# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_g180601a
_database_code_depnum_ccdc_archive 'CCDC 1847355'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-10-15 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         ?
_chemical_formula_sum            'C20 H12 F7 N3'
_chemical_formula_weight         427.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   8.5757(7)
_cell_length_b                   10.7240(9)
_cell_length_c                   11.5979(7)
_cell_angle_alpha                64.620(7)
_cell_angle_beta                 77.985(7)
_cell_angle_gamma                71.245(7)
_cell_volume                     909.41(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2385
_cell_measurement_theta_min      4.2050
_cell_measurement_theta_max      75.9130

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7258
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.234
_diffrn_reflns_theta_max         77.411
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3780
_reflns_number_gt                2830
_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)+(0.1529P)²+0.1191P] 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         3780
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2441
_refine_ls_wR_factor_gt          0.2192
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.9333(2) 0.9411(2) 0.21598(18) 0.0737(5) Uani 1 1 d . . . . .
F2 F 0.8842(3) 0.8437(2) 0.10308(17) 0.0740(5) Uani 1 1 d . . . . .
F3 F 0.5969(3) 1.0434(2) 0.26322(18) 0.0792(6) Uani 1 1 d . . . . .
F4 F 0.5536(2) 0.9524(2) 0.14205(19) 0.0760(5) Uani 1 1 d . . . . .
N1 N 0.7785(3) 0.5400(2) 0.55688(19) 0.0487(5) Uani 1 1 d . . . . .
N2 N 0.8231(3) 0.7691(2) 0.4296(2) 0.0512(5) Uani 1 1 d . . . . .
F5 F 0.5290(4) 1.2325(3) 0.0272(3) 0.1173(10) Uani 1 1 d . . . . .
F6 F 0.7319(4) 1.1142(4) -0.0558(2) 0.1255(11) Uani 1 1 d . . . . .
F7 F 0.7730(5) 1.2043(3) 0.0628(3) 0.1339(13) Uani 1 1 d . . . . .
C1 C 0.7495(3) 0.5302(2) 0.4518(2) 0.0460(5) Uani 1 1 d . . . . .
C2 C 0.7999(3) 0.7560(3) 0.3252(2) 0.0483(5) Uani 1 1 d . . . . .
C3 C 0.8444(3) 0.6711(3) 0.6566(2) 0.0503(6) Uani 1 1 d . . . . .
C4 C 0.7588(3) 0.6396(3) 0.3287(2) 0.0483(5) Uani 1 1 d . . . . .
C5 C 0.8131(3) 0.6596(3) 0.5407(2) 0.0470(5) Uani 1 1 d . . . . .
C6 C 0.7124(3) 0.3979(3) 0.4694(2) 0.0504(6) Uani 1 1 d . . . . .
C7 C 0.8357(4) 0.5789(3) 0.8862(2) 0.0662(7) Uani 1 1 d . . . . .
H7 H 0.8088 0.5136 0.9663 0.079 Uiso 1 1 calc R U . . .
C8 C 0.6468(3) 0.3948(3) 0.3702(3) 0.0534(6) Uani 1 1 d . . . . .
C9 C 0.7427(3) 0.2768(3) 0.5830(3) 0.0577(6) Uani 1 1 d . . . . .
H9 H 0.7851 0.2798 0.6490 0.069 Uiso 1 1 calc R U . . .
C10 C 0.9153(4) 0.7746(3) 0.6469(3) 0.0573(6) Uani 1 1 d . . . . .
H10 H 0.9411 0.8411 0.5671 0.069 Uiso 1 1 calc R U . . .
C11 C 0.7325(4) 0.6149(3) 0.2159(2) 0.0573(6) Uani 1 1 d . . . . .
H11A H 0.8371 0.5649 0.1851 0.069 Uiso 1 1 calc R U . . .
H11B H 0.6938 0.7065 0.1471 0.069 Uiso 1 1 calc R U . . .
C12 C 0.8224(4) 0.8834(3) 0.2032(2) 0.0548(6) Uani 1 1 d . . . . .
C13 C 0.6082(4) 0.5281(3) 0.2513(3) 0.0604(7) Uani 1 1 d . . . . .
H13A H 0.4986 0.5864 0.2645 0.073 Uiso 1 1 calc R U . . .
H13B H 0.6076 0.5021 0.1809 0.073 Uiso 1 1 calc R U . . .
C14 C 0.6621(4) 1.0046(3) 0.1644(2) 0.0575(6) Uani 1 1 d . . . . .
C15 C 0.6149(4) 0.2681(3) 0.3882(3) 0.0663(7) Uani 1 1 d . . . . .
H15 H 0.5709 0.2645 0.3232 0.080 Uiso 1 1 calc R U . . .
C16 C 0.7096(4) 0.1519(3) 0.5977(3) 0.0699(8) Uani 1 1 d . . . . .
H16 H 0.7297 0.0710 0.6733 0.084 Uiso 1 1 calc R U . . .
C17 C 0.8058(4) 0.5763(3) 0.7788(3) 0.0645(7) Uani 1 1 d . . . . .
H17 H 0.7564 0.5073 0.7861 0.077 Uiso 1 1 calc R U . . .
N3 N 0.9475(4) 0.7781(4) 0.7574(3) 0.0819(9) Uani 1 1 d . . . . .
C18 C 0.9050(5) 0.6780(4) 0.8738(3) 0.0737(9) Uani 1 1 d . . . . .
H18 H 0.9266 0.6807 0.9480 0.088 Uiso 1 1 calc R U . . .
C19 C 0.6462(4) 0.1495(3) 0.4980(4) 0.0758(9) Uani 1 1 d . . . . .
H19 H 0.6250 0.0661 0.5064 0.091 Uiso 1 1 calc R U . . .
C20 C 0.6761(5) 1.1419(4) 0.0470(3) 0.0782(9) 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
F1 C12 1.352(3) . ?
F2 C12 1.354(3) . ?
F3 C14 1.339(3) . ?
F4 C14 1.344(3) . ?
N1 C5 1.335(3) . ?
N1 C1 1.345(3) . ?
N2 C5 1.330(3) . ?
N2 C2 1.338(3) . ?
F5 C20 1.315(4) . ?
F6 C20 1.309(5) . ?
F7 C20 1.303(5) . ?
C1 C4 1.413(3) . ?
C1 C6 1.473(3) . ?
C2 C4 1.385(3) . ?
C2 C12 1.518(3) . ?
C3 C10 1.383(4) . ?
C3 C17 1.392(4) . ?
C3 C5 1.486(3) . ?
C4 C11 1.514(3) . ?
C6 C9 1.396(4) . ?
C6 C8 1.399(4) . ?
C7 C18 1.321(5) . ?
C7 C17 1.336(4) . ?
C7 H7 0.9300 . ?
C8 C15 1.391(4) . ?
C8 C13 1.500(4) . ?
C9 C16 1.390(4) . ?
C9 H9 0.9300 . ?
C10 N3 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.517(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.545(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C20 1.537(4) . ?
C15 C19 1.358(5) . ?
C15 H15 0.9300 . ?
C16 C19 1.389(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N3 C18 1.382(5) . ?
C18 H18 0.9300 . ?
C19 H19 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
C5 N1 C1 117.1(2) . . ?
C5 N2 C2 116.7(2) . . ?
N1 C1 C4 121.9(2) . . ?
N1 C1 C6 117.2(2) . . ?
C4 C1 C6 120.8(2) . . ?
N2 C2 C4 123.6(2) . . ?
N2 C2 C12 112.4(2) . . ?
C4 C2 C12 124.0(2) . . ?
C10 C3 C17 117.7(2) . . ?
C10 C3 C5 121.3(2) . . ?
C17 C3 C5 121.0(2) . . ?
C2 C4 C1 115.0(2) . . ?
C2 C4 C11 127.2(2) . . ?
C1 C4 C11 117.8(2) . . ?
N2 C5 N1 125.7(2) . . ?
N2 C5 C3 117.0(2) . . ?
N1 C5 C3 117.3(2) . . ?
C9 C6 C8 120.2(2) . . ?
C9 C6 C1 120.8(2) . . ?
C8 C6 C1 119.1(2) . . ?
C18 C7 C17 117.3(3) . . ?
C18 C7 H7 121.3 . . ?
C17 C7 H7 121.3 . . ?
C15 C8 C6 118.1(3) . . ?
C15 C8 C13 122.7(2) . . ?
C6 C8 C13 119.2(2) . . ?
C16 C9 C6 120.3(3) . . ?
C16 C9 H9 119.9 . . ?
C6 C9 H9 119.9 . . ?
C3 C10 N3 119.3(3) . . ?
C3 C10 H10 120.4 . . ?
N3 C10 H10 120.4 . . ?
C4 C11 C13 111.9(2) . . ?
C4 C11 H11A 109.2 . . ?
C13 C11 H11A 109.2 . . ?
C4 C11 H11B 109.2 . . ?
C13 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
F1 C12 F2 106.0(2) . . ?
F1 C12 C2 110.3(2) . . ?
F2 C12 C2 111.3(2) . . ?
F1 C12 C14 107.1(2) . . ?
F2 C12 C14 107.6(2) . . ?
C2 C12 C14 114.2(2) . . ?
C8 C13 C11 112.1(2) . . ?
C8 C13 H13A 109.2 . . ?
C11 C13 H13A 109.2 . . ?
C8 C13 H13B 109.2 . . ?
C11 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
F3 C14 F4 107.7(2) . . ?
F3 C14 C20 106.8(2) . . ?
F4 C14 C20 107.6(2) . . ?
F3 C14 C12 108.6(2) . . ?
F4 C14 C12 108.3(2) . . ?
C20 C14 C12 117.5(3) . . ?
C19 C15 C8 121.9(3) . . ?
C19 C15 H15 119.0 . . ?
C8 C15 H15 119.0 . . ?
C19 C16 C9 119.1(3) . . ?
C19 C16 H16 120.5 . . ?
C9 C16 H16 120.5 . . ?
C7 C17 C3 123.6(3) . . ?
C7 C17 H17 118.2 . . ?
C3 C17 H17 118.2 . . ?
C18 N3 C10 118.1(3) . . ?
C7 C18 N3 124.0(2) . . ?
C7 C18 H18 118.0 . . ?
N3 C18 H18 118.0 . . ?
C15 C19 C16 120.5(3) . . ?
C15 C19 H19 119.7 . . ?
C16 C19 H19 119.7 . . ?
F7 C20 F6 108.8(4) . . ?
F7 C20 F5 108.0(4) . . ?
F6 C20 F5 107.8(3) . . ?
F7 C20 C14 111.9(3) . . ?
F6 C20 C14 110.8(3) . . ?
F5 C20 C14 109.4(3) . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.071

