# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_fces140924_03
_database_code_depnum_ccdc_archive 'CCDC 1487974'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 1/2+x,1/2+y,z
4 1/2-x,1/2+y,1/2-z
5 -x,-y,-z
6 x,-y,1/2+z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
_cell_length_a                   23.5167(11)
_cell_length_b                   10.1022(3)
_cell_length_c                   17.5581(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.469(2)
_cell_angle_gamma                90
_cell_volume                     4114.45
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.17031(13) 0.2730(3) 0.05718(16)
C2 C 0.13373(14) 0.1613(3) 0.04421(18)
H2 H 0.0943 0.1729 0.0226
C3 C 0.15422(16) 0.0377(3) 0.0623(2)
H3 H 0.1293 -0.0366 0.0527
C4 C 0.21254(16) 0.0193(4) 0.0952(2)
H4 H 0.2265 -0.0673 0.1083
C5 C 0.24901(15) 0.1243(3) 0.10852(18)
H5 H 0.2883 0.1099 0.1299
C6 C 0.22907(13) 0.2551(3) 0.09078(16)
C7 C 0.26378(13) 0.3707(3) 0.10418(17)
C8 C 0.23995(14) 0.4916(3) 0.08433(18)
H8 H 0.2624 0.5699 0.0931
C9 C 0.18105(14) 0.4979(3) 0.05041(18)
C10 C 0.32673(15) 0.3591(4) 0.13928(18)
H10 H 0.3450 0.2878 0.1120
C11 C 0.15295(17) 0.6278(3) 0.0280(2)
H11 H 0.1114 0.6142 0.0057
N1 N 0.14689(11) 0.3941(2) 0.03728(14)
F1 F 0.35479(9) 0.4757(2) 0.13278(12)
F2 F 0.15768(12) 0.7093(2) 0.08999(15)
F3 F 0.18067(12) 0.6920(2) -0.02404(15)
Cl1 Cl 0.33433(4) 0.31957(11) 0.23963(5)
C12 C 0.00389(13) 0.2659(3) 0.12092(16)
C13 C -0.02356(14) 0.1542(3) 0.08407(18)
H13 H -0.0538 0.1655 0.0416
C14 C -0.00733(15) 0.0301(3) 0.10846(19)
H14 H -0.0263 -0.0446 0.0829
C15 C 0.03734(14) 0.0119(3) 0.17123(19)
H15 H 0.0484 -0.0752 0.1879
C16 C 0.06495(14) 0.1177(3) 0.20844(18)
H16 H 0.0952 0.1037 0.2507
C17 C 0.04902(13) 0.2487(3) 0.18480(17)
C18 C 0.07406(13) 0.3655(3) 0.22191(18)
C19 C 0.05506(14) 0.4867(3) 0.19379(18)
H19 H 0.0718 0.5657 0.2168
C20 C 0.01008(14) 0.4923(3) 0.12996(17)
C21 C 0.12004(14) 0.3532(4) 0.29309(19)
H21 H 0.1081 0.2853 0.3288
C22 C -0.01343(16) 0.6233(3) 0.0990(2)
H22 H -0.0400 0.6104 0.0489
N2 N -0.01507(11) 0.3884(2) 0.09431(14)
F4 F 0.12754(9) 0.4731(2) 0.33015(12)
F5 F -0.04171(11) 0.6854(2) 0.15068(15)
F6 F 0.02979(11) 0.70750(19) 0.08926(13)
Cl2 Cl 0.18687(4) 0.30683(12) 0.26652(5)

#END
####################################################################### 
# 
# 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_flfa150515
_database_code_depnum_ccdc_archive 'CCDC 1487975'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 Cl F4 N O2'
_chemical_formula_sum            'C12 H6 Cl F4 N O2'
_chemical_formula_weight         307.63

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3518(5)
_cell_length_b                   15.1942(7)
_cell_length_c                   7.8687(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.924(3)
_cell_angle_gamma                90
_cell_volume                     1156.03(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5072
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.384
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8837
_diffrn_reflns_av_unetI/netI     0.0944
_diffrn_reflns_av_R_equivalents  0.1620
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.106
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2640
_reflns_number_gt                1985
_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       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.1089P)²+0.0509P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2640
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
C1 C 0.5658(3) 0.70087(15) 0.4717(3) 0.0192(5) Uani 1 1 d . . . . .
C2 C 0.4310(3) 0.67425(16) 0.3608(3) 0.0211(5) Uani 1 1 d . . . . .
C3 C 0.3344(3) 0.73761(17) 0.2759(3) 0.0231(6) Uani 1 1 d . . . . .
C4 C 0.3642(3) 0.82767(17) 0.3002(4) 0.0274(6) Uani 1 1 d . . . . .
H4 H 0.2952 0.8699 0.2407 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4930(3) 0.85448(16) 0.4098(3) 0.0255(6) Uani 1 1 d . . . . .
H5 H 0.5124 0.9156 0.4279 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5979(3) 0.79243(15) 0.4969(3) 0.0201(5) Uani 1 1 d . . . . .
C7 C 0.7350(3) 0.81581(16) 0.6088(3) 0.0217(6) Uani 1 1 d . . . . .
C8 C 0.8323(3) 0.75109(16) 0.6795(3) 0.0256(6) Uani 1 1 d . . . . .
H8 H 0.9248 0.7657 0.7525 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7913(3) 0.66228(15) 0.6410(3) 0.0225(6) Uani 1 1 d . . . . .
C10 C 0.3923(3) 0.57810(16) 0.3324(3) 0.0213(5) Uani 1 1 d . . . . .
C11 C 0.7761(3) 0.91162(16) 0.6437(4) 0.0262(6) Uani 1 1 d . . . . .
H11 H 0.7619 0.9426 0.5263 0.031 Uiso 1 1 calc R U . . .
C12 C 0.8978(3) 0.59028(17) 0.7091(4) 0.0292(6) Uani 1 1 d . . . . .
H12 H 0.8613 0.5332 0.6472 0.035 Uiso 1 1 calc R U . . .
N1 N 0.6643(2) 0.63691(12) 0.5458(3) 0.0204(5) Uani 1 1 d . . . . .
O1 O 0.3817(2) 0.53814(12) 0.1964(2) 0.0314(5) Uani 1 1 d . . . . .
O2 O 0.3721(2) 0.54483(12) 0.4760(2) 0.0262(5) Uani 1 1 d . . . . .
F1 F 0.6987(2) 0.95090(10) 0.7324(2) 0.0399(5) Uani 1 1 d . . . . .
F2 F 0.90978(19) 0.91843(10) 0.7561(2) 0.0445(5) Uani 1 1 d . . . . .
F3 F 1.0148(2) 0.61318(12) 0.6828(3) 0.0471(5) Uani 1 1 d . . . . .
F4 F 0.9342(2) 0.58252(14) 0.8919(2) 0.0542(6) Uani 1 1 d . . . . .
Cl1 Cl 0.17101(7) 0.70511(4) 0.13470(10) 0.0360(3) Uani 1 1 d . . . . .
H2 H 0.360(6) 0.490(3) 0.464(7) 0.092(16) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.378(3) . ?
C1 C2 1.415(4) . ?
C1 C6 1.428(3) . ?
C2 C3 1.377(4) . ?
C2 C10 1.510(3) . ?
C3 C4 1.401(4) . ?
C3 Cl1 1.731(3) . ?
C4 C5 1.366(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.417(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.422(4) . ?
C7 C8 1.375(4) . ?
C7 C11 1.514(3) . ?
C8 C9 1.415(3) . ?
C8 H8 0.9500 . ?
C9 N1 1.317(3) . ?
C9 C12 1.509(4) . ?
C10 O1 1.201(3) . ?
C10 O2 1.321(3) . ?
C11 F2 1.354(3) . ?
C11 F1 1.373(3) . ?
C11 H11 1.0000 . ?
C12 F3 1.345(3) . ?
C12 F4 1.356(3) . ?
C12 H12 1.0000 . ?
O2 H2 0.85(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 118.5(2) . . ?
N1 C1 C6 121.9(2) . . ?
C2 C1 C6 119.6(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 C10 119.7(2) . . ?
C1 C2 C10 121.3(2) . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 Cl1 119.1(2) . . ?
C4 C3 Cl1 118.9(2) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 123.8(2) . . ?
C5 C6 C1 118.7(2) . . ?
C7 C6 C1 117.4(2) . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 C11 119.8(2) . . ?
C6 C7 C11 120.4(2) . . ?
C7 C8 C9 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
N1 C9 C8 124.3(2) . . ?
N1 C9 C12 116.4(2) . . ?
C8 C9 C12 119.4(2) . . ?
O1 C10 O2 125.2(2) . . ?
O1 C10 C2 123.8(2) . . ?
O2 C10 C2 111.0(2) . . ?
F2 C11 F1 106.3(2) . . ?
F2 C11 C7 110.3(2) . . ?
F1 C11 C7 109.5(2) . . ?
F2 C11 H11 110.2 . . ?
F1 C11 H11 110.2 . . ?
C7 C11 H11 110.2 . . ?
F3 C12 F4 105.2(2) . . ?
F3 C12 C9 110.0(2) . . ?
F4 C12 C9 109.3(2) . . ?
F3 C12 H12 110.8 . . ?
F4 C12 H12 110.8 . . ?
C9 C12 H12 110.8 . . ?
C9 N1 C1 118.2(2) . . ?
C10 O2 H2 110(3) . . ?

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
N1 C1 C2 C3 -175.6(2) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
N1 C1 C2 C10 3.7(3) . . . . ?
C6 C1 C2 C10 -179.2(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C10 C2 C3 C4 178.8(2) . . . . ?
C1 C2 C3 Cl1 178.06(17) . . . . ?
C10 C2 C3 Cl1 -1.2(3) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
Cl1 C3 C4 C5 -179.4(2) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C7 178.3(2) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
N1 C1 C6 C5 177.1(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C7 -2.6(3) . . . . ?
C2 C1 C6 C7 -179.6(2) . . . . ?
C5 C6 C7 C8 -176.3(2) . . . . ?
C1 C6 C7 C8 3.4(3) . . . . ?
C5 C6 C7 C11 1.0(4) . . . . ?
C1 C6 C7 C11 -179.2(2) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C11 C7 C8 C9 -178.6(2) . . . . ?
C7 C8 C9 N1 -2.1(4) . . . . ?
C7 C8 C9 C12 176.9(2) . . . . ?
C3 C2 C10 O1 76.1(3) . . . . ?
C1 C2 C10 O1 -103.2(3) . . . . ?
C3 C2 C10 O2 -103.9(3) . . . . ?
C1 C2 C10 O2 76.8(3) . . . . ?
C8 C7 C11 F2 -3.9(3) . . . . ?
C6 C7 C11 F2 178.8(2) . . . . ?
C8 C7 C11 F1 -120.5(3) . . . . ?
C6 C7 C11 F1 62.1(3) . . . . ?
N1 C9 C12 F3 136.1(2) . . . . ?
C8 C9 C12 F3 -43.0(3) . . . . ?
N1 C9 C12 F4 -108.9(3) . . . . ?
C8 C9 C12 F4 72.0(3) . . . . ?
C8 C9 N1 C1 3.0(3) . . . . ?
C12 C9 N1 C1 -176.1(2) . . . . ?
C2 C1 N1 C9 176.5(2) . . . . ?
C6 C1 N1 C9 -0.5(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
O2 H2 N1 0.85(5) 1.94(5) 2.784(3) 176(5) 3_666

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.114

_shelxl_version_number           2013-4



