# 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_xj72_0m
_database_code_depnum_ccdc_archive 'CCDC 1508601'
_audit_update_record             
;
2016-10-06 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_audit_creation_date             2016-10-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 F7 N2 O'
_chemical_formula_sum            'C20 H13 F7 N2 O'
_chemical_formula_weight         430.32
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.858(3)
_cell_length_b                   26.656(8)
_cell_length_c                   8.984(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.0010(10)
_cell_angle_gamma                90
_cell_volume                     1881.8(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2910
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.032
_cell_measurement_theta_min      2.393
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.725
_diffrn_reflns_Laue_measured_fraction_max 0.759
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8261
_diffrn_reflns_point_group_measured_fraction_full 0.725
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.640
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.725
_diffrn_measured_fraction_theta_max 0.759
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1595
_reflns_number_total             3334
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      0.887
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1523
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F01E F 0.3532(5) 0.73191(9) 0.1464(4) 0.191(2) Uani 1 1 d . . . . .
F01L F 0.4745(6) 0.71648(17) -0.0546(6) 0.230(2) Uani 1 1 d . . . . .
F010 F 0.2345(5) 0.68878(11) -0.0141(4) 0.1546(15) Uani 1 1 d . . . . .
F12 F 0.6068(3) 0.69107(5) 0.30294(19) 0.0726(5) Uani 1 1 d . . . . .
F13 F 0.7363(3) 0.67783(6) 0.0941(2) 0.0837(6) Uani 1 1 d . . . . .
F14 F 0.4719(4) 0.61780(7) 0.0064(2) 0.1043(9) Uani 1 1 d . . . . .
F15 F 0.3415(3) 0.63256(7) 0.2106(2) 0.0875(6) Uani 1 1 d . . . . .
O1 O 1.0026(3) 0.43638(7) 0.1560(2) 0.0700(6) Uani 1 1 d . . . . .
N1 N 0.7021(3) 0.51610(7) 0.5605(2) 0.0406(5) Uani 1 1 d . . . . .
N2 N 0.8826(3) 0.46546(7) 0.3681(2) 0.0440(5) Uani 1 1 d . . . . .
H2 H 0.8632 0.4579 0.4596 0.053 Uiso 1 1 calc R . . . .
C1 C 0.6084(3) 0.53825(9) 0.6619(2) 0.0427(6) Uani 1 1 d . . . . .
C2 C 0.5296(4) 0.58492(9) 0.6338(3) 0.0509(6) Uani 1 1 d . . . . .
H2A H 0.4610 0.5995 0.7062 0.061 Uiso 1 1 calc R . . . .
C3 C 0.5535(4) 0.60847(9) 0.5022(3) 0.0486(6) Uani 1 1 d . . . . .
H3 H 0.5008 0.6392 0.4845 0.058 Uiso 1 1 calc R . . . .
C4 C 0.6578(3) 0.58685(8) 0.3910(2) 0.0395(5) Uani 1 1 d . . . . .
C5 C 0.7281(3) 0.53940(8) 0.4272(2) 0.0374(5) Uani 1 1 d . . . . .
C6 C 0.8321(3) 0.51327(8) 0.3235(2) 0.0401(5) Uani 1 1 d . . . . .
C7 C 0.8726(4) 0.53513(9) 0.1907(3) 0.0496(6) Uani 1 1 d . . . . .
H7 H 0.9436 0.5187 0.1237 0.060 Uiso 1 1 calc R . . . .
C8 C 0.8068(4) 0.58224(9) 0.1563(3) 0.0505(6) Uani 1 1 d . . . . .
H8 H 0.8364 0.5969 0.0660 0.061 Uiso 1 1 calc R . . . .
C9 C 0.7004(3) 0.60787(8) 0.2499(3) 0.0442(6) Uani 1 1 d . . . . .
C10 C 0.6278(4) 0.65670(9) 0.1950(3) 0.0534(7) Uani 1 1 d . . . . .
C11 C 0.4588(5) 0.65154(11) 0.1141(3) 0.0628(8) Uani 1 1 d . . . . .
C12 C 0.3772(7) 0.69820(16) 0.0478(6) 0.1038(15) Uani 1 1 d . . . . .
C13 C 0.5901(4) 0.51288(10) 0.8102(3) 0.0581(7) Uani 1 1 d . . . . .
H13A H 0.6034 0.4773 0.7981 0.087 Uiso 1 1 calc GR . . . .
H13B H 0.4795 0.5199 0.8505 0.087 Uiso 1 1 calc GR . . . .
H13C H 0.6758 0.5252 0.8770 0.087 Uiso 1 1 calc GR . . . .
C14 C 0.9582(3) 0.42954(9) 0.2852(3) 0.0456(6) Uani 1 1 d . . . . .
C15 C 0.9888(3) 0.38023(9) 0.3602(3) 0.0448(6) Uani 1 1 d . . . . .
C16 C 0.9330(4) 0.36817(10) 0.4992(3) 0.0620(8) Uani 1 1 d . . . . .
H16 H 0.8720 0.3916 0.5543 0.074 Uiso 1 1 calc R . . . .
C17 C 0.9662(5) 0.32137(11) 0.5594(4) 0.0739(9) Uani 1 1 d . . . . .
H17 H 0.9278 0.3136 0.6546 0.089 Uiso 1 1 calc R . . . .
C18 C 1.0543(5) 0.28681(10) 0.4803(4) 0.0722(9) Uani 1 1 d . . . . .
H18 H 1.0737 0.2552 0.5205 0.087 Uiso 1 1 calc R . . . .
C19 C 1.1145(6) 0.29820(11) 0.3424(4) 0.0833(11) Uani 1 1 d . . . . .
H19 H 1.1781 0.2747 0.2897 0.100 Uiso 1 1 calc R . . . .
C20 C 1.0811(5) 0.34477(11) 0.2804(3) 0.0704(9) Uani 1 1 d . . . . .
H20 H 1.1204 0.3523 0.1854 0.084 Uiso 1 1 calc R . . . .


_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
F01E C12 1.276(6) . ?
F01L C12 1.292(7) . ?
F010 C12 1.277(5) . ?
F12 C10 1.344(3) . ?
F13 C10 1.366(4) . ?
F14 C11 1.325(3) . ?
F15 C11 1.363(4) . ?
O1 C14 1.226(3) . ?
N1 C1 1.311(3) . ?
N1 C5 1.365(3) . ?
N2 H2 0.8600 . ?
N2 C6 1.393(3) . ?
N2 C14 1.351(3) . ?
C1 C2 1.412(4) . ?
C1 C13 1.502(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.352(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.415(3) . ?
C4 C5 1.418(3) . ?
C4 C9 1.425(3) . ?
C5 C6 1.421(3) . ?
C6 C7 1.366(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(4) . ?
C9 C10 1.504(4) . ?
C10 C11 1.521(5) . ?
C11 C12 1.521(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.497(3) . ?
C15 C16 1.362(4) . ?
C15 C20 1.391(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.353(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.361(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(4) . ?
C20 H20 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
C1 N1 C5 119.3(2) . . ?
C6 N2 H2 116.0 . . ?
C14 N2 H2 116.0 . . ?
C14 N2 C6 127.9(2) . . ?
N1 C1 C2 121.3(2) . . ?
N1 C1 C13 117.9(2) . . ?
C2 C1 C13 120.9(2) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 115.3(2) . . ?
C3 C4 C9 127.1(2) . . ?
C5 C4 C9 117.6(2) . . ?
N1 C5 C4 123.3(2) . . ?
N1 C5 C6 116.01(19) . . ?
C4 C5 C6 120.7(2) . . ?
N2 C6 C5 115.1(2) . . ?
C7 C6 N2 125.1(2) . . ?
C7 C6 C5 119.8(2) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.5(2) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 118.6 . . ?
C9 C8 C7 122.7(2) . . ?
C9 C8 H8 118.6 . . ?
C4 C9 C10 122.9(2) . . ?
C8 C9 C4 119.6(2) . . ?
C8 C9 C10 117.5(2) . . ?
F12 C10 F13 105.9(2) . . ?
F12 C10 C9 113.6(2) . . ?
F12 C10 C11 107.4(2) . . ?
F13 C10 C9 109.8(3) . . ?
F13 C10 C11 105.4(2) . . ?
C9 C10 C11 114.2(2) . . ?
F14 C11 F15 105.4(3) . . ?
F14 C11 C10 110.0(3) . . ?
F14 C11 C12 107.6(3) . . ?
F15 C11 C10 108.7(2) . . ?
F15 C11 C12 105.5(3) . . ?
C10 C11 C12 118.8(3) . . ?
F01E C12 F01L 108.5(5) . . ?
F01E C12 F010 108.1(5) . . ?
F01E C12 C11 111.5(4) . . ?
F01L C12 C11 109.7(5) . . ?
F010 C12 F01L 106.5(4) . . ?
F010 C12 C11 112.3(4) . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 N2 122.8(2) . . ?
O1 C14 C15 120.8(2) . . ?
N2 C14 C15 116.4(2) . . ?
C16 C15 C14 124.7(2) . . ?
C16 C15 C20 118.7(2) . . ?
C20 C15 C14 116.6(2) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0(3) . . ?
C19 C20 H20 120.0 . . ?

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
F12 C10 C11 F14 -179.7(2) . . . . ?
F12 C10 C11 F15 -64.8(3) . . . . ?
F12 C10 C11 C12 55.7(4) . . . . ?
F13 C10 C11 F14 67.6(3) . . . . ?
F13 C10 C11 F15 -177.4(2) . . . . ?
F13 C10 C11 C12 -56.9(4) . . . . ?
F14 C11 C12 F01E 177.2(4) . . . . ?
F14 C11 C12 F01L -62.6(5) . . . . ?
F14 C11 C12 F010 55.6(6) . . . . ?
F15 C11 C12 F01E 65.0(5) . . . . ?
F15 C11 C12 F01L -174.8(4) . . . . ?
F15 C11 C12 F010 -56.5(5) . . . . ?
O1 C14 C15 C16 -175.0(3) . . . . ?
O1 C14 C15 C20 5.0(4) . . . . ?
N1 C1 C2 C3 -1.9(4) . . . . ?
N1 C5 C6 N2 4.8(3) . . . . ?
N1 C5 C6 C7 -176.3(2) . . . . ?
N2 C6 C7 C8 176.7(2) . . . . ?
N2 C14 C15 C16 6.0(4) . . . . ?
N2 C14 C15 C20 -174.0(2) . . . . ?
C1 N1 C5 C4 -0.3(3) . . . . ?
C1 N1 C5 C6 179.52(19) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 C9 -177.3(2) . . . . ?
C3 C4 C5 N1 -1.5(3) . . . . ?
C3 C4 C5 C6 178.6(2) . . . . ?
C3 C4 C9 C8 178.6(2) . . . . ?
C3 C4 C9 C10 -3.9(4) . . . . ?
C4 C5 C6 N2 -175.4(2) . . . . ?
C4 C5 C6 C7 3.6(3) . . . . ?
C4 C9 C10 F12 36.5(4) . . . . ?
C4 C9 C10 F13 154.8(2) . . . . ?
C4 C9 C10 C11 -87.2(3) . . . . ?
C5 N1 C1 C2 2.1(3) . . . . ?
C5 N1 C1 C13 -176.7(2) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
C5 C4 C9 C10 177.0(2) . . . . ?
C5 C6 C7 C8 -2.1(4) . . . . ?
C6 N2 C14 O1 4.7(4) . . . . ?
C6 N2 C14 C15 -176.4(2) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C4 2.0(4) . . . . ?
C7 C8 C9 C10 -175.6(2) . . . . ?
C8 C9 C10 F12 -146.0(2) . . . . ?
C8 C9 C10 F13 -27.6(3) . . . . ?
C8 C9 C10 C11 90.4(3) . . . . ?
C9 C4 C5 N1 177.6(2) . . . . ?
C9 C4 C5 C6 -2.2(3) . . . . ?
C9 C10 C11 F14 -52.9(3) . . . . ?
C9 C10 C11 F15 62.1(3) . . . . ?
C9 C10 C11 C12 -177.4(3) . . . . ?
C10 C11 C12 F01E -57.1(6) . . . . ?
C10 C11 C12 F01L 63.1(6) . . . . ?
C10 C11 C12 F010 -178.7(4) . . . . ?
C13 C1 C2 C3 176.9(2) . . . . ?
C14 N2 C6 C5 169.0(2) . . . . ?
C14 N2 C6 C7 -9.9(4) . . . . ?
C14 C15 C16 C17 179.5(3) . . . . ?
C14 C15 C20 C19 -179.9(3) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C16 C15 C20 C19 0.1(5) . . . . ?
C16 C17 C18 C19 1.6(6) . . . . ?
C17 C18 C19 C20 -2.0(6) . . . . ?
C18 C19 C20 C15 1.2(5) . . . . ?
C20 C15 C16 C17 -0.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
