# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mo_d8v18921_0m
_database_code_depnum_ccdc_archive 'CCDC 1878405'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-11-12 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N4 O2'
_chemical_formula_weight         444.48

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'

_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                   7.8352(4)
_cell_length_b                   11.9524(7)
_cell_length_c                   12.5240(7)
_cell_angle_alpha                86.602(2)
_cell_angle_beta                 78.708(2)
_cell_angle_gamma                75.444(2)
_cell_volume                     1113.18(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7360
_cell_measurement_theta_min      4.812
_cell_measurement_theta_max      54.857

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_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            16251
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.734
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4350
_reflns_number_gt                3545
_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-2013 (Sheldrick, 2013)'
_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)+(0.0521P)²+0.2226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.061(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4350
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O 0.2991(2) -0.03160(11) 0.99897(11) 0.0796(4) Uani 1 1 d . . . . .
O2 O 0.1519(2) -0.11266(11) 0.91279(13) 0.0863(5) Uani 1 1 d . . . . .
N1 N 0.42201(18) 0.32443(11) 0.94202(10) 0.0542(3) Uani 1 1 d . . . . .
N2 N 0.49040(16) 0.44966(11) 0.79380(10) 0.0473(3) Uani 1 1 d . . . . .
N3 N 0.24817(15) 0.36681(10) 0.80747(9) 0.0412(3) Uani 1 1 d . . . . .
N4 N 0.2086(2) -0.03006(12) 0.92981(13) 0.0602(4) Uani 1 1 d . . . . .
C1 C 0.5709(2) 0.33132(15) 0.97546(15) 0.0620(5) Uani 1 1 d . . . . .
H1 H 0.5993 0.2903 1.0377 0.074 Uiso 1 1 calc R U . . .
C2 C 0.6831(2) 0.39608(15) 0.92209(15) 0.0602(4) Uani 1 1 d . . . . .
H2 H 0.7871 0.3991 0.9458 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6347(2) 0.45584(14) 0.83243(14) 0.0554(4) Uani 1 1 d . . . . .
H3 H 0.7056 0.5033 0.7963 0.066 Uiso 1 1 calc R U . . .
C4 C 0.39445(18) 0.38211(11) 0.85055(11) 0.0395(3) Uani 1 1 d . . . . .
C5 C 0.17202(18) 0.43548(12) 0.72528(11) 0.0427(3) Uani 1 1 d . . . . .
C6 C 0.0744(2) 0.37685(13) 0.68269(12) 0.0489(4) Uani 1 1 d . . . . .
H6 H 0.0101 0.4037 0.6274 0.059 Uiso 1 1 calc R U . . .
C7 C 0.08603(19) 0.26768(13) 0.73622(12) 0.0460(3) Uani 1 1 d . . . . .
C8 C 0.19454(18) 0.26243(12) 0.81454(11) 0.0409(3) Uani 1 1 d . . . . .
C9 C 0.23772(19) 0.16489(12) 0.87904(12) 0.0452(3) Uani 1 1 d . . . . .
H9 H 0.3112 0.1606 0.9299 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1653(2) 0.07483(13) 0.86334(12) 0.0493(4) Uani 1 1 d . . . . .
C11 C 0.0538(2) 0.07770(15) 0.78932(14) 0.0584(4) Uani 1 1 d . . . . .
H11 H 0.0064 0.0149 0.7833 0.070 Uiso 1 1 calc R U . . .
C12 C 0.0142(2) 0.17399(15) 0.72512(14) 0.0579(4) Uani 1 1 d . . . . .
H12 H -0.0597 0.1770 0.6747 0.069 Uiso 1 1 calc R U . . .
C13 C 0.18898(19) 0.55434(12) 0.69795(11) 0.0437(3) Uani 1 1 d . . . . .
C14 C 0.1469(2) 0.63666(13) 0.78735(12) 0.0497(4) Uani 1 1 d . . . . .
H14 H 0.2084 0.6947 0.7796 0.060 Uiso 1 1 calc R U . . .
C15 C 0.0292(3) 0.63466(18) 0.87731(15) 0.0634(5) Uani 1 1 d . . . . .
C16 C 0.2343(2) 0.58177(12) 0.59216(12) 0.0475(4) Uani 1 1 d . . . . .
H16 H 0.2591 0.5210 0.5439 0.057 Uiso 1 1 calc R U . . .
C17 C 0.25033(19) 0.69319(12) 0.54202(11) 0.0443(3) Uani 1 1 d . . . . .
C18 C 0.1549(2) 0.80052(13) 0.58624(12) 0.0508(4) Uani 1 1 d . . . . .
H18 H 0.0720 0.8037 0.6509 0.061 Uiso 1 1 calc R U . . .
C19 C 0.1815(2) 0.90143(13) 0.53559(12) 0.0489(4) Uani 1 1 d . . . . .
H19 H 0.1183 0.9715 0.5681 0.059 Uiso 1 1 calc R U . . .
C20 C 0.30029(18) 0.90224(13) 0.43702(11) 0.0438(3) Uani 1 1 d . . . . .
C21 C 0.3915(2) 0.79535(13) 0.39160(12) 0.0500(4) Uani 1 1 d . . . . .
H21 H 0.4708 0.7925 0.3254 0.060 Uiso 1 1 calc R U . . .
C22 C 0.3670(2) 0.69403(13) 0.44225(12) 0.0498(4) Uani 1 1 d . . . . .
H22 H 0.4296 0.6241 0.4093 0.060 Uiso 1 1 calc R U . . .
C23 C 0.32260(19) 1.01209(13) 0.38183(12) 0.0482(4) Uani 1 1 d . . . . .
C24 C 0.3238(2) 1.10644(15) 0.44118(15) 0.0620(4) Uani 1 1 d . . . . .
H24 H 0.3113 1.1004 0.5165 0.074 Uiso 1 1 calc R U . . .
C25 C 0.3432(3) 1.20896(17) 0.3897(2) 0.0804(6) Uani 1 1 d . . . . .
H25 H 0.3447 1.2713 0.4302 0.096 Uiso 1 1 calc R U . . .
C26 C 0.3604(3) 1.2188(2) 0.2781(2) 0.0880(7) Uani 1 1 d . . . . .
H26 H 0.3739 1.2879 0.2433 0.106 Uiso 1 1 calc R U . . .
C27 C 0.3577(3) 1.12732(19) 0.21816(17) 0.0783(6) Uani 1 1 d . . . . .
H27 H 0.3672 1.1348 0.1430 0.094 Uiso 1 1 calc R U . . .
C28 C 0.3409(2) 1.02421(15) 0.26894(13) 0.0596(4) Uani 1 1 d . . . . .
H28 H 0.3419 0.9619 0.2275 0.071 Uiso 1 1 calc R U . . .
H15A H 0.002(2) 0.6927(16) 0.9343(15) 0.071(5) Uiso 1 1 d . . . . .
H15B H -0.036(3) 0.5737(18) 0.8906(15) 0.076(6) Uiso 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
O1 N4 1.2189(19) . ?
O2 N4 1.2246(17) . ?
N1 C4 1.3277(18) . ?
N1 C1 1.336(2) . ?
N2 C4 1.3229(18) . ?
N2 C3 1.3333(19) . ?
N3 C8 1.4060(17) . ?
N3 C5 1.4084(17) . ?
N3 C4 1.4132(17) . ?
N4 C10 1.467(2) . ?
C1 C2 1.367(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.354(2) . ?
C5 C13 1.474(2) . ?
C6 C7 1.421(2) . ?
C6 H6 0.9300 . ?
C7 C12 1.399(2) . ?
C7 C8 1.408(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.377(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(2) . ?
C11 C12 1.370(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C16 1.346(2) . ?
C13 C14 1.467(2) . ?
C14 C15 1.312(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.981(19) . ?
C15 H15B 0.98(2) . ?
C16 C17 1.462(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(2) . ?
C17 C22 1.397(2) . ?
C18 C19 1.373(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(2) . ?
C20 C23 1.481(2) . ?
C21 C22 1.373(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.390(2) . ?
C23 C28 1.395(2) . ?
C24 C25 1.379(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.369(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.377(2) . ?
C27 H27 0.9300 . ?
C28 H28 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
C4 N1 C1 114.83(14) . . ?
C4 N2 C3 114.91(13) . . ?
C8 N3 C5 107.91(11) . . ?
C8 N3 C4 123.76(11) . . ?
C5 N3 C4 125.61(11) . . ?
O1 N4 O2 122.90(15) . . ?
O1 N4 C10 119.02(14) . . ?
O2 N4 C10 118.09(16) . . ?
N1 C1 C2 122.80(15) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 116.51(15) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
N2 C3 C2 123.17(15) . . ?
N2 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
N2 C4 N1 127.63(13) . . ?
N2 C4 N3 116.40(12) . . ?
N1 C4 N3 115.95(12) . . ?
C6 C5 N3 108.68(12) . . ?
C6 C5 C13 127.11(13) . . ?
N3 C5 C13 124.08(12) . . ?
C5 C6 C7 108.95(13) . . ?
C5 C6 H6 125.5 . . ?
C7 C6 H6 125.5 . . ?
C12 C7 C8 119.54(14) . . ?
C12 C7 C6 133.38(14) . . ?
C8 C7 C6 107.08(12) . . ?
C9 C8 N3 130.81(13) . . ?
C9 C8 C7 121.76(13) . . ?
N3 C8 C7 107.37(12) . . ?
C10 C9 C8 116.04(14) . . ?
C10 C9 H9 122.0 . . ?
C8 C9 H9 122.0 . . ?
C9 C10 C11 124.02(15) . . ?
C9 C10 N4 117.62(14) . . ?
C11 C10 N4 118.36(14) . . ?
C12 C11 C10 119.31(14) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 119.29(15) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C16 C13 C14 124.17(13) . . ?
C16 C13 C5 117.88(13) . . ?
C14 C13 C5 117.88(12) . . ?
C15 C14 C13 125.04(16) . . ?
C15 C14 H14 117.5 . . ?
C13 C14 H14 117.5 . . ?
C14 C15 H15A 122.6(11) . . ?
C14 C15 H15B 120.7(11) . . ?
H15A C15 H15B 116.7(16) . . ?
C13 C16 C17 129.41(14) . . ?
C13 C16 H16 115.3 . . ?
C17 C16 H16 115.3 . . ?
C18 C17 C22 116.88(13) . . ?
C18 C17 C16 124.55(13) . . ?
C22 C17 C16 118.56(13) . . ?
C19 C18 C17 120.98(14) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 122.09(14) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 116.81(13) . . ?
C21 C20 C23 121.88(13) . . ?
C19 C20 C23 121.27(13) . . ?
C22 C21 C20 121.45(13) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C17 121.72(14) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
C24 C23 C28 118.15(15) . . ?
C24 C23 C20 120.91(14) . . ?
C28 C23 C20 120.94(14) . . ?
C25 C24 C23 120.82(18) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C26 C25 120.22(19) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 120.14(19) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.76(18) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?

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
C4 N1 C1 C2 2.3(2) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
C4 N2 C3 C2 1.2(2) . . . . ?
C1 C2 C3 N2 -2.8(3) . . . . ?
C3 N2 C4 N1 2.6(2) . . . . ?
C3 N2 C4 N3 -175.48(12) . . . . ?
C1 N1 C4 N2 -4.3(2) . . . . ?
C1 N1 C4 N3 173.82(13) . . . . ?
C8 N3 C4 N2 143.91(13) . . . . ?
C5 N3 C4 N2 -15.14(19) . . . . ?
C8 N3 C4 N1 -34.44(18) . . . . ?
C5 N3 C4 N1 166.51(13) . . . . ?
C8 N3 C5 C6 0.14(15) . . . . ?
C4 N3 C5 C6 161.93(13) . . . . ?
C8 N3 C5 C13 176.32(12) . . . . ?
C4 N3 C5 C13 -21.9(2) . . . . ?
N3 C5 C6 C7 -0.38(16) . . . . ?
C13 C5 C6 C7 -176.42(13) . . . . ?
C5 C6 C7 C12 -179.66(16) . . . . ?
C5 C6 C7 C8 0.48(16) . . . . ?
C5 N3 C8 C9 177.37(14) . . . . ?
C4 N3 C8 C9 15.2(2) . . . . ?
C5 N3 C8 C7 0.17(14) . . . . ?
C4 N3 C8 C7 -162.05(12) . . . . ?
C12 C7 C8 C9 2.2(2) . . . . ?
C6 C7 C8 C9 -177.90(13) . . . . ?
C12 C7 C8 N3 179.73(13) . . . . ?
C6 C7 C8 N3 -0.39(15) . . . . ?
N3 C8 C9 C10 -178.10(13) . . . . ?
C7 C8 C9 C10 -1.2(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C8 C9 C10 N4 179.76(12) . . . . ?
O1 N4 C10 C9 3.3(2) . . . . ?
O2 N4 C10 C9 -176.55(14) . . . . ?
O1 N4 C10 C11 -176.38(15) . . . . ?
O2 N4 C10 C11 3.8(2) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
N4 C10 C11 C12 -178.88(14) . . . . ?
C10 C11 C12 C7 -0.5(2) . . . . ?
C8 C7 C12 C11 -1.3(2) . . . . ?
C6 C7 C12 C11 178.86(16) . . . . ?
C6 C5 C13 C16 -51.5(2) . . . . ?
N3 C5 C13 C16 133.03(15) . . . . ?
C6 C5 C13 C14 125.60(16) . . . . ?
N3 C5 C13 C14 -49.86(19) . . . . ?
C16 C13 C14 C15 146.32(17) . . . . ?
C5 C13 C14 C15 -30.6(2) . . . . ?
C14 C13 C16 C17 -0.8(2) . . . . ?
C5 C13 C16 C17 176.15(13) . . . . ?
C13 C16 C17 C18 -27.6(2) . . . . ?
C13 C16 C17 C22 153.24(15) . . . . ?
C22 C17 C18 C19 -2.8(2) . . . . ?
C16 C17 C18 C19 178.05(14) . . . . ?
C17 C18 C19 C20 1.7(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C18 C19 C20 C23 177.92(14) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C23 C20 C21 C22 -178.57(13) . . . . ?
C20 C21 C22 C17 -0.4(2) . . . . ?
C18 C17 C22 C21 2.1(2) . . . . ?
C16 C17 C22 C21 -178.64(13) . . . . ?
C21 C20 C23 C24 -142.97(16) . . . . ?
C19 C20 C23 C24 39.3(2) . . . . ?
C21 C20 C23 C28 37.8(2) . . . . ?
C19 C20 C23 C28 -139.96(15) . . . . ?
C28 C23 C24 C25 -0.2(2) . . . . ?
C20 C23 C24 C25 -179.50(15) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C27 C28 C23 1.4(3) . . . . ?
C24 C23 C28 C27 -0.7(2) . . . . ?
C20 C23 C28 C27 178.56(15) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v19146_0m
_database_code_depnum_ccdc_archive 'CCDC 1899061'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2019-02-23 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 F N3'
_chemical_formula_weight         343.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.944(3)
_cell_length_b                   15.225(4)
_cell_length_c                   22.273(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.963(8)
_cell_angle_gamma                90
_cell_volume                     3616.6(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5806
_cell_measurement_theta_min      4.663
_cell_measurement_theta_max      48.306

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            39510
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6726
_reflns_number_gt                3702
_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-2013 (Sheldrick, 2013)'
_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)+(0.0556P)²+0.7933P] 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     SHELXL
_refine_ls_extinction_coef       0.0146(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6726
_refine_ls_number_parameters     472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.024
_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 0.9883(2) 0.47737(14) 0.70692(10) 0.1382(8) Uani 1 1 d . . . . .
N1 N 0.55377(19) 0.24807(13) 0.43969(10) 0.0652(6) Uani 1 1 d . . . . .
N2 N 0.5751(2) 0.09835(15) 0.46102(12) 0.0789(7) Uani 1 1 d . . . . .
N3 N 0.6416(2) 0.16044(15) 0.37559(12) 0.0815(7) Uani 1 1 d . . . . .
C1 C 0.5087(2) 0.31565(18) 0.39728(13) 0.0671(7) Uani 1 1 d . . . . .
C2 C 0.5055(3) 0.3238(2) 0.33475(15) 0.0861(9) Uani 1 1 d . . . . .
H2 H 0.5386 0.2805 0.3136 0.103 Uiso 1 1 calc R U . . .
C3 C 0.4516(3) 0.3982(3) 0.30559(17) 0.1027(11) Uani 1 1 d . . . . .
H3 H 0.4489 0.4050 0.2638 0.123 Uiso 1 1 calc R U . . .
C4 C 0.4011(3) 0.4636(2) 0.33573(18) 0.0992(11) Uani 1 1 d . . . . .
H4 H 0.3654 0.5131 0.3142 0.119 Uiso 1 1 calc R U . . .
C5 C 0.4037(3) 0.4554(2) 0.39746(16) 0.0857(9) Uani 1 1 d . . . . .
H5 H 0.3700 0.4991 0.4180 0.103 Uiso 1 1 calc R U . . .
C6 C 0.4576(2) 0.38068(18) 0.42884(14) 0.0697(7) Uani 1 1 d . . . . .
C7 C 0.4735(2) 0.35207(17) 0.49091(14) 0.0690(7) Uani 1 1 d . . . . .
H7 H 0.4489 0.3832 0.5221 0.083 Uiso 1 1 calc R U . . .
C8 C 0.5301(2) 0.27251(17) 0.49743(13) 0.0648(7) Uani 1 1 d . . . . .
C9 C 0.5919(2) 0.16407(18) 0.42498(14) 0.0663(7) Uani 1 1 d . . . . .
C10 C 0.6181(3) 0.0205(2) 0.44708(16) 0.0907(10) Uani 1 1 d . . . . .
H10 H 0.6099 -0.0278 0.4715 0.109 Uiso 1 1 calc R U . . .
C11 C 0.6735(3) 0.0089(2) 0.39858(18) 0.0972(11) Uani 1 1 d . . . . .
H11 H 0.7042 -0.0455 0.3900 0.117 Uiso 1 1 calc R U . . .
C12 C 0.6815(3) 0.0804(2) 0.36360(17) 0.0939(10) Uani 1 1 d . . . . .
H12 H 0.7165 0.0737 0.3295 0.113 Uiso 1 1 calc R U . . .
C13 C 0.5734(3) 0.22448(17) 0.55558(13) 0.0670(7) Uani 1 1 d . . . . .
C14 C 0.4935(3) 0.21500(19) 0.59230(14) 0.0832(9) Uani 1 1 d . . . . .
H14 H 0.4106 0.2307 0.5759 0.100 Uiso 1 1 calc R U . . .
C15 C 0.5231(4) 0.1816(2) 0.65727(16) 0.1135(12) Uani 1 1 d . . . . .
H15A H 0.5922 0.1413 0.6628 0.170 Uiso 1 1 calc R U . . .
H15B H 0.4511 0.1521 0.6655 0.170 Uiso 1 1 calc R U . . .
H15C H 0.5451 0.2301 0.6852 0.170 Uiso 1 1 calc R U . . .
C16 C 0.7110(3) 0.20138(17) 0.57494(13) 0.0724(8) Uani 1 1 d . . . . .
H16A H 0.7205 0.1490 0.6004 0.087 Uiso 1 1 calc R U . . .
H16B H 0.7424 0.1882 0.5385 0.087 Uiso 1 1 calc R U . . .
C17 C 0.7883(2) 0.27425(17) 0.61028(13) 0.0654(7) Uani 1 1 d . . . . .
C18 C 0.8315(3) 0.2698(2) 0.67285(15) 0.1020(11) Uani 1 1 d . . . . .
H18 H 0.8156 0.2196 0.6936 0.122 Uiso 1 1 calc R U . . .
C19 C 0.8982(4) 0.3380(3) 0.70590(16) 0.1216(14) Uani 1 1 d . . . . .
H19 H 0.9258 0.3343 0.7485 0.146 Uiso 1 1 calc R U . . .
C20 C 0.9223(3) 0.4098(2) 0.67518(16) 0.0910(10) Uani 1 1 d . . . . .
C21 C 0.8845(3) 0.41711(19) 0.61308(15) 0.0802(8) Uani 1 1 d . . . . .
H21 H 0.9035 0.4668 0.5927 0.096 Uiso 1 1 calc R U . . .
C22 C 0.8170(3) 0.34861(19) 0.58108(13) 0.0751(8) Uani 1 1 d . . . . .
H22 H 0.7900 0.3528 0.5385 0.090 Uiso 1 1 calc R U . . .
F2 F 0.3212(2) 0.02239(15) 0.29483(11) 0.1486(9) Uani 1 1 d . . . . .
N4 N 0.09929(19) 0.25536(12) 0.54777(9) 0.0584(5) Uani 1 1 d . . . . .
N5 N 0.2458(2) 0.33870(14) 0.61566(11) 0.0701(6) Uani 1 1 d . . . . .
N6 N 0.1060(2) 0.40601(13) 0.53094(10) 0.0681(6) Uani 1 1 d . . . . .
C23 C 0.0873(2) 0.18652(15) 0.58855(12) 0.0586(6) Uani 1 1 d . . . . .
C24 C 0.1377(3) 0.17518(17) 0.65127(13) 0.0709(7) Uani 1 1 d . . . . .
H24 H 0.1920 0.2164 0.6738 0.085 Uiso 1 1 calc R U . . .
C25 C 0.1040(3) 0.10061(19) 0.67868(15) 0.0826(9) Uani 1 1 d . . . . .
H25 H 0.1358 0.0919 0.7206 0.099 Uiso 1 1 calc R U . . .
C26 C 0.0242(3) 0.03819(19) 0.64571(16) 0.0836(9) Uani 1 1 d . . . . .
H26 H 0.0039 -0.0116 0.6657 0.100 Uiso 1 1 calc R U . . .
C27 C -0.0252(3) 0.04904(18) 0.58388(15) 0.0772(8) Uani 1 1 d . . . . .
H27 H -0.0785 0.0069 0.5619 0.093 Uiso 1 1 calc R U . . .
C28 C 0.0056(2) 0.12396(16) 0.55446(13) 0.0625(7) Uani 1 1 d . . . . .
C29 C -0.0305(2) 0.15537(16) 0.49300(13) 0.0653(7) Uani 1 1 d . . . . .
H29 H -0.0833 0.1262 0.4606 0.078 Uiso 1 1 calc R U . . .
C30 C 0.0238(2) 0.23434(15) 0.48896(12) 0.0590(6) Uani 1 1 d . . . . .
C31 C 0.1534(2) 0.33786(16) 0.56553(12) 0.0570(6) Uani 1 1 d . . . . .
C32 C 0.2986(3) 0.41697(19) 0.63072(13) 0.0762(8) Uani 1 1 d . . . . .
H32 H 0.3637 0.4211 0.6655 0.091 Uiso 1 1 calc R U . . .
C33 C 0.2617(3) 0.49112(18) 0.59748(14) 0.0756(8) Uani 1 1 d . . . . .
H33 H 0.3016 0.5447 0.6078 0.091 Uiso 1 1 calc R U . . .
C34 C 0.1628(3) 0.48250(17) 0.54815(13) 0.0751(8) Uani 1 1 d . . . . .
H34 H 0.1335 0.5324 0.5254 0.090 Uiso 1 1 calc R U . . .
C35 C 0.0198(3) 0.28445(16) 0.43156(12) 0.0605(7) Uani 1 1 d . . . . .
C36 C -0.0911(3) 0.29955(16) 0.39466(12) 0.0694(7) Uani 1 1 d . . . . .
H36 H -0.1607 0.2854 0.4102 0.083 Uiso 1 1 calc R U . . .
C37 C -0.1174(3) 0.3370(2) 0.33046(13) 0.0947(10) Uani 1 1 d . . . . .
H37A H -0.1685 0.2966 0.3025 0.142 Uiso 1 1 calc R U . . .
H37B H -0.0398 0.3463 0.3182 0.142 Uiso 1 1 calc R U . . .
H37C H -0.1608 0.3919 0.3298 0.142 Uiso 1 1 calc R U . . .
C38 C 0.1432(3) 0.30393(17) 0.41448(13) 0.0686(7) Uani 1 1 d . . . . .
H38A H 0.1329 0.3549 0.3876 0.082 Uiso 1 1 calc R U . . .
H38B H 0.2052 0.3186 0.4516 0.082 Uiso 1 1 calc R U . . .
C39 C 0.1915(2) 0.22859(17) 0.38268(12) 0.0621(7) Uani 1 1 d . . . . .
C40 C 0.2379(3) 0.15329(19) 0.41333(14) 0.0782(8) Uani 1 1 d . . . . .
H40 H 0.2400 0.1489 0.4552 0.094 Uiso 1 1 calc R U . . .
C41 C 0.2815(3) 0.0838(2) 0.38417(17) 0.0867(9) Uani 1 1 d . . . . .
H41 H 0.3126 0.0334 0.4059 0.104 Uiso 1 1 calc R U . . .
C42 C 0.2781(3) 0.0909(2) 0.32348(17) 0.0919(10) Uani 1 1 d . . . . .
C43 C 0.2349(4) 0.1627(3) 0.29150(17) 0.1304(16) Uani 1 1 d . . . . .
H43 H 0.2342 0.1664 0.2497 0.157 Uiso 1 1 calc R U . . .
C44 C 0.1911(4) 0.2317(2) 0.32116(15) 0.1032(11) Uani 1 1 d . . . . .
H44 H 0.1605 0.2817 0.2987 0.124 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 C20 1.360(3) . ?
N1 C9 1.407(3) . ?
N1 C1 1.409(3) . ?
N1 C8 1.418(3) . ?
N2 C9 1.321(3) . ?
N2 C10 1.338(3) . ?
N3 C9 1.333(3) . ?
N3 C12 1.341(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.401(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.422(4) . ?
C7 C8 1.353(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.470(4) . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.353(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.332(4) . ?
C13 C16 1.512(4) . ?
C14 C15 1.499(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.506(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.369(4) . ?
C17 C22 1.376(4) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.347(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.357(4) . ?
C21 C22 1.380(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
F2 C42 1.360(3) . ?
N4 C31 1.407(3) . ?
N4 C23 1.412(3) . ?
N4 C30 1.420(3) . ?
N5 C31 1.328(3) . ?
N5 C32 1.334(3) . ?
N6 C31 1.327(3) . ?
N6 C34 1.335(3) . ?
C23 C24 1.393(4) . ?
C23 C28 1.407(3) . ?
C24 C25 1.378(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.394(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.420(4) . ?
C29 C30 1.353(3) . ?
C29 H29 0.9300 . ?
C30 C35 1.481(3) . ?
C32 C33 1.361(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.324(3) . ?
C35 C38 1.513(3) . ?
C36 C37 1.506(4) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.505(3) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C44 1.370(4) . ?
C39 C40 1.372(4) . ?
C40 C41 1.382(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.348(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.333(4) . ?
C43 C44 1.383(4) . ?
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
C9 N1 C1 125.8(2) . . ?
C9 N1 C8 125.1(2) . . ?
C1 N1 C8 108.0(2) . . ?
C9 N2 C10 115.2(3) . . ?
C9 N3 C12 114.4(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 N1 131.5(3) . . ?
C6 C1 N1 107.4(2) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 122.7(3) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 133.0(3) . . ?
C1 C6 C7 107.2(2) . . ?
C8 C7 C6 109.4(2) . . ?
C8 C7 H7 125.3 . . ?
C6 C7 H7 125.3 . . ?
C7 C8 N1 108.1(2) . . ?
C7 C8 C13 126.1(2) . . ?
N1 C8 C13 125.5(2) . . ?
N2 C9 N3 127.5(3) . . ?
N2 C9 N1 117.3(3) . . ?
N3 C9 N1 115.3(3) . . ?
N2 C10 C11 122.7(3) . . ?
N2 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C12 C11 C10 116.7(3) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
N3 C12 C11 123.4(3) . . ?
N3 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C14 C13 C8 117.9(3) . . ?
C14 C13 C16 123.3(3) . . ?
C8 C13 C16 118.1(2) . . ?
C13 C14 C15 126.8(3) . . ?
C13 C14 H14 116.6 . . ?
C15 C14 H14 116.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 112.6(2) . . ?
C17 C16 H16A 109.1 . . ?
C13 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C22 117.3(3) . . ?
C18 C17 C16 121.4(3) . . ?
C22 C17 C16 121.3(3) . . ?
C17 C18 C19 121.7(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 122.3(3) . . ?
C19 C20 F1 119.5(3) . . ?
C21 C20 F1 118.2(3) . . ?
C20 C21 C22 118.0(3) . . ?
C20 C21 H21 121.0 . . ?
C22 C21 H21 121.0 . . ?
C17 C22 C21 122.0(3) . . ?
C17 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C31 N4 C23 125.2(2) . . ?
C31 N4 C30 125.6(2) . . ?
C23 N4 C30 107.89(19) . . ?
C31 N5 C32 115.2(2) . . ?
C31 N6 C34 114.8(2) . . ?
C24 C23 C28 121.2(2) . . ?
C24 C23 N4 131.6(2) . . ?
C28 C23 N4 107.2(2) . . ?
C25 C24 C23 117.5(3) . . ?
C25 C24 H24 121.3 . . ?
C23 C24 H24 121.3 . . ?
C24 C25 C26 122.0(3) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C27 C26 C25 120.6(3) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.2(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C27 C28 C23 119.4(3) . . ?
C27 C28 C29 133.2(3) . . ?
C23 C28 C29 107.3(2) . . ?
C30 C29 C28 109.4(2) . . ?
C30 C29 H29 125.3 . . ?
C28 C29 H29 125.3 . . ?
C29 C30 N4 108.2(2) . . ?
C29 C30 C35 125.9(2) . . ?
N4 C30 C35 125.4(2) . . ?
N6 C31 N5 127.3(2) . . ?
N6 C31 N4 116.7(2) . . ?
N5 C31 N4 116.0(2) . . ?
N5 C32 C33 123.0(3) . . ?
N5 C32 H32 118.5 . . ?
C33 C32 H32 118.5 . . ?
C32 C33 C34 116.3(3) . . ?
C32 C33 H33 121.8 . . ?
C34 C33 H33 121.8 . . ?
N6 C34 C33 123.3(3) . . ?
N6 C34 H34 118.3 . . ?
C33 C34 H34 118.3 . . ?
C36 C35 C30 118.1(2) . . ?
C36 C35 C38 123.7(2) . . ?
C30 C35 C38 117.6(2) . . ?
C35 C36 C37 127.5(3) . . ?
C35 C36 H36 116.2 . . ?
C37 C36 H36 116.2 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 C35 113.3(2) . . ?
C39 C38 H38A 108.9 . . ?
C35 C38 H38A 108.9 . . ?
C39 C38 H38B 108.9 . . ?
C35 C38 H38B 108.9 . . ?
H38A C38 H38B 107.7 . . ?
C44 C39 C40 116.4(3) . . ?
C44 C39 C38 121.4(3) . . ?
C40 C39 C38 122.2(3) . . ?
C39 C40 C41 122.3(3) . . ?
C39 C40 H40 118.9 . . ?
C41 C40 H40 118.9 . . ?
C42 C41 C40 118.4(3) . . ?
C42 C41 H41 120.8 . . ?
C40 C41 H41 120.8 . . ?
C43 C42 C41 121.8(3) . . ?
C43 C42 F2 119.8(3) . . ?
C41 C42 F2 118.3(3) . . ?
C42 C43 C44 119.2(3) . . ?
C42 C43 H43 120.4 . . ?
C44 C43 H43 120.4 . . ?
C39 C44 C43 121.9(3) . . ?
C39 C44 H44 119.1 . . ?
C43 C44 H44 119.1 . . ?

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
C9 N1 C1 C2 -9.9(5) . . . . ?
C8 N1 C1 C2 -178.1(3) . . . . ?
C9 N1 C1 C6 168.1(2) . . . . ?
C8 N1 C1 C6 -0.2(3) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
N1 C1 C2 C3 178.4(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -179.0(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
N1 C1 C6 C5 -178.9(2) . . . . ?
C2 C1 C6 C7 178.8(3) . . . . ?
N1 C1 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 178.6(3) . . . . ?
C1 C6 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 N1 0.8(3) . . . . ?
C6 C7 C8 C13 174.0(3) . . . . ?
C9 N1 C8 C7 -168.7(2) . . . . ?
C1 N1 C8 C7 -0.4(3) . . . . ?
C9 N1 C8 C13 18.0(4) . . . . ?
C1 N1 C8 C13 -173.6(2) . . . . ?
C10 N2 C9 N3 3.0(4) . . . . ?
C10 N2 C9 N1 -177.0(2) . . . . ?
C12 N3 C9 N2 -2.2(4) . . . . ?
C12 N3 C9 N1 177.7(2) . . . . ?
C1 N1 C9 N2 -148.8(3) . . . . ?
C8 N1 C9 N2 17.5(4) . . . . ?
C1 N1 C9 N3 31.2(4) . . . . ?
C8 N1 C9 N3 -162.5(2) . . . . ?
C9 N2 C10 C11 -1.1(4) . . . . ?
N2 C10 C11 C12 -1.2(5) . . . . ?
C9 N3 C12 C11 -0.5(5) . . . . ?
C10 C11 C12 N3 2.0(5) . . . . ?
C7 C8 C13 C14 49.8(4) . . . . ?
N1 C8 C13 C14 -138.1(3) . . . . ?
C7 C8 C13 C16 -120.7(3) . . . . ?
N1 C8 C13 C16 51.4(4) . . . . ?
C8 C13 C14 C15 -169.6(3) . . . . ?
C16 C13 C14 C15 0.4(5) . . . . ?
C14 C13 C16 C17 -83.8(3) . . . . ?
C8 C13 C16 C17 86.1(3) . . . . ?
C13 C16 C17 C18 104.4(3) . . . . ?
C13 C16 C17 C22 -74.7(3) . . . . ?
C22 C17 C18 C19 1.8(5) . . . . ?
C16 C17 C18 C19 -177.3(3) . . . . ?
C17 C18 C19 C20 -1.0(6) . . . . ?
C18 C19 C20 C21 -0.6(6) . . . . ?
C18 C19 C20 F1 -179.7(3) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
F1 C20 C21 C22 -179.6(3) . . . . ?
C18 C17 C22 C21 -1.1(4) . . . . ?
C16 C17 C22 C21 178.0(3) . . . . ?
C20 C21 C22 C17 -0.3(5) . . . . ?
C31 N4 C23 C24 -10.7(4) . . . . ?
C30 N4 C23 C24 -177.9(3) . . . . ?
C31 N4 C23 C28 167.6(2) . . . . ?
C30 N4 C23 C28 0.4(3) . . . . ?
C28 C23 C24 C25 -0.3(4) . . . . ?
N4 C23 C24 C25 177.8(3) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C27 -0.4(5) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
C26 C27 C28 C23 0.5(4) . . . . ?
C26 C27 C28 C29 -178.4(3) . . . . ?
C24 C23 C28 C27 -0.3(4) . . . . ?
N4 C23 C28 C27 -178.8(2) . . . . ?
C24 C23 C28 C29 178.9(2) . . . . ?
N4 C23 C28 C29 0.4(3) . . . . ?
C27 C28 C29 C30 177.9(3) . . . . ?
C23 C28 C29 C30 -1.1(3) . . . . ?
C28 C29 C30 N4 1.3(3) . . . . ?
C28 C29 C30 C35 173.5(2) . . . . ?
C31 N4 C30 C29 -168.2(2) . . . . ?
C23 N4 C30 C29 -1.1(3) . . . . ?
C31 N4 C30 C35 19.6(4) . . . . ?
C23 N4 C30 C35 -173.3(2) . . . . ?
C34 N6 C31 N5 3.0(4) . . . . ?
C34 N6 C31 N4 -177.8(2) . . . . ?
C32 N5 C31 N6 -2.8(4) . . . . ?
C32 N5 C31 N4 178.0(2) . . . . ?
C23 N4 C31 N6 -147.2(2) . . . . ?
C30 N4 C31 N6 17.8(3) . . . . ?
C23 N4 C31 N5 32.0(3) . . . . ?
C30 N4 C31 N5 -163.0(2) . . . . ?
C31 N5 C32 C33 -0.1(4) . . . . ?
N5 C32 C33 C34 2.4(4) . . . . ?
C31 N6 C34 C33 -0.3(4) . . . . ?
C32 C33 C34 N6 -2.2(4) . . . . ?
C29 C30 C35 C36 52.4(4) . . . . ?
N4 C30 C35 C36 -136.7(3) . . . . ?
C29 C30 C35 C38 -119.2(3) . . . . ?
N4 C30 C35 C38 51.7(3) . . . . ?
C30 C35 C36 C37 -170.5(2) . . . . ?
C38 C35 C36 C37 0.5(4) . . . . ?
C36 C35 C38 C39 -89.2(3) . . . . ?
C30 C35 C38 C39 81.9(3) . . . . ?
C35 C38 C39 C44 108.5(3) . . . . ?
C35 C38 C39 C40 -71.4(3) . . . . ?
C44 C39 C40 C41 -0.3(4) . . . . ?
C38 C39 C40 C41 179.6(3) . . . . ?
C39 C40 C41 C42 0.0(5) . . . . ?
C40 C41 C42 C43 0.4(6) . . . . ?
C40 C41 C42 F2 -180.0(3) . . . . ?
C41 C42 C43 C44 -0.6(7) . . . . ?
F2 C42 C43 C44 179.8(3) . . . . ?
C40 C39 C44 C43 0.1(5) . . . . ?
C38 C39 C44 C43 -179.8(3) . . . . ?
C42 C43 C44 C39 0.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C24 H24 N5 0.93 2.42 2.941(4) 115.7 .
C2 H2 N3 0.93 2.41 2.937(4) 115.5 .

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

