# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1njhb0
_database_code_depnum_ccdc_archive 'CCDC 1535192'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-06-12 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 H11 F N2'
_chemical_formula_sum            'C18 H11 F N2'
_chemical_formula_weight         274.29

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'

_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                   9.9724(6)
_cell_length_b                   11.0543(11)
_cell_length_c                   12.3031(11)
_cell_angle_alpha                90
_cell_angle_beta                 112.490(3)
_cell_angle_gamma                90
_cell_volume                     1253.12(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    2942
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      30.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_measurement_method       Omega-Scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4515
_diffrn_reflns_av_unetI/netI     0.1400
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.570
_diffrn_reflns_theta_max         30.520
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.767
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.767
_diffrn_reflns_Laue_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.767
_diffrn_reflns_point_group_measured_fraction_full 0.874
_reflns_number_total             2942
_reflns_number_gt                1582
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0619P)²+0.2057P] 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         2942
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1683
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.1732
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
F1 F 0.23800(17) 0.58764(17) 0.39924(13) 0.0236(5) Uani 1 1 d . . . . .
N2 N 0.4235(2) 0.7666(2) 0.41066(18) 0.0129(5) Uani 1 1 d . . . . .
N1 N 0.4951(2) 0.5400(2) 0.69928(18) 0.0144(6) Uani 1 1 d . . . . .
C8 C 0.3536(3) 0.5996(3) 0.5028(2) 0.0125(6) Uani 1 1 d . . . . .
C6 C 0.2750(3) 0.4237(3) 0.5981(2) 0.0124(6) Uani 1 1 d . . . . .
C14 C 0.5215(3) 0.8552(3) 0.4204(2) 0.0113(6) Uani 1 1 d . . . . .
C10 C 0.5756(3) 0.7066(3) 0.6117(2) 0.0112(6) Uani 1 1 d . . . . .
C13 C 0.6520(3) 0.8724(3) 0.5229(2) 0.0122(6) Uani 1 1 d . . . . .
C9 C 0.4517(3) 0.6948(3) 0.5051(2) 0.0101(6) Uani 1 1 d . . . . .
C7 C 0.3730(3) 0.5244(3) 0.5956(2) 0.0114(6) Uani 1 1 d . . . . .
C12 C 0.6764(3) 0.7957(3) 0.6191(2) 0.0134(6) Uani 1 1 d . . . . .
H12 H 0.7611 0.8046 0.6886 0.016 Uiso 1 1 calc R U . . .
C11 C 0.5878(3) 0.6252(3) 0.7052(2) 0.0138(6) Uani 1 1 d . . . . .
H11 H 0.6696 0.6338 0.7770 0.017 Uiso 1 1 calc R U . . .
C4 C 0.2357(3) 0.2448(3) 0.6971(2) 0.0158(6) Uani 1 1 d . . . . .
H4 H 0.2701 0.1898 0.7612 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3219(3) 0.3404(3) 0.6912(2) 0.0162(7) Uani 1 1 d . . . . .
H5 H 0.4154 0.3499 0.7517 0.019 Uiso 1 1 calc R U . . .
C1 C 0.1362(3) 0.4062(3) 0.5111(2) 0.0158(6) Uani 1 1 d . . . . .
H1 H 0.1007 0.4609 0.4467 0.019 Uiso 1 1 calc R U . . .
C18 C 0.7499(3) 0.9670(3) 0.5229(2) 0.0147(6) Uani 1 1 d . . . . .
H18 H 0.8376 0.9784 0.5894 0.018 Uiso 1 1 calc R U . . .
C3 C 0.0984(3) 0.2289(3) 0.6094(2) 0.0170(7) Uani 1 1 d . . . . .
H3 H 0.0388 0.1631 0.6126 0.020 Uiso 1 1 calc R U . . .
C16 C 0.5882(3) 1.0245(3) 0.3270(2) 0.0181(7) Uani 1 1 d . . . . .
H16 H 0.5671 1.0772 0.2615 0.022 Uiso 1 1 calc R U . . .
C15 C 0.4935(3) 0.9342(3) 0.3227(2) 0.0155(6) Uani 1 1 d . . . . .
H15 H 0.4080 0.9238 0.2541 0.019 Uiso 1 1 calc R U . . .
C17 C 0.7176(3) 1.0411(3) 0.4274(2) 0.0169(7) Uani 1 1 d . . . . .
H17 H 0.7825 1.1044 0.4283 0.020 Uiso 1 1 calc R U . . .
C2 C 0.0503(3) 0.3106(3) 0.5176(3) 0.0197(7) Uani 1 1 d . . . . .
H2 H -0.0435 0.3008 0.4577 0.024 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
F1 C8 1.359(3) . ?
N2 C9 1.345(3) . ?
N2 C14 1.356(3) . ?
N1 C11 1.302(3) . ?
N1 C7 1.397(3) . ?
C8 C7 1.365(4) . ?
C8 C9 1.430(4) . ?
C6 C1 1.402(4) . ?
C6 C5 1.404(4) . ?
C6 C7 1.488(4) . ?
C14 C15 1.424(4) . ?
C14 C13 1.437(4) . ?
C10 C12 1.385(4) . ?
C10 C9 1.422(4) . ?
C10 C11 1.429(4) . ?
C13 C12 1.399(4) . ?
C13 C18 1.431(4) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C4 C5 1.382(4) . ?
C4 C3 1.393(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C1 C2 1.382(4) . ?
C1 H1 0.9500 . ?
C18 C17 1.365(4) . ?
C18 H18 0.9500 . ?
C3 C2 1.380(4) . ?
C3 H3 0.9500 . ?
C16 C15 1.361(4) . ?
C16 C17 1.416(4) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C2 H2 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
C9 N2 C14 116.4(2) . . ?
C11 N1 C7 119.5(2) . . ?
F1 C8 C7 121.5(3) . . ?
F1 C8 C9 114.8(2) . . ?
C7 C8 C9 123.7(2) . . ?
C1 C6 C5 117.1(3) . . ?
C1 C6 C7 123.5(3) . . ?
C5 C6 C7 119.4(2) . . ?
N2 C14 C15 117.8(2) . . ?
N2 C14 C13 123.6(2) . . ?
C15 C14 C13 118.6(3) . . ?
C12 C10 C9 118.6(2) . . ?
C12 C10 C11 124.0(2) . . ?
C9 C10 C11 117.5(2) . . ?
C12 C13 C18 123.1(2) . . ?
C12 C13 C14 117.9(3) . . ?
C18 C13 C14 119.0(2) . . ?
N2 C9 C10 124.3(3) . . ?
N2 C9 C8 120.1(2) . . ?
C10 C9 C8 115.6(2) . . ?
C8 C7 N1 118.9(3) . . ?
C8 C7 C6 126.0(2) . . ?
N1 C7 C6 115.1(2) . . ?
C10 C12 C13 119.3(2) . . ?
C10 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
N1 C11 C10 124.8(2) . . ?
N1 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.076



