# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_KN1-3B
_database_code_depnum_ccdc_archive 'CCDC 1991016'
loop_
_audit_author_name
_audit_author_address
'Boris Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 F2 N2 O2 Sn'
_chemical_formula_sum            'C18 H12 F2 N2 O2 Sn'
_chemical_formula_weight         444.99

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   13.4420(11)
_cell_length_b                   9.4200(7)
_cell_length_c                   13.5862(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.526(8)
_cell_angle_gamma                90
_cell_volume                     1631.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4309
_cell_measurement_theta_min      2.7490
_cell_measurement_theta_max      32.1370

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.602
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6917
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.850
_diffrn_reflns_theta_max         27.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1977
_reflns_number_gt                1735
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1977
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.5000 0.08823(3) 0.2500 0.03247(10) Uani 1 2 d S T P . .
F1 F 0.39003(15) -0.0523(2) 0.19717(15) 0.0505(4) Uani 1 1 d . . . . .
O1 O 0.45657(17) 0.1160(2) 0.37890(15) 0.0404(5) Uani 1 1 d . . . . .
N1 N 0.60882(17) 0.2565(2) 0.33228(16) 0.0338(5) Uani 1 1 d . . . . .
C1 C 0.6837(2) 0.3220(3) 0.3053(2) 0.0430(7) Uani 1 1 d . . . . .
H1A H 0.6953 0.2970 0.2436 0.052 Uiso 1 1 calc R U . . .
C2 C 0.7455(3) 0.4275(4) 0.3676(3) 0.0537(9) Uani 1 1 d . . . . .
H2A H 0.7972 0.4728 0.3471 0.064 Uiso 1 1 calc R U . . .
C3 C 0.7298(3) 0.4637(4) 0.4587(3) 0.0508(8) Uani 1 1 d . . . . .
H3A H 0.7708 0.5341 0.5003 0.061 Uiso 1 1 calc R U . . .
C4 C 0.6512(2) 0.3948(3) 0.4907(2) 0.0424(7) Uani 1 1 d . . . . .
C5 C 0.6306(3) 0.4209(3) 0.5838(3) 0.0544(9) Uani 1 1 d . . . . .
H5A H 0.6691 0.4889 0.6299 0.065 Uiso 1 1 calc R U . . .
C6 C 0.5535(3) 0.3457(4) 0.6067(2) 0.0552(8) Uani 1 1 d . . . . .
H6A H 0.5406 0.3635 0.6689 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4935(2) 0.2426(4) 0.5388(2) 0.0455(7) Uani 1 1 d . . . . .
H7A H 0.4417 0.1935 0.5566 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5106(2) 0.2136(3) 0.44682(19) 0.0337(5) Uani 1 1 d . . . . .
C9 C 0.5914(2) 0.2910(3) 0.42277(18) 0.0323(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 F1 1.9436(18) 2_655 ?
Sn1 F1 1.9436(18) . ?
Sn1 O1 2.0313(19) 2_655 ?
Sn1 O1 2.0313(19) . ?
Sn1 N1 2.205(2) 2_655 ?
Sn1 N1 2.205(2) . ?
O1 C8 1.341(3) . ?
N1 C1 1.328(3) . ?
N1 C9 1.362(3) . ?
C1 C2 1.395(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.364(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.420(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.400(5) . ?
C4 C9 1.408(4) . ?
C5 C6 1.370(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.404(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.368(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.429(4) . ?

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
F1 Sn1 F1 94.16(12) 2_655 . ?
F1 Sn1 O1 90.75(8) 2_655 2_655 ?
F1 Sn1 O1 99.36(8) . 2_655 ?
F1 Sn1 O1 99.36(8) 2_655 . ?
F1 Sn1 O1 90.75(8) . . ?
O1 Sn1 O1 165.18(11) 2_655 . ?
F1 Sn1 N1 168.77(8) 2_655 2_655 ?
F1 Sn1 N1 89.89(9) . 2_655 ?
O1 Sn1 N1 78.25(8) 2_655 2_655 ?
O1 Sn1 N1 91.05(8) . 2_655 ?
F1 Sn1 N1 89.89(9) 2_655 . ?
F1 Sn1 N1 168.77(8) . . ?
O1 Sn1 N1 91.05(8) 2_655 . ?
O1 Sn1 N1 78.25(8) . . ?
N1 Sn1 N1 88.08(12) 2_655 . ?
C8 O1 Sn1 116.13(16) . . ?
C1 N1 C9 120.1(2) . . ?
C1 N1 Sn1 129.3(2) . . ?
C9 N1 Sn1 110.64(16) . . ?
N1 C1 C2 121.4(3) . . ?
N1 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C9 118.6(3) . . ?
C5 C4 C3 125.2(3) . . ?
C9 C4 C3 116.3(3) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H6A 119.1 . . ?
C7 C6 H6A 119.1 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
O1 C8 C7 123.6(3) . . ?
O1 C8 C9 118.5(2) . . ?
C7 C8 C9 117.8(2) . . ?
N1 C9 C4 122.1(2) . . ?
N1 C9 C8 116.5(2) . . ?
C4 C9 C8 121.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -0.5(4) . . . . ?
Sn1 N1 C1 C2 179.8(2) . . . . ?
N1 C1 C2 C3 0.6(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C2 C3 C4 C9 -1.0(5) . . . . ?
C9 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
Sn1 O1 C8 C7 -178.0(2) . . . . ?
Sn1 O1 C8 C9 1.3(3) . . . . ?
C6 C7 C8 O1 179.6(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C1 N1 C9 C4 -0.5(4) . . . . ?
Sn1 N1 C9 C4 179.3(2) . . . . ?
C1 N1 C9 C8 -178.9(2) . . . . ?
Sn1 N1 C9 C8 0.9(3) . . . . ?
C5 C4 C9 N1 -178.0(3) . . . . ?
C3 C4 C9 N1 1.2(4) . . . . ?
C5 C4 C9 C8 0.4(4) . . . . ?
C3 C4 C9 C8 179.5(3) . . . . ?
O1 C8 C9 N1 -1.5(4) . . . . ?
C7 C8 C9 N1 177.9(2) . . . . ?
O1 C8 C9 C4 -179.9(2) . . . . ?
C7 C8 C9 C4 -0.5(4) . . . . ?

_refine_diff_density_max         1.017
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.104



