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

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

data_10a
_database_code_depnum_ccdc_archive 'CCDC 1900132'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-06
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H14 F5 N3 O3 S Se'
_chemical_formula_moiety         'C22 H14 F5 N3 O3 S Se'
_chemical_formula_weight         574.38
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.9213(9)
_cell_length_b                   7.5643(5)
_cell_length_c                   22.5143(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.433(7)
_cell_angle_gamma                90.0000
_cell_volume                     2186.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5484
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144.00
_exptl_absorpt_coefficient_mu    1.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_T_max  0.893

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            18254
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_theta_max         25.405
_diffrn_reflns_theta_min         1.738
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4005
_reflns_number_gt                3385
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0577
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4005
_refine_ls_number_parameters     316
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0249P)²+0.7044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.004
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 1.11197(2) 0.19117(3) 0.47077(2) 0.02394(7) Uani 1 1 d . . . . .
S1 S 0.44642(4) 0.22957(7) 0.42480(2) 0.02948(13) Uani 1 1 d . . . . .
F1 F 0.32370(9) 0.2389(2) 0.42438(7) 0.0490(4) Uani 1 1 d . . . . .
F2 F 0.42746(9) 0.19755(18) 0.35491(6) 0.0390(3) Uani 1 1 d . . . . .
F3 F 0.45597(10) 0.2661(2) 0.49461(6) 0.0433(3) Uani 1 1 d . . . . .
F4 F 0.44263(8) 0.43632(17) 0.41322(6) 0.0388(3) Uani 1 1 d . . . . .
F5 F 0.43785(9) 0.02587(17) 0.43642(6) 0.0387(3) Uani 1 1 d . . . . .
O7 O 1.09271(10) 0.28369(19) 0.58136(6) 0.0288(3) Uani 1 1 d . . . . .
O11 O 0.86930(14) 0.6575(2) 0.81568(8) 0.0494(4) Uani 1 1 d . . . . .
O12 O 0.72167(14) 0.5435(3) 0.78136(9) 0.0633(6) Uani 1 1 d . . . . .
N3 N 0.91071(11) 0.2079(2) 0.42558(7) 0.0207(3) Uani 1 1 d . . . . .
N6 N 0.93045(12) 0.2841(2) 0.52670(7) 0.0234(4) Uani 1 1 d . . . . .
N11 N 0.81383(15) 0.5743(3) 0.77795(9) 0.0390(5) Uani 1 1 d . . . . .
C2 C 0.97140(13) 0.2361(2) 0.47844(9) 0.0213(4) Uani 1 1 d . . . . .
C4 C 0.96377(14) 0.1582(2) 0.37647(9) 0.0212(4) Uani 1 1 d . . . . .
C5 C 1.06723(14) 0.1416(3) 0.39057(9) 0.0249(4) Uani 1 1 d . . . . .
H5 H 1.113230 0.107965 0.362476 0.030 Uiso 1 1 calc R U . . .
C7 C 0.99734(14) 0.3083(2) 0.57715(9) 0.0221(4) Uani 1 1 d . . . . .
C8 C 0.94701(14) 0.3738(3) 0.62954(9) 0.0230(4) Uani 1 1 d . . . . .
C9 C 1.00955(15) 0.4156(3) 0.68219(9) 0.0262(4) Uani 1 1 d . . . . .
H9 H 1.082583 0.396569 0.684645 0.031 Uiso 1 1 calc R U . . .
C10 C 0.96707(16) 0.4839(3) 0.73062(10) 0.0294(4) Uani 1 1 d . . . . .
H10 H 1.009807 0.515577 0.766128 0.035 Uiso 1 1 calc R U . . .
C11 C 0.86005(15) 0.5049(3) 0.72599(9) 0.0290(5) Uani 1 1 d . . . . .
C12 C 0.79560(15) 0.4633(3) 0.67532(10) 0.0307(5) Uani 1 1 d . . . . .
H12 H 0.722381 0.478772 0.673783 0.037 Uiso 1 1 calc R U . . .
C13 C 0.83968(15) 0.3982(3) 0.62648(9) 0.0289(4) Uani 1 1 d . . . . .
H13 H 0.796576 0.370129 0.590735 0.035 Uiso 1 1 calc R U . . .
C14 C 0.79852(13) 0.2118(2) 0.42467(8) 0.0209(4) Uani 1 1 d . . . . .
C15 C 0.75214(14) 0.3634(3) 0.44375(9) 0.0238(4) Uani 1 1 d . . . . .
H15 H 0.793290 0.463497 0.456303 0.029 Uiso 1 1 calc R U . . .
C16 C 0.64504(14) 0.3675(3) 0.44436(9) 0.0254(4) Uani 1 1 d . . . . .
H16 H 0.612202 0.469916 0.457957 0.030 Uiso 1 1 calc R U . . .
C17 C 0.58625(13) 0.2211(3) 0.42497(8) 0.0223(4) Uani 1 1 d . . . . .
C18 C 0.63275(14) 0.0696(3) 0.40536(9) 0.0232(4) Uani 1 1 d . . . . .
H18 H 0.591584 -0.029395 0.391647 0.028 Uiso 1 1 calc R U . . .
C19 C 0.74025(14) 0.0650(3) 0.40610(8) 0.0217(4) Uani 1 1 d . . . . .
H19 H 0.773563 -0.038645 0.393884 0.026 Uiso 1 1 calc R U . . .
C20 C 0.91119(14) 0.1472(3) 0.31480(9) 0.0222(4) Uani 1 1 d . . . . .
C21 C 0.82749(14) 0.2546(3) 0.29332(9) 0.0253(4) Uani 1 1 d . . . . .
H21 H 0.796435 0.329644 0.320146 0.030 Uiso 1 1 calc R U . . .
C22 C 0.78906(15) 0.2531(3) 0.23328(10) 0.0293(4) Uani 1 1 d . . . . .
H22 H 0.731991 0.326983 0.219344 0.035 Uiso 1 1 calc R U . . .
C23 C 0.83311(16) 0.1453(3) 0.19380(10) 0.0323(5) Uani 1 1 d . . . . .
H23 H 0.806910 0.145267 0.152653 0.039 Uiso 1 1 calc R U . . .
C24 C 0.91587(16) 0.0369(3) 0.21432(10) 0.0336(5) Uani 1 1 d . . . . .
H24 H 0.946360 -0.037809 0.187159 0.040 Uiso 1 1 calc R U . . .
C25 C 0.95441(15) 0.0368(3) 0.27437(9) 0.0274(4) Uani 1 1 d . . . . .
H25 H 1.010692 -0.038920 0.288116 0.033 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.871(2) . ?
Se1 C2 1.8748(17) . ?
S1 F5 1.5689(14) . ?
S1 F2 1.5839(14) . ?
S1 F4 1.5854(14) . ?
S1 F1 1.5863(12) . ?
S1 F3 1.5868(14) . ?
S1 C17 1.8075(18) . ?
O7 C7 1.239(2) . ?
O11 N11 1.222(3) . ?
O12 N11 1.224(2) . ?
N3 C2 1.367(3) . ?
N3 C4 1.415(2) . ?
N3 C14 1.448(2) . ?
N6 C2 1.312(2) . ?
N6 C7 1.360(3) . ?
N11 C11 1.469(3) . ?
C4 C5 1.345(3) . ?
C4 C20 1.478(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.494(3) . ?
C8 C13 1.393(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.380(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.395(3) . ?
C20 C25 1.397(3) . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(3) . ?
C24 H24 0.9500 . ?
C25 H25 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
C5 Se1 C2 85.84(8) . . ?
F5 S1 F2 90.55(8) . . ?
F5 S1 F4 174.16(7) . . ?
F2 S1 F4 89.36(8) . . ?
F5 S1 F1 87.45(7) . . ?
F2 S1 F1 87.57(7) . . ?
F4 S1 F1 86.72(7) . . ?
F5 S1 F3 90.28(8) . . ?
F2 S1 F3 175.45(7) . . ?
F4 S1 F3 89.36(8) . . ?
F1 S1 F3 87.99(8) . . ?
F5 S1 C17 93.10(8) . . ?
F2 S1 C17 92.29(8) . . ?
F4 S1 C17 92.74(8) . . ?
F1 S1 C17 179.44(10) . . ?
F3 S1 C17 92.14(8) . . ?
C2 N3 C4 116.16(15) . . ?
C2 N3 C14 119.01(15) . . ?
C4 N3 C14 124.49(15) . . ?
C2 N6 C7 116.83(16) . . ?
O11 N11 O12 123.59(19) . . ?
O11 N11 C11 118.57(18) . . ?
O12 N11 C11 117.83(19) . . ?
N6 C2 N3 121.28(16) . . ?
N6 C2 Se1 127.68(15) . . ?
N3 C2 Se1 111.02(13) . . ?
C5 C4 N3 113.33(17) . . ?
C5 C4 C20 123.82(17) . . ?
N3 C4 C20 122.46(16) . . ?
C4 C5 Se1 113.62(14) . . ?
C4 C5 H5 123.2 . . ?
Se1 C5 H5 123.2 . . ?
O7 C7 N6 125.22(18) . . ?
O7 C7 C8 120.45(17) . . ?
N6 C7 C8 114.32(16) . . ?
C13 C8 C9 119.42(18) . . ?
C13 C8 C7 121.60(18) . . ?
C9 C8 C7 118.96(17) . . ?
C10 C9 C8 120.96(18) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 117.88(19) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C12 C11 C10 123.00(19) . . ?
C12 C11 N11 118.77(18) . . ?
C10 C11 N11 118.23(19) . . ?
C11 C12 C13 118.48(19) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C8 120.25(19) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C19 C14 C15 121.34(17) . . ?
C19 C14 N3 119.95(16) . . ?
C15 C14 N3 118.71(16) . . ?
C14 C15 C16 119.31(18) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 119.44(18) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.22(16) . . ?
C16 C17 S1 119.00(14) . . ?
C18 C17 S1 119.78(15) . . ?
C19 C18 C17 119.01(18) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C14 C19 C18 119.66(17) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C25 118.23(19) . . ?
C21 C20 C4 123.35(18) . . ?
C25 C20 C4 118.06(17) . . ?
C22 C21 C20 120.82(19) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.7(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 120.30(19) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 120.58(19) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 179.78(17) . . . . ?
C7 N6 C2 Se1 1.6(3) . . . . ?
C4 N3 C2 N6 179.41(17) . . . . ?
C14 N3 C2 N6 -7.0(3) . . . . ?
C4 N3 C2 Se1 -2.1(2) . . . . ?
C14 N3 C2 Se1 171.48(13) . . . . ?
C5 Se1 C2 N6 179.73(19) . . . . ?
C5 Se1 C2 N3 1.38(14) . . . . ?
C2 N3 C4 C5 1.8(2) . . . . ?
C14 N3 C4 C5 -171.37(17) . . . . ?
C2 N3 C4 C20 -171.33(17) . . . . ?
C14 N3 C4 C20 15.5(3) . . . . ?
N3 C4 C5 Se1 -0.6(2) . . . . ?
C20 C4 C5 Se1 172.42(15) . . . . ?
C2 Se1 C5 C4 -0.41(15) . . . . ?
C2 N6 C7 O7 -2.2(3) . . . . ?
C2 N6 C7 C8 176.31(16) . . . . ?
O7 C7 C8 C13 -178.30(18) . . . . ?
N6 C7 C8 C13 3.1(3) . . . . ?
O7 C7 C8 C9 3.3(3) . . . . ?
N6 C7 C8 C9 -175.30(17) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?
C7 C8 C9 C10 177.04(18) . . . . ?
C8 C9 C10 C11 1.8(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 N11 178.76(19) . . . . ?
O11 N11 C11 C12 -159.3(2) . . . . ?
O12 N11 C11 C12 21.6(3) . . . . ?
O11 N11 C11 C10 21.0(3) . . . . ?
O12 N11 C11 C10 -158.1(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
N11 C11 C12 C13 179.89(19) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
C7 C8 C13 C12 -178.40(19) . . . . ?
C2 N3 C14 C19 -120.8(2) . . . . ?
C4 N3 C14 C19 52.2(3) . . . . ?
C2 N3 C14 C15 58.0(2) . . . . ?
C4 N3 C14 C15 -128.98(19) . . . . ?
C19 C14 C15 C16 0.2(3) . . . . ?
N3 C14 C15 C16 -178.59(17) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C15 C16 C17 S1 -178.97(15) . . . . ?
F5 S1 C17 C16 -149.54(16) . . . . ?
F2 S1 C17 C16 119.79(16) . . . . ?
F4 S1 C17 C16 30.32(16) . . . . ?
F3 S1 C17 C16 -59.15(17) . . . . ?
F5 S1 C17 C18 30.97(17) . . . . ?
F2 S1 C17 C18 -59.70(17) . . . . ?
F4 S1 C17 C18 -149.17(16) . . . . ?
F3 S1 C17 C18 121.37(16) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
S1 C17 C18 C19 -179.65(14) . . . . ?
C15 C14 C19 C18 1.2(3) . . . . ?
N3 C14 C19 C18 179.97(17) . . . . ?
C17 C18 C19 C14 -1.7(3) . . . . ?
C5 C4 C20 C21 -141.3(2) . . . . ?
N3 C4 C20 C21 31.1(3) . . . . ?
C5 C4 C20 C25 31.8(3) . . . . ?
N3 C4 C20 C25 -155.79(17) . . . . ?
C25 C20 C21 C22 -0.7(3) . . . . ?
C4 C20 C21 C22 172.35(18) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 -0.7(3) . . . . ?
C21 C20 C25 C24 1.1(3) . . . . ?
C4 C20 C25 C24 -172.37(18) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_10d
_database_code_depnum_ccdc_archive 'CCDC 1900135'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-04
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H16 F5 N3 O3 S Se'
_chemical_formula_moiety         'C23 H16 F5 N3 O3 S Se'
_chemical_formula_weight         588.41
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.2003(7)
_cell_length_b                   17.8940(13)
_cell_length_c                   12.5877(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.325(3)
_cell_angle_gamma                90.0000
_cell_volume                     2287.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12623
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176.00
_exptl_absorpt_coefficient_mu    1.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.947

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            16920
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4177
_reflns_number_gt                2636
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0661
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4177
_refine_ls_number_parameters     326
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0267P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.67557(4) 0.09888(2) 0.20293(3) 0.02799(13) Uani 1 1 d . . . . .
S1 S 0.76331(10) 0.54767(5) 0.43542(8) 0.0228(2) Uani 1 1 d . . . . .
F1 F 0.7766(2) 0.62644(10) 0.49328(16) 0.0322(6) Uani 1 1 d . . . . .
F2 F 0.6308(2) 0.53654(11) 0.48985(18) 0.0367(6) Uani 1 1 d . . . . .
F3 F 0.6853(2) 0.58828(11) 0.33786(17) 0.0401(6) Uani 1 1 d . . . . .
F4 F 0.8977(2) 0.56577(11) 0.38778(17) 0.0335(6) Uani 1 1 d . . . . .
F5 F 0.8429(2) 0.51274(10) 0.53803(15) 0.0279(5) Uani 1 1 d . . . . .
O7 O 0.5311(2) 0.07395(13) 0.3538(2) 0.0275(6) Uani 1 1 d . . . . .
O11 O 0.1499(3) 0.11917(17) 0.7692(2) 0.0456(8) Uani 1 1 d . . . . .
O12 O 0.1917(3) 0.23729(18) 0.7742(3) 0.0587(10) Uani 1 1 d . . . . .
N3 N 0.7136(3) 0.24663(15) 0.2285(2) 0.0183(7) Uani 1 1 d . . . . .
N6 N 0.5754(3) 0.20104(15) 0.3524(2) 0.0198(7) Uani 1 1 d . . . . .
N11 N 0.2043(3) 0.1744(2) 0.7380(3) 0.0348(9) Uani 1 1 d . . . . .
C2 C 0.6458(4) 0.19011(18) 0.2720(3) 0.0203(9) Uani 1 1 d . . . . .
C4 C 0.7862(4) 0.22700(19) 0.1424(3) 0.0236(9) Uani 1 1 d . . . . .
C5 C 0.7792(4) 0.1548(2) 0.1181(3) 0.0291(10) Uani 1 1 d . . . . .
H5 H 0.823401 0.133508 0.062191 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5189(4) 0.1381(2) 0.3901(3) 0.0224(9) Uani 1 1 d . . . . .
C8 C 0.4401(3) 0.14953(18) 0.4828(3) 0.0201(8) Uani 1 1 d . . . . .
C9 C 0.4256(4) 0.21978(19) 0.5278(3) 0.0239(9) Uani 1 1 d . . . . .
H9 H 0.467586 0.261978 0.500157 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3499(4) 0.2282(2) 0.6130(3) 0.0269(9) Uani 1 1 d . . . . .
H10 H 0.339619 0.275782 0.644560 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2898(3) 0.1657(2) 0.6508(3) 0.0234(9) Uani 1 1 d . . . . .
C12 C 0.3048(3) 0.0955(2) 0.6099(3) 0.0257(9) Uani 1 1 d . . . . .
H12 H 0.263980 0.053438 0.639059 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3803(3) 0.08742(19) 0.5255(3) 0.0245(9) Uani 1 1 d . . . . .
H13 H 0.391931 0.039269 0.496015 0.029 Uiso 1 1 calc R U . . .
C14 C 0.7247(3) 0.31886(18) 0.2789(3) 0.0179(8) Uani 1 1 d . . . . .
C15 C 0.8476(3) 0.34523(18) 0.3152(3) 0.0185(8) Uani 1 1 d . . . . .
H15 H 0.923656 0.315531 0.308652 0.022 Uiso 1 1 calc R U . . .
C16 C 0.8592(4) 0.41557(18) 0.3612(3) 0.0202(8) Uani 1 1 d . . . . .
H16 H 0.943334 0.434553 0.386432 0.024 Uiso 1 1 calc R U . . .
C17 C 0.7480(3) 0.45766(18) 0.3702(3) 0.0179(8) Uani 1 1 d . . . . .
C18 C 0.6248(4) 0.43202(19) 0.3343(3) 0.0252(9) Uani 1 1 d . . . . .
H18 H 0.549181 0.462021 0.340820 0.030 Uiso 1 1 calc R U . . .
C19 C 0.6128(3) 0.36168(19) 0.2884(3) 0.0215(9) Uani 1 1 d . . . . .
H19 H 0.528413 0.342830 0.263534 0.026 Uiso 1 1 calc R U . . .
C20 C 0.8525(3) 0.28390(18) 0.0808(3) 0.0195(8) Uani 1 1 d . . . . .
C21 C 0.9706(4) 0.2645(2) 0.0405(3) 0.0246(9) Uani 1 1 d . . . . .
H21 H 1.012232 0.218543 0.061004 0.029 Uiso 1 1 calc R U . . .
C22 C 1.0278(4) 0.3116(2) -0.0292(3) 0.0286(10) Uani 1 1 d . . . . .
H22 H 1.107477 0.297003 -0.056862 0.034 Uiso 1 1 calc R U . . .
C23 C 0.9709(4) 0.3798(2) -0.0596(3) 0.0298(10) Uani 1 1 d . . . . .
C24 C 0.8556(4) 0.3990(2) -0.0168(3) 0.0287(9) Uani 1 1 d . . . . .
H24 H 0.815949 0.445858 -0.035215 0.034 Uiso 1 1 calc R U . . .
C25 C 0.7961(4) 0.3525(2) 0.0519(3) 0.0245(9) Uani 1 1 d . . . . .
H25 H 0.716502 0.367433 0.079512 0.029 Uiso 1 1 calc R U . . .
C26 C 1.0324(4) 0.4297(2) -0.1386(3) 0.0454(12) Uani 1 1 d . . . . .
H26A H 0.998298 0.416087 -0.211388 0.054 Uiso 1 1 calc R U . . .
H26B H 1.128256 0.423457 -0.130490 0.054 Uiso 1 1 calc R U . . .
H26C H 1.010448 0.481998 -0.125103 0.054 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.863(4) . ?
Se1 C2 1.887(3) . ?
S1 F3 1.577(2) . ?
S1 F4 1.580(2) . ?
S1 F2 1.584(2) . ?
S1 F1 1.586(2) . ?
S1 F5 1.589(2) . ?
S1 C17 1.808(3) . ?
O7 C7 1.245(4) . ?
O11 N11 1.217(4) . ?
O12 N11 1.225(4) . ?
N3 C2 1.368(4) . ?
N3 C4 1.413(4) . ?
N3 C14 1.440(4) . ?
N6 C2 1.309(4) . ?
N6 C7 1.370(4) . ?
N11 C11 1.472(5) . ?
C4 C5 1.328(5) . ?
C4 C20 1.481(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.492(5) . ?
C8 C9 1.392(5) . ?
C8 C13 1.399(5) . ?
C9 C10 1.386(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.378(5) . ?
C14 C19 1.389(5) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(5) . ?
C18 C19 1.386(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.390(5) . ?
C20 C21 1.394(5) . ?
C21 C22 1.384(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(5) . ?
C23 C26 1.516(5) . ?
C24 C25 1.381(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Se1 C2 85.61(16) . . ?
F3 S1 F4 90.16(13) . . ?
F3 S1 F2 90.33(13) . . ?
F4 S1 F2 174.52(12) . . ?
F3 S1 F1 87.92(11) . . ?
F4 S1 F1 87.24(12) . . ?
F2 S1 F1 87.33(12) . . ?
F3 S1 F5 175.68(11) . . ?
F4 S1 F5 89.60(12) . . ?
F2 S1 F5 89.51(12) . . ?
F1 S1 F5 87.76(11) . . ?
F3 S1 C17 92.33(14) . . ?
F4 S1 C17 92.95(14) . . ?
F2 S1 C17 92.48(14) . . ?
F1 S1 C17 179.69(15) . . ?
F5 S1 C17 92.00(13) . . ?
C2 N3 C4 116.3(3) . . ?
C2 N3 C14 120.6(3) . . ?
C4 N3 C14 122.4(3) . . ?
C2 N6 C7 115.0(3) . . ?
O11 N11 O12 124.0(3) . . ?
O11 N11 C11 118.3(3) . . ?
O12 N11 C11 117.7(3) . . ?
N6 C2 N3 122.2(3) . . ?
N6 C2 Se1 127.5(3) . . ?
N3 C2 Se1 110.3(3) . . ?
C5 C4 N3 113.5(3) . . ?
C5 C4 C20 124.4(3) . . ?
N3 C4 C20 121.9(3) . . ?
C4 C5 Se1 114.3(3) . . ?
C4 C5 H5 122.8 . . ?
Se1 C5 H5 122.8 . . ?
O7 C7 N6 124.9(3) . . ?
O7 C7 C8 119.5(3) . . ?
N6 C7 C8 115.6(3) . . ?
C9 C8 C13 119.6(3) . . ?
C9 C8 C7 121.9(3) . . ?
C13 C8 C7 118.5(3) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C12 C11 C10 122.9(3) . . ?
C12 C11 N11 118.1(3) . . ?
C10 C11 N11 118.9(3) . . ?
C11 C12 C13 118.4(3) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C15 C14 C19 120.8(3) . . ?
C15 C14 N3 119.0(3) . . ?
C19 C14 N3 120.1(3) . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 S1 119.0(3) . . ?
C16 C17 S1 119.2(3) . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 119.7(3) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C25 C20 C21 118.4(3) . . ?
C25 C20 C4 123.1(3) . . ?
C21 C20 C4 118.1(3) . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 121.3(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 117.4(4) . . ?
C24 C23 C26 121.9(4) . . ?
C22 C23 C26 120.7(4) . . ?
C25 C24 C23 122.3(4) . . ?
C25 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C24 C25 C20 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C20 C25 H25 120.0 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 -176.9(3) . . . . ?
C7 N6 C2 Se1 0.7(5) . . . . ?
C4 N3 C2 N6 179.7(3) . . . . ?
C14 N3 C2 N6 8.5(5) . . . . ?
C4 N3 C2 Se1 1.7(4) . . . . ?
C14 N3 C2 Se1 -169.5(2) . . . . ?
C5 Se1 C2 N6 -179.0(3) . . . . ?
C5 Se1 C2 N3 -1.2(3) . . . . ?
C2 N3 C4 C5 -1.3(5) . . . . ?
C14 N3 C4 C5 169.7(3) . . . . ?
C2 N3 C4 C20 173.5(3) . . . . ?
C14 N3 C4 C20 -15.5(5) . . . . ?
N3 C4 C5 Se1 0.3(4) . . . . ?
C20 C4 C5 Se1 -174.4(3) . . . . ?
C2 Se1 C5 C4 0.5(3) . . . . ?
C2 N6 C7 O7 0.4(5) . . . . ?
C2 N6 C7 C8 179.1(3) . . . . ?
O7 C7 C8 C9 178.7(3) . . . . ?
N6 C7 C8 C9 -0.1(5) . . . . ?
O7 C7 C8 C13 -0.9(5) . . . . ?
N6 C7 C8 C13 -179.7(3) . . . . ?
C13 C8 C9 C10 -1.4(5) . . . . ?
C7 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 1.9(6) . . . . ?
C9 C10 C11 N11 -177.3(3) . . . . ?
O11 N11 C11 C12 -0.6(5) . . . . ?
O12 N11 C11 C12 179.9(4) . . . . ?
O11 N11 C11 C10 178.6(3) . . . . ?
O12 N11 C11 C10 -0.9(5) . . . . ?
C10 C11 C12 C13 -1.7(6) . . . . ?
N11 C11 C12 C13 177.4(3) . . . . ?
C11 C12 C13 C8 0.0(5) . . . . ?
C9 C8 C13 C12 1.5(5) . . . . ?
C7 C8 C13 C12 -178.9(3) . . . . ?
C2 N3 C14 C15 117.9(4) . . . . ?
C4 N3 C14 C15 -52.7(5) . . . . ?
C2 N3 C14 C19 -63.5(4) . . . . ?
C4 N3 C14 C19 125.8(4) . . . . ?
C19 C14 C15 C16 -0.3(5) . . . . ?
N3 C14 C15 C16 178.3(3) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C15 C16 C17 S1 177.4(3) . . . . ?
F3 S1 C17 C18 -55.0(3) . . . . ?
F4 S1 C17 C18 -145.2(3) . . . . ?
F2 S1 C17 C18 35.5(3) . . . . ?
F5 S1 C17 C18 125.0(3) . . . . ?
F3 S1 C17 C16 127.4(3) . . . . ?
F4 S1 C17 C16 37.1(3) . . . . ?
F2 S1 C17 C16 -142.2(3) . . . . ?
F5 S1 C17 C16 -52.6(3) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
S1 C17 C18 C19 -177.3(3) . . . . ?
C17 C18 C19 C14 -0.4(5) . . . . ?
C15 C14 C19 C18 0.4(5) . . . . ?
N3 C14 C19 C18 -178.2(3) . . . . ?
C5 C4 C20 C25 133.8(4) . . . . ?
N3 C4 C20 C25 -40.4(5) . . . . ?
C5 C4 C20 C21 -39.2(5) . . . . ?
N3 C4 C20 C21 146.5(3) . . . . ?
C25 C20 C21 C22 -2.0(5) . . . . ?
C4 C20 C21 C22 171.4(3) . . . . ?
C20 C21 C22 C23 1.1(6) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C21 C22 C23 C26 -178.1(3) . . . . ?
C22 C23 C24 C25 -1.3(6) . . . . ?
C26 C23 C24 C25 177.4(4) . . . . ?
C23 C24 C25 C20 0.4(6) . . . . ?
C21 C20 C25 C24 1.2(5) . . . . ?
C4 C20 C25 C24 -171.8(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1900137'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-06
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H14 Br Cl N2 O Se'
_chemical_formula_moiety         'C22 H14 Br Cl N2 O Se'
_chemical_formula_weight         516.68
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.3066(7)
_cell_length_b                   11.8464(8)
_cell_length_c                   15.0693(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.197(7)
_cell_angle_gamma                90.0000
_cell_volume                     2015.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5309
_cell_measurement_theta_min      1.40
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016.00
_exptl_absorpt_coefficient_mu    4.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_T_max  0.619

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            17162
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_theta_max         25.412
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3680
_reflns_number_gt                3114
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0612
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3680
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0311P)²+0.5042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br17 Br 0.57943(2) 1.05558(2) 0.66732(2) 0.04201(9) Uani 1 1 d . . . . .
Se1 Se 0.68709(2) 0.34404(2) 0.55507(2) 0.03692(9) Uani 1 1 d . . . . .
Cl23 Cl 1.10894(6) 0.91694(6) 0.41544(4) 0.04482(16) Uani 1 1 d . . . . .
O7 O 0.51896(17) 0.29358(13) 0.65341(12) 0.0432(4) Uani 1 1 d . . . . .
N3 N 0.69567(16) 0.56736(15) 0.58422(13) 0.0287(4) Uani 1 1 d . . . . .
N6 N 0.54160(17) 0.48638(16) 0.66041(12) 0.0309(4) Uani 1 1 d . . . . .
C2 C 0.6311(2) 0.47705(19) 0.60869(14) 0.0291(5) Uani 1 1 d . . . . .
C4 C 0.7887(2) 0.54602(19) 0.52709(15) 0.0315(5) Uani 1 1 d . . . . .
C5 C 0.7983(2) 0.4384(2) 0.50395(17) 0.0379(6) Uani 1 1 d . . . . .
H5 H 0.855728 0.411739 0.465329 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4885(2) 0.38710(19) 0.68155(14) 0.0316(5) Uani 1 1 d . . . . .
C8 C 0.3888(2) 0.39431(19) 0.74194(15) 0.0311(5) Uani 1 1 d . . . . .
C9 C 0.3292(2) 0.2956(2) 0.76368(16) 0.0381(6) Uani 1 1 d . . . . .
H9 H 0.350421 0.225765 0.737910 0.046 Uiso 1 1 calc R U . . .
C10 C 0.2398(2) 0.2988(2) 0.82230(17) 0.0439(6) Uani 1 1 d . . . . .
H10 H 0.198882 0.231489 0.836049 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2096(2) 0.3999(3) 0.86112(19) 0.0484(7) Uani 1 1 d . . . . .
H11 H 0.149252 0.401676 0.902531 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2672(2) 0.4984(2) 0.8397(2) 0.0475(7) Uani 1 1 d . . . . .
H12 H 0.245634 0.567867 0.865777 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3562(2) 0.4958(2) 0.78010(17) 0.0373(6) Uani 1 1 d . . . . .
H13 H 0.395259 0.563708 0.765274 0.045 Uiso 1 1 calc R U . . .
C14 C 0.66281(19) 0.68130(18) 0.60658(14) 0.0260(5) Uani 1 1 d . . . . .
C15 C 0.6754(2) 0.71863(19) 0.69335(15) 0.0321(5) Uani 1 1 d . . . . .
H15 H 0.700124 0.668289 0.739833 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6513(2) 0.8311(2) 0.71167(15) 0.0329(5) Uani 1 1 d . . . . .
H16 H 0.660345 0.858478 0.770912 0.040 Uiso 1 1 calc R U . . .
C17 C 0.61444(19) 0.90260(18) 0.64366(16) 0.0300(5) Uani 1 1 d . . . . .
C18 C 0.6008(2) 0.8644(2) 0.55711(16) 0.0340(5) Uani 1 1 d . . . . .
H18 H 0.575369 0.914434 0.510620 0.041 Uiso 1 1 calc R U . . .
C19 C 0.62445(19) 0.7529(2) 0.53889(15) 0.0318(5) Uani 1 1 d . . . . .
H19 H 0.614318 0.725473 0.479722 0.038 Uiso 1 1 calc R U . . .
C20 C 0.86660(19) 0.63942(19) 0.50108(15) 0.0298(5) Uani 1 1 d . . . . .
C21 C 0.9213(2) 0.7123(2) 0.56353(15) 0.0328(5) Uani 1 1 d . . . . .
H21 H 0.907754 0.703079 0.624764 0.039 Uiso 1 1 calc R U . . .
C22 C 0.9947(2) 0.7977(2) 0.53733(15) 0.0332(5) Uani 1 1 d . . . . .
H22 H 1.031181 0.847558 0.580037 0.040 Uiso 1 1 calc R U . . .
C23 C 1.0146(2) 0.8098(2) 0.44821(16) 0.0331(5) Uani 1 1 d . . . . .
C24 C 0.9631(2) 0.7381(2) 0.38535(16) 0.0365(5) Uani 1 1 d . . . . .
H24 H 0.978054 0.747152 0.324355 0.044 Uiso 1 1 calc R U . . .
C25 C 0.8894(2) 0.6529(2) 0.41186(15) 0.0338(5) Uani 1 1 d . . . . .
H25 H 0.853864 0.603092 0.368765 0.041 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br17 C17 1.893(2) . ?
Se1 C5 1.879(3) . ?
Se1 C2 1.896(2) . ?
Cl23 C23 1.747(2) . ?
O7 C7 1.242(3) . ?
N3 C2 1.358(3) . ?
N3 C4 1.419(3) . ?
N3 C14 1.445(3) . ?
N6 C2 1.316(3) . ?
N6 C7 1.366(3) . ?
C4 C5 1.328(3) . ?
C4 C20 1.481(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.490(3) . ?
C8 C13 1.391(3) . ?
C8 C9 1.398(3) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.378(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.392(3) . ?
C20 C21 1.396(3) . ?
C21 C22 1.381(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(3) . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 H25 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
C5 Se1 C2 85.83(10) . . ?
C2 N3 C4 116.91(18) . . ?
C2 N3 C14 121.57(18) . . ?
C4 N3 C14 121.13(18) . . ?
C2 N6 C7 115.36(19) . . ?
N6 C2 N3 122.5(2) . . ?
N6 C2 Se1 127.48(17) . . ?
N3 C2 Se1 109.98(15) . . ?
C5 C4 N3 113.9(2) . . ?
C5 C4 C20 126.1(2) . . ?
N3 C4 C20 119.97(19) . . ?
C4 C5 Se1 113.40(18) . . ?
C4 C5 H5 123.3 . . ?
Se1 C5 H5 123.3 . . ?
O7 C7 N6 123.7(2) . . ?
O7 C7 C8 119.6(2) . . ?
N6 C7 C8 116.8(2) . . ?
C13 C8 C9 119.0(2) . . ?
C13 C8 C7 121.9(2) . . ?
C9 C8 C7 119.1(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C19 C14 C15 121.0(2) . . ?
C19 C14 N3 118.49(19) . . ?
C15 C14 N3 120.4(2) . . ?
C14 C15 C16 118.9(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 Br17 120.45(17) . . ?
C18 C17 Br17 118.56(17) . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C14 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C25 C20 C21 118.8(2) . . ?
C25 C20 C4 119.1(2) . . ?
C21 C20 C4 122.1(2) . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 119.1(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 121.3(2) . . ?
C24 C23 Cl23 119.68(19) . . ?
C22 C23 Cl23 119.00(19) . . ?
C23 C24 C25 119.4(2) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C20 120.7(2) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 -177.7(2) . . . . ?
C7 N6 C2 Se1 4.3(3) . . . . ?
C4 N3 C2 N6 -179.0(2) . . . . ?
C14 N3 C2 N6 -6.1(3) . . . . ?
C4 N3 C2 Se1 -0.7(2) . . . . ?
C14 N3 C2 Se1 172.25(16) . . . . ?
C5 Se1 C2 N6 178.4(2) . . . . ?
C5 Se1 C2 N3 0.13(17) . . . . ?
C2 N3 C4 C5 1.1(3) . . . . ?
C14 N3 C4 C5 -171.9(2) . . . . ?
C2 N3 C4 C20 -177.1(2) . . . . ?
C14 N3 C4 C20 10.0(3) . . . . ?
N3 C4 C5 Se1 -0.9(3) . . . . ?
C20 C4 C5 Se1 177.08(19) . . . . ?
C2 Se1 C5 C4 0.5(2) . . . . ?
C2 N6 C7 O7 -1.5(3) . . . . ?
C2 N6 C7 C8 178.47(19) . . . . ?
O7 C7 C8 C13 175.6(2) . . . . ?
N6 C7 C8 C13 -4.4(3) . . . . ?
O7 C7 C8 C9 -1.8(3) . . . . ?
N6 C7 C8 C9 178.2(2) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 C10 177.3(2) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 C12 1.5(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
C9 C8 C13 C12 0.9(4) . . . . ?
C7 C8 C13 C12 -176.6(2) . . . . ?
C2 N3 C14 C19 -112.3(2) . . . . ?
C4 N3 C14 C19 60.3(3) . . . . ?
C2 N3 C14 C15 70.8(3) . . . . ?
C4 N3 C14 C15 -116.5(2) . . . . ?
C19 C14 C15 C16 -1.5(3) . . . . ?
N3 C14 C15 C16 175.3(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C15 C16 C17 Br17 179.26(18) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
Br17 C17 C18 C19 -179.18(17) . . . . ?
C17 C18 C19 C14 -0.9(3) . . . . ?
C15 C14 C19 C18 1.6(4) . . . . ?
N3 C14 C19 C18 -175.2(2) . . . . ?
C5 C4 C20 C25 50.2(3) . . . . ?
N3 C4 C20 C25 -131.9(2) . . . . ?
C5 C4 C20 C21 -127.7(3) . . . . ?
N3 C4 C20 C21 50.2(3) . . . . ?
C25 C20 C21 C22 1.3(3) . . . . ?
C4 C20 C21 C22 179.1(2) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C21 C22 C23 Cl23 -179.26(18) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
Cl23 C23 C24 C25 179.41(18) . . . . ?
C23 C24 C25 C20 0.2(3) . . . . ?
C21 C20 C25 C24 -1.1(3) . . . . ?
C4 C20 C25 C24 -179.0(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1900136'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-07
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H17 Br N2 O2 Se'
_chemical_formula_moiety         'C23 H17 Br N2 O2 Se'
_chemical_formula_weight         512.26
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.5971(6)
_cell_length_b                   10.5881(7)
_cell_length_c                   11.4042(7)
_cell_angle_alpha                65.702(6)
_cell_angle_beta                 79.265(6)
_cell_angle_gamma                87.524(7)
_cell_volume                     1036.98(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6261
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.310
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508.00
_exptl_absorpt_coefficient_mu    3.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.231
_exptl_absorpt_correction_T_max  0.311

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            8659
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_theta_max         25.389
_diffrn_reflns_theta_min         2.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3657
_reflns_number_gt                3082
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0834
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3657
_refine_ls_number_parameters     263
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0289P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br17 Br 0.42625(3) 0.03719(3) 0.76168(2) 0.03179(12) Uani 1 1 d . . . . .
Se1 Se 0.62687(3) 0.69722(3) -0.02135(2) 0.03117(11) Uani 1 1 d . . . . .
O7 O 0.36534(19) 0.7692(2) 0.00018(18) 0.0362(5) Uani 1 1 d . . . . .
O23 O 1.1606(2) 0.10199(19) 0.3540(2) 0.0366(5) Uani 1 1 d . . . . .
N3 N 0.6070(2) 0.4750(2) 0.20748(19) 0.0210(4) Uani 1 1 d . . . . .
N6 N 0.3913(2) 0.5872(2) 0.19373(19) 0.0236(5) Uani 1 1 d . . . . .
C2 C 0.5220(3) 0.5773(2) 0.1423(2) 0.0229(5) Uani 1 1 d . . . . .
C4 C 0.7497(3) 0.4818(3) 0.1463(2) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.7827(3) 0.5886(3) 0.0298(3) 0.0331(6) Uani 1 1 d . . . . .
H5 H 0.875477 0.607658 -0.021906 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3185(3) 0.6925(2) 0.1156(2) 0.0256(6) Uani 1 1 d . . . . .
C8 C 0.1752(3) 0.7132(2) 0.1798(2) 0.0240(5) Uani 1 1 d . . . . .
C9 C 0.0821(3) 0.7981(3) 0.1027(3) 0.0326(6) Uani 1 1 d . . . . .
H9 H 0.111835 0.843449 0.010514 0.039 Uiso 1 1 calc R U . . .
C10 C -0.0520(3) 0.8166(3) 0.1594(3) 0.0404(7) Uani 1 1 d . . . . .
H10 H -0.115286 0.872401 0.105737 0.048 Uiso 1 1 calc R U . . .
C11 C -0.0961(3) 0.7547(3) 0.2940(3) 0.0389(7) Uani 1 1 d . . . . .
H11 H -0.188785 0.768619 0.332603 0.047 Uiso 1 1 calc R U . . .
C12 C -0.0038(3) 0.6722(3) 0.3722(3) 0.0329(6) Uani 1 1 d . . . . .
H12 H -0.032601 0.630898 0.464732 0.039 Uiso 1 1 calc R U . . .
C13 C 0.1301(3) 0.6502(2) 0.3154(2) 0.0251(5) Uani 1 1 d . . . . .
H13 H 0.191964 0.591753 0.369097 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5559(2) 0.3749(2) 0.3395(2) 0.0202(5) Uani 1 1 d . . . . .
C15 C 0.4683(3) 0.2656(3) 0.3607(2) 0.0273(6) Uani 1 1 d . . . . .
H15 H 0.437139 0.258276 0.289309 0.033 Uiso 1 1 calc R U . . .
C16 C 0.4251(3) 0.1645(3) 0.4886(3) 0.0288(6) Uani 1 1 d . . . . .
H16 H 0.363987 0.088276 0.505547 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4738(2) 0.1790(3) 0.5890(2) 0.0225(5) Uani 1 1 d . . . . .
C18 C 0.5570(3) 0.2901(3) 0.5691(2) 0.0263(5) Uani 1 1 d . . . . .
H18 H 0.585133 0.299310 0.640919 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6002(3) 0.3900(3) 0.4417(2) 0.0245(5) Uani 1 1 d . . . . .
H19 H 0.659218 0.467336 0.425484 0.029 Uiso 1 1 calc R U . . .
C20 C 0.8485(2) 0.3753(3) 0.2089(2) 0.0222(5) Uani 1 1 d . . . . .
C21 C 0.8356(3) 0.2390(3) 0.2254(3) 0.0297(6) Uani 1 1 d . . . . .
H21 H 0.755914 0.209838 0.203199 0.036 Uiso 1 1 calc R U . . .
C22 C 0.9375(3) 0.1443(3) 0.2740(3) 0.0311(6) Uani 1 1 d . . . . .
H22 H 0.927531 0.051145 0.284611 0.037 Uiso 1 1 calc R U . . .
C23 C 1.0535(3) 0.1861(3) 0.3070(2) 0.0260(5) Uani 1 1 d . . . . .
C24 C 1.0673(3) 0.3221(3) 0.2921(2) 0.0269(5) Uani 1 1 d . . . . .
H24 H 1.146613 0.350890 0.315168 0.032 Uiso 1 1 calc R U . . .
C25 C 0.9654(3) 0.4154(3) 0.2435(2) 0.0264(5) Uani 1 1 d . . . . .
H25 H 0.975155 0.508315 0.233594 0.032 Uiso 1 1 calc R U . . .
C26 C 1.1553(3) -0.0356(3) 0.3622(3) 0.0431(8) Uani 1 1 d . . . . .
H26A H 1.236385 -0.085620 0.398386 0.052 Uiso 1 1 calc R U . . .
H26B H 1.159139 -0.032473 0.274537 0.052 Uiso 1 1 calc R U . . .
H26C H 1.066870 -0.083356 0.419180 0.052 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br17 C17 1.906(2) . ?
Se1 C5 1.877(3) . ?
Se1 C2 1.889(2) . ?
O7 C7 1.235(3) . ?
O23 C23 1.367(3) . ?
O23 C26 1.423(4) . ?
N3 C2 1.370(3) . ?
N3 C4 1.407(3) . ?
N3 C14 1.445(3) . ?
N6 C2 1.302(3) . ?
N6 C7 1.368(3) . ?
C4 C5 1.335(3) . ?
C4 C20 1.475(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.485(4) . ?
C8 C13 1.397(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.372(4) . ?
C14 C19 1.381(4) . ?
C15 C16 1.405(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.367(4) . ?
C18 C19 1.397(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.384(4) . ?
C20 C25 1.392(4) . ?
C21 C22 1.389(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(4) . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Se1 C2 86.23(10) . . ?
C23 O23 C26 117.2(2) . . ?
C2 N3 C4 117.02(19) . . ?
C2 N3 C14 121.0(2) . . ?
C4 N3 C14 121.63(18) . . ?
C2 N6 C7 115.60(19) . . ?
N6 C2 N3 122.3(2) . . ?
N6 C2 Se1 128.08(17) . . ?
N3 C2 Se1 109.59(17) . . ?
C5 C4 N3 114.1(2) . . ?
C5 C4 C20 125.2(2) . . ?
N3 C4 C20 120.7(2) . . ?
C4 C5 Se1 113.0(2) . . ?
C4 C5 H5 123.5 . . ?
Se1 C5 H5 123.5 . . ?
O7 C7 N6 124.5(2) . . ?
O7 C7 C8 120.3(2) . . ?
N6 C7 C8 115.3(2) . . ?
C13 C8 C9 118.7(2) . . ?
C13 C8 C7 122.1(2) . . ?
C9 C8 C7 119.3(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C15 C14 C19 121.5(2) . . ?
C15 C14 N3 119.8(2) . . ?
C19 C14 N3 118.7(2) . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 118.1(2) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C18 C17 C16 122.5(2) . . ?
C18 C17 Br17 118.62(19) . . ?
C16 C17 Br17 118.8(2) . . ?
C17 C18 C19 119.0(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C14 C19 C18 119.2(2) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C25 118.5(2) . . ?
C21 C20 C4 122.5(2) . . ?
C25 C20 C4 118.8(2) . . ?
C20 C21 C22 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
O23 C23 C22 124.5(2) . . ?
O23 C23 C24 115.5(2) . . ?
C22 C23 C24 119.9(2) . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
O23 C26 H26A 109.5 . . ?
O23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 -178.4(2) . . . . ?
C7 N6 C2 Se1 4.8(3) . . . . ?
C4 N3 C2 N6 -174.8(2) . . . . ?
C14 N3 C2 N6 -1.9(4) . . . . ?
C4 N3 C2 Se1 2.6(3) . . . . ?
C14 N3 C2 Se1 175.49(19) . . . . ?
C5 Se1 C2 N6 174.5(3) . . . . ?
C5 Se1 C2 N3 -2.66(19) . . . . ?
C2 N3 C4 C5 -0.7(4) . . . . ?
C14 N3 C4 C5 -173.6(3) . . . . ?
C2 N3 C4 C20 -179.5(2) . . . . ?
C14 N3 C4 C20 7.7(4) . . . . ?
N3 C4 C5 Se1 -1.6(3) . . . . ?
C20 C4 C5 Se1 177.1(2) . . . . ?
C2 Se1 C5 C4 2.4(2) . . . . ?
C2 N6 C7 O7 5.2(4) . . . . ?
C2 N6 C7 C8 -173.4(2) . . . . ?
O7 C7 C8 C13 -165.9(3) . . . . ?
N6 C7 C8 C13 12.8(4) . . . . ?
O7 C7 C8 C9 14.0(4) . . . . ?
N6 C7 C8 C9 -167.2(2) . . . . ?
C13 C8 C9 C10 -1.4(4) . . . . ?
C7 C8 C9 C10 178.6(3) . . . . ?
C8 C9 C10 C11 1.9(5) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 -1.2(5) . . . . ?
C11 C12 C13 C8 1.7(4) . . . . ?
C9 C8 C13 C12 -0.3(4) . . . . ?
C7 C8 C13 C12 179.6(2) . . . . ?
C2 N3 C14 C15 78.6(3) . . . . ?
C4 N3 C14 C15 -108.8(3) . . . . ?
C2 N3 C14 C19 -103.2(3) . . . . ?
C4 N3 C14 C19 69.4(3) . . . . ?
C19 C14 C15 C16 -1.5(4) . . . . ?
N3 C14 C15 C16 176.6(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 2.7(4) . . . . ?
C15 C16 C17 Br17 -176.1(2) . . . . ?
C16 C17 C18 C19 -3.0(4) . . . . ?
Br17 C17 C18 C19 175.84(19) . . . . ?
C15 C14 C19 C18 1.3(4) . . . . ?
N3 C14 C19 C18 -176.9(2) . . . . ?
C17 C18 C19 C14 1.0(4) . . . . ?
C5 C4 C20 C21 -111.0(3) . . . . ?
N3 C4 C20 C21 67.6(3) . . . . ?
C5 C4 C20 C25 63.9(4) . . . . ?
N3 C4 C20 C25 -117.6(3) . . . . ?
C25 C20 C21 C22 -0.7(4) . . . . ?
C4 C20 C21 C22 174.2(2) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C26 O23 C23 C22 3.7(4) . . . . ?
C26 O23 C23 C24 -175.8(3) . . . . ?
C21 C22 C23 O23 -179.1(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
O23 C23 C24 C25 179.1(2) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C20 -0.1(4) . . . . ?
C21 C20 C25 C24 0.6(4) . . . . ?
C4 C20 C25 C24 -174.4(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_10c
_database_code_depnum_ccdc_archive 'CCDC 1900134'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H18 F5 N3 O5 S Se'
_chemical_formula_moiety         'C24 H18 F5 N3 O5 S Se'
_chemical_formula_weight         634.44
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.2430(12)
_cell_length_b                   7.5672(5)
_cell_length_c                   20.083(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 116.938(6)
_cell_angle_gamma                90.0000
_cell_volume                     2471.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8131
_cell_measurement_theta_min      1.30
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272.00
_exptl_absorpt_coefficient_mu    1.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  0.845

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            4465
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4465
_reflns_number_gt                3912
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1451
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     355
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+14.6511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.65
_refine_diff_density_min         -0.97
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.53693(3) -0.02133(7) 0.72341(3) 0.02980(18) Uani 1 1 d . . . . .
S1 S 0.89003(10) 0.7205(2) 0.73571(10) 0.0392(4) Uani 1 1 d . . . . .
F1 F 0.9475(3) 0.8542(5) 0.7202(3) 0.0610(12) Uani 1 1 d . . . . .
F2 F 0.8158(3) 0.7936(6) 0.6630(3) 0.0623(12) Uani 1 1 d . . . . .
F3 F 0.9699(2) 0.6567(5) 0.8076(2) 0.0519(10) Uani 1 1 d . . . . .
F4 F 0.9088(3) 0.5817(5) 0.6869(2) 0.0518(10) Uani 1 1 d . . . . .
F5 F 0.8774(3) 0.8711(5) 0.7842(3) 0.0620(12) Uani 1 1 d . . . . .
O7 O 0.4385(2) 0.1534(5) 0.6045(2) 0.0365(10) Uani 1 1 d . . . . .
O11 O 0.2652(5) 0.8651(8) 0.3725(3) 0.098(3) Uani 1 1 d . . . . .
O12 O 0.3814(5) 1.0022(9) 0.4215(4) 0.081(2) Uani 1 1 d . . . . .
O21 O 0.7366(3) 0.3430(6) 0.9289(2) 0.0400(10) Uani 1 1 d . . . . .
O24 O 0.9337(3) -0.2499(6) 0.9929(3) 0.0482(11) Uani 1 1 d . . . . .
N3 N 0.6661(3) 0.2028(6) 0.7766(2) 0.0246(9) Uani 1 1 d . . . . .
N6 N 0.5589(3) 0.3120(6) 0.6660(2) 0.0256(9) Uani 1 1 d . . . . .
N11 N 0.3385(5) 0.8750(9) 0.4170(3) 0.065(2) Uani 1 1 d . . . . .
C2 C 0.5885(3) 0.1911(7) 0.7174(3) 0.0249(11) Uani 1 1 d . . . . .
C4 C 0.6898(3) 0.0637(7) 0.8291(3) 0.0279(12) Uani 1 1 d . . . . .
C5 C 0.6333(4) -0.0634(8) 0.8122(3) 0.0321(13) Uani 1 1 d . . . . .
H5 H 0.641070 -0.165333 0.842302 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4803(3) 0.2865(7) 0.6109(3) 0.0271(11) Uani 1 1 d . . . . .
C8 C 0.4443(4) 0.4420(8) 0.5598(3) 0.0310(12) Uani 1 1 d . . . . .
C9 C 0.3674(4) 0.4253(9) 0.4983(3) 0.0404(14) Uani 1 1 d . . . . .
H9 H 0.339048 0.315653 0.488582 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3321(4) 0.5678(10) 0.4514(3) 0.0480(17) Uani 1 1 d . . . . .
H10 H 0.279915 0.557532 0.409037 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3748(4) 0.7249(8) 0.4678(3) 0.0425(16) Uani 1 1 d . . . . .
C12 C 0.4511(4) 0.7468(9) 0.5278(3) 0.0436(16) Uani 1 1 d . . . . .
H12 H 0.479064 0.856749 0.536852 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4858(4) 0.6027(8) 0.5746(3) 0.0354(13) Uani 1 1 d . . . . .
H13 H 0.538028 0.614110 0.616839 0.043 Uiso 1 1 calc R U . . .
C14 C 0.7220(3) 0.3328(7) 0.7739(3) 0.0244(11) Uani 1 1 d . . . . .
C15 C 0.7008(3) 0.5097(7) 0.7623(3) 0.0290(12) Uani 1 1 d . . . . .
H15 H 0.651209 0.549291 0.761963 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7518(3) 0.6293(7) 0.7512(3) 0.0283(12) Uani 1 1 d . . . . .
H16 H 0.737073 0.750537 0.742262 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8247(3) 0.5692(7) 0.7534(3) 0.0279(12) Uani 1 1 d . . . . .
C18 C 0.8480(3) 0.3936(7) 0.7680(3) 0.0283(12) Uani 1 1 d . . . . .
H18 H 0.899099 0.354955 0.771324 0.034 Uiso 1 1 calc R U . . .
C19 C 0.7958(3) 0.2754(7) 0.7777(3) 0.0281(12) Uani 1 1 d . . . . .
H19 H 0.810752 0.154272 0.787077 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7688(3) 0.0655(8) 0.8984(3) 0.0302(12) Uani 1 1 d . . . . .
C21 C 0.7911(4) 0.2063(8) 0.9492(3) 0.0344(13) Uani 1 1 d . . . . .
C22 C 0.8632(4) 0.1943(9) 1.0162(3) 0.0406(14) Uani 1 1 d . . . . .
H22 H 0.878883 0.289592 1.050684 0.049 Uiso 1 1 calc R U . . .
C23 C 0.9121(4) 0.0444(9) 1.0329(3) 0.0388(14) Uani 1 1 d . . . . .
H23 H 0.960949 0.037747 1.078830 0.047 Uiso 1 1 calc R U . . .
C24 C 0.8904(4) -0.0954(8) 0.9832(3) 0.0364(14) Uani 1 1 d . . . . .
C25 C 0.8185(3) -0.0834(8) 0.9161(3) 0.0330(13) Uani 1 1 d . . . . .
H25 H 0.803230 -0.179130 0.881756 0.040 Uiso 1 1 calc R U . . .
C26 C 0.7622(5) 0.5002(9) 0.9734(4) 0.0550(18) Uani 1 1 d . . . . .
H26A H 0.716888 0.585583 0.955115 0.066 Uiso 1 1 calc R U . . .
H26B H 0.809579 0.551539 0.969787 0.066 Uiso 1 1 calc R U . . .
H26C H 0.777557 0.470879 1.025558 0.066 Uiso 1 1 calc R U . . .
C27 C 1.0002(4) -0.2800(10) 1.0656(4) 0.0509(18) Uani 1 1 d . . . . .
H27A H 1.025628 -0.394637 1.066377 0.061 Uiso 1 1 calc R U . . .
H27B H 0.979334 -0.279847 1.102767 0.061 Uiso 1 1 calc R U . . .
H27C H 1.041316 -0.186214 1.077423 0.061 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.879(6) . ?
Se1 C2 1.894(5) . ?
S1 F2 1.575(4) . ?
S1 F4 1.576(4) . ?
S1 F5 1.582(4) . ?
S1 F1 1.586(4) . ?
S1 F3 1.592(4) . ?
S1 C17 1.801(6) . ?
O7 C7 1.234(7) . ?
O11 N11 1.228(10) . ?
O12 N11 1.218(10) . ?
O21 C21 1.364(7) . ?
O21 C26 1.432(8) . ?
O24 C24 1.375(7) . ?
O24 C27 1.432(8) . ?
N3 C2 1.378(7) . ?
N3 C4 1.412(7) . ?
N3 C14 1.435(7) . ?
N6 C2 1.300(7) . ?
N6 C7 1.370(7) . ?
N11 C11 1.470(8) . ?
C4 C5 1.336(8) . ?
C4 C20 1.483(8) . ?
C5 H5 0.9500 . ?
C7 C8 1.504(8) . ?
C8 C13 1.392(8) . ?
C8 C9 1.392(8) . ?
C9 C10 1.384(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(10) . ?
C12 C13 1.391(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.384(8) . ?
C14 C19 1.384(7) . ?
C15 C16 1.387(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(8) . ?
C18 C19 1.383(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.387(8) . ?
C20 C21 1.403(8) . ?
C21 C22 1.394(9) . ?
C22 C23 1.387(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(8) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Se1 C2 85.8(2) . . ?
F2 S1 F4 89.7(3) . . ?
F2 S1 F5 90.8(3) . . ?
F4 S1 F5 174.7(2) . . ?
F2 S1 F1 87.7(2) . . ?
F4 S1 F1 87.4(2) . . ?
F5 S1 F1 87.4(2) . . ?
F2 S1 F3 175.3(2) . . ?
F4 S1 F3 89.7(2) . . ?
F5 S1 F3 89.3(3) . . ?
F1 S1 F3 87.5(2) . . ?
F2 S1 C17 92.2(2) . . ?
F4 S1 C17 92.8(2) . . ?
F5 S1 C17 92.4(2) . . ?
F1 S1 C17 179.8(3) . . ?
F3 S1 C17 92.5(2) . . ?
C21 O21 C26 117.1(5) . . ?
C24 O24 C27 116.6(5) . . ?
C2 N3 C4 116.3(4) . . ?
C2 N3 C14 118.7(4) . . ?
C4 N3 C14 123.8(4) . . ?
C2 N6 C7 116.6(5) . . ?
O12 N11 O11 123.6(7) . . ?
O12 N11 C11 119.1(7) . . ?
O11 N11 C11 117.3(8) . . ?
N6 C2 N3 122.4(5) . . ?
N6 C2 Se1 127.4(4) . . ?
N3 C2 Se1 110.2(4) . . ?
C5 C4 N3 114.0(5) . . ?
C5 C4 C20 123.7(5) . . ?
N3 C4 C20 122.2(5) . . ?
C4 C5 Se1 113.6(4) . . ?
C4 C5 H5 123.2 . . ?
Se1 C5 H5 123.2 . . ?
O7 C7 N6 124.8(5) . . ?
O7 C7 C8 120.6(5) . . ?
N6 C7 C8 114.5(5) . . ?
C13 C8 C9 120.1(6) . . ?
C13 C8 C7 120.7(5) . . ?
C9 C8 C7 119.2(5) . . ?
C10 C9 C8 120.2(6) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 118.1(6) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C12 C11 C10 123.5(6) . . ?
C12 C11 N11 118.3(7) . . ?
C10 C11 N11 118.2(6) . . ?
C11 C12 C13 117.9(6) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C8 120.2(6) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C15 C14 C19 120.3(5) . . ?
C15 C14 N3 121.3(5) . . ?
C19 C14 N3 118.2(5) . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.0(5) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 121.3(5) . . ?
C18 C17 S1 119.0(4) . . ?
C16 C17 S1 119.8(4) . . ?
C19 C18 C17 119.0(5) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C14 120.3(5) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C25 C20 C21 119.4(5) . . ?
C25 C20 C4 118.6(5) . . ?
C21 C20 C4 121.9(5) . . ?
O21 C21 C22 125.4(6) . . ?
O21 C21 C20 115.3(5) . . ?
C22 C21 C20 119.3(6) . . ?
C23 C22 C21 120.6(6) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.5(6) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
O24 C24 C23 126.1(6) . . ?
O24 C24 C25 114.9(6) . . ?
C23 C24 C25 119.0(6) . . ?
C20 C25 C24 121.3(6) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
O21 C26 H26A 109.5 . . ?
O21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O24 C27 H27A 109.5 . . ?
O24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 -178.7(5) . . . . ?
C7 N6 C2 Se1 2.3(7) . . . . ?
C4 N3 C2 N6 178.8(5) . . . . ?
C14 N3 C2 N6 -12.7(7) . . . . ?
C4 N3 C2 Se1 -2.1(6) . . . . ?
C14 N3 C2 Se1 166.5(4) . . . . ?
C5 Se1 C2 N6 -179.5(5) . . . . ?
C5 Se1 C2 N3 1.4(4) . . . . ?
C2 N3 C4 C5 1.8(7) . . . . ?
C14 N3 C4 C5 -166.1(5) . . . . ?
C2 N3 C4 C20 -175.4(5) . . . . ?
C14 N3 C4 C20 16.8(8) . . . . ?
N3 C4 C5 Se1 -0.6(6) . . . . ?
C20 C4 C5 Se1 176.5(4) . . . . ?
C2 Se1 C5 C4 -0.5(4) . . . . ?
C2 N6 C7 O7 -4.7(8) . . . . ?
C2 N6 C7 C8 171.1(4) . . . . ?
O7 C7 C8 C13 168.8(5) . . . . ?
N6 C7 C8 C13 -7.1(7) . . . . ?
O7 C7 C8 C9 -9.2(8) . . . . ?
N6 C7 C8 C9 174.9(5) . . . . ?
C13 C8 C9 C10 0.5(9) . . . . ?
C7 C8 C9 C10 178.5(5) . . . . ?
C8 C9 C10 C11 -0.6(10) . . . . ?
C9 C10 C11 C12 0.9(10) . . . . ?
C9 C10 C11 N11 178.4(6) . . . . ?
O12 N11 C11 C12 12.2(10) . . . . ?
O11 N11 C11 C12 -166.8(7) . . . . ?
O12 N11 C11 C10 -165.4(7) . . . . ?
O11 N11 C11 C10 15.6(9) . . . . ?
C10 C11 C12 C13 -1.0(10) . . . . ?
N11 C11 C12 C13 -178.6(6) . . . . ?
C11 C12 C13 C8 0.9(9) . . . . ?
C9 C8 C13 C12 -0.6(9) . . . . ?
C7 C8 C13 C12 -178.6(5) . . . . ?
C2 N3 C14 C15 54.7(7) . . . . ?
C4 N3 C14 C15 -137.7(5) . . . . ?
C2 N3 C14 C19 -120.6(5) . . . . ?
C4 N3 C14 C19 47.0(7) . . . . ?
C19 C14 C15 C16 2.8(8) . . . . ?
N3 C14 C15 C16 -172.4(5) . . . . ?
C14 C15 C16 C17 -1.2(8) . . . . ?
C15 C16 C17 C18 -1.5(8) . . . . ?
C15 C16 C17 S1 177.7(4) . . . . ?
F2 S1 C17 C18 130.5(5) . . . . ?
F4 S1 C17 C18 40.6(5) . . . . ?
F5 S1 C17 C18 -138.6(5) . . . . ?
F3 S1 C17 C18 -49.2(5) . . . . ?
F2 S1 C17 C16 -48.7(5) . . . . ?
F4 S1 C17 C16 -138.6(5) . . . . ?
F5 S1 C17 C16 42.2(5) . . . . ?
F3 S1 C17 C16 131.6(5) . . . . ?
C16 C17 C18 C19 2.5(8) . . . . ?
S1 C17 C18 C19 -176.7(4) . . . . ?
C17 C18 C19 C14 -0.9(8) . . . . ?
C15 C14 C19 C18 -1.8(8) . . . . ?
N3 C14 C19 C18 173.7(5) . . . . ?
C5 C4 C20 C25 52.4(8) . . . . ?
N3 C4 C20 C25 -130.7(6) . . . . ?
C5 C4 C20 C21 -122.0(6) . . . . ?
N3 C4 C20 C21 54.9(8) . . . . ?
C26 O21 C21 C22 11.8(9) . . . . ?
C26 O21 C21 C20 -171.0(5) . . . . ?
C25 C20 C21 O21 -176.7(5) . . . . ?
C4 C20 C21 O21 -2.4(8) . . . . ?
C25 C20 C21 C22 0.6(8) . . . . ?
C4 C20 C21 C22 175.0(5) . . . . ?
O21 C21 C22 C23 176.5(6) . . . . ?
C20 C21 C22 C23 -0.5(9) . . . . ?
C21 C22 C23 C24 0.3(10) . . . . ?
C27 O24 C24 C23 10.2(9) . . . . ?
C27 O24 C24 C25 -170.2(6) . . . . ?
C22 C23 C24 O24 179.6(6) . . . . ?
C22 C23 C24 C25 0.0(9) . . . . ?
C21 C20 C25 C24 -0.4(9) . . . . ?
C4 C20 C25 C24 -174.9(5) . . . . ?
O24 C24 C25 C20 -179.5(5) . . . . ?
C23 C24 C25 C20 0.1(9) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_10b
_database_code_depnum_ccdc_archive 'CCDC 1900133'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-06
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H15 Cl3 F5 N3 O3 S Se'
_chemical_formula_moiety         'C22 H13 Cl F5 N3 O3 S Se, C H2 Cl2'
_chemical_formula_weight         693.76
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.4201(5)
_cell_length_b                   12.6297(9)
_cell_length_c                   14.6868(11)
_cell_angle_alpha                96.558(6)
_cell_angle_beta                 90.345(6)
_cell_angle_gamma                95.925(6)
_cell_volume                     1359.82(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4633
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    1.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.865

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            11817
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4925
_reflns_number_gt                4381
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0811
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4925
_refine_ls_number_parameters     371
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0399P)²+0.5900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.71681(3) 1.10813(2) 0.44741(2) 0.03039(9) Uani 1 1 d . . . . .
Cl2A Cl 0.0493(5) 0.6138(6) 0.1916(3) 0.0937(14) Uani 0.533(10) 1 d D . P A 1
Cl2B Cl 0.1209(9) 0.6759(6) 0.1950(2) 0.091(2) Uani 0.467(10) 1 d D . P A 2
Cl23 Cl 0.49983(11) 0.75684(7) -0.08395(5) 0.0612(2) Uani 1 1 d . . . . .
Cl26 Cl 0.33009(17) 0.52500(9) 0.08699(9) 0.1005(4) Uani 1 1 d D . . . .
S1 S 0.61347(12) 0.42266(5) 0.35418(5) 0.0565(2) Uani 1 1 d . . . . .
F1 F 0.5929(4) 0.29528(13) 0.34558(16) 0.0896(7) Uani 1 1 d . . . . .
F2 F 0.7270(3) 0.42186(13) 0.44575(14) 0.0790(6) Uani 1 1 d . . . . .
F3 F 0.4978(3) 0.41220(12) 0.26293(12) 0.0758(6) Uani 1 1 d . . . . .
F4 F 0.7918(3) 0.41622(14) 0.29793(16) 0.0883(7) Uani 1 1 d . . . . .
F5 F 0.4334(3) 0.41778(13) 0.41069(14) 0.0722(5) Uani 1 1 d . . . . .
O7 O 0.8090(2) 1.08532(12) 0.61735(11) 0.0379(4) Uani 1 1 d . . . . .
O11 O 1.0472(3) 0.8395(2) 0.99101(13) 0.0629(6) Uani 1 1 d . . . . .
O12 O 1.0069(4) 0.6862(2) 0.90952(16) 0.0750(7) Uani 1 1 d . . . . .
N3 N 0.6915(2) 0.90130(13) 0.37745(12) 0.0270(4) Uani 1 1 d . . . . .
N6 N 0.7754(2) 0.91914(14) 0.53169(13) 0.0304(4) Uani 1 1 d . . . . .
N11 N 1.0087(3) 0.7833(2) 0.91857(15) 0.0500(6) Uani 1 1 d . . . . .
C2 C 0.7345(3) 0.96241(16) 0.45844(15) 0.0271(4) Uani 1 1 d . . . . .
C4 C 0.6480(3) 0.95603(16) 0.30279(15) 0.0272(4) Uani 1 1 d . . . . .
C5 C 0.6523(3) 1.06228(17) 0.32487(16) 0.0313(5) Uani 1 1 d . . . . .
H5 H 0.625104 1.109817 0.282247 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8134(3) 0.98682(17) 0.60985(15) 0.0305(5) Uani 1 1 d . . . . .
C8 C 0.8645(3) 0.93230(18) 0.69017(15) 0.0314(5) Uani 1 1 d . . . . .
C9 C 0.9235(3) 0.9943(2) 0.77152(16) 0.0361(5) Uani 1 1 d . . . . .
H9 H 0.930007 1.070222 0.775478 0.043 Uiso 1 1 calc R U . . .
C10 C 0.9726(3) 0.9461(2) 0.84640(16) 0.0402(6) Uani 1 1 d . . . . .
H10 H 1.013271 0.988001 0.901969 0.048 Uiso 1 1 calc R U . . .
C11 C 0.9611(3) 0.8362(2) 0.83863(16) 0.0394(5) Uani 1 1 d . . . . .
C12 C 0.9029(4) 0.7719(2) 0.75870(17) 0.0425(6) Uani 1 1 d . . . . .
H12 H 0.896075 0.696049 0.755302 0.051 Uiso 1 1 calc R U . . .
C13 C 0.8552(3) 0.82122(19) 0.68443(17) 0.0379(5) Uani 1 1 d . . . . .
H13 H 0.815671 0.778964 0.628844 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6727(3) 0.78578(16) 0.37427(14) 0.0279(4) Uani 1 1 d . . . . .
C15 C 0.8221(3) 0.73452(18) 0.39219(16) 0.0354(5) Uani 1 1 d . . . . .
H15 H 0.935774 0.774549 0.407760 0.042 Uiso 1 1 calc R U . . .
C16 C 0.8038(4) 0.62353(19) 0.38712(17) 0.0412(6) Uani 1 1 d . . . . .
H16 H 0.904835 0.586583 0.399498 0.049 Uiso 1 1 calc R U . . .
C17 C 0.6364(4) 0.56715(17) 0.36376(15) 0.0371(5) Uani 1 1 d . . . . .
C18 C 0.4872(3) 0.61880(17) 0.34708(15) 0.0357(5) Uani 1 1 d . . . . .
H18 H 0.373487 0.578782 0.331574 0.043 Uiso 1 1 calc R U . . .
C19 C 0.5043(3) 0.72987(16) 0.35309(14) 0.0300(5) Uani 1 1 d . . . . .
H19 H 0.402244 0.766923 0.342870 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6103(3) 0.90079(16) 0.20945(15) 0.0285(4) Uani 1 1 d . . . . .
C21 C 0.7002(3) 0.81426(17) 0.17179(16) 0.0331(5) Uani 1 1 d . . . . .
H21 H 0.785098 0.785645 0.208311 0.040 Uiso 1 1 calc R U . . .
C22 C 0.6665(3) 0.77003(19) 0.08191(17) 0.0383(5) Uani 1 1 d . . . . .
H22 H 0.727461 0.711141 0.056781 0.046 Uiso 1 1 calc R U . . .
C23 C 0.5431(3) 0.8125(2) 0.02897(16) 0.0399(6) Uani 1 1 d . . . . .
C24 C 0.4531(3) 0.8981(2) 0.06474(17) 0.0396(5) Uani 1 1 d . . . . .
H24 H 0.368319 0.926530 0.027992 0.048 Uiso 1 1 calc R U . . .
C25 C 0.4877(3) 0.94153(18) 0.15416(16) 0.0340(5) Uani 1 1 d . . . . .
H25 H 0.426567 1.000621 0.178646 0.041 Uiso 1 1 calc R U . . .
C26A C 0.2180(14) 0.6374(8) 0.1117(7) 0.078(3) Uani 0.533(10) 1 d D . P A 1
H26A H 0.162736 0.655972 0.054833 0.093 Uiso 0.533(10) 1 calc R U P A 1
H26B H 0.305155 0.698652 0.136675 0.093 Uiso 0.533(10) 1 calc R U P A 1
C26B C 0.1312(16) 0.5855(9) 0.0919(6) 0.077(3) Uani 0.467(10) 1 d D . P A 2
H26C H 0.026747 0.529718 0.089090 0.092 Uiso 0.467(10) 1 calc R U P A 2
H26D H 0.122455 0.625517 0.038132 0.092 Uiso 0.467(10) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.870(2) . ?
Se1 C2 1.884(2) . ?
Cl2A C26A 1.748(7) . ?
Cl2B C26B 1.796(9) . ?
Cl23 C23 1.740(2) . ?
Cl26 C26A 1.723(8) . ?
Cl26 C26B 1.729(9) . ?
S1 F4 1.569(2) . ?
S1 F3 1.572(2) . ?
S1 F5 1.576(2) . ?
S1 F2 1.584(2) . ?
S1 F1 1.5907(16) . ?
S1 C17 1.804(2) . ?
O7 C7 1.240(3) . ?
O11 N11 1.224(3) . ?
O12 N11 1.217(3) . ?
N3 C2 1.359(3) . ?
N3 C4 1.414(3) . ?
N3 C14 1.447(3) . ?
N6 C2 1.309(3) . ?
N6 C7 1.360(3) . ?
N11 C11 1.474(3) . ?
C4 C5 1.341(3) . ?
C4 C20 1.477(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.498(3) . ?
C8 C13 1.390(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(4) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 C19 1.386(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(4) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.391(3) . ?
C20 C21 1.401(3) . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(4) . ?
C24 C25 1.376(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C26B H26C 0.9900 . ?
C26B H26D 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
C5 Se1 C2 85.72(9) . . ?
F4 S1 F3 90.58(14) . . ?
F4 S1 F5 174.81(10) . . ?
F3 S1 F5 89.66(13) . . ?
F4 S1 F2 89.59(14) . . ?
F3 S1 F2 174.86(9) . . ?
F5 S1 F2 89.71(13) . . ?
F4 S1 F1 87.74(12) . . ?
F3 S1 F1 87.28(11) . . ?
F5 S1 F1 87.09(12) . . ?
F2 S1 F1 87.59(11) . . ?
F4 S1 C17 92.30(11) . . ?
F3 S1 C17 92.59(10) . . ?
F5 S1 C17 92.87(10) . . ?
F2 S1 C17 92.53(11) . . ?
F1 S1 C17 179.87(15) . . ?
C2 N3 C4 116.71(17) . . ?
C2 N3 C14 119.35(17) . . ?
C4 N3 C14 123.56(17) . . ?
C2 N6 C7 116.89(19) . . ?
O12 N11 O11 123.3(2) . . ?
O12 N11 C11 118.5(2) . . ?
O11 N11 C11 118.2(3) . . ?
N6 C2 N3 121.29(18) . . ?
N6 C2 Se1 128.07(16) . . ?
N3 C2 Se1 110.61(15) . . ?
C5 C4 N3 113.2(2) . . ?
C5 C4 C20 124.2(2) . . ?
N3 C4 C20 122.58(18) . . ?
C4 C5 Se1 113.73(17) . . ?
C4 C5 H5 123.1 . . ?
Se1 C5 H5 123.1 . . ?
O7 C7 N6 125.2(2) . . ?
O7 C7 C8 120.7(2) . . ?
N6 C7 C8 114.03(19) . . ?
C13 C8 C9 119.7(2) . . ?
C13 C8 C7 121.0(2) . . ?
C9 C8 C7 119.2(2) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 118.4(2) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 122.7(2) . . ?
C10 C11 N11 119.1(2) . . ?
C12 C11 N11 118.1(2) . . ?
C13 C12 C11 118.2(2) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C8 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C15 C14 C19 121.9(2) . . ?
C15 C14 N3 119.30(19) . . ?
C19 C14 N3 118.77(19) . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 S1 119.05(19) . . ?
C16 C17 S1 119.40(19) . . ?
C17 C18 C19 119.4(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C18 118.9(2) . . ?
C14 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C25 C20 C21 118.4(2) . . ?
C25 C20 C4 118.01(19) . . ?
C21 C20 C4 123.4(2) . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.9(2) . . ?
C24 C23 Cl23 119.5(2) . . ?
C22 C23 Cl23 119.51(19) . . ?
C25 C24 C23 119.2(2) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C20 121.4(2) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?
Cl26 C26A Cl2A 110.0(5) . . ?
Cl26 C26A H26A 109.7 . . ?
Cl2A C26A H26A 109.7 . . ?
Cl26 C26A H26B 109.7 . . ?
Cl2A C26A H26B 109.7 . . ?
H26A C26A H26B 108.2 . . ?
Cl26 C26B Cl2B 111.7(5) . . ?
Cl26 C26B H26C 109.3 . . ?
Cl2B C26B H26C 109.3 . . ?
Cl26 C26B H26D 109.3 . . ?
Cl2B C26B H26D 109.3 . . ?
H26C C26B H26D 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 -178.87(18) . . . . ?
C7 N6 C2 Se1 -1.3(3) . . . . ?
C4 N3 C2 N6 179.49(19) . . . . ?
C14 N3 C2 N6 6.3(3) . . . . ?
C4 N3 C2 Se1 1.5(2) . . . . ?
C14 N3 C2 Se1 -171.67(15) . . . . ?
C5 Se1 C2 N6 -178.7(2) . . . . ?
C5 Se1 C2 N3 -0.90(15) . . . . ?
C2 N3 C4 C5 -1.4(3) . . . . ?
C14 N3 C4 C5 171.43(19) . . . . ?
C2 N3 C4 C20 175.92(19) . . . . ?
C14 N3 C4 C20 -11.2(3) . . . . ?
N3 C4 C5 Se1 0.6(2) . . . . ?
C20 C4 C5 Se1 -176.67(16) . . . . ?
C2 Se1 C5 C4 0.15(17) . . . . ?
C2 N6 C7 O7 1.4(3) . . . . ?
C2 N6 C7 C8 -178.26(18) . . . . ?
O7 C7 C8 C13 174.6(2) . . . . ?
N6 C7 C8 C13 -5.7(3) . . . . ?
O7 C7 C8 C9 -5.9(3) . . . . ?
N6 C7 C8 C9 173.75(19) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 N11 -178.5(2) . . . . ?
O12 N11 C11 C10 -176.3(3) . . . . ?
O11 N11 C11 C10 4.1(3) . . . . ?
O12 N11 C11 C12 4.9(4) . . . . ?
O11 N11 C11 C12 -174.7(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
N11 C11 C12 C13 178.9(2) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
C9 C8 C13 C12 0.4(4) . . . . ?
C7 C8 C13 C12 179.9(2) . . . . ?
C2 N3 C14 C15 -64.8(3) . . . . ?
C4 N3 C14 C15 122.5(2) . . . . ?
C2 N3 C14 C19 115.3(2) . . . . ?
C4 N3 C14 C19 -57.4(3) . . . . ?
C19 C14 C15 C16 1.3(3) . . . . ?
N3 C14 C15 C16 -178.7(2) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C15 C16 C17 S1 178.40(18) . . . . ?
F4 S1 C17 C18 134.3(2) . . . . ?
F3 S1 C17 C18 43.6(2) . . . . ?
F5 S1 C17 C18 -46.2(2) . . . . ?
F2 S1 C17 C18 -136.0(2) . . . . ?
F4 S1 C17 C16 -45.3(2) . . . . ?
F3 S1 C17 C16 -136.0(2) . . . . ?
F5 S1 C17 C16 134.2(2) . . . . ?
F2 S1 C17 C16 44.4(2) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
S1 C17 C18 C19 -179.14(17) . . . . ?
C15 C14 C19 C18 -2.0(3) . . . . ?
N3 C14 C19 C18 177.93(19) . . . . ?
C17 C18 C19 C14 1.1(3) . . . . ?
C5 C4 C20 C25 -34.6(3) . . . . ?
N3 C4 C20 C25 148.3(2) . . . . ?
C5 C4 C20 C21 141.0(2) . . . . ?
N3 C4 C20 C21 -36.0(3) . . . . ?
C25 C20 C21 C22 -0.5(3) . . . . ?
C4 C20 C21 C22 -176.1(2) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C21 C22 C23 Cl23 -179.79(18) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
Cl23 C23 C24 C25 179.87(18) . . . . ?
C23 C24 C25 C20 -0.4(4) . . . . ?
C21 C20 C25 C24 0.6(3) . . . . ?
C4 C20 C25 C24 176.4(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1900140'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24.5 H20 Cl F5 N2 O3 S Se'
_chemical_formula_moiety         'C24 H19 F5 N2 O3 S Se, 0.5(C H2 Cl2)'
_chemical_formula_weight         631.90
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.4893(8)
_cell_length_b                   10.2641(9)
_cell_length_c                   13.4203(11)
_cell_angle_alpha                104.147(14)
_cell_angle_beta                 95.793(13)
_cell_angle_gamma                98.240(13)
_cell_volume                     1241.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2564
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             634.00
_exptl_absorpt_coefficient_mu    1.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_T_max  0.899

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            9104
_diffrn_reflns_av_unetI/netI     0.1954
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         2.924
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4483
_reflns_number_gt                2246
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1822
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1236
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4483
_refine_ls_number_parameters     345
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0521P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.73
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.70573(9) 0.43334(10) 0.61962(7) 0.0331(3) Uani 1 1 d . . . . .
Cl28 Cl 0.6380(3) 0.5394(3) 0.0651(2) 0.0733(9) Uani 1 1 d D . . . .
S1 S 0.2548(2) 0.0368(2) 0.01544(15) 0.0265(5) Uani 1 1 d . . . . .
F1 F 0.1456(5) -0.0401(5) -0.0861(3) 0.0358(12) Uani 1 1 d . . . . .
F2 F 0.3414(4) -0.0853(4) -0.0109(3) 0.0334(11) Uani 1 1 d . . . . .
F3 F 0.1557(4) -0.0456(5) 0.0765(3) 0.0351(12) Uani 1 1 d . . . . .
F4 F 0.1571(4) 0.1514(5) 0.0320(4) 0.0356(12) Uani 1 1 d . . . . .
F5 F 0.3438(5) 0.1138(5) -0.0534(3) 0.0366(12) Uani 1 1 d . . . . .
O7 O 0.5040(6) 0.2931(6) 0.6821(4) 0.0400(16) Uani 1 1 d . . . . .
O11 O -0.0439(6) -0.1774(5) 0.5927(4) 0.0314(14) Uani 1 1 d . . . . .
O24 O 1.0795(7) 0.5221(6) 0.1115(4) 0.0419(16) Uani 1 1 d . . . . .
N3 N 0.6360(6) 0.3269(6) 0.4136(5) 0.0226(15) Uani 1 1 d . . . . .
N6 N 0.4756(6) 0.2214(6) 0.5035(5) 0.0230(15) Uani 1 1 d . . . . .
C2 C 0.5885(8) 0.3125(9) 0.5046(6) 0.028(2) Uani 1 1 d . . . . .
C4 C 0.7593(8) 0.4280(8) 0.4251(6) 0.0245(19) Uani 1 1 d . . . . .
C5 C 0.8121(9) 0.4913(9) 0.5241(6) 0.035(2) Uani 1 1 d . . . . .
H5 H 0.896181 0.559450 0.543929 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4380(8) 0.2169(8) 0.5995(6) 0.027(2) Uani 1 1 d . . . . .
C8 C 0.3142(8) 0.1097(8) 0.5980(6) 0.0256(19) Uani 1 1 d . . . . .
C9 C 0.2442(8) 0.1223(8) 0.6863(6) 0.0259(19) Uani 1 1 d . . . . .
H9 H 0.279009 0.196163 0.745990 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1248(8) 0.0276(8) 0.6870(6) 0.0269(19) Uani 1 1 d . . . . .
H10 H 0.076699 0.036929 0.746437 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0766(8) -0.0800(8) 0.6007(6) 0.027(2) Uani 1 1 d . . . . .
C12 C 0.1481(8) -0.0961(8) 0.5143(6) 0.0272(19) Uani 1 1 d . . . . .
H12 H 0.116943 -0.173181 0.456485 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2646(8) 0.0003(8) 0.5128(6) 0.0248(19) Uani 1 1 d . . . . .
H13 H 0.311014 -0.008729 0.452624 0.030 Uiso 1 1 calc R U . . .
C14 C -0.1326(8) -0.1540(8) 0.6732(6) 0.031(2) Uani 1 1 d . . . . .
H14A H -0.157731 -0.062879 0.682745 0.038 Uiso 1 1 calc R U . . .
H14B H -0.080185 -0.160483 0.738072 0.038 Uiso 1 1 calc R U . . .
H14C H -0.220596 -0.222769 0.653809 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5516(7) 0.2565(8) 0.3144(6) 0.0204(18) Uani 1 1 d . . . . .
C16 C 0.5174(7) 0.1159(8) 0.2871(6) 0.0221(18) Uani 1 1 d . . . . .
H16 H 0.554438 0.065682 0.331345 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4292(8) 0.0484(8) 0.1953(6) 0.0222(18) Uani 1 1 d . . . . .
H17 H 0.404872 -0.048344 0.176079 0.027 Uiso 1 1 calc R U . . .
C18 C 0.3767(8) 0.1231(8) 0.1316(6) 0.0242(19) Uani 1 1 d . . . . .
C19 C 0.4139(8) 0.2653(8) 0.1575(6) 0.0241(19) Uani 1 1 d . . . . .
H19 H 0.377911 0.315728 0.113002 0.029 Uiso 1 1 calc R U . . .
C20 C 0.5029(8) 0.3307(8) 0.2480(6) 0.0231(18) Uani 1 1 d . . . . .
H20 H 0.531605 0.426944 0.265585 0.028 Uiso 1 1 calc R U . . .
C21 C 0.8285(8) 0.4500(8) 0.3353(6) 0.0242(19) Uani 1 1 d . . . . .
C22 C 0.8619(8) 0.3444(8) 0.2595(6) 0.0256(19) Uani 1 1 d . . . . .
H22 H 0.826667 0.252626 0.258601 0.031 Uiso 1 1 calc R U . . .
C23 C 0.9453(8) 0.3699(8) 0.1852(6) 0.0275(19) Uani 1 1 d . . . . .
H23 H 0.968775 0.296488 0.134983 0.033 Uiso 1 1 calc R U . . .
C24 C 0.9952(8) 0.5061(9) 0.1849(6) 0.0259(19) Uani 1 1 d . . . . .
C25 C 0.9572(8) 0.6111(9) 0.2561(7) 0.030(2) Uani 1 1 d . . . . .
H25 H 0.986221 0.702567 0.253454 0.036 Uiso 1 1 calc R U . . .
C26 C 0.8768(8) 0.5847(8) 0.3320(6) 0.029(2) Uani 1 1 d . . . . .
H26 H 0.854122 0.658537 0.382357 0.035 Uiso 1 1 calc R U . . .
C27 C 1.1211(11) 0.6581(10) 0.1023(7) 0.061(3) Uani 1 1 d . . . . .
H27A H 1.193798 0.709660 0.161077 0.073 Uiso 1 1 calc R U . . .
H27B H 1.036703 0.703153 0.102073 0.073 Uiso 1 1 calc R U . . .
H27C H 1.161078 0.654524 0.037323 0.073 Uiso 1 1 calc R U . . .
C28 C 0.4621(14) 0.5808(18) 0.0561(13) 0.055(6) Uani 0.5 1 d D . P . .
H28A H 0.465844 0.676404 0.052543 0.066 Uiso 0.5 1 calc R U P . .
H28B H 0.415825 0.568735 0.116911 0.066 Uiso 0.5 1 calc R U P . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.865(8) . ?
Se1 C2 1.866(8) . ?
Cl28 C28 1.780(14) . ?
Cl28 C28 1.855(14) 2_665 ?
S1 F1 1.584(4) . ?
S1 F2 1.584(5) . ?
S1 F5 1.586(4) . ?
S1 F4 1.587(5) . ?
S1 F3 1.593(4) . ?
S1 C18 1.795(8) . ?
O7 C7 1.237(9) . ?
O11 C11 1.383(8) . ?
O11 C14 1.430(9) . ?
O24 C24 1.355(9) . ?
O24 C27 1.434(10) . ?
N3 C2 1.377(9) . ?
N3 C4 1.416(9) . ?
N3 C15 1.443(9) . ?
N6 C2 1.314(9) . ?
N6 C7 1.380(9) . ?
C4 C5 1.337(11) . ?
C4 C21 1.478(10) . ?
C5 H5 0.9500 . ?
C7 C8 1.484(10) . ?
C8 C13 1.379(11) . ?
C8 C9 1.404(10) . ?
C9 C10 1.385(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(11) . ?
C12 C13 1.379(10) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.380(10) . ?
C15 C20 1.391(10) . ?
C16 C17 1.381(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(10) . ?
C19 C20 1.368(10) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.392(11) . ?
C21 C26 1.406(10) . ?
C22 C23 1.384(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.411(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.372(11) . ?
C25 C26 1.388(11) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Se1 C2 86.0(3) . . ?
C28 Cl28 C28 74.8(9) . 2_665 ?
F1 S1 F2 87.3(3) . . ?
F1 S1 F5 88.3(2) . . ?
F2 S1 F5 90.4(3) . . ?
F1 S1 F4 87.1(3) . . ?
F2 S1 F4 174.4(3) . . ?
F5 S1 F4 89.6(3) . . ?
F1 S1 F3 87.1(2) . . ?
F2 S1 F3 89.9(3) . . ?
F5 S1 F3 175.3(3) . . ?
F4 S1 F3 89.7(3) . . ?
F1 S1 C18 179.1(3) . . ?
F2 S1 C18 92.8(3) . . ?
F5 S1 C18 92.6(3) . . ?
F4 S1 C18 92.8(3) . . ?
F3 S1 C18 92.0(3) . . ?
C11 O11 C14 117.4(6) . . ?
C24 O24 C27 117.2(7) . . ?
C2 N3 C4 115.5(6) . . ?
C2 N3 C15 120.7(6) . . ?
C4 N3 C15 123.1(6) . . ?
C2 N6 C7 115.7(6) . . ?
N6 C2 N3 121.0(7) . . ?
N6 C2 Se1 127.9(6) . . ?
N3 C2 Se1 111.1(5) . . ?
C5 C4 N3 113.5(7) . . ?
C5 C4 C21 124.2(7) . . ?
N3 C4 C21 122.0(7) . . ?
C4 C5 Se1 113.8(6) . . ?
C4 C5 H5 123.1 . . ?
Se1 C5 H5 123.1 . . ?
O7 C7 N6 123.3(7) . . ?
O7 C7 C8 121.3(7) . . ?
N6 C7 C8 115.4(6) . . ?
C13 C8 C9 119.2(7) . . ?
C13 C8 C7 122.5(7) . . ?
C9 C8 C7 118.3(7) . . ?
C10 C9 C8 120.4(7) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.3(7) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 O11 123.7(7) . . ?
C10 C11 C12 120.7(7) . . ?
O11 C11 C12 115.6(7) . . ?
C13 C12 C11 119.7(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 120.6(7) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
O11 C14 H14A 109.5 . . ?
O11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 120.4(7) . . ?
C16 C15 N3 119.6(6) . . ?
C20 C15 N3 119.9(7) . . ?
C15 C16 C17 119.9(7) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 119.2(7) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 121.1(7) . . ?
C17 C18 S1 119.5(6) . . ?
C19 C18 S1 119.3(6) . . ?
C20 C19 C18 119.0(7) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C15 120.2(7) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
C22 C21 C26 118.0(7) . . ?
C22 C21 C4 123.2(7) . . ?
C26 C21 C4 118.4(7) . . ?
C23 C22 C21 121.5(7) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 119.4(8) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
O24 C24 C25 124.7(7) . . ?
O24 C24 C23 115.6(8) . . ?
C25 C24 C23 119.7(7) . . ?
C24 C25 C26 120.5(7) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.8(8) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
O24 C27 H27A 109.5 . . ?
O24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Cl28 C28 Cl28 105.2(9) . 2_665 ?
Cl28 C28 H28A 110.7 . . ?
Cl28 C28 H28A 110.7 2_665 . ?
Cl28 C28 H28B 110.7 . . ?
Cl28 C28 H28B 110.7 2_665 . ?
H28A C28 H28B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 -179.7(7) . . . . ?
C7 N6 C2 Se1 1.3(10) . . . . ?
C4 N3 C2 N6 -179.6(7) . . . . ?
C15 N3 C2 N6 8.9(11) . . . . ?
C4 N3 C2 Se1 -0.5(8) . . . . ?
C15 N3 C2 Se1 -172.0(5) . . . . ?
C5 Se1 C2 N6 178.6(8) . . . . ?
C5 Se1 C2 N3 -0.4(6) . . . . ?
C2 N3 C4 C5 1.6(10) . . . . ?
C15 N3 C4 C5 172.9(7) . . . . ?
C2 N3 C4 C21 176.2(7) . . . . ?
C15 N3 C4 C21 -12.6(10) . . . . ?
N3 C4 C5 Se1 -1.9(9) . . . . ?
C21 C4 C5 Se1 -176.3(6) . . . . ?
C2 Se1 C5 C4 1.4(7) . . . . ?
C2 N6 C7 O7 0.5(11) . . . . ?
C2 N6 C7 C8 -177.4(7) . . . . ?
O7 C7 C8 C13 -161.2(8) . . . . ?
N6 C7 C8 C13 16.8(11) . . . . ?
O7 C7 C8 C9 19.9(11) . . . . ?
N6 C7 C8 C9 -162.2(7) . . . . ?
C13 C8 C9 C10 -1.5(11) . . . . ?
C7 C8 C9 C10 177.5(7) . . . . ?
C8 C9 C10 C11 0.9(11) . . . . ?
C9 C10 C11 O11 -178.0(7) . . . . ?
C9 C10 C11 C12 1.4(11) . . . . ?
C14 O11 C11 C10 8.4(10) . . . . ?
C14 O11 C11 C12 -171.1(6) . . . . ?
C10 C11 C12 C13 -3.2(11) . . . . ?
O11 C11 C12 C13 176.3(6) . . . . ?
C11 C12 C13 C8 2.6(11) . . . . ?
C9 C8 C13 C12 -0.3(11) . . . . ?
C7 C8 C13 C12 -179.2(7) . . . . ?
C2 N3 C15 C16 -58.9(10) . . . . ?
C4 N3 C15 C16 130.2(7) . . . . ?
C2 N3 C15 C20 119.8(7) . . . . ?
C4 N3 C15 C20 -51.0(9) . . . . ?
C20 C15 C16 C17 -2.8(10) . . . . ?
N3 C15 C16 C17 175.9(6) . . . . ?
C15 C16 C17 C18 0.2(10) . . . . ?
C16 C17 C18 C19 1.4(11) . . . . ?
C16 C17 C18 S1 -176.9(6) . . . . ?
F2 S1 C18 C17 -40.6(6) . . . . ?
F5 S1 C18 C17 -131.1(6) . . . . ?
F4 S1 C18 C17 139.2(6) . . . . ?
F3 S1 C18 C17 49.4(6) . . . . ?
F2 S1 C18 C19 141.0(6) . . . . ?
F5 S1 C18 C19 50.5(6) . . . . ?
F4 S1 C18 C19 -39.2(6) . . . . ?
F3 S1 C18 C19 -129.0(6) . . . . ?
C17 C18 C19 C20 -0.6(11) . . . . ?
S1 C18 C19 C20 177.8(6) . . . . ?
C18 C19 C20 C15 -2.0(11) . . . . ?
C16 C15 C20 C19 3.7(10) . . . . ?
N3 C15 C20 C19 -175.0(7) . . . . ?
C5 C4 C21 C22 125.8(9) . . . . ?
N3 C4 C21 C22 -48.1(10) . . . . ?
C5 C4 C21 C26 -47.2(11) . . . . ?
N3 C4 C21 C26 138.9(7) . . . . ?
C26 C21 C22 C23 2.7(11) . . . . ?
C4 C21 C22 C23 -170.3(7) . . . . ?
C21 C22 C23 C24 -1.4(11) . . . . ?
C27 O24 C24 C25 -5.8(11) . . . . ?
C27 O24 C24 C23 174.3(7) . . . . ?
C22 C23 C24 O24 178.2(7) . . . . ?
C22 C23 C24 C25 -1.8(11) . . . . ?
O24 C24 C25 C26 -176.4(7) . . . . ?
C23 C24 C25 C26 3.5(11) . . . . ?
C24 C25 C26 C21 -2.2(11) . . . . ?
C22 C21 C26 C25 -0.9(11) . . . . ?
C4 C21 C26 C25 172.4(7) . . . . ?
C28 Cl28 C28 Cl28 0.000(1) 2_665 . . 2_665 ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1900139'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H13 F5 N2 O2 S Se'
_chemical_formula_moiety         'C15 H13 F5 N2 O2 S Se'
_chemical_formula_weight         459.29
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   17.4151(11)
_cell_length_b                   6.5384(5)
_cell_length_c                   15.8481(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.850(3)
_cell_angle_gamma                90.0000
_cell_volume                     1697.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4263
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912.00
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.931

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            11794
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_theta_max         25.291
_diffrn_reflns_theta_min         2.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3064
_reflns_number_gt                2038
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0826
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3064
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0473P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.76
_refine_diff_density_min         -0.73
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.42355(3) 0.59168(7) 0.73243(3) 0.02125(16) Uani 1 1 d . . . . .
S1 S 0.11181(8) 1.22768(19) 0.58031(8) 0.0262(3) Uani 1 1 d . . . . .
F1 F 0.03025(18) 1.3357(5) 0.58033(18) 0.0379(8) Uani 1 1 d . . . . .
F2 F 0.08339(18) 1.0315(4) 0.62043(18) 0.0375(8) Uani 1 1 d . . . . .
F3 F 0.15444(18) 1.3142(5) 0.67907(17) 0.0355(7) Uani 1 1 d . . . . .
F4 F 0.13443(17) 1.4333(4) 0.54065(17) 0.0315(7) Uani 1 1 d . . . . .
F5 F 0.06288(17) 1.1519(4) 0.48140(16) 0.0325(7) Uani 1 1 d . . . . .
O4 O 0.5638(2) 0.8421(5) 0.5500(2) 0.0361(9) Uani 1 1 d . . . . .
O14 O 0.9058(2) 0.3864(5) 0.6834(2) 0.0282(8) Uani 1 1 d . . . . .
N1 N 0.4222(3) 0.8224(6) 0.5825(2) 0.0222(9) Uani 1 1 d D . . . .
H1 H 0.456(4) 0.878(9) 0.551(4) 0.08(2) Uiso 1 1 d D . . . .
N3 N 0.5355(2) 0.6128(6) 0.6440(2) 0.0224(9) Uani 1 1 d D . . . .
H3 H 0.561(3) 0.511(6) 0.688(3) 0.054(17) Uiso 1 1 d D . . . .
C2 C 0.4611(3) 0.6857(7) 0.6446(3) 0.0211(11) Uani 1 1 d . . . . .
C4 C 0.5872(3) 0.6977(7) 0.6017(3) 0.0236(11) Uani 1 1 d . . . . .
C5 C 0.3471(3) 0.9163(7) 0.5820(3) 0.0195(10) Uani 1 1 d . . . . .
C6 C 0.3501(3) 1.1142(7) 0.6150(3) 0.0208(11) Uani 1 1 d . . . . .
H6 H 0.400619 1.184690 0.637765 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2784(3) 1.2073(7) 0.6141(3) 0.0221(11) Uani 1 1 d . . . . .
H7 H 0.279594 1.342434 0.636550 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2053(3) 1.1035(7) 0.5807(3) 0.0193(10) Uani 1 1 d . . . . .
C9 C 0.2018(3) 0.9072(7) 0.5465(3) 0.0226(11) Uani 1 1 d . . . . .
H9 H 0.151114 0.837436 0.523013 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2733(3) 0.8149(7) 0.5473(3) 0.0247(12) Uani 1 1 d . . . . .
H10 H 0.271867 0.680695 0.523839 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6684(3) 0.6058(7) 0.6238(3) 0.0221(11) Uani 1 1 d . . . . .
C12 C 0.6883(3) 0.4110(8) 0.6609(3) 0.0305(12) Uani 1 1 d . . . . .
H12 H 0.647251 0.330530 0.671912 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7659(3) 0.3325(8) 0.6821(3) 0.0308(13) Uani 1 1 d . . . . .
H13 H 0.777884 0.200088 0.707822 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8268(3) 0.4462(7) 0.6659(3) 0.0244(12) Uani 1 1 d . . . . .
C15 C 0.8081(3) 0.6425(7) 0.6289(3) 0.0241(12) Uani 1 1 d . . . . .
H15 H 0.849361 0.722790 0.618248 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7304(3) 0.7193(7) 0.6082(3) 0.0232(11) Uani 1 1 d . . . . .
H16 H 0.718511 0.852032 0.582727 0.028 Uiso 1 1 calc R U . . .
C17 C 0.9294(4) 0.1917(8) 0.7253(4) 0.0391(14) Uani 1 1 d . . . . .
H17A H 0.920907 0.190308 0.783391 0.047 Uiso 1 1 calc R U . . .
H17B H 0.987169 0.167136 0.734529 0.047 Uiso 1 1 calc R U . . .
H17C H 0.896212 0.084257 0.686821 0.047 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.834(5) . ?
S1 F2 1.584(3) . ?
S1 F1 1.587(3) . ?
S1 F5 1.588(3) . ?
S1 F4 1.589(3) . ?
S1 F3 1.591(3) . ?
S1 C8 1.817(5) . ?
O4 C4 1.225(5) . ?
O14 C14 1.366(6) . ?
O14 C17 1.430(6) . ?
N1 C2 1.332(6) . ?
N1 C5 1.443(6) . ?
N1 H1 0.97(2) . ?
N3 C2 1.383(6) . ?
N3 C4 1.406(6) . ?
N3 H3 0.96(2) . ?
C4 C11 1.465(7) . ?
C5 C10 1.383(7) . ?
C5 C6 1.390(6) . ?
C6 C7 1.384(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(6) . ?
C9 C10 1.380(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.397(7) . ?
C11 C16 1.400(7) . ?
C12 C13 1.377(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(6) . ?
C15 C16 1.375(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 S1 F1 87.64(17) . . ?
F2 S1 F5 90.43(16) . . ?
F1 S1 F5 87.64(16) . . ?
F2 S1 F4 175.64(18) . . ?
F1 S1 F4 88.02(16) . . ?
F5 S1 F4 89.74(15) . . ?
F2 S1 F3 89.89(16) . . ?
F1 S1 F3 87.71(16) . . ?
F5 S1 F3 175.32(18) . . ?
F4 S1 F3 89.58(16) . . ?
F2 S1 C8 92.19(19) . . ?
F1 S1 C8 179.78(18) . . ?
F5 S1 C8 92.51(18) . . ?
F4 S1 C8 92.15(18) . . ?
F3 S1 C8 92.14(18) . . ?
C14 O14 C17 117.4(4) . . ?
C2 N1 C5 121.6(4) . . ?
C2 N1 H1 113(4) . . ?
C5 N1 H1 124(4) . . ?
C2 N3 C4 128.3(4) . . ?
C2 N3 H3 116(4) . . ?
C4 N3 H3 114(4) . . ?
N1 C2 N3 118.0(4) . . ?
N1 C2 Se2 124.2(4) . . ?
N3 C2 Se2 117.8(3) . . ?
O4 C4 N3 120.1(4) . . ?
O4 C4 C11 123.4(4) . . ?
N3 C4 C11 116.5(4) . . ?
C10 C5 C6 120.5(4) . . ?
C10 C5 N1 121.1(4) . . ?
C6 C5 N1 118.4(4) . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.1(4) . . ?
C7 C8 S1 119.4(4) . . ?
C9 C8 S1 119.5(4) . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C5 120.5(4) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C16 117.5(5) . . ?
C12 C11 C4 123.8(5) . . ?
C16 C11 C4 118.7(4) . . ?
C13 C12 C11 121.7(5) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O14 C14 C13 126.1(4) . . ?
O14 C14 C15 114.9(4) . . ?
C13 C14 C15 119.0(5) . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.4(5) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
O14 C17 H17A 109.5 . . ?
O14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -175.8(4) . . . . ?
C5 N1 C2 Se2 2.8(6) . . . . ?
C4 N3 C2 N1 17.7(7) . . . . ?
C4 N3 C2 Se2 -161.0(4) . . . . ?
C2 N3 C4 O4 -8.7(7) . . . . ?
C2 N3 C4 C11 170.7(4) . . . . ?
C2 N1 C5 C10 -80.0(5) . . . . ?
C2 N1 C5 C6 101.8(5) . . . . ?
C10 C5 C6 C7 1.2(6) . . . . ?
N1 C5 C6 C7 179.4(4) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C6 C7 C8 C9 -0.9(6) . . . . ?
C6 C7 C8 S1 179.9(3) . . . . ?
F2 S1 C8 C7 -133.4(3) . . . . ?
F5 S1 C8 C7 136.0(3) . . . . ?
F4 S1 C8 C7 46.2(4) . . . . ?
F3 S1 C8 C7 -43.5(4) . . . . ?
F2 S1 C8 C9 47.3(4) . . . . ?
F5 S1 C8 C9 -43.2(3) . . . . ?
F4 S1 C8 C9 -133.1(3) . . . . ?
F3 S1 C8 C9 137.3(3) . . . . ?
C7 C8 C9 C10 0.7(6) . . . . ?
S1 C8 C9 C10 180.0(3) . . . . ?
C8 C9 C10 C5 0.3(6) . . . . ?
C6 C5 C10 C9 -1.3(6) . . . . ?
N1 C5 C10 C9 -179.5(4) . . . . ?
O4 C4 C11 C12 -161.2(5) . . . . ?
N3 C4 C11 C12 19.4(6) . . . . ?
O4 C4 C11 C16 19.7(7) . . . . ?
N3 C4 C11 C16 -159.7(4) . . . . ?
C16 C11 C12 C13 0.3(7) . . . . ?
C4 C11 C12 C13 -178.8(4) . . . . ?
C11 C12 C13 C14 -0.6(7) . . . . ?
C17 O14 C14 C13 -2.4(6) . . . . ?
C17 O14 C14 C15 176.9(4) . . . . ?
C12 C13 C14 O14 -179.9(4) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
O14 C14 C15 C16 179.8(4) . . . . ?
C13 C14 C15 C16 -0.9(6) . . . . ?
C14 C15 C16 C11 0.5(6) . . . . ?
C12 C11 C16 C15 -0.3(6) . . . . ?
C4 C11 C16 C15 178.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O4 0.97(2) 1.89(5) 2.687(6) 138(6) . yes
N1 H1 O4 0.97(2) 2.38(5) 3.104(5) 131(5) 3_676 yes
N3 H3 Se2 0.96(2) 2.99(3) 3.874(4) 154(4) 2_646 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1900138'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-06
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H14 Br2 N2 O Se'
_chemical_formula_moiety         'C22 H14 Br2 N2 O Se'
_chemical_formula_weight         561.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.3990(7)
_cell_length_b                   11.8584(8)
_cell_length_c                   15.0948(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.183(6)
_cell_angle_gamma                90.0000
_cell_volume                     2037.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6071
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088.00
_exptl_absorpt_coefficient_mu    5.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_T_max  0.560

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            17055
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  0.1577
_diffrn_reflns_theta_max         25.359
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3668
_reflns_number_gt                3123
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0998
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3668
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.90
_refine_diff_density_min         -0.77
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br17 Br 0.42384(3) -0.05209(3) 0.33123(3) 0.04088(14) Uani 1 1 d . . . . .
Br23 Br -0.11647(3) 0.07630(3) 0.58270(3) 0.04096(14) Uani 1 1 d . . . . .
Se1 Se 0.31315(3) 0.65756(3) 0.44524(2) 0.03623(14) Uani 1 1 d . . . . .
O7 O 0.4804(2) 0.7078(2) 0.34727(18) 0.0422(6) Uani 1 1 d . . . . .
N3 N 0.3044(2) 0.4347(2) 0.4155(2) 0.0292(6) Uani 1 1 d . . . . .
N6 N 0.4571(2) 0.5152(2) 0.34070(19) 0.0300(6) Uani 1 1 d . . . . .
C2 C 0.3687(3) 0.5248(3) 0.3919(2) 0.0280(7) Uani 1 1 d . . . . .
C4 C 0.2123(3) 0.4558(3) 0.4726(2) 0.0300(7) Uani 1 1 d . . . . .
C5 C 0.2030(3) 0.5636(3) 0.4963(3) 0.0386(8) Uani 1 1 d . . . . .
H5 H 0.146190 0.590164 0.535043 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5102(3) 0.6147(3) 0.3194(2) 0.0303(7) Uani 1 1 d . . . . .
C8 C 0.6095(3) 0.6075(3) 0.2601(2) 0.0295(7) Uani 1 1 d . . . . .
C9 C 0.6689(3) 0.7061(3) 0.2390(2) 0.0385(8) Uani 1 1 d . . . . .
H9 H 0.647518 0.775804 0.264537 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7580(3) 0.7027(4) 0.1816(3) 0.0442(9) Uani 1 1 d . . . . .
H10 H 0.798447 0.769967 0.167952 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7895(3) 0.6012(4) 0.1433(3) 0.0465(10) Uani 1 1 d . . . . .
H11 H 0.849952 0.599482 0.102523 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7323(3) 0.5027(4) 0.1649(3) 0.0462(9) Uani 1 1 d . . . . .
H12 H 0.754506 0.433078 0.139475 0.055 Uiso 1 1 calc R U . . .
C13 C 0.6430(3) 0.5053(3) 0.2232(3) 0.0357(8) Uani 1 1 d . . . . .
H13 H 0.604378 0.437495 0.238223 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3369(2) 0.3207(3) 0.3933(2) 0.0258(6) Uani 1 1 d . . . . .
C15 C 0.3235(3) 0.2833(3) 0.3070(2) 0.0315(7) Uani 1 1 d . . . . .
H15 H 0.297054 0.333407 0.260972 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3490(3) 0.1721(3) 0.2878(2) 0.0325(7) Uani 1 1 d . . . . .
H16 H 0.340184 0.145038 0.228614 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3877(2) 0.1006(3) 0.3563(2) 0.0296(7) Uani 1 1 d . . . . .
C18 C 0.4010(3) 0.1378(3) 0.4418(2) 0.0330(7) Uani 1 1 d . . . . .
H18 H 0.427086 0.087511 0.487730 0.040 Uiso 1 1 calc R U . . .
C19 C 0.3761(3) 0.2492(3) 0.4612(2) 0.0309(7) Uani 1 1 d . . . . .
H19 H 0.385951 0.276139 0.520440 0.037 Uiso 1 1 calc R U . . .
C20 C 0.1341(3) 0.3631(3) 0.4978(2) 0.0296(7) Uani 1 1 d . . . . .
C21 C 0.0799(3) 0.2922(3) 0.4348(2) 0.0319(7) Uani 1 1 d . . . . .
H21 H 0.093755 0.302336 0.373867 0.038 Uiso 1 1 calc R U . . .
C22 C 0.0054(3) 0.2063(3) 0.4600(2) 0.0307(7) Uani 1 1 d . . . . .
H22 H -0.031217 0.157661 0.416786 0.037 Uiso 1 1 calc R U . . .
C23 C -0.0144(3) 0.1931(3) 0.5492(2) 0.0318(7) Uani 1 1 d . . . . .
C24 C 0.0387(3) 0.2632(3) 0.6131(2) 0.0341(8) Uani 1 1 d . . . . .
H24 H 0.024414 0.253009 0.674045 0.041 Uiso 1 1 calc R U . . .
C25 C 0.1124(3) 0.3478(3) 0.5872(2) 0.0331(7) Uani 1 1 d . . . . .
H25 H 0.148925 0.396206 0.630686 0.040 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br17 C17 1.900(3) . ?
Br23 C23 1.896(3) . ?
Se1 C5 1.876(4) . ?
Se1 C2 1.893(3) . ?
O7 C7 1.236(4) . ?
N3 C2 1.354(4) . ?
N3 C4 1.417(4) . ?
N3 C14 1.446(4) . ?
N6 C2 1.309(4) . ?
N6 C7 1.373(4) . ?
C4 C5 1.333(5) . ?
C4 C20 1.478(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.483(5) . ?
C8 C13 1.395(5) . ?
C8 C9 1.397(5) . ?
C9 C10 1.372(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.377(5) . ?
C14 C19 1.386(5) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.364(5) . ?
C18 C19 1.386(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.388(5) . ?
C20 C25 1.398(5) . ?
C21 C22 1.391(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(5) . ?
C24 C25 1.380(5) . ?
C24 H24 0.9500 . ?
C25 H25 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
C5 Se1 C2 85.86(14) . . ?
C2 N3 C4 116.8(3) . . ?
C2 N3 C14 121.9(2) . . ?
C4 N3 C14 120.9(3) . . ?
C2 N6 C7 115.3(3) . . ?
N6 C2 N3 122.2(3) . . ?
N6 C2 Se1 127.6(3) . . ?
N3 C2 Se1 110.2(2) . . ?
C5 C4 N3 113.9(3) . . ?
C5 C4 C20 125.9(3) . . ?
N3 C4 C20 120.2(3) . . ?
C4 C5 Se1 113.2(3) . . ?
C4 C5 H5 123.4 . . ?
Se1 C5 H5 123.4 . . ?
O7 C7 N6 123.7(3) . . ?
O7 C7 C8 119.4(3) . . ?
N6 C7 C8 116.9(3) . . ?
C13 C8 C9 119.3(3) . . ?
C13 C8 C7 121.7(3) . . ?
C9 C8 C7 119.0(3) . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C15 C14 C19 121.1(3) . . ?
C15 C14 N3 120.2(3) . . ?
C19 C14 N3 118.6(3) . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 Br17 118.8(3) . . ?
C16 C17 Br17 119.8(3) . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 119.2(3) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C25 119.1(3) . . ?
C21 C20 C4 121.8(3) . . ?
C25 C20 C4 119.1(3) . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C24 C23 C22 121.3(3) . . ?
C24 C23 Br23 120.2(3) . . ?
C22 C23 Br23 118.5(3) . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C20 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 C2 N3 177.1(3) . . . . ?
C7 N6 C2 Se1 -4.3(4) . . . . ?
C4 N3 C2 N6 178.8(3) . . . . ?
C14 N3 C2 N6 6.7(5) . . . . ?
C4 N3 C2 Se1 0.0(4) . . . . ?
C14 N3 C2 Se1 -172.1(2) . . . . ?
C5 Se1 C2 N6 -178.3(3) . . . . ?
C5 Se1 C2 N3 0.4(2) . . . . ?
C2 N3 C4 C5 -0.7(4) . . . . ?
C14 N3 C4 C5 171.5(3) . . . . ?
C2 N3 C4 C20 176.8(3) . . . . ?
C14 N3 C4 C20 -11.0(5) . . . . ?
N3 C4 C5 Se1 1.0(4) . . . . ?
C20 C4 C5 Se1 -176.3(3) . . . . ?
C2 Se1 C5 C4 -0.8(3) . . . . ?
C2 N6 C7 O7 1.6(5) . . . . ?
C2 N6 C7 C8 -178.9(3) . . . . ?
O7 C7 C8 C13 -176.7(3) . . . . ?
N6 C7 C8 C13 3.8(5) . . . . ?
O7 C7 C8 C9 1.6(5) . . . . ?
N6 C7 C8 C9 -177.8(3) . . . . ?
C13 C8 C9 C10 1.0(5) . . . . ?
C7 C8 C9 C10 -177.4(3) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C13 1.0(6) . . . . ?
C11 C12 C13 C8 0.5(6) . . . . ?
C9 C8 C13 C12 -1.5(5) . . . . ?
C7 C8 C13 C12 176.9(3) . . . . ?
C2 N3 C14 C15 -72.0(4) . . . . ?
C4 N3 C14 C15 116.2(3) . . . . ?
C2 N3 C14 C19 111.0(3) . . . . ?
C4 N3 C14 C19 -60.8(4) . . . . ?
C19 C14 C15 C16 0.4(5) . . . . ?
N3 C14 C15 C16 -176.5(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C15 C16 C17 Br17 -179.7(2) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
Br17 C17 C18 C19 179.4(2) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?
N3 C14 C19 C18 176.2(3) . . . . ?
C17 C18 C19 C14 0.7(5) . . . . ?
C5 C4 C20 C21 127.2(4) . . . . ?
N3 C4 C20 C21 -50.0(4) . . . . ?
C5 C4 C20 C25 -51.6(5) . . . . ?
N3 C4 C20 C25 131.2(3) . . . . ?
C25 C20 C21 C22 -0.4(5) . . . . ?
C4 C20 C21 C22 -179.2(3) . . . . ?
C20 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C21 C22 C23 Br23 179.7(2) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
Br23 C23 C24 C25 -179.8(2) . . . . ?
C23 C24 C25 C20 -0.2(5) . . . . ?
C21 C20 C25 C24 0.3(5) . . . . ?
C4 C20 C25 C24 179.1(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1900141'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H11 Br N2'
_chemical_formula_moiety         'C10 H11 Br N2'
_chemical_formula_weight         239.11
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.1222(10)
_cell_length_b                   11.956(2)
_cell_length_c                   14.3610(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1051.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2738
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480.00
_exptl_absorpt_coefficient_mu    3.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.890

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            12853
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_theta_max         25.370
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1926
_reflns_number_gt                1603
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.994

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0465
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1926
_refine_ls_number_parameters     124
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0237P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br7 Br 0.88843(7) 0.52610(4) 0.38985(3) 0.05593(16) Uani 1 1 d . . . . .
N1 N 1.2582(6) 0.7194(3) 0.8374(2) 0.0559(9) Uani 1 1 d . . . . .
N3 N 0.7308(5) 0.7394(3) 0.7666(2) 0.0342(7) Uani 1 1 d D . . . .
H3 H 0.599(4) 0.726(3) 0.791(2) 0.031(9) Uiso 1 1 d D . . . .
C1 C 1.0908(7) 0.7577(3) 0.8299(2) 0.0374(8) Uani 1 1 d . . . . .
C2 C 0.8707(6) 0.8111(3) 0.8208(2) 0.0313(8) Uani 1 1 d . . . . .
C4 C 0.7712(5) 0.6965(3) 0.6790(2) 0.0274(8) Uani 1 1 d . . . . .
C5 C 0.9644(5) 0.7140(3) 0.6296(2) 0.0285(8) Uani 1 1 d . . . . .
H5 H 1.074640 0.760796 0.655078 0.034 Uiso 1 1 calc R U . . .
C6 C 0.9974(6) 0.6636(3) 0.5436(2) 0.0314(8) Uani 1 1 d . . . . .
H6 H 1.129424 0.676143 0.510419 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8396(6) 0.5960(3) 0.5069(2) 0.0325(8) Uani 1 1 d . . . . .
C8 C 0.6445(6) 0.5787(3) 0.5530(2) 0.0361(8) Uani 1 1 d . . . . .
H8 H 0.533964 0.533058 0.526349 0.043 Uiso 1 1 calc R U . . .
C9 C 0.6127(6) 0.6288(3) 0.6383(2) 0.0320(8) Uani 1 1 d . . . . .
H9 H 0.478896 0.616798 0.670224 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7740(6) 0.8183(4) 0.9190(3) 0.0474(11) Uani 1 1 d . . . . .
H10A H 0.866722 0.866085 0.957840 0.057 Uiso 1 1 calc R U . . .
H10B H 0.766860 0.743183 0.946167 0.057 Uiso 1 1 calc R U . . .
H10C H 0.626725 0.850097 0.915733 0.057 Uiso 1 1 calc R U . . .
C11 C 0.8959(8) 0.9272(3) 0.7786(3) 0.0501(10) Uani 1 1 d . . . . .
H11A H 0.754301 0.965447 0.779053 0.060 Uiso 1 1 calc R U . . .
H11B H 0.948305 0.920547 0.714397 0.060 Uiso 1 1 calc R U . . .
H11C H 1.001274 0.970374 0.815329 0.060 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br7 C7 1.900(3) . ?
N1 C1 1.128(5) . ?
N3 C4 1.380(4) . ?
N3 C2 1.440(4) . ?
N3 H3 0.90(2) . ?
C1 C2 1.497(6) . ?
C2 C11 1.522(5) . ?
C2 C10 1.532(5) . ?
C4 C9 1.393(5) . ?
C4 C5 1.395(4) . ?
C5 C6 1.389(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(5) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N3 C2 127.4(3) . . ?
C4 N3 H3 117(2) . . ?
C2 N3 H3 116(2) . . ?
N1 C1 C2 178.6(4) . . ?
N3 C2 C1 109.2(3) . . ?
N3 C2 C11 112.9(3) . . ?
C1 C2 C11 109.4(3) . . ?
N3 C2 C10 107.5(3) . . ?
C1 C2 C10 106.9(3) . . ?
C11 C2 C10 110.8(3) . . ?
N3 C4 C9 118.3(3) . . ?
N3 C4 C5 124.0(3) . . ?
C9 C4 C5 117.6(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 Br7 119.4(3) . . ?
C8 C7 Br7 119.6(3) . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C4 121.9(3) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N3 C2 C1 -54.2(4) . . . . ?
C4 N3 C2 C11 67.8(5) . . . . ?
C4 N3 C2 C10 -169.8(3) . . . . ?
C2 N3 C4 C9 -179.6(3) . . . . ?
C2 N3 C4 C5 2.4(5) . . . . ?
N3 C4 C5 C6 176.9(3) . . . . ?
C9 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C8 1.5(5) . . . . ?
C5 C6 C7 Br7 -179.2(3) . . . . ?
C6 C7 C8 C9 -1.6(5) . . . . ?
Br7 C7 C8 C9 179.2(2) . . . . ?
C7 C8 C9 C4 0.2(5) . . . . ?
N3 C4 C9 C8 -177.0(3) . . . . ?
C5 C4 C9 C8 1.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 N1 0.90(2) 2.19(2) 3.076(4) 170(3) 1_455 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1900142'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H14 Br N'
_chemical_formula_moiety         'C12 H14 Br N'
_chemical_formula_weight         252.15
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.9086(12)
_cell_length_b                   17.787(3)
_cell_length_c                   7.9416(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.047(5)
_cell_angle_gamma                90.0000
_cell_volume                     1117.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3141
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.60
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.00
_exptl_absorpt_coefficient_mu    3.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_T_max  0.720

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            13382
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         2.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2031
_reflns_number_gt                1733
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0647
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     134
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0524P)²+0.0212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br7 Br 0.85232(3) 0.57740(2) 0.07518(3) 0.04014(14) Uani 1 1 d . . . . .
N1 N 0.4639(3) 0.70197(11) 0.6621(3) 0.0331(5) Uani 1 1 d D . . . .
C2 C 0.3217(3) 0.66340(12) 0.7412(3) 0.0271(5) Uani 1 1 d . . . . .
C3 C 0.2443(3) 0.60882(12) 0.6176(3) 0.0266(5) Uani 1 1 d . . . . .
H3 H 0.134735 0.590105 0.641193 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3170(3) 0.58452(11) 0.4774(3) 0.0243(5) Uani 1 1 d . . . . .
C5 C 0.4850(3) 0.61269(11) 0.4348(3) 0.0220(4) Uani 1 1 d . . . . .
C6 C 0.5754(3) 0.58585(11) 0.2990(3) 0.0242(5) Uani 1 1 d . . . . .
H6 H 0.527307 0.548189 0.228107 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7345(3) 0.61342(13) 0.2661(3) 0.0280(5) Uani 1 1 d . . . . .
C8 C 0.8084(3) 0.66722(13) 0.3676(3) 0.0334(5) Uani 1 1 d . . . . .
H8 H 0.919517 0.684596 0.345955 0.040 Uiso 1 1 calc R U . . .
C9 C 0.7196(3) 0.69572(13) 0.5014(3) 0.0337(5) Uani 1 1 d . . . . .
H9 H 0.769789 0.733538 0.570478 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5571(3) 0.66988(12) 0.5370(3) 0.0254(5) Uani 1 1 d . . . . .
C11 C 0.1909(3) 0.72313(14) 0.7875(3) 0.0382(6) Uani 1 1 d . . . . .
H11A H 0.242811 0.759645 0.865012 0.046 Uiso 1 1 calc R U . . .
H11B H 0.094859 0.698937 0.841859 0.046 Uiso 1 1 calc R U . . .
H11C H 0.151339 0.749001 0.685179 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3810(3) 0.62221(14) 0.9007(3) 0.0405(6) Uani 1 1 d . . . . .
H12A H 0.285980 0.594528 0.948180 0.049 Uiso 1 1 calc R U . . .
H12B H 0.423762 0.658799 0.983333 0.049 Uiso 1 1 calc R U . . .
H12C H 0.471443 0.586913 0.872709 0.049 Uiso 1 1 calc R U . . .
C13 C 0.2315(3) 0.52837(13) 0.3630(3) 0.0308(5) Uani 1 1 d . . . . .
H13A H 0.215268 0.550452 0.250846 0.037 Uiso 1 1 calc R U . . .
H13B H 0.121374 0.514766 0.408758 0.037 Uiso 1 1 calc R U . . .
H13C H 0.302072 0.483281 0.354911 0.037 Uiso 1 1 calc R U . . .
H1 H 0.519(3) 0.7321(13) 0.739(3) 0.040(7) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br7 C7 1.905(2) . ?
N1 C10 1.372(3) . ?
N1 C2 1.468(3) . ?
N1 H1 0.917(17) . ?
C2 C3 1.503(3) . ?
C2 C12 1.530(3) . ?
C2 C11 1.532(3) . ?
C3 C4 1.334(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.466(3) . ?
C4 C13 1.502(3) . ?
C5 C6 1.390(3) . ?
C5 C10 1.415(3) . ?
C6 C7 1.379(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C2 122.77(18) . . ?
C10 N1 H1 117.8(17) . . ?
C2 N1 H1 110.6(18) . . ?
N1 C2 C3 109.18(18) . . ?
N1 C2 C12 110.61(19) . . ?
C3 C2 C12 110.28(19) . . ?
N1 C2 C11 107.72(19) . . ?
C3 C2 C11 109.63(19) . . ?
C12 C2 C11 109.38(19) . . ?
C4 C3 C2 125.29(19) . . ?
C4 C3 H3 117.4 . . ?
C2 C3 H3 117.4 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 C13 121.6(2) . . ?
C5 C4 C13 119.19(19) . . ?
C6 C5 C10 118.99(19) . . ?
C6 C5 C4 122.92(19) . . ?
C10 C5 C4 118.09(19) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 Br7 119.45(17) . . ?
C6 C7 Br7 119.46(17) . . ?
C7 C8 C9 119.3(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
N1 C10 C9 121.2(2) . . ?
N1 C10 C5 119.88(19) . . ?
C9 C10 C5 118.8(2) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C3 -28.0(3) . . . . ?
C10 N1 C2 C12 93.6(2) . . . . ?
C10 N1 C2 C11 -146.9(2) . . . . ?
N1 C2 C3 C4 16.2(3) . . . . ?
C12 C2 C3 C4 -105.5(3) . . . . ?
C11 C2 C3 C4 134.0(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C13 178.6(2) . . . . ?
C3 C4 C5 C6 174.6(2) . . . . ?
C13 C4 C5 C6 -4.8(3) . . . . ?
C3 C4 C5 C10 -5.5(3) . . . . ?
C13 C4 C5 C10 175.08(19) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
C4 C5 C6 C7 -178.87(19) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C5 C6 C7 Br7 -178.25(16) . . . . ?
C6 C7 C8 C9 -2.1(4) . . . . ?
Br7 C7 C8 C9 177.05(18) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
C2 N1 C10 C9 -159.5(2) . . . . ?
C2 N1 C10 C5 24.4(3) . . . . ?
C8 C9 C10 N1 -175.2(2) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C6 C5 C10 N1 174.0(2) . . . . ?
C4 C5 C10 N1 -5.8(3) . . . . ?
C6 C5 C10 C9 -2.2(3) . . . . ?
C4 C5 C10 C9 178.0(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1900143'
loop_
_audit_author_name
_audit_author_address
'J. Derek Woollins'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2019-02-12
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H9 F5 N4 O3 S Se2'
_chemical_formula_moiety         'C15 H9 F5 N4 O3 S Se2'
_chemical_formula_weight         578.23
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.680(4)
_cell_length_b                   10.671(10)
_cell_length_c                   13.825(8)
_cell_angle_alpha                95.96(10)
_cell_angle_beta                 100.66(8)
_cell_angle_gamma                109.54(6)
_cell_volume                     1032.4(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3585
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      26.37
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560.00
_exptl_absorpt_coefficient_mu    3.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_T_max  0.894

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            8540
_diffrn_reflns_av_unetI/netI     0.1099
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_theta_max         26.385
_diffrn_reflns_theta_min         1.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4089
_reflns_number_gt                2807
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0883
_refine_ls_wR_factor_ref         0.2546
_refine_ls_wR_factor_gt          0.1942
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4089
_refine_ls_number_parameters     271
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0719P)²+15.9343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.00
_refine_diff_density_min         -1.10
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.40913(18) 0.13115(12) 0.26951(9) 0.0363(4) Uani 1 1 d . . . . .
Se2 Se 0.53153(19) 0.35062(12) 0.22657(9) 0.0396(4) Uani 1 1 d . . . . .
S1 S 0.7276(5) 0.9125(3) 0.0658(2) 0.0411(8) Uani 1 1 d . . . . .
F1 F 0.7638(12) 1.0005(8) -0.0193(6) 0.057(2) Uani 1 1 d . . . . .
F2 F 0.6638(12) 1.0218(8) 0.1180(6) 0.054(2) Uani 1 1 d . . . . .
F3 F 0.5183(12) 0.8327(8) 0.0006(6) 0.056(2) Uani 1 1 d . . . . .
F4 F 0.8011(12) 0.8113(8) 0.0074(6) 0.053(2) Uani 1 1 d . . . . .
F5 F 0.9397(10) 0.9966(7) 0.1233(5) 0.0457(18) Uani 1 1 d . . . . .
O14 O 0.2912(12) -0.0469(8) 0.3506(6) 0.041(2) Uani 1 1 d . . . . .
O18 O -0.0754(13) -0.4775(8) 0.6576(7) 0.047(2) Uani 1 1 d . . . . .
O19 O -0.0636(17) -0.3112(9) 0.7639(8) 0.065(3) Uani 1 1 d . . . . .
N4 N 0.4630(13) 0.3509(9) 0.4201(7) 0.031(2) Uani 1 1 d . . . . .
N6 N 0.5681(15) 0.5598(10) 0.3762(8) 0.040(2) Uani 1 1 d . . . . .
H6 H 0.574483 0.599343 0.444581 0.048 Uiso 1 1 calc R U . . .
N13 N 0.3415(13) 0.1385(9) 0.4654(7) 0.031(2) Uani 1 1 d . . . . .
N18 N -0.0298(13) -0.3544(10) 0.6868(8) 0.035(2) Uani 1 1 d . . . . .
C3 C 0.5155(19) 0.4258(15) 0.3529(10) 0.048(3) Uani 1 1 d . . . . .
C5 C 0.4068(16) 0.2175(11) 0.3979(8) 0.029(2) Uani 1 1 d . . . . .
C7 C 0.6159(18) 0.6495(12) 0.3064(9) 0.038(3) Uani 1 1 d . . . . .
C8 C 0.483(2) 0.7034(14) 0.2673(10) 0.046(3) Uani 1 1 d . . . . .
H8 H 0.369214 0.686290 0.289768 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5198(19) 0.7845(14) 0.1932(10) 0.044(3) Uani 1 1 d . . . . .
H9 H 0.429027 0.820395 0.164079 0.053 Uiso 1 1 calc R U . . .
C10 C 0.6855(17) 0.8103(12) 0.1643(9) 0.038(3) Uani 1 1 d . . . . .
C11 C 0.8230(19) 0.7588(13) 0.2043(9) 0.043(3) Uani 1 1 d . . . . .
H11 H 0.938226 0.778573 0.182716 0.051 Uiso 1 1 calc R U . . .
C12 C 0.7859(15) 0.6758(12) 0.2781(8) 0.032(3) Uani 1 1 d . . . . .
H12 H 0.876282 0.639479 0.307182 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2844(16) 0.0033(11) 0.4331(8) 0.031(2) Uani 1 1 d . . . . .
C15 C 0.2128(15) -0.0835(11) 0.5034(9) 0.030(2) Uani 1 1 d . . . . .
C16 C 0.1891(15) -0.2220(11) 0.4814(9) 0.035(3) Uani 1 1 d . . . . .
H16 H 0.227464 -0.254607 0.425495 0.042 Uiso 1 1 calc R U . . .
C17 C 0.1076(16) -0.3112(11) 0.5436(8) 0.032(3) Uani 1 1 d . . . . .
H17 H 0.092047 -0.404018 0.530903 0.038 Uiso 1 1 calc R U . . .
C18 C 0.0522(16) -0.2605(12) 0.6218(9) 0.037(3) Uani 1 1 d . . . . .
C19 C 0.0784(18) -0.1262(12) 0.6478(9) 0.042(3) Uani 1 1 d . . . . .
H19 H 0.041771 -0.094706 0.704766 0.050 Uiso 1 1 calc R U . . .
C20 C 0.1622(16) -0.0365(12) 0.5862(9) 0.035(3) Uani 1 1 d . . . . .
H20 H 0.183448 0.056951 0.602409 0.042 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.920(11) . ?
Se1 O14 2.313(8) . ?
Se1 Se2 2.397(3) . ?
Se2 C3 1.889(15) . ?
S1 F2 1.568(8) . ?
S1 F5 1.576(8) . ?
S1 F3 1.584(9) . ?
S1 F1 1.587(8) . ?
S1 F4 1.591(8) . ?
S1 C10 1.840(13) . ?
O14 C14 1.227(13) . ?
O18 N18 1.241(12) . ?
O19 N18 1.224(14) . ?
N4 C3 1.320(15) . ?
N4 C5 1.325(14) . ?
N6 C3 1.335(17) . ?
N6 C7 1.438(14) . ?
N6 H6 0.9800 . ?
N13 C14 1.358(14) . ?
N13 C5 1.374(14) . ?
N18 C18 1.477(15) . ?
C7 C12 1.380(17) . ?
C7 C8 1.384(18) . ?
C8 C9 1.415(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.353(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(17) . ?
C11 C12 1.426(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.465(16) . ?
C15 C20 1.375(17) . ?
C15 C16 1.420(15) . ?
C16 C17 1.417(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.359(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(17) . ?
C19 C20 1.419(16) . ?
C19 H19 0.9500 . ?
C20 H20 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
C5 Se1 O14 76.1(4) . . ?
C5 Se1 Se2 88.4(3) . . ?
O14 Se1 Se2 164.5(2) . . ?
C3 Se2 Se1 88.5(4) . . ?
F2 S1 F5 89.5(5) . . ?
F2 S1 F3 91.4(5) . . ?
F5 S1 F3 175.6(4) . . ?
F2 S1 F1 88.0(4) . . ?
F5 S1 F1 87.5(4) . . ?
F3 S1 F1 88.2(4) . . ?
F2 S1 F4 174.9(4) . . ?
F5 S1 F4 88.8(5) . . ?
F3 S1 F4 90.0(5) . . ?
F1 S1 F4 87.1(4) . . ?
F2 S1 C10 92.0(5) . . ?
F5 S1 C10 92.6(5) . . ?
F3 S1 C10 91.7(5) . . ?
F1 S1 C10 179.9(7) . . ?
F4 S1 C10 92.8(5) . . ?
C14 O14 Se1 106.4(7) . . ?
C3 N4 C5 120.3(11) . . ?
C3 N6 C7 123.6(11) . . ?
C3 N6 H6 118.2 . . ?
C7 N6 H6 118.2 . . ?
C14 N13 C5 115.1(9) . . ?
O19 N18 O18 121.4(10) . . ?
O19 N18 C18 120.0(10) . . ?
O18 N18 C18 118.4(11) . . ?
N4 C3 N6 119.4(13) . . ?
N4 C3 Se2 122.1(11) . . ?
N6 C3 Se2 118.4(9) . . ?
N4 C5 N13 120.6(10) . . ?
N4 C5 Se1 120.5(8) . . ?
N13 C5 Se1 118.8(8) . . ?
C12 C7 C8 122.2(11) . . ?
C12 C7 N6 120.2(11) . . ?
C8 C7 N6 117.5(11) . . ?
C7 C8 C9 119.0(12) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.3(12) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 122.5(12) . . ?
C9 C10 S1 118.6(10) . . ?
C11 C10 S1 118.9(9) . . ?
C10 C11 C12 118.4(11) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C7 C12 C11 118.5(10) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
O14 C14 N13 123.6(10) . . ?
O14 C14 C15 120.2(10) . . ?
N13 C14 C15 116.2(10) . . ?
C20 C15 C16 119.8(11) . . ?
C20 C15 C14 122.4(10) . . ?
C16 C15 C14 117.7(10) . . ?
C17 C16 C15 119.4(11) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 118.2(11) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C18 C19 124.2(11) . . ?
C17 C18 N18 117.5(11) . . ?
C19 C18 N18 118.1(12) . . ?
C18 C19 C20 117.5(12) . . ?
C18 C19 H19 121.3 . . ?
C20 C19 H19 121.3 . . ?
C15 C20 C19 120.7(11) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N4 C3 N6 178.7(11) . . . . ?
C5 N4 C3 Se2 -4.6(16) . . . . ?
C7 N6 C3 N4 -175.9(11) . . . . ?
C7 N6 C3 Se2 7.4(17) . . . . ?
Se1 Se2 C3 N4 3.9(10) . . . . ?
Se1 Se2 C3 N6 -179.4(10) . . . . ?
C3 N4 C5 N13 -176.2(11) . . . . ?
C3 N4 C5 Se1 2.2(15) . . . . ?
C14 N13 C5 N4 178.7(10) . . . . ?
C14 N13 C5 Se1 0.3(13) . . . . ?
C3 N6 C7 C12 -73.7(17) . . . . ?
C3 N6 C7 C8 104.3(15) . . . . ?
C12 C7 C8 C9 2(2) . . . . ?
N6 C7 C8 C9 -175.7(12) . . . . ?
C7 C8 C9 C10 -2(2) . . . . ?
C8 C9 C10 C11 1(2) . . . . ?
C8 C9 C10 S1 178.6(11) . . . . ?
F2 S1 C10 C9 47.6(11) . . . . ?
F5 S1 C10 C9 137.1(11) . . . . ?
F3 S1 C10 C9 -43.9(11) . . . . ?
F4 S1 C10 C9 -133.9(11) . . . . ?
F2 S1 C10 C11 -134.3(10) . . . . ?
F5 S1 C10 C11 -44.8(10) . . . . ?
F3 S1 C10 C11 134.2(10) . . . . ?
F4 S1 C10 C11 44.1(10) . . . . ?
C9 C10 C11 C12 0.1(19) . . . . ?
S1 C10 C11 C12 -177.9(9) . . . . ?
C8 C7 C12 C11 -1.6(19) . . . . ?
N6 C7 C12 C11 176.3(11) . . . . ?
C10 C11 C12 C7 0.4(18) . . . . ?
Se1 O14 C14 N13 -1.1(14) . . . . ?
Se1 O14 C14 C15 179.2(9) . . . . ?
C5 N13 C14 O14 0.7(17) . . . . ?
C5 N13 C14 C15 -179.6(10) . . . . ?
O14 C14 C15 C20 -165.1(11) . . . . ?
N13 C14 C15 C20 15.2(16) . . . . ?
O14 C14 C15 C16 12.4(16) . . . . ?
N13 C14 C15 C16 -167.3(10) . . . . ?
C20 C15 C16 C17 2.0(16) . . . . ?
C14 C15 C16 C17 -175.6(10) . . . . ?
C15 C16 C17 C18 0.9(16) . . . . ?
C16 C17 C18 C19 -3.3(18) . . . . ?
C16 C17 C18 N18 -179.1(10) . . . . ?
O19 N18 C18 C17 172.5(11) . . . . ?
O18 N18 C18 C17 -12.6(15) . . . . ?
O19 N18 C18 C19 -3.7(16) . . . . ?
O18 N18 C18 C19 171.3(10) . . . . ?
C17 C18 C19 C20 2.5(18) . . . . ?
N18 C18 C19 C20 178.3(10) . . . . ?
C16 C15 C20 C19 -2.8(17) . . . . ?
C14 C15 C20 C19 174.6(11) . . . . ?
C18 C19 C20 C15 0.7(17) . . . . ?

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
_geom_hbond_publ_flag
N6 H6 N4 0.98 1.99 2.956(15) 168.3 2_666 yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
