# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Yong-Ming Wu'
_publ_contact_author_email       ymwu@sioc.ac.cn
_publ_author_name                'Yong Ming Wu'

data_cd29513
_database_code_depnum_ccdc_archive 'CCDC 769650'
#TrackingRef '3a.cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 F N2'
_chemical_formula_weight         340.39

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'
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                   7.4524(10)
_cell_length_b                   19.810(3)
_cell_length_c                   11.8050(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.816(3)
_cell_angle_gamma                90.00
_cell_volume                     1742.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1328
_cell_measurement_theta_min      5.841
_cell_measurement_theta_max      41.406

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3688
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10195
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3792
_reflns_number_gt                1811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0279P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3792
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_restrained_S_all      0.802
_refine_ls_shift/su_max          0.001
_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
F1 F 0.24892(15) 0.47209(5) -0.25395(9) 0.0674(4) Uani 1 1 d . . .
N1 N 0.22759(19) 0.55910(7) 0.01437(12) 0.0478(4) Uani 1 1 d . . .
N2 N 0.2977(3) 0.36496(9) -0.11845(17) 0.0654(6) Uani 1 1 d . . .
C1 C 0.2213(2) 0.54747(10) -0.09842(16) 0.0470(5) Uani 1 1 d . . .
C2 C 0.2478(2) 0.48363(10) -0.13937(15) 0.0495(5) Uani 1 1 d . . .
C3 C 0.2784(2) 0.42850(10) -0.07022(16) 0.0496(5) Uani 1 1 d . . .
C4 C 0.2858(2) 0.44181(9) 0.04509(15) 0.0503(5) Uani 1 1 d . . .
H4 H 0.3069 0.4069 0.0963 0.060 Uiso 1 1 calc R . .
C5 C 0.2617(2) 0.50680(9) 0.08364(15) 0.0437(5) Uani 1 1 d . . .
C6 C 0.1819(2) 0.60760(9) -0.17038(15) 0.0469(5) Uani 1 1 d . . .
C7 C 0.2466(3) 0.67048(10) -0.13690(16) 0.0556(5) Uani 1 1 d . . .
H7 H 0.3183 0.6741 -0.0721 0.067 Uiso 1 1 calc R . .
C8 C 0.2052(3) 0.72737(10) -0.19919(19) 0.0643(6) Uani 1 1 d . . .
H8 H 0.2504 0.7691 -0.1766 0.077 Uiso 1 1 calc R . .
C9 C 0.0981(3) 0.72293(11) -0.29403(19) 0.0676(6) Uani 1 1 d . . .
H9 H 0.0706 0.7615 -0.3357 0.081 Uiso 1 1 calc R . .
C10 C 0.0315(3) 0.66164(11) -0.32747(17) 0.0658(6) Uani 1 1 d . . .
H10 H -0.0430 0.6588 -0.3912 0.079 Uiso 1 1 calc R . .
C11 C 0.0743(3) 0.60381(10) -0.26720(16) 0.0563(5) Uani 1 1 d . . .
H11 H 0.0309 0.5622 -0.2916 0.068 Uiso 1 1 calc R . .
C12 C 0.2602(2) 0.52135(9) 0.20700(15) 0.0451(5) Uani 1 1 d . . .
C13 C 0.3416(3) 0.47870(9) 0.28508(16) 0.0540(5) Uani 1 1 d . . .
H13 H 0.4084 0.4422 0.2596 0.065 Uiso 1 1 calc R . .
C14 C 0.3257(3) 0.48928(10) 0.39930(18) 0.0656(6) Uani 1 1 d . . .
H14 H 0.3807 0.4597 0.4502 0.079 Uiso 1 1 calc R . .
C15 C 0.2297(3) 0.54290(11) 0.43886(17) 0.0691(7) Uani 1 1 d . . .
H15 H 0.2184 0.5498 0.5164 0.083 Uiso 1 1 calc R . .
C16 C 0.1500(3) 0.58647(10) 0.36308(18) 0.0681(6) Uani 1 1 d . . .
H16 H 0.0849 0.6232 0.3893 0.082 Uiso 1 1 calc R . .
C17 C 0.1663(3) 0.57600(9) 0.24811(16) 0.0577(6) Uani 1 1 d . . .
H17 H 0.1132 0.6062 0.1975 0.069 Uiso 1 1 calc R . .
C18 C 0.3248(3) 0.30387(10) -0.05969(17) 0.0521(5) Uani 1 1 d . . .
C19 C 0.4517(3) 0.25909(10) -0.09914(18) 0.0658(6) Uani 1 1 d . . .
H19 H 0.5182 0.2700 -0.1626 0.079 Uiso 1 1 calc R . .
C20 C 0.4801(3) 0.19855(11) -0.0450(2) 0.0742(7) Uani 1 1 d . . .
H20 H 0.5649 0.1686 -0.0726 0.089 Uiso 1 1 calc R . .
C21 C 0.3845(3) 0.18203(11) 0.0489(2) 0.0733(7) Uani 1 1 d . . .
H21 H 0.4059 0.1415 0.0865 0.088 Uiso 1 1 calc R . .
C22 C 0.2571(3) 0.22582(11) 0.08715(18) 0.0670(6) Uani 1 1 d . . .
H22 H 0.1915 0.2147 0.1509 0.080 Uiso 1 1 calc R . .
C23 C 0.2244(3) 0.28619(10) 0.03279(18) 0.0589(6) Uani 1 1 d . . .
H23 H 0.1349 0.3149 0.0584 0.071 Uiso 1 1 calc R . .
H2 H 0.334(3) 0.3702(10) -0.1855(18) 0.079(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0793(9) 0.0803(8) 0.0426(7) -0.0070(6) 0.0022(6) 0.0025(7)
N1 0.0494(10) 0.0500(10) 0.0439(10) -0.0009(8) -0.0027(8) -0.0036(8)
N2 0.0921(15) 0.0585(12) 0.0456(13) -0.0091(10) 0.0039(11) 0.0105(10)
C1 0.0403(12) 0.0569(13) 0.0439(12) -0.0012(10) -0.0004(9) -0.0057(9)
C2 0.0470(12) 0.0656(13) 0.0359(11) -0.0089(11) -0.0005(9) -0.0036(10)
C3 0.0483(13) 0.0542(12) 0.0461(13) -0.0082(11) -0.0016(10) 0.0031(10)
C4 0.0510(13) 0.0533(12) 0.0466(13) -0.0047(10) -0.0034(10) 0.0014(10)
C5 0.0397(11) 0.0481(12) 0.0431(12) -0.0016(10) -0.0009(9) -0.0028(9)
C6 0.0425(12) 0.0569(12) 0.0412(12) 0.0034(10) 0.0015(9) -0.0047(10)
C7 0.0559(14) 0.0586(13) 0.0521(13) -0.0012(11) -0.0038(10) -0.0044(11)
C8 0.0695(16) 0.0532(13) 0.0702(16) 0.0027(12) 0.0030(13) -0.0049(11)
C9 0.0697(16) 0.0654(15) 0.0679(16) 0.0165(13) 0.0045(13) 0.0082(12)
C10 0.0679(16) 0.0788(16) 0.0506(14) 0.0087(13) -0.0051(11) 0.0012(13)
C11 0.0610(14) 0.0613(13) 0.0465(13) 0.0046(11) -0.0016(10) -0.0074(11)
C12 0.0493(12) 0.0424(11) 0.0434(12) -0.0019(9) -0.0030(9) -0.0056(9)
C13 0.0616(14) 0.0513(12) 0.0488(13) -0.0074(10) -0.0075(10) -0.0003(10)
C14 0.0874(18) 0.0588(14) 0.0500(14) 0.0029(11) -0.0172(12) -0.0069(12)
C15 0.1015(19) 0.0631(14) 0.0425(13) -0.0075(12) -0.0021(13) -0.0135(14)
C16 0.0918(19) 0.0553(13) 0.0571(15) -0.0128(12) 0.0039(13) 0.0046(12)
C17 0.0772(16) 0.0463(12) 0.0495(14) -0.0030(10) -0.0009(11) -0.0001(11)
C18 0.0574(14) 0.0509(13) 0.0478(13) -0.0127(10) -0.0038(11) 0.0033(11)
C19 0.0716(16) 0.0689(15) 0.0572(15) -0.0134(12) 0.0109(12) 0.0111(12)
C20 0.0826(18) 0.0639(15) 0.0760(18) -0.0138(14) 0.0034(14) 0.0210(13)
C21 0.093(2) 0.0611(15) 0.0658(17) -0.0083(13) -0.0045(14) 0.0071(14)
C22 0.0847(18) 0.0605(14) 0.0561(15) -0.0118(12) 0.0087(12) -0.0081(13)
C23 0.0633(15) 0.0553(13) 0.0584(15) -0.0161(11) 0.0064(12) 0.0026(11)

_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 C2 1.3719(19) . ?
N1 C5 1.342(2) . ?
N1 C1 1.351(2) . ?
N2 C3 1.390(2) . ?
N2 C18 1.408(2) . ?
N2 H2 0.85(2) . ?
C1 C2 1.369(2) . ?
C1 C6 1.490(2) . ?
C2 C3 1.381(2) . ?
C3 C4 1.387(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C12 1.485(2) . ?
C6 C11 1.389(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.378(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.381(2) . ?
C12 C13 1.384(2) . ?
C13 C14 1.371(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.377(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 118.19(15) . . ?
C3 N2 C18 126.26(19) . . ?
C3 N2 H2 108.0(15) . . ?
C18 N2 H2 121.4(15) . . ?
N1 C1 C2 120.14(17) . . ?
N1 C1 C6 115.41(16) . . ?
C2 C1 C6 124.44(17) . . ?
C1 C2 F1 120.32(18) . . ?
C1 C2 C3 123.05(17) . . ?
F1 C2 C3 116.61(17) . . ?
C2 C3 C4 115.71(17) . . ?
C2 C3 N2 119.43(18) . . ?
C4 C3 N2 124.85(19) . . ?
C5 C4 C3 119.88(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 122.99(17) . . ?
N1 C5 C12 116.35(16) . . ?
C4 C5 C12 120.54(17) . . ?
C11 C6 C7 118.44(17) . . ?
C11 C6 C1 122.20(17) . . ?
C7 C6 C1 119.27(16) . . ?
C8 C7 C6 120.43(18) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.50(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.88(19) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.44(19) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 120.30(19) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C17 C12 C13 117.66(18) . . ?
C17 C12 C5 120.51(17) . . ?
C13 C12 C5 121.70(17) . . ?
C14 C13 C12 121.21(19) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 121.03(18) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C23 C18 C19 119.1(2) . . ?
C23 C18 N2 122.2(2) . . ?
C19 C18 N2 118.6(2) . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 121.1(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C18 C23 C22 119.7(2) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?

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
C5 N1 C1 C2 0.6(3) . . . . ?
C5 N1 C1 C6 179.64(15) . . . . ?
N1 C1 C2 F1 -177.31(15) . . . . ?
C6 C1 C2 F1 3.7(3) . . . . ?
N1 C1 C2 C3 1.2(3) . . . . ?
C6 C1 C2 C3 -177.81(17) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
F1 C2 C3 C4 176.87(15) . . . . ?
C1 C2 C3 N2 177.76(18) . . . . ?
F1 C2 C3 N2 -3.7(3) . . . . ?
C18 N2 C3 C2 -178.3(2) . . . . ?
C18 N2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
N2 C3 C4 C5 -178.89(18) . . . . ?
C1 N1 C5 C4 -1.7(3) . . . . ?
C1 N1 C5 C12 -177.69(15) . . . . ?
C3 C4 C5 N1 1.2(3) . . . . ?
C3 C4 C5 C12 176.98(16) . . . . ?
N1 C1 C6 C11 -142.07(19) . . . . ?
C2 C1 C6 C11 37.0(3) . . . . ?
N1 C1 C6 C7 34.5(2) . . . . ?
C2 C1 C6 C7 -146.46(19) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C1 C6 C7 C8 -177.05(18) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C6 1.6(3) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
C1 C6 C11 C10 175.78(19) . . . . ?
N1 C5 C12 C17 23.3(2) . . . . ?
C4 C5 C12 C17 -152.72(18) . . . . ?
N1 C5 C12 C13 -161.09(17) . . . . ?
C4 C5 C12 C13 22.9(3) . . . . ?
C17 C12 C13 C14 1.7(3) . . . . ?
C5 C12 C13 C14 -174.01(17) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C12 0.9(3) . . . . ?
C13 C12 C17 C16 -1.8(3) . . . . ?
C5 C12 C17 C16 173.91(18) . . . . ?
C3 N2 C18 C23 46.4(3) . . . . ?
C3 N2 C18 C19 -136.2(2) . . . . ?
C23 C18 C19 C20 -1.6(3) . . . . ?
N2 C18 C19 C20 -179.06(19) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 C20 C21 C22 1.5(3) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C19 C18 C23 C22 2.8(3) . . . . ?
N2 C18 C23 C22 -179.82(17) . . . . ?
C21 C22 C23 C18 -1.9(3) . . . . ?

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
N2 H2 F1 0.85(2) 2.26(2) 2.679(2) 110.6(17) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042

# Attachment '5a.cif.cif'

data_cd201285
_database_code_depnum_ccdc_archive 'CCDC 778755'
#TrackingRef '5a.cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 F2 N2'
_chemical_formula_weight         360.39

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'
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   C2/c

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

_cell_length_a                   23.699(2)
_cell_length_b                   10.1868(9)
_cell_length_c                   17.9095(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.0200(10)
_cell_angle_gamma                90.00
_cell_volume                     3625.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3525
_cell_measurement_theta_min      4.636
_cell_measurement_theta_max      54.785

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5244
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9634
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3558
_reflns_number_gt                2851
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0681P)^2^+1.7597P] where P=(Fo^2^+2Fc^2^)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3558
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
F1 F 0.04141(8) 0.67366(18) 0.08355(11) 0.1026(7) Uani 1 1 d . . .
F2 F 0.08874(8) 0.79069(16) 0.20209(10) 0.0844(5) Uani 1 1 d . . .
N1 N 0.16307(8) 0.53523(14) 0.14447(9) 0.0358(4) Uani 1 1 d . . .
N2 N 0.25351(7) 0.43418(14) 0.28069(9) 0.0335(4) Uani 1 1 d . . .
C1 C 0.19427(9) 0.41103(16) 0.19036(11) 0.0319(4) Uani 1 1 d . . .
H1 H 0.2100 0.3664 0.1565 0.038 Uiso 1 1 calc R . .
C2 C 0.24575(9) 0.52569(17) 0.32377(11) 0.0337(4) Uani 1 1 d . . .
C3 C 0.18799(9) 0.61169(18) 0.28289(12) 0.0381(4) Uani 1 1 d . . .
H3 H 0.1761 0.6579 0.3171 0.046 Uiso 1 1 calc R . .
C4 C 0.15199(9) 0.62257(17) 0.19360(12) 0.0357(4) Uani 1 1 d . . .
C5 C 0.09919(11) 0.7266(2) 0.14582(14) 0.0530(6) Uani 1 1 d . . .
H5 H 0.1140 0.7890 0.1182 0.064 Uiso 1 1 calc R . .
C6 C 0.14479(9) 0.31955(16) 0.19335(11) 0.0310(4) Uani 1 1 d . . .
C7 C 0.07583(10) 0.3374(2) 0.14043(14) 0.0463(5) Uani 1 1 d . . .
H7 H 0.0582 0.4092 0.1023 0.056 Uiso 1 1 calc R . .
C8 C 0.03310(11) 0.2494(3) 0.14387(16) 0.0609(6) Uani 1 1 d . . .
H8 H -0.0132 0.2623 0.1079 0.073 Uiso 1 1 calc R . .
C9 C 0.05801(13) 0.1432(3) 0.19967(17) 0.0622(7) Uani 1 1 d . . .
H9 H 0.0289 0.0851 0.2024 0.075 Uiso 1 1 calc R . .
C10 C 0.12652(13) 0.1231(2) 0.25171(15) 0.0552(6) Uani 1 1 d . . .
H10 H 0.1438 0.0504 0.2890 0.066 Uiso 1 1 calc R . .
C11 C 0.16929(10) 0.21050(18) 0.24846(13) 0.0409(5) Uani 1 1 d . . .
H11 H 0.2155 0.1962 0.2839 0.049 Uiso 1 1 calc R . .
C12 C 0.30159(9) 0.55356(17) 0.41766(12) 0.0376(4) Uani 1 1 d . . .
C13 C 0.36843(10) 0.54490(19) 0.44293(13) 0.0457(5) Uani 1 1 d . . .
H13 H 0.3785 0.5205 0.4015 0.055 Uiso 1 1 calc R . .
C14 C 0.41965(12) 0.5725(2) 0.52950(15) 0.0607(6) Uani 1 1 d . . .
H14 H 0.4641 0.5668 0.5458 0.073 Uiso 1 1 calc R . .
C15 C 0.40583(14) 0.6080(2) 0.59167(15) 0.0675(8) Uani 1 1 d . . .
H15 H 0.4407 0.6267 0.6498 0.081 Uiso 1 1 calc R . .
C16 C 0.33988(14) 0.6161(2) 0.56762(14) 0.0623(7) Uani 1 1 d . . .
H16 H 0.3303 0.6390 0.6098 0.075 Uiso 1 1 calc R . .
C17 C 0.28804(12) 0.5901(2) 0.48096(13) 0.0502(5) Uani 1 1 d . . .
H17 H 0.2437 0.5972 0.4649 0.060 Uiso 1 1 calc R . .
C18 C 0.14957(9) 0.56029(18) 0.05780(11) 0.0361(4) Uani 1 1 d . . .
C19 C 0.16683(10) 0.6796(2) 0.03768(13) 0.0448(5) Uani 1 1 d . . .
H19 H 0.1873 0.7446 0.0810 0.054 Uiso 1 1 calc R . .
C20 C 0.15367(11) 0.7014(2) -0.04608(14) 0.0532(6) Uani 1 1 d . . .
H20 H 0.1650 0.7817 -0.0592 0.064 Uiso 1 1 calc R . .
C21 C 0.12405(12) 0.6062(2) -0.11064(15) 0.0564(6) Uani 1 1 d . . .
H21 H 0.1153 0.6215 -0.1672 0.068 Uiso 1 1 calc R . .
C22 C 0.10745(12) 0.4874(2) -0.09040(14) 0.0545(6) Uani 1 1 d . . .
H22 H 0.0874 0.4223 -0.1337 0.065 Uiso 1 1 calc R . .
C23 C 0.12017(10) 0.4640(2) -0.00690(13) 0.0437(5) Uani 1 1 d . . .
H23 H 0.1090 0.3834 0.0060 0.052 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0611(9) 0.0893(12) 0.0858(11) -0.0193(9) -0.0062(8) 0.0325(8)
F2 0.0853(10) 0.0810(11) 0.0664(9) -0.0086(8) 0.0282(8) 0.0439(8)
N1 0.0444(9) 0.0289(8) 0.0304(8) 0.0027(6) 0.0180(7) 0.0029(6)
N2 0.0318(8) 0.0282(7) 0.0349(8) 0.0011(6) 0.0146(7) -0.0008(6)
C1 0.0363(9) 0.0265(8) 0.0316(9) -0.0001(7) 0.0177(8) 0.0029(7)
C2 0.0368(9) 0.0287(9) 0.0325(9) 0.0016(7) 0.0170(8) -0.0035(7)
C3 0.0397(10) 0.0358(10) 0.0368(10) -0.0036(8) 0.0196(8) 0.0021(8)
C4 0.0383(10) 0.0283(9) 0.0379(10) -0.0005(7) 0.0191(8) 0.0005(7)
C5 0.0571(13) 0.0456(12) 0.0457(12) 0.0015(10) 0.0212(11) 0.0129(10)
C6 0.0344(9) 0.0289(9) 0.0272(8) -0.0058(7) 0.0152(7) -0.0016(7)
C7 0.0364(10) 0.0498(12) 0.0453(11) 0.0003(9) 0.0175(9) 0.0002(9)
C8 0.0396(12) 0.0749(17) 0.0665(15) -0.0126(13) 0.0278(11) -0.0127(11)
C9 0.0711(16) 0.0611(15) 0.0695(16) -0.0186(13) 0.0481(14) -0.0308(13)
C10 0.0782(16) 0.0362(11) 0.0525(13) -0.0019(9) 0.0365(12) -0.0131(10)
C11 0.0450(11) 0.0331(10) 0.0394(10) -0.0018(8) 0.0196(9) -0.0022(8)
C12 0.0432(10) 0.0256(9) 0.0348(9) 0.0021(7) 0.0153(8) -0.0013(7)
C13 0.0433(11) 0.0385(11) 0.0425(11) 0.0055(8) 0.0150(9) -0.0018(8)
C14 0.0457(12) 0.0511(13) 0.0525(13) 0.0054(11) 0.0054(10) -0.0046(10)
C15 0.0718(17) 0.0462(13) 0.0368(12) -0.0009(10) -0.0012(11) -0.0012(11)
C16 0.0883(19) 0.0432(12) 0.0374(11) -0.0013(10) 0.0227(12) 0.0089(12)
C17 0.0576(13) 0.0452(12) 0.0400(11) 0.0000(9) 0.0216(10) 0.0046(10)
C18 0.0345(9) 0.0376(10) 0.0318(9) 0.0037(8) 0.0154(8) 0.0022(7)
C19 0.0424(11) 0.0408(11) 0.0403(11) 0.0054(9) 0.0155(9) -0.0052(8)
C20 0.0517(12) 0.0550(13) 0.0516(12) 0.0168(11) 0.0272(10) 0.0007(10)
C21 0.0661(14) 0.0696(16) 0.0423(12) 0.0157(11) 0.0352(11) 0.0141(12)
C22 0.0662(14) 0.0565(13) 0.0406(11) -0.0057(10) 0.0289(11) 0.0025(11)
C23 0.0519(12) 0.0398(11) 0.0410(11) -0.0018(8) 0.0263(9) -0.0033(9)

_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 C5 1.321(3) . ?
F2 C5 1.332(3) . ?
N1 C4 1.374(2) . ?
N1 C18 1.427(2) . ?
N1 C1 1.470(2) . ?
N2 C2 1.286(2) . ?
N2 C1 1.473(2) . ?
C1 C6 1.522(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.444(3) . ?
C2 C12 1.495(2) . ?
C3 C4 1.345(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.502(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.383(3) . ?
C6 C11 1.386(2) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.387(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.382(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9300 . ?
C23 H23 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 C18 124.98(15) . . ?
C4 N1 C1 114.39(14) . . ?
C18 N1 C1 120.57(14) . . ?
C2 N2 C1 114.38(14) . . ?
N1 C1 N2 111.37(14) . . ?
N1 C1 C6 112.60(14) . . ?
N2 C1 C6 110.55(13) . . ?
N1 C1 H1 107.3 . . ?
N2 C1 H1 107.3 . . ?
C6 C1 H1 107.3 . . ?
N2 C2 C3 122.80(16) . . ?
N2 C2 C12 118.97(16) . . ?
C3 C2 C12 117.95(16) . . ?
C4 C3 C2 117.68(17) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 N1 119.29(16) . . ?
C3 C4 C5 121.82(17) . . ?
N1 C4 C5 118.88(16) . . ?
F1 C5 F2 107.7(2) . . ?
F1 C5 C4 110.56(19) . . ?
F2 C5 C4 110.82(17) . . ?
F1 C5 H5 109.2 . . ?
F2 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
C7 C6 C11 118.25(17) . . ?
C7 C6 C1 122.74(16) . . ?
C11 C6 C1 118.96(15) . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 121.15(19) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C17 C12 C13 118.70(18) . . ?
C17 C12 C2 120.88(18) . . ?
C13 C12 C2 120.42(17) . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C23 C18 C19 119.20(17) . . ?
C23 C18 N1 119.79(17) . . ?
C19 C18 N1 120.99(17) . . ?
C20 C19 C18 120.04(19) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.09(19) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C18 120.01(19) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 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
C4 N1 C1 N2 -48.9(2) . . . . ?
C18 N1 C1 N2 128.17(16) . . . . ?
C4 N1 C1 C6 75.93(18) . . . . ?
C18 N1 C1 C6 -106.99(18) . . . . ?
C2 N2 C1 N1 41.8(2) . . . . ?
C2 N2 C1 C6 -84.14(18) . . . . ?
C1 N2 C2 C3 -8.9(2) . . . . ?
C1 N2 C2 C12 177.30(15) . . . . ?
N2 C2 C3 C4 -19.9(3) . . . . ?
C12 C2 C3 C4 153.97(17) . . . . ?
C2 C3 C4 N1 12.2(3) . . . . ?
C2 C3 C4 C5 -168.62(18) . . . . ?
C18 N1 C4 C3 -155.12(18) . . . . ?
C1 N1 C4 C3 21.8(2) . . . . ?
C18 N1 C4 C5 25.7(3) . . . . ?
C1 N1 C4 C5 -157.35(17) . . . . ?
C3 C4 C5 F1 -127.0(2) . . . . ?
N1 C4 C5 F1 52.1(3) . . . . ?
C3 C4 C5 F2 -7.6(3) . . . . ?
N1 C4 C5 F2 171.50(18) . . . . ?
N1 C1 C6 C7 14.9(2) . . . . ?
N2 C1 C6 C7 140.18(17) . . . . ?
N1 C1 C6 C11 -167.93(15) . . . . ?
N2 C1 C6 C11 -42.6(2) . . . . ?
C11 C6 C7 C8 0.9(3) . . . . ?
C1 C6 C7 C8 178.09(18) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
C7 C6 C11 C10 -0.9(3) . . . . ?
C1 C6 C11 C10 -178.24(18) . . . . ?
N2 C2 C12 C17 -144.23(19) . . . . ?
C3 C2 C12 C17 41.6(3) . . . . ?
N2 C2 C12 C13 36.6(2) . . . . ?
C3 C2 C12 C13 -137.52(19) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C2 C12 C13 C14 179.15(18) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C16 C17 C12 1.1(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C2 C12 C17 C16 -179.83(18) . . . . ?
C4 N1 C18 C23 -137.83(19) . . . . ?
C1 N1 C18 C23 45.4(2) . . . . ?
C4 N1 C18 C19 43.5(3) . . . . ?
C1 N1 C18 C19 -133.24(18) . . . . ?
C23 C18 C19 C20 1.0(3) . . . . ?
N1 C18 C19 C20 179.68(18) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C22 C23 C18 0.4(3) . . . . ?
C19 C18 C23 C22 -0.9(3) . . . . ?
N1 C18 C23 C22 -179.58(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.049