# 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_jx3
_database_code_depnum_ccdc_archive 'CCDC 1053855'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '3ak in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 F12 N2'
_chemical_formula_weight         434.24

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'
F F 0.0171 0.0103 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.0639(19)
_cell_length_b                   8.1630(16)
_cell_length_c                   20.469(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.995(3)
_cell_angle_gamma                90
_cell_volume                     1644.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4030
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.65

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.761480
_exptl_absorpt_correction_T_max  0.980151
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11766
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         26.758
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 0.892
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.892
_reflns_number_total             3013
_reflns_number_gt                1716
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0719P)²+0.2264P] 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         3013
_refine_ls_number_parameters     283
_refine_ls_number_restraints     282
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.5946(3) 0.6663(4) 0.40584(15) 0.0242(8) Uani 1 1 d . U . . .
N2 N 0.6122(3) 0.7545(3) 0.45930(13) 0.0297(7) Uani 1 1 d . U . . .
N3 N 0.7047(3) 0.7218(4) 0.51504(13) 0.0388(8) Uani 1 1 d . U . . .
C4 C 0.8309(4) 0.6359(5) 0.51530(17) 0.0451(11) Uani 1 1 d . U . . .
H4A H 0.8135 0.5178 0.5113 0.068 Uiso 1 1 calc R U . . .
H4B H 0.8955 0.6586 0.5572 0.068 Uiso 1 1 calc R U . . .
H4C H 0.8691 0.6732 0.4776 0.068 Uiso 1 1 calc R U . . .
C5 C 0.7142(5) 0.8550(5) 0.56365(17) 0.0535(12) Uani 1 1 d . U . . .
H5A H 0.7845 0.9326 0.5570 0.080 Uiso 1 1 calc R U . . .
H5B H 0.7379 0.8100 0.6090 0.080 Uiso 1 1 calc R U . . .
H5C H 0.6267 0.9116 0.5575 0.080 Uiso 1 1 calc R U . . .
C6 C 0.4814(4) 0.7360(4) 0.35167(15) 0.0270(8) Uani 1 1 d . U . . .
F1 F 0.5048(2) 0.6960(3) 0.29042(9) 0.0398(6) Uani 1 1 d . U . . .
F2 F 0.4757(2) 0.9007(2) 0.35409(9) 0.0393(6) Uani 1 1 d . U . . .
C7 C 0.3399(3) 0.6709(4) 0.35444(15) 0.0254(8) Uani 1 1 d . U . . .
F3 F 0.3414(2) 0.5071(2) 0.34887(10) 0.0446(6) Uani 1 1 d . U . . .
F4 F 0.3149(2) 0.7071(3) 0.41538(8) 0.0423(6) Uani 1 1 d . U . . .
C8 C 0.2171(4) 0.7372(4) 0.30281(16) 0.0293(8) Uani 1 1 d . U . . .
F5 F 0.2381(2) 0.7101(3) 0.24095(9) 0.0469(6) Uani 1 1 d . U . . .
F6 F 0.2064(2) 0.8979(2) 0.31102(10) 0.0450(6) Uani 1 1 d . U . . .
C9 C 0.0807(4) 0.6621(5) 0.30579(19) 0.0413(10) Uani 1 1 d . U . . .
F7 F 0.0785(2) 0.5021(3) 0.29578(12) 0.0629(7) Uani 1 1 d . U . . .
F8 F 0.0464(2) 0.6892(3) 0.36399(11) 0.0586(7) Uani 1 1 d . U . . .
F9 F -0.0159(2) 0.7279(3) 0.25925(11) 0.0662(8) Uani 1 1 d . U . . .
C11 C 0.6549(3) 0.5076(4) 0.39268(14) 0.0209(8) Uani 1 1 d . U . . .
C12 C 0.6252(4) 0.3677(4) 0.42630(15) 0.0300(9) Uani 1 1 d . U . . .
H12 H 0.5634 0.3747 0.4555 0.036 Uiso 1 1 calc R U . . .
C13 C 0.6845(4) 0.2206(4) 0.41745(15) 0.0296(8) Uani 1 1 d . U . . .
H13 H 0.6638 0.1263 0.4406 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7745(3) 0.2086(4) 0.37486(15) 0.0250(8) Uani 1 1 d . U . . .
C15 C 0.8008(4) 0.3439(4) 0.33931(15) 0.0295(9) Uani 1 1 d . U . . .
H15 H 0.8601 0.3358 0.3089 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7398(4) 0.4917(4) 0.34829(15) 0.0301(9) Uani 1 1 d . U . . .
H16 H 0.7569 0.5845 0.3232 0.036 Uiso 1 1 calc R U . . .
C18 C 0.8404(4) 0.0495(5) 0.36604(17) 0.0379(9) Uani 1 1 d D U . . .
F10 F 0.7610(3) -0.0514(3) 0.32445(14) 0.0687(9) Uani 0.962(3) 1 d D U P A 1
F11 F 0.9524(3) 0.0655(3) 0.34230(15) 0.0615(9) Uani 0.962(3) 1 d D U P A 1
F12 F 0.8753(3) -0.0338(3) 0.42276(12) 0.0753(11) Uani 0.962(3) 1 d D U P A 1
F10B F 0.965(3) 0.048(6) 0.402(2) 0.041(7) Uani 0.038(3) 1 d D U P A 2
F11B F 0.780(4) -0.085(4) 0.380(2) 0.033(7) Uani 0.038(3) 1 d D U P A 2
F12B F 0.849(6) 0.029(6) 0.3027(10) 0.042(7) Uani 0.038(3) 1 d D U P A 2


_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 N2 1.291(4) . ?
C1 C11 1.479(4) . ?
C1 C6 1.525(4) . ?
N2 N3 1.341(4) . ?
N3 C4 1.450(5) . ?
N3 C5 1.464(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 F2 1.347(4) . ?
C6 F1 1.363(4) . ?
C6 C7 1.532(5) . ?
C7 F3 1.342(4) . ?
C7 F4 1.355(4) . ?
C7 C8 1.547(5) . ?
C8 F6 1.330(4) . ?
C8 F5 1.345(4) . ?
C8 C9 1.516(5) . ?
C9 F7 1.322(4) . ?
C9 F9 1.325(4) . ?
C9 F8 1.326(4) . ?
C11 C16 1.377(4) . ?
C11 C12 1.397(4) . ?
C12 C13 1.370(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 C18 1.487(5) . ?
C15 C16 1.383(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 F11B 1.319(15) . ?
C18 F10B 1.322(15) . ?
C18 F11 1.324(4) . ?
C18 F10 1.326(4) . ?
C18 F12B 1.326(15) . ?
C18 F12 1.328(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
N2 C1 C11 130.8(3) . . ?
N2 C1 C6 111.0(3) . . ?
C11 C1 C6 117.8(3) . . ?
C1 N2 N3 124.0(3) . . ?
N2 N3 C4 123.5(3) . . ?
N2 N3 C5 111.5(3) . . ?
C4 N3 C5 115.0(3) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
F2 C6 F1 106.8(3) . . ?
F2 C6 C1 112.1(3) . . ?
F1 C6 C1 109.5(3) . . ?
F2 C6 C7 107.3(3) . . ?
F1 C6 C7 106.9(2) . . ?
C1 C6 C7 113.8(3) . . ?
F3 C7 F4 107.6(3) . . ?
F3 C7 C6 108.4(3) . . ?
F4 C7 C6 108.1(2) . . ?
F3 C7 C8 108.2(3) . . ?
F4 C7 C8 106.1(3) . . ?
C6 C7 C8 118.0(3) . . ?
F6 C8 F5 108.3(3) . . ?
F6 C8 C9 107.2(3) . . ?
F5 C8 C9 107.0(3) . . ?
F6 C8 C7 109.5(3) . . ?
F5 C8 C7 109.0(3) . . ?
C9 C8 C7 115.6(3) . . ?
F7 C9 F9 107.6(3) . . ?
F7 C9 F8 107.8(3) . . ?
F9 C9 F8 106.8(3) . . ?
F7 C9 C8 112.3(3) . . ?
F9 C9 C8 110.0(3) . . ?
F8 C9 C8 112.1(3) . . ?
C16 C11 C12 118.3(3) . . ?
C16 C11 C1 122.5(3) . . ?
C12 C11 C1 119.3(3) . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 C18 119.8(3) . . ?
C13 C14 C18 120.3(3) . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 121.5(3) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
F11B C18 F10B 108(2) . . ?
F11 C18 F10 105.7(3) . . ?
F11B C18 F12B 103(2) . . ?
F10B C18 F12B 108(2) . . ?
F11 C18 F12 106.3(3) . . ?
F10 C18 F12 105.0(3) . . ?
F11B C18 C14 118(2) . . ?
F10B C18 C14 110(2) . . ?
F11 C18 C14 113.2(3) . . ?
F10 C18 C14 113.4(3) . . ?
F12B C18 C14 110(2) . . ?
F12 C18 C14 112.6(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
C11 C1 N2 N3 6.7(6) . . . . ?
C6 C1 N2 N3 179.8(3) . . . . ?
C1 N2 N3 C4 28.2(5) . . . . ?
C1 N2 N3 C5 171.9(3) . . . . ?
N2 C1 C6 F2 33.3(4) . . . . ?
C11 C1 C6 F2 -152.6(3) . . . . ?
N2 C1 C6 F1 151.6(3) . . . . ?
C11 C1 C6 F1 -34.3(4) . . . . ?
N2 C1 C6 C7 -88.8(3) . . . . ?
C11 C1 C6 C7 85.3(4) . . . . ?
F2 C6 C7 F3 177.1(2) . . . . ?
F1 C6 C7 F3 62.8(3) . . . . ?
C1 C6 C7 F3 -58.3(3) . . . . ?
F2 C6 C7 F4 -66.5(3) . . . . ?
F1 C6 C7 F4 179.1(2) . . . . ?
C1 C6 C7 F4 58.1(4) . . . . ?
F2 C6 C7 C8 53.8(3) . . . . ?
F1 C6 C7 C8 -60.6(4) . . . . ?
C1 C6 C7 C8 178.4(3) . . . . ?
F3 C7 C8 F6 174.8(3) . . . . ?
F4 C7 C8 F6 59.5(3) . . . . ?
C6 C7 C8 F6 -61.8(4) . . . . ?
F3 C7 C8 F5 -66.9(4) . . . . ?
F4 C7 C8 F5 177.8(3) . . . . ?
C6 C7 C8 F5 56.5(4) . . . . ?
F3 C7 C8 C9 53.6(4) . . . . ?
F4 C7 C8 C9 -61.6(4) . . . . ?
C6 C7 C8 C9 177.1(3) . . . . ?
F6 C8 C9 F7 177.8(3) . . . . ?
F5 C8 C9 F7 61.8(4) . . . . ?
C7 C8 C9 F7 -59.9(4) . . . . ?
F6 C8 C9 F9 57.9(4) . . . . ?
F5 C8 C9 F9 -58.1(4) . . . . ?
C7 C8 C9 F9 -179.7(3) . . . . ?
F6 C8 C9 F8 -60.8(4) . . . . ?
F5 C8 C9 F8 -176.8(3) . . . . ?
C7 C8 C9 F8 61.6(4) . . . . ?
N2 C1 C11 C16 -114.7(4) . . . . ?
C6 C1 C11 C16 72.6(4) . . . . ?
N2 C1 C11 C12 65.3(5) . . . . ?
C6 C1 C11 C12 -107.4(3) . . . . ?
C16 C11 C12 C13 3.0(5) . . . . ?
C1 C11 C12 C13 -177.0(3) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 -2.4(5) . . . . ?
C12 C13 C14 C18 179.1(3) . . . . ?
C13 C14 C15 C16 2.0(5) . . . . ?
C18 C14 C15 C16 -179.5(3) . . . . ?
C12 C11 C16 C15 -3.4(5) . . . . ?
C1 C11 C16 C15 176.5(3) . . . . ?
C14 C15 C16 C11 0.9(5) . . . . ?
C15 C14 C18 F11B -156(2) . . . . ?
C13 C14 C18 F11B 23(2) . . . . ?
C15 C14 C18 F10B 81(2) . . . . ?
C13 C14 C18 F10B -100(3) . . . . ?
C15 C14 C18 F11 21.9(4) . . . . ?
C13 C14 C18 F11 -159.6(3) . . . . ?
C15 C14 C18 F10 -98.5(4) . . . . ?
C13 C14 C18 F10 80.0(4) . . . . ?
C15 C14 C18 F12B -37(2) . . . . ?
C13 C14 C18 F12B 141(2) . . . . ?
C15 C14 C18 F12 142.5(4) . . . . ?
C13 C14 C18 F12 -39.0(5) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.069



# start Validation Reply Form
_vrf_PLAT029_jx3                 
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.892 Note
RESPONSE: The measured crystal suffers from multiple domain twinning. 
There is a dominating main component that we used for structure data, 
but beyond that main pattern we tried to index as many components as 
possible in order to identify overlaps and partial overlaps. In the cases 
where neither a complete overlap nor a clear separation of intensities 
originating from different domains was possible the reflection have 
been omitted. This way a clean however slightly incomplete data set 
results. We prefer this over a complete but contaminated data set. 
;
# end Validation Reply Form


#==================================================================

