ?
C14 C13 C12 C11 0.0(13) . . . . ?
C7 N2 C6 C1 177.6(6) . . . . ?
C7 N2 C6 C5 -3.5(11) . . . . ?
C8 N4 C14 C9 175.9(6) . . . . ?
C8 N4 C14 C13 -6.9(11) . . . . ?
C9 C14 C13 C12 -2.1(11) . . . . ?
C9 C10 C11 C12 -0.4(15) . . . . ?
C2 C1 C6 N2 179.1(6) . . . . ?
C2 C1 C6 C5 0.1(9) . . . . ?
C2 C3 C4 C5 -2.1(12) . . . . ?
C13 C14 C9 N3 -177.3(7) . . . . ?
C13 C14 C9 C10 3.0(11) . . . . ?
C13 C12 C11 C10 1.3(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9722(8)
2 0.0278(8)
####################################################################### 
# 
# 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_ll055_01_a-2
_database_code_depnum_ccdc_archive 'CCDC 1912323'
loop_
_audit_author_name
_audit_author_address
'Myongwon Lucia Lee'
;McMaster University
Canada
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N4 Se2, 2(C F3 O3 S)'
_chemical_formula_sum            'C16 H12 F6 N4 O6 S2 Se2'
_chemical_formula_weight         692.34
_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'
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'
O O 0.0106 0.0060 '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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3966(16)
_cell_length_b                   11.300(2)
_cell_length_c                   11.9466(19)
_cell_angle_alpha                90.953(3)
_cell_angle_beta                 90.846(4)
_cell_angle_gamma                94.122(4)
_cell_volume                     1130.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4710
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.675
_exptl_absorpt_coefficient_mu    3.549
_exptl_absorpt_correction_T_max  0.8082
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0418 before and 0.0350 after correction.
The Ratio of minimum to maximum transmission is 0.7971.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.034
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22026
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.448
_diffrn_reflns_theta_min         2.924
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3748
_reflns_number_total             4636
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.016
_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)+(0.0333P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0592
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C12(H12), C2(H2), C11(H11), C5(H5), C10(H10), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.29825(3) 0.48516(2) 0.59559(2) 0.01294(7) Uani 1 1 d . . . . .
Se2 Se 0.04217(3) 0.51707(2) 0.14559(2) 0.01349(7) Uani 1 1 d . . . . .
S2 S 0.16083(8) 0.29008(5) 0.34430(5) 0.01796(15) Uani 1 1 d . . . . .
S1 S 0.31675(8) 0.23151(5) 0.78649(5) 0.01656(14) Uani 1 1 d . . . . .
F5 F 0.23853(18) 0.07774(12) 0.39934(12) 0.0236(4) Uani 1 1 d . . . . .
F6 F -0.01258(19) 0.09151(14) 0.37514(17) 0.0454(5) Uani 1 1 d . . . . .
O2 O 0.4415(2) 0.18953(15) 0.71818(14) 0.0204(4) Uani 1 1 d . . . . .
O4 O 0.3100(2) 0.33627(15) 0.39472(15) 0.0208(4) Uani 1 1 d . . . . .
F3 F 0.5356(2) 0.39022(18) 0.86572(16) 0.0477(5) Uani 1 1 d . . . . .
O3 O 0.2321(2) 0.32559(15) 0.73746(14) 0.0190(4) Uani 1 1 d . . . . .
F4 F 0.1056(2) 0.16466(14) 0.52457(14) 0.0440(5) Uani 1 1 d . . . . .
O5 O 0.0270(2) 0.35758(16) 0.37436(18) 0.0328(5) Uani 1 1 d . . . . .
O6 O 0.1671(3) 0.25641(17) 0.22834(15) 0.0345(5) Uani 1 1 d . . . . .
O1 O 0.2150(2) 0.14263(17) 0.83870(18) 0.0355(5) Uani 1 1 d . . . . .
N2 N 0.3215(2) 0.61941(17) 0.50858(16) 0.0124(4) Uani 1 1 d . . . . .
N4 N 0.1091(2) 0.64663(17) 0.23366(16) 0.0129(4) Uani 1 1 d . . . . .
F1 F 0.5062(2) 0.2303(2) 0.96082(15) 0.0652(7) Uani 1 1 d . . . . .
F2 F 0.3309(2) 0.3595(2) 0.97212(14) 0.0589(6) Uani 1 1 d . . . . .
C3 C 0.3946(3) 0.8958(2) 0.7357(2) 0.0191(6) Uani 1 1 d . . . . .
H3 H 0.4103 0.9576 0.7879 0.023 Uiso 1 1 calc R . . . .
N1 N 0.3276(2) 0.57586(18) 0.71721(16) 0.0153(5) Uani 1 1 d . . . . .
C4 C 0.3870(3) 0.9222(2) 0.6185(2) 0.0175(6) Uani 1 1 d . . . . .
H4 H 0.3970 1.0011 0.5972 0.021 Uiso 1 1 calc R . . . .
C12 C 0.1934(3) 0.9490(2) 0.1363(2) 0.0192(6) Uani 1 1 d . . . . .
H12 H 0.2274 1.0255 0.1602 0.023 Uiso 1 1 calc R . . . .
N3 N 0.0467(2) 0.61200(18) 0.02843(16) 0.0151(5) Uani 1 1 d . . . . .
C6 C 0.3466(3) 0.7170(2) 0.5730(2) 0.0129(5) Uani 1 1 d . . . . .
C7 C 0.3027(3) 0.6200(2) 0.38617(19) 0.0127(5) Uani 1 1 d . . . . .
H7A H 0.3303 0.5448 0.3545 0.015 Uiso 1 1 calc R . . . .
H7B H 0.3735 0.6825 0.3555 0.015 Uiso 1 1 calc R . . . .
C2 C 0.3795(3) 0.7831(2) 0.7712(2) 0.0188(6) Uani 1 1 d . . . . .
H2 H 0.3873 0.7669 0.8471 0.023 Uiso 1 1 calc R . . . .
C11 C 0.1582(3) 0.9276(2) 0.0194(2) 0.0188(6) Uani 1 1 d . . . . .
H11 H 0.1712 0.9899 -0.0302 0.023 Uiso 1 1 calc R . . . .
C9 C 0.0914(3) 0.7234(2) 0.0572(2) 0.0135(5) Uani 1 1 d . . . . .
C1 C 0.3512(3) 0.6891(2) 0.6905(2) 0.0139(5) Uani 1 1 d . . . . .
C14 C 0.1284(3) 0.7457(2) 0.1740(2) 0.0138(5) Uani 1 1 d . . . . .
C5 C 0.3658(3) 0.8362(2) 0.5377(2) 0.0155(5) Uani 1 1 d . . . . .
H5 H 0.3640 0.8548 0.4621 0.019 Uiso 1 1 calc R . . . .
C0AA C 0.1203(3) 0.1493(2) 0.4145(2) 0.0214(6) Uani 1 1 d . . . . .
C8 C 0.1295(3) 0.6407(2) 0.35624(19) 0.0148(5) Uani 1 1 d . . . . .
H8A H 0.0594 0.5765 0.3847 0.018 Uiso 1 1 calc R . . . .
H8B H 0.1009 0.7143 0.3908 0.018 Uiso 1 1 calc R . . . .
C10 C 0.1062(3) 0.8179(2) -0.0198(2) 0.0159(5) Uani 1 1 d . . . . .
H10 H 0.0809 0.8049 -0.0953 0.019 Uiso 1 1 calc R . . . .
C13 C 0.1792(3) 0.8621(2) 0.2132(2) 0.0174(6) Uani 1 1 d . . . . .
H13 H 0.2019 0.8780 0.2886 0.021 Uiso 1 1 calc R . . . .
C15 C 0.4276(4) 0.3077(3) 0.9026(2) 0.0369(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 N2 1.854(2) . ?
Se1 N1 1.7680(19) . ?
Se2 N4 1.8383(19) . ?
Se2 N3 1.777(2) . ?
S2 O4 1.4415(18) . ?
S2 O5 1.449(2) . ?
S2 O6 1.433(2) . ?
S2 C0AA 1.824(3) . ?
S1 O2 1.4398(18) . ?
S1 O3 1.4475(17) . ?
S1 O1 1.429(2) . ?
S1 C15 1.827(3) . ?
F5 C0AA 1.337(3) . ?
F6 C0AA 1.327(3) . ?
F3 C15 1.338(4) . ?
F4 C0AA 1.333(3) . ?
N2 C6 1.337(3) . ?
N2 C7 1.469(3) . ?
N4 C14 1.338(3) . ?
N4 C8 1.475(3) . ?
F1 C15 1.331(4) . ?
F2 C15 1.328(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.438(3) . ?
C3 C2 1.346(4) . ?
N1 C1 1.326(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.360(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.435(4) . ?
C12 C13 1.356(4) . ?
N3 C9 1.326(3) . ?
C6 C1 1.444(3) . ?
C6 C5 1.417(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.527(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.427(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.358(3) . ?
C9 C14 1.440(3) . ?
C9 C10 1.420(3) . ?
C14 C13 1.422(3) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10 0.9300 . ?
C13 H13 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 Se1 N2 89.44(9) . . ?
N3 Se2 N4 88.28(9) . . ?
O4 S2 O5 113.32(11) . . ?
O4 S2 C0AA 103.18(11) . . ?
O5 S2 C0AA 103.71(12) . . ?
O6 S2 O4 115.65(12) . . ?
O6 S2 O5 115.18(13) . . ?
O6 S2 C0AA 103.64(12) . . ?
O2 S1 O3 114.51(11) . . ?
O2 S1 C15 102.87(12) . . ?
O3 S1 C15 102.67(13) . . ?
O1 S1 O2 116.27(11) . . ?
O1 S1 O3 113.77(11) . . ?
O1 S1 C15 104.44(15) . . ?
C6 N2 Se1 110.69(16) . . ?
C6 N2 C7 124.3(2) . . ?
C7 N2 Se1 124.86(15) . . ?
C14 N4 Se2 111.96(16) . . ?
C14 N4 C8 125.0(2) . . ?
C8 N4 Se2 122.93(15) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(2) . . ?
C1 N1 Se1 110.79(16) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 H4 118.8 . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C13 C12 C11 122.7(2) . . ?
C9 N3 Se2 111.99(16) . . ?
N2 C6 C1 111.8(2) . . ?
N2 C6 C5 127.4(2) . . ?
C5 C6 C1 120.8(2) . . ?
N2 C7 H7A 109.9 . . ?
N2 C7 H7B 109.9 . . ?
N2 C7 C8 109.01(19) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C3 C2 H2 120.5 . . ?
C3 C2 C1 118.9(2) . . ?
C1 C2 H2 120.5 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.5 . . ?
N3 C9 C14 116.1(2) . . ?
N3 C9 C10 123.9(2) . . ?
C10 C9 C14 120.0(2) . . ?
N1 C1 C6 117.3(2) . . ?
N1 C1 C2 123.6(2) . . ?
C2 C1 C6 119.2(2) . . ?
N4 C14 C9 111.7(2) . . ?
N4 C14 C13 127.9(2) . . ?
C13 C14 C9 120.4(2) . . ?
C4 C5 C6 117.4(2) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
F5 C0AA S2 111.27(18) . . ?
F6 C0AA S2 111.53(19) . . ?
F6 C0AA F5 107.0(2) . . ?
F6 C0AA F4 108.1(2) . . ?
F4 C0AA S2 111.71(17) . . ?
F4 C0AA F5 107.1(2) . . ?
N4 C8 C7 110.05(19) . . ?
N4 C8 H8A 109.6 . . ?
N4 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C11 C10 C9 118.4(2) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C12 C13 C14 117.4(2) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
F3 C15 S1 111.3(2) . . ?
F1 C15 S1 110.0(2) . . ?
F1 C15 F3 107.4(3) . . ?
F2 C15 S1 111.5(2) . . ?
F2 C15 F3 108.5(3) . . ?
F2 C15 F1 107.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 N2 C6 C1 1.1(3) . . . . ?
Se1 N2 C6 C5 -178.3(2) . . . . ?
Se1 N2 C7 C8 91.6(2) . . . . ?
Se1 N1 C1 C6 0.9(3) . . . . ?
Se1 N1 C1 C2 -179.5(2) . . . . ?
Se2 N4 C14 C9 0.0(3) . . . . ?
Se2 N4 C14 C13 -179.7(2) . . . . ?
Se2 N4 C8 C7 94.0(2) . . . . ?
Se2 N3 C9 C14 0.7(3) . . . . ?
Se2 N3 C9 C10 179.63(19) . . . . ?
O2 S1 C15 F3 54.7(2) . . . . ?
O2 S1 C15 F1 -64.2(2) . . . . ?
O2 S1 C15 F2 176.1(2) . . . . ?
O4 S2 C0AA F5 -58.6(2) . . . . ?
O4 S2 C0AA F6 -177.93(18) . . . . ?
O4 S2 C0AA F4 61.0(2) . . . . ?
O3 S1 C15 F3 -64.5(2) . . . . ?
O3 S1 C15 F1 176.6(2) . . . . ?
O3 S1 C15 F2 56.9(3) . . . . ?
O5 S2 C0AA F5 -176.98(17) . . . . ?
O5 S2 C0AA F6 63.7(2) . . . . ?
O5 S2 C0AA F4 -57.4(2) . . . . ?
O6 S2 C0AA F5 62.4(2) . . . . ?
O6 S2 C0AA F6 -57.0(2) . . . . ?
O6 S2 C0AA F4 -178.04(19) . . . . ?
O1 S1 C15 F3 176.6(2) . . . . ?
O1 S1 C15 F1 57.6(2) . . . . ?
O1 S1 C15 F2 -62.1(3) . . . . ?
N2 Se1 N1 C1 -0.20(17) . . . . ?
N2 C6 C1 N1 -1.3(3) . . . . ?
N2 C6 C1 C2 179.1(2) . . . . ?
N2 C6 C5 C4 178.7(2) . . . . ?
N2 C7 C8 N4 177.67(18) . . . . ?
N4 Se2 N3 C9 -0.55(18) . . . . ?
N4 C14 C13 C12 178.6(2) . . . . ?
C3 C4 C5 C6 1.7(4) . . . . ?
C3 C2 C1 N1 -176.9(2) . . . . ?
C3 C2 C1 C6 2.7(4) . . . . ?
N1 Se1 N2 C6 -0.55(17) . . . . ?
N1 Se1 N2 C7 -176.16(19) . . . . ?
C4 C3 C2 C1 -1.7(4) . . . . ?
C12 C11 C10 C9 -1.7(4) . . . . ?
N3 Se2 N4 C14 0.31(17) . . . . ?
N3 Se2 N4 C8 177.18(19) . . . . ?
N3 C9 C14 N4 -0.4(3) . . . . ?
N3 C9 C14 C13 179.3(2) . . . . ?
N3 C9 C10 C11 -177.8(2) . . . . ?
C6 N2 C7 C8 -83.4(3) . . . . ?
C7 N2 C6 C1 176.7(2) . . . . ?
C7 N2 C6 C5 -2.6(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C9 C14 C13 C12 -1.0(4) . . . . ?
C1 C6 C5 C4 -0.6(4) . . . . ?
C14 N4 C8 C7 -89.5(3) . . . . ?
C14 C9 C10 C11 1.1(4) . . . . ?
C5 C6 C1 N1 178.0(2) . . . . ?
C5 C6 C1 C2 -1.5(4) . . . . ?
C8 N4 C14 C9 -176.8(2) . . . . ?
C8 N4 C14 C13 3.5(4) . . . . ?
C10 C9 C14 N4 -179.4(2) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C13 C12 C11 C10 0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT430_ll055_01_a-2        
;
PROBLEM: Short Inter D...A Contact  Se1      ..O3       .       2.53 Ang.  
RESPONSE: A short contact between O/N and Se is expected.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_ll60
_database_code_depnum_ccdc_archive 'CCDC 1912324'
loop_
_audit_author_name
_audit_author_address
'Myongwon Lucia Lee'
;McMaster University
Canada
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N4 Se2, 2(C F3 O3 S)'
_chemical_formula_sum            'C17 H14 F6 N4 O6 S2 Se2'
_chemical_formula_weight         706.36
_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'
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'
O O 0.0106 0.0060 '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'
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                   11.9799(2)
_cell_length_b                   29.8901(6)
_cell_length_c                   6.63540(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.9400(10)
_cell_angle_gamma                90
_cell_volume                     2370.39(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9529
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.687
_shelx_estimated_absorpt_T_min   0.282
_exptl_absorpt_coefficient_mu    3.387
_exptl_absorpt_correction_T_max  0.5801
_exptl_absorpt_correction_T_min  0.4094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0989 before and 0.0386 after correction.
The Ratio of minimum to maximum transmission is 0.7057.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            84643
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.605
_diffrn_reflns_theta_min         1.363
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6582
_reflns_number_total             7252
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         7252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0266P)²+3.1442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0669
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
Se2 Se 0.28176(2) 0.47567(2) 0.31703(3) 0.01352(5) Uani 1 1 d . . . . .
Se1 Se 0.39436(2) 0.26945(2) -0.11263(3) 0.01417(5) Uani 1 1 d . . . . .
S2 S 0.37519(4) 0.54816(2) 0.74091(7) 0.01441(9) Uani 1 1 d . . . . .
S1 S 0.21629(4) 0.16997(2) -0.03742(7) 0.01470(9) Uani 1 1 d . . . . .
F5 F 0.23284(12) 0.61177(5) 0.6228(2) 0.0290(3) Uani 1 1 d . . . . .
F6 F 0.40630(13) 0.63081(5) 0.6181(2) 0.0354(3) Uani 1 1 d . . . . .
O4 O 0.29025(12) 0.51562(5) 0.6767(2) 0.0175(3) Uani 1 1 d . . . . .
F4 F 0.33208(15) 0.58647(5) 0.3887(2) 0.0356(3) Uani 1 1 d . . . . .
O6 O 0.36867(12) 0.56387(5) 0.9461(2) 0.0195(3) Uani 1 1 d . . . . .
O3 O 0.21792(15) 0.18449(6) 0.1698(2) 0.0310(4) Uani 1 1 d . . . . .
O5 O 0.48655(13) 0.53843(6) 0.6833(3) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.29031(14) 0.19458(5) -0.1611(3) 0.0288(4) Uani 1 1 d . . . . .
N4 N 0.25351(13) 0.44668(5) 0.0749(2) 0.0132(3) Uani 1 1 d . . . . .
F3 F 0.06314(16) 0.23013(7) -0.1328(3) 0.0571(5) Uani 1 1 d . . . . .
O1 O 0.21858(16) 0.12230(5) -0.0647(3) 0.0306(4) Uani 1 1 d . . . . .
N3 N 0.13732(13) 0.47845(5) 0.3491(2) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.48873(13) 0.31819(5) -0.1055(2) 0.0132(3) Uani 1 1 d . . . . .
F2 F -0.00225(14) 0.16732(8) -0.0433(4) 0.0640(6) Uani 1 1 d . . . . .
F1 F 0.06418(18) 0.17375(10) -0.3358(3) 0.0722(7) Uani 1 1 d . . . . .
N1 N 0.51055(15) 0.23389(5) -0.0585(2) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.79405(17) 0.31233(8) -0.0111(3) 0.0207(4) Uani 1 1 d . . . . .
C5 C 0.69269(16) 0.33303(7) -0.0510(3) 0.0176(4) Uani 1 1 d . . . . .
H5 H 0.6873 0.3646 -0.0670 0.021 Uiso 1 1 calc R . . . .
C3 C 0.80491(18) 0.26507(8) 0.0117(3) 0.0217(4) Uani 1 1 d . . . . .
C10 C 0.07947(15) 0.45902(6) 0.1934(3) 0.0145(3) Uani 1 1 d . . . . .
C15 C 0.14300(15) 0.44088(6) 0.0352(3) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.45115(15) 0.36454(6) -0.1511(3) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.71370(18) 0.23770(7) -0.0037(3) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.33990(16) 0.42950(6) -0.0534(3) 0.0140(3) Uani 1 1 d . . . . .
C1 C 0.60534(17) 0.25754(7) -0.0425(3) 0.0158(3) Uani 1 1 d . . . . .
C8 C 0.36722(16) 0.38061(6) -0.0037(3) 0.0139(3) Uani 1 1 d . . . . .
C11 C -0.03998(16) 0.45666(7) 0.1750(3) 0.0175(4) Uani 1 1 d . . . . .
C6 C 0.59598(16) 0.30525(6) -0.0674(3) 0.0139(3) Uani 1 1 d . . . . .
C14 C 0.08874(17) 0.42089(7) -0.1392(3) 0.0176(4) Uani 1 1 d . . . . .
C13 C -0.02546(17) 0.41972(7) -0.1507(3) 0.0206(4) Uani 1 1 d . . . . .
C12 C -0.09005(17) 0.43734(7) 0.0060(3) 0.0198(4) Uani 1 1 d . . . . .
C16 C 0.33431(19) 0.59671(7) 0.5851(3) 0.0220(4) Uani 1 1 d . . . . .
C17 C 0.0779(2) 0.18622(11) -0.1425(4) 0.0363(6) Uani 1 1 d . . . . .
H3 H 0.878(2) 0.2515(9) 0.038(4) 0.024(7) Uiso 1 1 d . . . . .
H4 H 0.859(2) 0.3306(10) 0.001(4) 0.029(7) Uiso 1 1 d . . . . .
H13 H -0.061(2) 0.4073(9) -0.262(4) 0.022(7) Uiso 1 1 d . . . . .
H2 H 0.716(2) 0.2059(10) 0.010(4) 0.027(7) Uiso 1 1 d . . . . .
H12 H -0.169(2) 0.4375(9) -0.010(4) 0.025(7) Uiso 1 1 d . . . . .
H11 H -0.078(2) 0.4672(9) 0.280(4) 0.024(7) Uiso 1 1 d . . . . .
H9A H 0.3101(19) 0.4319(8) -0.190(3) 0.007(5) Uiso 1 1 d . . . . .
H9B H 0.405(2) 0.4472(8) -0.033(4) 0.012(6) Uiso 1 1 d . . . . .
H14 H 0.128(2) 0.4084(10) -0.239(4) 0.026(7) Uiso 1 1 d . . . . .
H7A H 0.518(2) 0.3825(8) -0.142(4) 0.015(6) Uiso 1 1 d . . . . .
H7B H 0.419(2) 0.3652(8) -0.289(4) 0.013(6) Uiso 1 1 d . . . . .
H8A H 0.4000(19) 0.3771(8) 0.132(4) 0.010(5) Uiso 1 1 d . . . . .
H8B H 0.302(2) 0.3644(9) -0.018(4) 0.025(7) Uiso 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
Se2 N4 1.8360(16) . ?
Se2 N3 1.7598(16) . ?
Se1 N2 1.8427(16) . ?
Se1 N1 1.7684(17) . ?
S2 O4 1.4501(14) . ?
S2 O6 1.4472(15) . ?
S2 O5 1.4424(16) . ?
S2 C16 1.829(2) . ?
S1 O3 1.4408(16) . ?
S1 O2 1.4496(16) . ?
S1 O1 1.4367(16) . ?
S1 C17 1.820(2) . ?
F5 C16 1.336(3) . ?
F6 C16 1.343(2) . ?
F4 C16 1.337(2) . ?
N4 C15 1.343(2) . ?
N4 C9 1.477(2) . ?
F3 C17 1.326(4) . ?
N3 C10 1.337(2) . ?
N2 C7 1.482(2) . ?
N2 C6 1.349(2) . ?
F2 C17 1.327(3) . ?
F1 C17 1.335(3) . ?
N1 C1 1.336(3) . ?
C4 C5 1.372(3) . ?
C4 C3 1.426(3) . ?
C4 H4 0.95(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.423(3) . ?
C3 C2 1.363(3) . ?
C3 H3 0.97(3) . ?
C10 C15 1.444(3) . ?
C10 C11 1.430(3) . ?
C15 C14 1.420(3) . ?
C7 C8 1.528(3) . ?
C7 H7A 0.96(3) . ?
C7 H7B 0.97(2) . ?
C2 C1 1.434(3) . ?
C2 H2 0.96(3) . ?
C9 C8 1.529(3) . ?
C9 H9A 0.95(2) . ?
C9 H9B 0.94(2) . ?
C1 C6 1.439(3) . ?
C8 H8A 0.96(2) . ?
C8 H8B 0.92(3) . ?
C11 C12 1.364(3) . ?
C11 H11 0.91(3) . ?
C14 C13 1.365(3) . ?
C14 H14 0.92(3) . ?
C13 C12 1.438(3) . ?
C13 H13 0.91(3) . ?
C12 H12 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Se2 N4 90.24(7) . . ?
N1 Se1 N2 89.83(8) . . ?
O4 S2 C16 102.17(9) . . ?
O6 S2 O4 114.32(9) . . ?
O6 S2 C16 104.15(9) . . ?
O5 S2 O4 115.47(9) . . ?
O5 S2 O6 115.17(9) . . ?
O5 S2 C16 103.11(11) . . ?
O3 S1 O2 114.75(11) . . ?
O3 S1 C17 103.74(12) . . ?
O2 S1 C17 102.96(12) . . ?
O1 S1 O3 114.84(11) . . ?
O1 S1 O2 114.47(10) . . ?
O1 S1 C17 103.95(13) . . ?
C15 N4 Se2 110.64(12) . . ?
C15 N4 C9 124.21(16) . . ?
C9 N4 Se2 125.04(12) . . ?
C10 N3 Se2 110.37(13) . . ?
C7 N2 Se1 123.83(12) . . ?
C6 N2 Se1 110.67(12) . . ?
C6 N2 C7 125.35(16) . . ?
C1 N1 Se1 110.55(13) . . ?
C5 C4 C3 122.7(2) . . ?
C5 C4 H4 117.6(18) . . ?
C3 C4 H4 119.7(18) . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.17(19) . . ?
C6 C5 H5 121.4 . . ?
C4 C3 H3 120.4(17) . . ?
C2 C3 C4 121.31(19) . . ?
C2 C3 H3 118.3(17) . . ?
N3 C10 C15 116.98(16) . . ?
N3 C10 C11 123.38(17) . . ?
C11 C10 C15 119.61(17) . . ?
N4 C15 C10 111.75(16) . . ?
N4 C15 C14 127.17(17) . . ?
C14 C15 C10 121.05(17) . . ?
N2 C7 C8 111.54(15) . . ?
N2 C7 H7A 105.6(15) . . ?
N2 C7 H7B 108.0(14) . . ?
C8 C7 H7A 111.4(15) . . ?
C8 C7 H7B 111.4(15) . . ?
H7A C7 H7B 109(2) . . ?
C3 C2 C1 118.45(19) . . ?
C3 C2 H2 124.6(17) . . ?
C1 C2 H2 116.9(17) . . ?
N4 C9 C8 110.87(15) . . ?
N4 C9 H9A 106.8(14) . . ?
N4 C9 H9B 109.0(15) . . ?
C8 C9 H9A 109.8(14) . . ?
C8 C9 H9B 110.1(15) . . ?
H9A C9 H9B 110(2) . . ?
N1 C1 C2 123.33(18) . . ?
N1 C1 C6 117.15(17) . . ?
C2 C1 C6 119.52(19) . . ?
C7 C8 C9 107.64(15) . . ?
C7 C8 H8A 108.6(14) . . ?
C7 C8 H8B 111.1(17) . . ?
C9 C8 H8A 111.9(14) . . ?
C9 C8 H8B 108.2(17) . . ?
H8A C8 H8B 109(2) . . ?
C10 C11 H11 117.6(18) . . ?
C12 C11 C10 118.18(18) . . ?
C12 C11 H11 124.2(18) . . ?
N2 C6 C5 127.37(17) . . ?
N2 C6 C1 111.79(17) . . ?
C5 C6 C1 120.84(17) . . ?
C15 C14 H14 121.8(18) . . ?
C13 C14 C15 117.21(19) . . ?
C13 C14 H14 120.9(18) . . ?
C14 C13 C12 122.50(19) . . ?
C14 C13 H13 118.1(17) . . ?
C12 C13 H13 119.4(17) . . ?
C11 C12 C13 121.44(18) . . ?
C11 C12 H12 117.9(17) . . ?
C13 C12 H12 120.5(17) . . ?
F5 C16 S2 111.93(15) . . ?
F5 C16 F6 107.24(18) . . ?
F5 C16 F4 107.57(18) . . ?
F6 C16 S2 111.47(15) . . ?
F4 C16 S2 110.83(15) . . ?
F4 C16 F6 107.58(17) . . ?
F3 C17 S1 111.48(19) . . ?
F3 C17 F2 107.1(2) . . ?
F3 C17 F1 108.3(2) . . ?
F2 C17 S1 111.5(2) . . ?
F2 C17 F1 108.2(2) . . ?
F1 C17 S1 109.99(19) . . ?

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
Se2 N4 C15 C10 0.01(19) . . . . ?
Se2 N4 C15 C14 178.36(16) . . . . ?
Se2 N4 C9 C8 92.55(17) . . . . ?
Se2 N3 C10 C15 -0.8(2) . . . . ?
Se2 N3 C10 C11 -178.99(15) . . . . ?
Se1 N2 C7 C8 61.48(19) . . . . ?
Se1 N2 C6 C5 179.76(15) . . . . ?
Se1 N2 C6 C1 -0.29(18) . . . . ?
Se1 N1 C1 C2 -178.60(14) . . . . ?
Se1 N1 C1 C6 1.0(2) . . . . ?
O4 S2 C16 F5 61.90(16) . . . . ?
O4 S2 C16 F6 -177.99(15) . . . . ?
O4 S2 C16 F4 -58.19(17) . . . . ?
O6 S2 C16 F5 -57.36(16) . . . . ?
O6 S2 C16 F6 62.74(17) . . . . ?
O6 S2 C16 F4 -177.46(15) . . . . ?
O3 S1 C17 F3 61.0(2) . . . . ?
O3 S1 C17 F2 -58.7(2) . . . . ?
O3 S1 C17 F1 -178.8(2) . . . . ?
O5 S2 C16 F5 -177.97(15) . . . . ?
O5 S2 C16 F6 -57.86(17) . . . . ?
O5 S2 C16 F4 61.94(17) . . . . ?
O2 S1 C17 F3 -58.9(2) . . . . ?
O2 S1 C17 F2 -178.6(2) . . . . ?
O2 S1 C17 F1 61.3(2) . . . . ?
N4 Se2 N3 C10 0.61(14) . . . . ?
N4 C15 C14 C13 -178.05(19) . . . . ?
N4 C9 C8 C7 176.42(15) . . . . ?
O1 S1 C17 F3 -178.56(19) . . . . ?
O1 S1 C17 F2 61.7(2) . . . . ?
O1 S1 C17 F1 -58.4(2) . . . . ?
N3 Se2 N4 C15 -0.35(13) . . . . ?
N3 Se2 N4 C9 -176.83(15) . . . . ?
N3 C10 C15 N4 0.5(2) . . . . ?
N3 C10 C15 C14 -177.96(17) . . . . ?
N3 C10 C11 C12 177.79(19) . . . . ?
N2 Se1 N1 C1 -0.97(13) . . . . ?
N2 C7 C8 C9 176.09(15) . . . . ?
N1 Se1 N2 C7 176.45(14) . . . . ?
N1 Se1 N2 C6 0.72(13) . . . . ?
N1 C1 C6 N2 -0.5(2) . . . . ?
N1 C1 C6 C5 179.46(17) . . . . ?
C4 C5 C6 N2 -179.99(18) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C2 C1 N1 -179.36(18) . . . . ?
C3 C2 C1 C6 1.0(3) . . . . ?
C10 C15 C14 C13 0.2(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C15 N4 C9 C8 -83.5(2) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C15 C14 C13 C12 -0.6(3) . . . . ?
C7 N2 C6 C5 4.1(3) . . . . ?
C7 N2 C6 C1 -175.94(16) . . . . ?
C2 C1 C6 N2 179.17(16) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C9 N4 C15 C10 176.53(16) . . . . ?
C9 N4 C15 C14 -5.1(3) . . . . ?
C11 C10 C15 N4 178.79(17) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C6 N2 C7 C8 -123.41(18) . . . . ?
C14 C13 C12 C11 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT430_ll60                
;
PROBLEM: Short Inter D...A Contact  Se1      ..O2       .       2.57 Ang.  
RESPONSE: A short contact between O and Se is expected.
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# end Validation Reply Form
