# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd16760
_database_code_depnum_ccdc_archive 'CCDC 1879465'
_audit_update_record             
;
2018-11-16 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 F3 N O6 Se'
_chemical_formula_weight         400.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.809(8)
_cell_length_b                   9.877(8)
_cell_length_c                   9.925(8)
_cell_angle_alpha                66.084(14)
_cell_angle_beta                 65.463(14)
_cell_angle_gamma                64.347(15)
_cell_volume                     758.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1502
_cell_measurement_theta_min      4.760
_cell_measurement_theta_max      48.291

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.539
_shelx_estimated_absorpt_T_min   0.631
_shelx_estimated_absorpt_T_max   0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4158
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2778
_reflns_number_gt                2231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2778
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.85801(5) 0.91231(4) 0.68364(4) 0.02829(15) Uani 1 1 d . . . . .
F1 F 0.5884(4) 1.1341(3) 0.6137(3) 0.0655(9) Uani 1 1 d . . . . .
F2 F 0.5331(3) 1.0033(3) 0.8487(3) 0.0510(7) Uani 1 1 d . . . . .
F3 F 0.5835(3) 0.9016(4) 0.6728(3) 0.0605(8) Uani 1 1 d . . . . .
N1 N 0.7901(5) 1.0515(5) 1.2623(4) 0.0454(10) Uani 1 1 d . . . . .
O1 O 1.1232(4) 0.7382(4) 0.4920(3) 0.0498(9) Uani 1 1 d . . . . .
O2 O 1.1056(4) 0.4969(3) 0.6097(4) 0.0548(10) Uani 1 1 d . . . . .
O3 O 0.8583(4) 0.4625(3) 0.8705(4) 0.0588(10) Uani 1 1 d . . . . .
O4 O 0.7054(4) 0.6828(3) 0.9400(3) 0.0436(8) Uani 1 1 d . . . . .
O5 O 0.8217(5) 0.9412(5) 1.3721(4) 0.0729(12) Uani 1 1 d . . . . .
O6 O 0.7496(6) 1.1858(5) 1.2595(4) 0.0828(14) Uani 1 1 d . . . . .
C1 C 0.6221(6) 0.9922(5) 0.7096(5) 0.0394(11) Uani 1 1 d . . . . .
C2 C 0.9160(5) 0.6978(4) 0.7193(4) 0.0316(10) Uani 1 1 d . . . . .
C3 C 1.0546(6) 0.6496(5) 0.5976(5) 0.0364(11) Uani 1 1 d . . . . .
C4 C 1.2437(8) 0.4464(6) 0.4873(6) 0.0733(19) Uani 1 1 d . . . . .
H4A H 1.2180 0.4930 0.3917 0.110 Uiso 1 1 calc R U . . .
H4B H 1.2775 0.3347 0.5101 0.110 Uiso 1 1 calc R U . . .
H4C H 1.3273 0.4780 0.4792 0.110 Uiso 1 1 calc R U . . .
C5 C 0.8289(5) 0.6017(5) 0.8447(5) 0.0371(11) Uani 1 1 d . . . . .
C6 C 0.6253(7) 0.5935(6) 1.0822(6) 0.0663(17) Uani 1 1 d . . . . .
H6A H 0.5689 0.5488 1.0615 0.099 Uiso 1 1 calc R U . . .
H6B H 0.5521 0.6604 1.1475 0.099 Uiso 1 1 calc R U . . .
H6C H 0.7012 0.5114 1.1328 0.099 Uiso 1 1 calc R U . . .
C7 C 0.8344(5) 0.9497(4) 0.8722(4) 0.0287(9) Uani 1 1 d . . . . .
C8 C 0.8789(5) 0.8279(5) 0.9945(5) 0.0333(10) Uani 1 1 d . . . . .
H8 H 0.9177 0.7251 0.9901 0.040 Uiso 1 1 calc R U . . .
C9 C 0.8650(5) 0.8609(5) 1.1243(5) 0.0356(10) Uani 1 1 d . . . . .
H9 H 0.8948 0.7814 1.2079 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8058(5) 1.0146(5) 1.1248(4) 0.0314(10) Uani 1 1 d . . . . .
C11 C 0.7677(5) 1.1384(5) 0.9999(5) 0.0353(10) Uani 1 1 d . . . . .
H11 H 0.7333 1.2412 1.0029 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7823(5) 1.1050(5) 0.8708(4) 0.0326(10) Uani 1 1 d . . . . .
H12 H 0.7577 1.1849 0.7852 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C2 1.858(4) . ?
Se1 C7 1.954(4) . ?
Se1 C1 2.033(5) . ?
F1 C1 1.326(5) . ?
F2 C1 1.311(5) . ?
F3 C1 1.324(5) . ?
N1 O6 1.201(5) . ?
N1 O5 1.223(5) . ?
N1 C10 1.483(5) . ?
O1 C3 1.223(5) . ?
O2 C3 1.338(5) . ?
O2 C4 1.449(6) . ?
O3 C5 1.213(5) . ?
O4 C5 1.352(5) . ?
O4 C6 1.434(5) . ?
C2 C5 1.429(6) . ?
C2 C3 1.440(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.382(6) . ?
C7 C12 1.387(5) . ?
C8 C9 1.393(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(6) . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Se1 C7 107.55(17) . . ?
C2 Se1 C1 104.85(19) . . ?
C7 Se1 C1 94.69(17) . . ?
O6 N1 O5 123.8(4) . . ?
O6 N1 C10 118.9(4) . . ?
O5 N1 C10 117.2(4) . . ?
C3 O2 C4 115.2(4) . . ?
C5 O4 C6 116.7(3) . . ?
F2 C1 F3 108.6(4) . . ?
F2 C1 F1 107.4(4) . . ?
F3 C1 F1 108.1(4) . . ?
F2 C1 Se1 114.1(3) . . ?
F3 C1 Se1 110.5(3) . . ?
F1 C1 Se1 107.9(3) . . ?
C5 C2 C3 127.0(4) . . ?
C5 C2 Se1 123.8(3) . . ?
C3 C2 Se1 109.1(3) . . ?
O1 C3 O2 121.7(4) . . ?
O1 C3 C2 124.0(4) . . ?
O2 C3 C2 114.4(4) . . ?
O2 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 O4 121.1(4) . . ?
O3 C5 C2 126.6(4) . . ?
O4 C5 C2 112.3(3) . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 122.4(4) . . ?
C8 C7 Se1 121.4(3) . . ?
C12 C7 Se1 116.0(3) . . ?
C7 C8 C9 119.2(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.8(4) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 123.5(3) . . ?
C9 C10 N1 118.4(4) . . ?
C11 C10 N1 118.0(4) . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 118.5(4) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?

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 Se1 C2 C5 54.4(4) . . . . ?
C1 Se1 C2 C5 -45.5(4) . . . . ?
C7 Se1 C2 C3 -128.5(3) . . . . ?
C1 Se1 C2 C3 131.6(3) . . . . ?
C4 O2 C3 O1 -1.6(7) . . . . ?
C4 O2 C3 C2 179.3(5) . . . . ?
C5 C2 C3 O1 179.1(5) . . . . ?
Se1 C2 C3 O1 2.1(6) . . . . ?
C5 C2 C3 O2 -1.8(7) . . . . ?
Se1 C2 C3 O2 -178.8(3) . . . . ?
C6 O4 C5 O3 8.2(7) . . . . ?
C6 O4 C5 C2 -170.4(4) . . . . ?
C3 C2 C5 O3 0.9(8) . . . . ?
Se1 C2 C5 O3 177.4(4) . . . . ?
C3 C2 C5 O4 179.4(4) . . . . ?
Se1 C2 C5 O4 -4.0(6) . . . . ?
C12 C7 C8 C9 2.8(6) . . . . ?
Se1 C7 C8 C9 177.8(3) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C8 C9 C10 C11 -3.7(6) . . . . ?
C8 C9 C10 N1 179.9(4) . . . . ?
O6 N1 C10 C9 174.5(4) . . . . ?
O5 N1 C10 C9 -4.5(6) . . . . ?
O6 N1 C10 C11 -2.1(6) . . . . ?
O5 N1 C10 C11 178.9(4) . . . . ?
C9 C10 C11 C12 3.5(7) . . . . ?
N1 C10 C11 C12 179.9(4) . . . . ?
C10 C11 C12 C7 -0.1(6) . . . . ?
C8 C7 C12 C11 -3.0(6) . . . . ?
Se1 C7 C12 C11 -178.2(3) . . . . ?

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
C9 H9 O2 0.93 2.61 3.425(6) 146.9 2_767
C11 H11 O3 0.93 2.58 3.297(6) 134.1 1_565
C12 H12 O1 0.93 2.43 3.190(5) 138.6 2_776

_refine_diff_density_max         1.051
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.100

_shelxl_version_number           2013-4



