# 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_mo_60926b
_database_code_depnum_ccdc_archive 'CCDC 1527960'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2017-04-05 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            'C26 H20 F3 N O'
_chemical_formula_weight         419.43

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      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                   9.3089(19)
_cell_length_b                   10.692(2)
_cell_length_c                   10.826(2)
_cell_angle_alpha                98.780(4)
_cell_angle_beta                 90.325(4)
_cell_angle_gamma                108.111(4)
_cell_volume                     1010.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1255
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      22.55

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6671
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.906
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3930
_reflns_number_gt                2252
_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)+(0.1628P)²] 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         3930
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.2556
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.002
_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 1.0644(4) 0.9071(2) 0.2114(3) 0.1064(12) Uani 1 1 d . . . . .
F2 F 1.0916(4) 0.9411(3) 0.4067(3) 0.1147(12) Uani 1 1 d . . . . .
F3 F 1.2724(3) 0.9268(3) 0.2984(3) 0.1023(10) Uani 1 1 d . . . . .
N1 N 0.9387(3) 0.3149(3) 0.3021(3) 0.0457(7) Uani 1 1 d . . . . .
O1 O 0.8106(3) 0.1117(3) 0.1959(3) 0.0774(10) Uani 1 1 d . . . . .
C1 C 0.8266(4) 0.2301(3) 0.2184(3) 0.0477(9) Uani 1 1 d . . . . .
C2 C 0.7172(4) 0.2867(3) 0.1561(3) 0.0402(8) Uani 1 1 d . . . . .
C3 C 0.5585(4) 0.1882(3) 0.1661(3) 0.0471(9) Uani 1 1 d . . . . .
H3A H 0.5498 0.1037 0.1138 0.057 Uiso 1 1 calc R U . . .
H3B H 0.5465 0.1727 0.2519 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4347(4) 0.2379(3) 0.1271(3) 0.0423(8) Uani 1 1 d . . . . .
C5 C 0.3006(4) 0.1516(4) 0.0665(3) 0.0525(9) Uani 1 1 d . . . . .
H5 H 0.2891 0.0613 0.0456 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1833(4) 0.1987(4) 0.0368(3) 0.0577(10) Uani 1 1 d . . . . .
H6 H 0.0941 0.1406 -0.0044 0.069 Uiso 1 1 calc R U . . .
C7 C 0.2011(4) 0.3321(4) 0.0692(3) 0.0526(9) Uani 1 1 d . . . . .
H7 H 0.1230 0.3643 0.0502 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3331(4) 0.4189(4) 0.1295(3) 0.0443(8) Uani 1 1 d . . . . .
H8 H 0.3427 0.5088 0.1513 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4523(3) 0.3736(3) 0.1582(3) 0.0367(7) Uani 1 1 d . . . . .
C10 C 0.5993(3) 0.4659(3) 0.2208(3) 0.0347(7) Uani 1 1 d . . . . .
C11 C 0.7245(3) 0.4257(3) 0.2182(3) 0.0346(7) Uani 1 1 d . . . . .
C12 C 0.8788(3) 0.5128(3) 0.2642(3) 0.0352(7) Uani 1 1 d . . . . .
C13 C 0.9310(3) 0.6483(3) 0.2616(3) 0.0385(7) Uani 1 1 d . . . . .
H13 H 0.8666 0.6879 0.2289 0.046 Uiso 1 1 calc R U . . .
C14 C 1.0760(4) 0.7273(3) 0.3061(3) 0.0421(8) Uani 1 1 d . . . . .
C15 C 1.1724(4) 0.6697(4) 0.3571(3) 0.0511(9) Uani 1 1 d . . . . .
H15 H 1.2678 0.7222 0.3915 0.061 Uiso 1 1 calc R U . . .
C16 C 1.1252(4) 0.5342(4) 0.3562(3) 0.0484(9) Uani 1 1 d . . . . .
H16 H 1.1909 0.4953 0.3881 0.058 Uiso 1 1 calc R U . . .
C17 C 0.9811(4) 0.4540(3) 0.3085(3) 0.0391(8) Uani 1 1 d . . . . .
C18 C 1.0369(5) 0.2542(4) 0.3619(4) 0.0611(11) Uani 1 1 d . . . . .
H18A H 0.9854 0.1606 0.3584 0.092 Uiso 1 1 calc R U . . .
H18B H 1.0606 0.2961 0.4477 0.092 Uiso 1 1 calc R U . . .
H18C H 1.1287 0.2662 0.3186 0.092 Uiso 1 1 calc R U . . .
C19 C 0.7578(4) 0.2889(4) 0.0190(3) 0.0520(9) Uani 1 1 d . . . . .
H19A H 0.6780 0.3034 -0.0277 0.078 Uiso 1 1 calc R U . . .
H19B H 0.7703 0.2051 -0.0161 0.078 Uiso 1 1 calc R U . . .
H19C H 0.8504 0.3595 0.0150 0.078 Uiso 1 1 calc R U . . .
C20 C 0.5993(3) 0.5991(3) 0.2847(3) 0.0360(7) Uani 1 1 d . . . . .
C21 C 0.5900(4) 0.6977(3) 0.2166(3) 0.0431(8) Uani 1 1 d . . . . .
H21 H 0.5812 0.6796 0.1296 0.052 Uiso 1 1 calc R U . . .
C22 C 0.5937(4) 0.8217(4) 0.2780(4) 0.0585(10) Uani 1 1 d . . . . .
H22 H 0.5865 0.8862 0.2317 0.070 Uiso 1 1 calc R U . . .
C23 C 0.6077(5) 0.8510(4) 0.4034(5) 0.0715(13) Uani 1 1 d . . . . .
H23 H 0.6125 0.9358 0.4431 0.086 Uiso 1 1 calc R U . . .
C24 C 0.6149(4) 0.7548(4) 0.4736(4) 0.0646(12) Uani 1 1 d . . . . .
H24 H 0.6222 0.7746 0.5605 0.078 Uiso 1 1 calc R U . . .
C25 C 0.6114(4) 0.6295(4) 0.4149(3) 0.0465(8) Uani 1 1 d . . . . .
H25 H 0.6172 0.5655 0.4623 0.056 Uiso 1 1 calc R U . . .
C26 C 1.1241(4) 0.8732(4) 0.3065(3) 0.0523(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 C26 1.316(4) . ?
F2 C26 1.303(5) . ?
F3 C26 1.329(4) . ?
N1 C1 1.372(4) . ?
N1 C17 1.406(4) . ?
N1 C18 1.472(4) . ?
O1 C1 1.214(4) . ?
C1 C2 1.536(5) . ?
C2 C11 1.516(4) . ?
C2 C19 1.536(5) . ?
C2 C3 1.540(4) . ?
C3 C4 1.494(5) . ?
C4 C5 1.388(5) . ?
C4 C9 1.396(4) . ?
C5 C6 1.392(6) . ?
C6 C7 1.373(5) . ?
C7 C8 1.376(5) . ?
C8 C9 1.392(5) . ?
C9 C10 1.501(4) . ?
C10 C11 1.361(4) . ?
C10 C20 1.485(4) . ?
C11 C12 1.482(4) . ?
C12 C13 1.382(4) . ?
C12 C17 1.411(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.390(5) . ?
C14 C26 1.482(5) . ?
C15 C16 1.375(5) . ?
C16 C17 1.395(5) . ?
C20 C25 1.392(4) . ?
C20 C21 1.399(4) . ?
C21 C22 1.380(5) . ?
C22 C23 1.341(6) . ?
C23 C24 1.386(6) . ?
C24 C25 1.383(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
C1 N1 C17 121.6(3) . . ?
C1 N1 C18 116.4(3) . . ?
C17 N1 C18 120.3(3) . . ?
O1 C1 N1 121.1(3) . . ?
O1 C1 C2 120.0(3) . . ?
N1 C1 C2 118.9(3) . . ?
C11 C2 C19 109.6(3) . . ?
C11 C2 C1 113.5(3) . . ?
C19 C2 C1 107.2(3) . . ?
C11 C2 C3 110.0(3) . . ?
C19 C2 C3 111.3(3) . . ?
C1 C2 C3 105.1(3) . . ?
C4 C3 C2 112.6(3) . . ?
C5 C4 C9 119.6(3) . . ?
C5 C4 C3 121.6(3) . . ?
C9 C4 C3 118.7(3) . . ?
C4 C5 C6 120.8(3) . . ?
C7 C6 C5 119.0(3) . . ?
C6 C7 C8 120.9(4) . . ?
C7 C8 C9 120.7(3) . . ?
C8 C9 C4 118.9(3) . . ?
C8 C9 C10 122.2(3) . . ?
C4 C9 C10 118.9(3) . . ?
C11 C10 C20 123.0(3) . . ?
C11 C10 C9 120.0(3) . . ?
C20 C10 C9 117.0(3) . . ?
C10 C11 C12 124.7(3) . . ?
C10 C11 C2 121.0(3) . . ?
C12 C11 C2 114.2(3) . . ?
C13 C12 C17 117.7(3) . . ?
C13 C12 C11 123.8(3) . . ?
C17 C12 C11 118.5(3) . . ?
C12 C13 C14 122.4(3) . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 C26 120.3(3) . . ?
C15 C14 C26 120.3(3) . . ?
C16 C15 C14 119.3(3) . . ?
C15 C16 C17 121.4(3) . . ?
C16 C17 N1 120.2(3) . . ?
C16 C17 C12 119.7(3) . . ?
N1 C17 C12 120.0(3) . . ?
C25 C20 C21 118.3(3) . . ?
C25 C20 C10 120.4(3) . . ?
C21 C20 C10 121.2(3) . . ?
C22 C21 C20 120.2(3) . . ?
C23 C22 C21 121.2(4) . . ?
C22 C23 C24 120.0(4) . . ?
C25 C24 C23 120.3(4) . . ?
C24 C25 C20 120.0(4) . . ?
F2 C26 F1 105.9(4) . . ?
F2 C26 F3 105.0(3) . . ?
F1 C26 F3 104.0(3) . . ?
F2 C26 C14 114.0(3) . . ?
F1 C26 C14 113.5(3) . . ?
F3 C26 C14 113.5(3) . . ?

_refine_diff_density_max         0.557
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.073



