# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_180628a
_audit_block_doi                 10.5517/ccdc.csd.cc21dbyr
_database_code_depnum_ccdc_archive 'CCDC 1888704'
loop_
_audit_author_name
_audit_author_address
'Wen Wan'
;Shanghai University
China
;
_audit_update_record             
;
2019-01-04 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 F2 N'
_chemical_formula_weight         331.35

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.086(11)
_cell_length_b                   21.938(16)
_cell_length_c                   10.094(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.185(10)
_cell_angle_gamma                90.00
_cell_volume                     3336(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3064
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      21.58

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16982
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.05
_reflns_number_total             5895
_reflns_number_gt                3450
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1045P)²+1.3889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5895
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2228
_refine_ls_wR_factor_gt          0.1835
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4303(2) 0.30223(14) 0.0758(3) 0.0591(8) Uani 1 1 d . . .
C2 C 0.4174(2) 0.35149(15) -0.0308(3) 0.0585(8) Uani 1 1 d . . .
C3 C 0.38824(16) 0.40502(12) 0.0073(3) 0.0395(6) Uani 1 1 d . . .
H3 H 0.3784 0.4121 0.0961 0.047 Uiso 1 1 calc R . .
C4 C 0.3728(2) 0.44910(15) -0.0829(3) 0.0606(8) Uani 1 1 d . . .
C5 C 0.3876(3) 0.43897(19) -0.2162(4) 0.0814(11) Uani 1 1 d . . .
H5 H 0.3761 0.4696 -0.2786 0.098 Uiso 1 1 calc R . .
C6 C 0.4196(3) 0.3833(2) -0.2548(4) 0.0932(13) Uani 1 1 d . . .
H6 H 0.4304 0.3760 -0.3432 0.112 Uiso 1 1 calc R . .
C7 C 0.4352(3) 0.33834(19) -0.1603(4) 0.0793(11) Uani 1 1 d . . .
H7 H 0.4571 0.3004 -0.1834 0.095 Uiso 1 1 calc R . .
C8 C 0.3384(2) 0.50809(15) -0.0356(3) 0.0618(9) Uani 1 1 d . . .
C9 C 0.3690(3) 0.53239(17) 0.0859(4) 0.0793(11) Uani 1 1 d . . .
H9 H 0.4114 0.5113 0.1382 0.095 Uiso 1 1 calc R . .
C10 C 0.3374(3) 0.58708(19) 0.1295(4) 0.0980(14) Uani 1 1 d . . .
H10 H 0.3605 0.6037 0.2089 0.118 Uiso 1 1 calc R . .
C11 C 0.2710(3) 0.61785(19) 0.0555(5) 0.1008(14) Uani 1 1 d . . .
H11 H 0.2480 0.6541 0.0871 0.121 Uiso 1 1 calc R . .
C12 C 0.2398(3) 0.59479(19) -0.0628(5) 0.0977(14) Uani 1 1 d . . .
H12 H 0.1959 0.6158 -0.1124 0.117 Uiso 1 1 calc R . .
C13 C 0.5199(2) 0.29928(13) 0.1480(3) 0.0574(8) Uani 1 1 d . . .
C14 C 0.5779(2) 0.25507(16) 0.1098(4) 0.0764(10) Uani 1 1 d . . .
H14 H 0.5604 0.2286 0.0413 0.092 Uiso 1 1 calc R . .
C15 C 0.6624(3) 0.2492(2) 0.1717(5) 0.0956(13) Uani 1 1 d . . .
H15 H 0.7005 0.2188 0.1448 0.115 Uiso 1 1 calc R . .
C16 C 0.6891(3) 0.2877(2) 0.2714(5) 0.0929(14) Uani 1 1 d . . .
H16 H 0.7453 0.2830 0.3129 0.112 Uiso 1 1 calc R . .
C17 C 0.6327(2) 0.33516(17) 0.3139(4) 0.0707(10) Uani 1 1 d . . .
C18 C 0.6596(3) 0.3755(2) 0.4171(5) 0.0928(14) Uani 1 1 d . . .
H18 H 0.7160 0.3714 0.4581 0.111 Uiso 1 1 calc R . .
C19 C 0.6054(3) 0.4199(2) 0.4580(4) 0.0927(14) Uani 1 1 d . . .
H19 H 0.6245 0.4461 0.5261 0.111 Uiso 1 1 calc R . .
C20 C 0.5198(3) 0.42622(17) 0.3970(4) 0.0834(12) Uani 1 1 d . . .
H20 H 0.4821 0.4564 0.4256 0.100 Uiso 1 1 calc R . .
C21 C 0.4921(2) 0.38868(15) 0.2971(3) 0.0654(9) Uani 1 1 d . . .
H21 H 0.4356 0.3940 0.2569 0.079 Uiso 1 1 calc R . .
C22 C 0.5465(2) 0.34153(14) 0.2519(3) 0.0568(8) Uani 1 1 d . . .
C23 C 0.9287(2) 0.20036(14) 0.1056(3) 0.0605(8) Uani 1 1 d . . .
C24 C 0.9287(2) 0.14662(16) 0.0104(3) 0.0592(8) Uani 1 1 d . . .
C25 C 0.9768(3) 0.15111(19) -0.1026(4) 0.0805(11) Uani 1 1 d . . .
H25 H 1.0057 0.1870 -0.1233 0.097 Uiso 1 1 calc R . .
C26 C 0.9799(3) 0.1009(2) -0.1823(4) 0.0943(13) Uani 1 1 d . . .
H26 H 1.0113 0.1023 -0.2590 0.113 Uiso 1 1 calc R . .
C27 C 0.9367(3) 0.04820(19) -0.1493(4) 0.0791(11) Uani 1 1 d . . .
H27 H 0.9390 0.0138 -0.2030 0.095 Uiso 1 1 calc R . .
C28 C 0.8894(2) 0.04695(15) -0.0345(3) 0.0582(8) Uani 1 1 d . . .
C29 C 0.88671(16) 0.09610(12) 0.0439(2) 0.0382(6) Uani 1 1 d . . .
H29 H 0.8557 0.0949 0.1210 0.046 Uiso 1 1 calc R . .
C30 C 0.8401(2) -0.00794(15) 0.0080(3) 0.0561(8) Uani 1 1 d . . .
C31 C 0.8318(3) -0.05999(16) -0.0696(4) 0.0759(10) Uani 1 1 d . . .
H31 H 0.8579 -0.0611 -0.1509 0.091 Uiso 1 1 calc R . .
C32 C 0.7859(3) -0.10992(17) -0.0287(4) 0.0874(12) Uani 1 1 d . . .
H32 H 0.7816 -0.1443 -0.0826 0.105 Uiso 1 1 calc R . .
C33 C 0.7460(3) -0.11013(16) 0.0905(4) 0.0780(11) Uani 1 1 d . . .
H33 H 0.7152 -0.1443 0.1174 0.094 Uiso 1 1 calc R . .
C34 C 0.7525(2) -0.05903(16) 0.1692(4) 0.0721(10) Uani 1 1 d . . .
H34 H 0.7252 -0.0586 0.2495 0.086 Uiso 1 1 calc R . .
C35 C 1.0153(2) 0.20805(13) 0.1850(3) 0.0552(8) Uani 1 1 d . . .
C36 C 1.04226(19) 0.16538(13) 0.2877(3) 0.0531(8) Uani 1 1 d . . .
C37 C 0.9877(2) 0.11769(14) 0.3320(3) 0.0614(9) Uani 1 1 d . . .
H37 H 0.9302 0.1135 0.2949 0.074 Uiso 1 1 calc R . .
C38 C 1.0179(3) 0.07806(16) 0.4276(4) 0.0764(10) Uani 1 1 d . . .
H38 H 0.9807 0.0474 0.4557 0.092 Uiso 1 1 calc R . .
C39 C 1.1045(3) 0.08302(19) 0.4843(4) 0.0864(12) Uani 1 1 d . . .
H39 H 1.1253 0.0549 0.5477 0.104 Uiso 1 1 calc R . .
C40 C 1.1579(3) 0.1286(2) 0.4467(4) 0.0812(11) Uani 1 1 d . . .
H40 H 1.2149 0.1319 0.4861 0.097 Uiso 1 1 calc R . .
C41 C 1.1289(2) 0.17143(16) 0.3486(3) 0.0652(9) Uani 1 1 d . . .
C42 C 1.1838(2) 0.2204(2) 0.3106(4) 0.0816(12) Uani 1 1 d . . .
H42 H 1.2400 0.2250 0.3521 0.098 Uiso 1 1 calc R . .
C43 C 1.1557(3) 0.26065(19) 0.2149(4) 0.0838(12) Uani 1 1 d . . .
H43 H 1.1923 0.2926 0.1920 0.101 Uiso 1 1 calc R . .
C44 C 1.0718(2) 0.25392(15) 0.1510(4) 0.0683(9) Uani 1 1 d . . .
H44 H 1.0537 0.2810 0.0840 0.082 Uiso 1 1 calc R . .
F1 F 0.36475(11) 0.30782(8) 0.16443(19) 0.0676(5) Uani 1 1 d . . .
F2 F 0.41180(14) 0.24676(8) 0.0147(2) 0.0837(7) Uani 1 1 d . . .
F3 F 0.85963(12) 0.19571(8) 0.1875(2) 0.0721(6) Uani 1 1 d . . .
F4 F 0.91019(15) 0.25230(9) 0.0322(2) 0.0938(7) Uani 1 1 d . . .
N1 N 0.2727(3) 0.53966(18) -0.1121(4) 0.1079(12) Uani 1 1 d . . .
N2 N 0.7999(2) -0.00727(16) 0.1303(3) 0.0899(10) 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
C1 F1 1.375(4) . ?
C1 F2 1.386(4) . ?
C1 C13 1.500(4) . ?
C1 C2 1.530(5) . ?
C2 C3 1.319(4) . ?
C2 C7 1.380(5) . ?
C3 C4 1.339(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(5) . ?
C4 C8 1.483(5) . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.393(5) . ?
C8 N1 1.404(5) . ?
C9 C10 1.372(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.357(6) . ?
C11 H11 0.9300 . ?
C12 N1 1.408(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(5) . ?
C13 C22 1.441(4) . ?
C14 C15 1.395(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.425(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.409(6) . ?
C17 C22 1.418(4) . ?
C18 C19 1.352(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.405(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.351(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.412(5) . ?
C21 H21 0.9300 . ?
C23 F3 1.370(4) . ?
C23 F4 1.379(4) . ?
C23 C35 1.503(4) . ?
C23 C24 1.521(5) . ?
C24 C29 1.330(4) . ?
C24 C25 1.388(5) . ?
C25 C26 1.367(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.377(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.394(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.339(4) . ?
C28 C30 1.491(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.386(5) . ?
C30 N2 1.406(5) . ?
C31 C32 1.372(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.374(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(5) . ?
C33 H33 0.9300 . ?
C34 N2 1.409(5) . ?
C34 H34 0.9300 . ?
C35 C44 1.375(4) . ?
C35 C36 1.439(4) . ?
C36 C37 1.419(4) . ?
C36 C41 1.419(4) . ?
C37 C38 1.359(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.402(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.350(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.418(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.422(5) . ?
C42 C43 1.360(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.396(5) . ?
C43 H43 0.9300 . ?
C44 H44 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
F1 C1 F2 103.5(2) . . ?
F1 C1 C13 110.4(3) . . ?
F2 C1 C13 109.4(3) . . ?
F1 C1 C2 109.1(3) . . ?
F2 C1 C2 107.0(3) . . ?
C13 C1 C2 116.6(3) . . ?
C3 C2 C7 123.2(3) . . ?
C3 C2 C1 117.1(3) . . ?
C7 C2 C1 119.7(3) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 C8 117.5(3) . . ?
C5 C4 C8 121.8(3) . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 118.0(4) . . ?
C2 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C9 C8 N1 119.0(3) . . ?
C9 C8 C4 120.8(3) . . ?
N1 C8 C4 120.2(3) . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 N1 121.3(4) . . ?
C11 C12 H12 119.3 . . ?
N1 C12 H12 119.3 . . ?
C14 C13 C22 120.1(3) . . ?
C14 C13 C1 117.7(3) . . ?
C22 C13 C1 122.2(3) . . ?
C13 C14 C15 121.3(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C22 118.9(4) . . ?
C18 C17 C16 121.9(4) . . ?
C22 C17 C16 119.1(4) . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.7(3) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C21 C22 C17 117.7(3) . . ?
C21 C22 C13 124.2(3) . . ?
C17 C22 C13 118.0(3) . . ?
F3 C23 F4 104.3(2) . . ?
F3 C23 C35 110.7(3) . . ?
F4 C23 C35 109.8(3) . . ?
F3 C23 C24 110.5(3) . . ?
F4 C23 C24 108.0(3) . . ?
C35 C23 C24 113.2(3) . . ?
C29 C24 C25 123.1(3) . . ?
C29 C24 C23 118.0(3) . . ?
C25 C24 C23 118.8(3) . . ?
C26 C25 C24 117.6(4) . . ?
C26 C25 H25 121.2 . . ?
C24 C25 H25 121.2 . . ?
C25 C26 C27 120.1(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 119.2(4) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C29 C28 C27 120.6(3) . . ?
C29 C28 C30 116.6(3) . . ?
C27 C28 C30 122.8(3) . . ?
C24 C29 C28 119.3(3) . . ?
C24 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C31 C30 N2 118.3(3) . . ?
C31 C30 C28 122.3(3) . . ?
N2 C30 C28 119.4(3) . . ?
C32 C31 C30 121.2(4) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C33 121.3(4) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C32 C33 C34 118.8(4) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
C33 C34 N2 121.2(4) . . ?
C33 C34 H34 119.4 . . ?
N2 C34 H34 119.4 . . ?
C44 C35 C36 120.1(3) . . ?
C44 C35 C23 118.7(3) . . ?
C36 C35 C23 120.9(3) . . ?
C37 C36 C41 118.0(3) . . ?
C37 C36 C35 124.1(3) . . ?
C41 C36 C35 117.9(3) . . ?
C38 C37 C36 121.2(3) . . ?
C38 C37 H37 119.4 . . ?
C36 C37 H37 119.4 . . ?
C37 C38 C39 120.6(4) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C40 C39 C38 120.0(4) . . ?
C40 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?
C39 C40 C41 121.4(4) . . ?
C39 C40 H40 119.3 . . ?
C41 C40 H40 119.3 . . ?
C40 C41 C36 118.8(3) . . ?
C40 C41 C42 121.8(3) . . ?
C36 C41 C42 119.4(3) . . ?
C43 C42 C41 121.2(3) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C42 C43 C44 120.0(4) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C35 C44 C43 121.4(4) . . ?
C35 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C8 N1 C12 118.8(4) . . ?
C30 N2 C34 119.1(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
F1 C1 C2 C3 35.9(4) . . . . ?
F2 C1 C2 C3 147.3(3) . . . . ?
C13 C1 C2 C3 -90.0(3) . . . . ?
F1 C1 C2 C7 -143.3(3) . . . . ?
F2 C1 C2 C7 -31.9(4) . . . . ?
C13 C1 C2 C7 90.9(4) . . . . ?
C7 C2 C3 C4 1.5(5) . . . . ?
C1 C2 C3 C4 -177.7(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C8 178.8(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C8 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 C7 0.7(6) . . . . ?
C3 C2 C7 C6 -1.6(5) . . . . ?
C1 C2 C7 C6 177.5(3) . . . . ?
C5 C6 C7 C2 0.4(6) . . . . ?
C3 C4 C8 C9 38.6(4) . . . . ?
C5 C4 C8 C9 -142.4(4) . . . . ?
C3 C4 C8 N1 -140.0(3) . . . . ?
C5 C4 C8 N1 39.0(5) . . . . ?
N1 C8 C9 C10 -1.6(6) . . . . ?
C4 C8 C9 C10 179.8(4) . . . . ?
C8 C9 C10 C11 3.1(7) . . . . ?
C9 C10 C11 C12 -2.7(7) . . . . ?
C10 C11 C12 N1 0.8(7) . . . . ?
F1 C1 C13 C14 133.8(3) . . . . ?
F2 C1 C13 C14 20.5(4) . . . . ?
C2 C1 C13 C14 -101.0(4) . . . . ?
F1 C1 C13 C22 -47.5(4) . . . . ?
F2 C1 C13 C22 -160.8(3) . . . . ?
C2 C1 C13 C22 77.7(4) . . . . ?
C22 C13 C14 C15 1.3(5) . . . . ?
C1 C13 C14 C15 -180.0(3) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C15 C16 C17 C18 -179.9(4) . . . . ?
C15 C16 C17 C22 1.0(6) . . . . ?
C22 C17 C18 C19 -0.1(6) . . . . ?
C16 C17 C18 C19 -179.1(4) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C19 C20 C21 -0.8(6) . . . . ?
C19 C20 C21 C22 1.1(6) . . . . ?
C20 C21 C22 C17 -0.9(5) . . . . ?
C20 C21 C22 C13 178.6(3) . . . . ?
C18 C17 C22 C21 0.4(5) . . . . ?
C16 C17 C22 C21 179.5(3) . . . . ?
C18 C17 C22 C13 -179.1(3) . . . . ?
C16 C17 C22 C13 0.0(5) . . . . ?
C14 C13 C22 C21 179.4(3) . . . . ?
C1 C13 C22 C21 0.8(5) . . . . ?
C14 C13 C22 C17 -1.1(5) . . . . ?
C1 C13 C22 C17 -179.8(3) . . . . ?
F3 C23 C24 C29 -21.6(4) . . . . ?
F4 C23 C24 C29 -135.1(3) . . . . ?
C35 C23 C24 C29 103.2(3) . . . . ?
F3 C23 C24 C25 162.3(3) . . . . ?
F4 C23 C24 C25 48.8(4) . . . . ?
C35 C23 C24 C25 -72.9(4) . . . . ?
C29 C24 C25 C26 0.3(5) . . . . ?
C23 C24 C25 C26 176.2(3) . . . . ?
C24 C25 C26 C27 -0.2(6) . . . . ?
C25 C26 C27 C28 0.4(6) . . . . ?
C26 C27 C28 C29 -0.7(5) . . . . ?
C26 C27 C28 C30 179.4(3) . . . . ?
C25 C24 C29 C28 -0.6(4) . . . . ?
C23 C24 C29 C28 -176.6(3) . . . . ?
C27 C28 C29 C24 0.8(4) . . . . ?
C30 C28 C29 C24 -179.4(2) . . . . ?
C29 C28 C30 C31 174.7(3) . . . . ?
C27 C28 C30 C31 -5.4(5) . . . . ?
C29 C28 C30 N2 -4.8(4) . . . . ?
C27 C28 C30 N2 175.0(3) . . . . ?
N2 C30 C31 C32 -0.2(5) . . . . ?
C28 C30 C31 C32 -179.8(3) . . . . ?
C30 C31 C32 C33 0.3(6) . . . . ?
C31 C32 C33 C34 0.2(6) . . . . ?
C32 C33 C34 N2 -0.7(6) . . . . ?
F3 C23 C35 C44 -131.0(3) . . . . ?
F4 C23 C35 C44 -16.4(4) . . . . ?
C24 C23 C35 C44 104.3(3) . . . . ?
F3 C23 C35 C36 54.0(4) . . . . ?
F4 C23 C35 C36 168.7(3) . . . . ?
C24 C23 C35 C36 -70.6(4) . . . . ?
C44 C35 C36 C37 178.2(3) . . . . ?
C23 C35 C36 C37 -7.0(5) . . . . ?
C44 C35 C36 C41 -1.7(4) . . . . ?
C23 C35 C36 C41 173.1(3) . . . . ?
C41 C36 C37 C38 -1.5(5) . . . . ?
C35 C36 C37 C38 178.6(3) . . . . ?
C36 C37 C38 C39 -0.6(5) . . . . ?
C37 C38 C39 C40 2.0(6) . . . . ?
C38 C39 C40 C41 -1.2(6) . . . . ?
C39 C40 C41 C36 -0.9(5) . . . . ?
C39 C40 C41 C42 178.5(3) . . . . ?
C37 C36 C41 C40 2.2(4) . . . . ?
C35 C36 C41 C40 -177.8(3) . . . . ?
C37 C36 C41 C42 -177.2(3) . . . . ?
C35 C36 C41 C42 2.7(4) . . . . ?
C40 C41 C42 C43 179.0(3) . . . . ?
C36 C41 C42 C43 -1.6(5) . . . . ?
C41 C42 C43 C44 -0.7(6) . . . . ?
C36 C35 C44 C43 -0.5(5) . . . . ?
C23 C35 C44 C43 -175.4(3) . . . . ?
C42 C43 C44 C35 1.7(6) . . . . ?
C9 C8 N1 C12 -0.2(6) . . . . ?
C4 C8 N1 C12 178.4(3) . . . . ?
C11 C12 N1 C8 0.6(7) . . . . ?
C31 C30 N2 C34 -0.3(5) . . . . ?
C28 C30 N2 C34 179.3(3) . . . . ?
C33 C34 N2 C30 0.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_180518b_0m
_database_code_depnum_ccdc_archive 'CCDC 1888703'
loop_
_audit_author_name
_audit_author_address
'Wen Wan'
;Shanghai University
China
;
_audit_update_record             
;
2019-01-04 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 F2 N2 O'
_chemical_formula_weight         312.31

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.552(5)
_cell_length_b                   6.143(4)
_cell_length_c                   31.83(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.706(8)
_cell_angle_gamma                90.00
_cell_volume                     1471.9(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3389
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.53

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7260
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2604
_reflns_number_gt                2171
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.3083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0100(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2604
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24685(17) 1.0552(2) 0.09726(4) 0.0428(3) Uani 1 1 d . . .
C2 C 0.13371(19) 1.3476(2) 0.06133(5) 0.0509(4) Uani 1 1 d . . .
H2 H 0.0836 1.4859 0.0612 0.061 Uiso 1 1 calc R . .
C3 C 0.16046(18) 1.2542(2) 0.02294(4) 0.0457(3) Uani 1 1 d . . .
H3 H 0.1293 1.3291 -0.0020 0.055 Uiso 1 1 calc R . .
C4 C 0.23407(15) 1.0482(2) 0.02179(4) 0.0379(3) Uani 1 1 d . . .
C5 C 0.27764(17) 0.9479(2) 0.06057(4) 0.0400(3) Uani 1 1 d . . .
H5 H 0.3272 0.8092 0.0616 0.048 Uiso 1 1 calc R . .
C6 C 0.27009(16) 0.9362(2) -0.01806(4) 0.0389(3) Uani 1 1 d . . .
C7 C 0.23005(19) 1.0280(3) -0.05756(4) 0.0501(4) Uani 1 1 d . . .
H7 H 0.1783 1.1653 -0.0601 0.060 Uiso 1 1 calc R . .
C8 C 0.2678(2) 0.9137(3) -0.09299(5) 0.0609(4) Uani 1 1 d . . .
H8 H 0.2415 0.9724 -0.1197 0.073 Uiso 1 1 calc R . .
C9 C 0.3448(2) 0.7120(3) -0.08825(5) 0.0600(4) Uani 1 1 d . . .
H9 H 0.3718 0.6314 -0.1116 0.072 Uiso 1 1 calc R . .
C10 C 0.3809(2) 0.6322(3) -0.04828(5) 0.0553(4) Uani 1 1 d . . .
H10 H 0.4335 0.4956 -0.0452 0.066 Uiso 1 1 calc R . .
C11 C 0.2929(2) 0.9540(3) 0.14036(4) 0.0539(4) Uani 1 1 d . . .
C12 C 0.13521(19) 0.8966(2) 0.16411(4) 0.0462(3) Uani 1 1 d . . .
C13 C 0.0563(2) 0.6950(3) 0.15953(4) 0.0545(4) Uani 1 1 d . . .
H13 H 0.1046 0.5911 0.1426 0.065 Uiso 1 1 calc R . .
C14 C -0.0938(2) 0.6448(2) 0.17978(5) 0.0554(4) Uani 1 1 d . . .
H14 H -0.1461 0.5082 0.1763 0.066 Uiso 1 1 calc R . .
C15 C -0.1655(2) 0.7978(2) 0.20519(4) 0.0494(4) Uani 1 1 d . . .
C16 C -0.0857(2) 0.9997(3) 0.21016(4) 0.0535(4) Uani 1 1 d . . .
H16 H -0.1327 1.1028 0.2275 0.064 Uiso 1 1 calc R . .
C17 C 0.0624(2) 1.0498(2) 0.18971(4) 0.0516(4) Uani 1 1 d . . .
H17 H 0.1140 1.1869 0.1930 0.062 Uiso 1 1 calc R . .
C18 C -0.3991(3) 0.5616(3) 0.22329(6) 0.0787(5) Uani 1 1 d . . .
H18A H -0.4388 0.5353 0.1943 0.118 Uiso 1 1 calc R . .
H18B H -0.4995 0.5627 0.2399 0.118 Uiso 1 1 calc R . .
H18C H -0.3184 0.4485 0.2332 0.118 Uiso 1 1 calc R . .
F1 F 0.39326(13) 0.77128(17) 0.13514(3) 0.0738(3) Uani 1 1 d . . .
F2 F 0.40215(12) 1.09423(19) 0.16372(3) 0.0776(3) Uani 1 1 d . . .
N1 N 0.17476(16) 1.25337(19) 0.09846(4) 0.0494(3) Uani 1 1 d . . .
N2 N 0.34482(16) 0.73910(19) -0.01346(4) 0.0481(3) Uani 1 1 d . . .
O1 O -0.31123(15) 0.76630(19) 0.22692(3) 0.0662(3) 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
C1 N1 1.3354(19) . ?
C1 C5 1.3775(19) . ?
C1 C11 1.520(2) . ?
C2 N1 1.3298(19) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3948(19) . ?
C4 C6 1.488(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.3386(19) . ?
C6 C7 1.389(2) . ?
C7 C8 1.378(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(2) . ?
C9 H9 0.9300 . ?
C10 N2 1.3355(19) . ?
C10 H10 0.9300 . ?
C11 F2 1.3692(19) . ?
C11 F1 1.3722(19) . ?
C11 C12 1.504(2) . ?
C12 C13 1.377(2) . ?
C12 C17 1.388(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 O1 1.3609(19) . ?
C15 C16 1.383(2) . ?
C16 C17 1.374(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O1 1.422(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
N1 C1 C5 123.94(12) . . ?
N1 C1 C11 114.23(12) . . ?
C5 C1 C11 121.82(13) . . ?
N1 C2 C3 124.45(14) . . ?
N1 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
C2 C3 C4 119.47(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 116.54(12) . . ?
C3 C4 C6 123.20(12) . . ?
C5 C4 C6 120.25(13) . . ?
C1 C5 C4 119.65(13) . . ?
C1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C7 121.68(13) . . ?
N2 C6 C4 115.47(11) . . ?
C7 C6 C4 122.85(13) . . ?
C8 C7 C6 119.31(15) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 118.98(15) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 118.41(14) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
N2 C10 C9 123.79(16) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
F2 C11 F1 105.44(12) . . ?
F2 C11 C12 109.95(12) . . ?
F1 C11 C12 109.70(13) . . ?
F2 C11 C1 108.42(13) . . ?
F1 C11 C1 108.24(12) . . ?
C12 C11 C1 114.68(12) . . ?
C13 C12 C17 118.90(14) . . ?
C13 C12 C11 120.76(13) . . ?
C17 C12 C11 120.29(14) . . ?
C12 C13 C14 121.02(14) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.80(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O1 C15 C14 125.02(15) . . ?
O1 C15 C16 115.64(13) . . ?
C14 C15 C16 119.33(14) . . ?
C17 C16 C15 120.72(13) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 120.22(15) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 N1 C1 115.94(12) . . ?
C10 N2 C6 117.82(13) . . ?
C15 O1 C18 118.42(13) . . ?

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
N1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C5 -0.27(19) . . . . ?
C2 C3 C4 C6 -179.09(12) . . . . ?
N1 C1 C5 C4 0.6(2) . . . . ?
C11 C1 C5 C4 -179.60(12) . . . . ?
C3 C4 C5 C1 -0.16(18) . . . . ?
C6 C4 C5 C1 178.71(11) . . . . ?
C3 C4 C6 N2 178.77(11) . . . . ?
C5 C4 C6 N2 -0.01(17) . . . . ?
C3 C4 C6 C7 -1.1(2) . . . . ?
C5 C4 C6 C7 -179.85(12) . . . . ?
N2 C6 C7 C8 0.1(2) . . . . ?
C4 C6 C7 C8 179.93(12) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 N2 0.3(2) . . . . ?
N1 C1 C11 F2 -55.52(16) . . . . ?
C5 C1 C11 F2 124.69(14) . . . . ?
N1 C1 C11 F1 -169.42(12) . . . . ?
C5 C1 C11 F1 10.79(19) . . . . ?
N1 C1 C11 C12 67.76(17) . . . . ?
C5 C1 C11 C12 -112.03(15) . . . . ?
F2 C11 C12 C13 -148.01(13) . . . . ?
F1 C11 C12 C13 -32.50(18) . . . . ?
C1 C11 C12 C13 89.53(17) . . . . ?
F2 C11 C12 C17 34.67(18) . . . . ?
F1 C11 C12 C17 150.19(13) . . . . ?
C1 C11 C12 C17 -87.78(17) . . . . ?
C17 C12 C13 C14 0.4(2) . . . . ?
C11 C12 C13 C14 -176.98(14) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 O1 -179.36(13) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
O1 C15 C16 C17 -179.97(13) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C16 C17 C12 -0.8(2) . . . . ?
C13 C12 C17 C16 0.2(2) . . . . ?
C11 C12 C17 C16 177.59(13) . . . . ?
C3 C2 N1 C1 0.2(2) . . . . ?
C5 C1 N1 C2 -0.6(2) . . . . ?
C11 C1 N1 C2 179.60(12) . . . . ?
C9 C10 N2 C6 -0.4(2) . . . . ?
C7 C6 N2 C10 0.23(19) . . . . ?
C4 C6 N2 C10 -179.61(12) . . . . ?
C14 C15 O1 C18 -0.6(2) . . . . ?
C16 C15 O1 C18 -179.75(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.026
