# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-(4-Methylpiperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-
7-(trifluoromethyl)quinoline
;

_chemical_name_common            ?
_chemical_formula_moiety         'C23 H20 F3 N5 O'
_chemical_formula_sum            'C23 H20 F3 N5 O'
_chemical_formula_iupac          'C23 H20 F3 N5 O'
_chemical_formula_weight         439.44
_chemical_melting_point          ?
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz

'x, y, z'
'-x, -y, -z'


_cell_length_a                   8.5065(15)

_cell_length_b                   10.2176(17)

_cell_length_c                   13.709(3)

_cell_angle_alpha                103.840(5)

_cell_angle_beta                 98.515(5)

_cell_angle_gamma                109.034(4)

_cell_volume                     1060.0(4)

_cell_formula_units_Z            2

_cell_measurement_reflns_used    4219

_cell_measurement_theta_min      2.29

_cell_measurement_theta_max      26.86

_cell_measurement_temperature    296(2)

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.44

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.13

_exptl_crystal_density_diffrn    1.377

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             456

_exptl_absorpt_coefficient_mu    0.106

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_absorpt_correction_T_min  0.954

_exptl_absorpt_correction_T_max  0.987

_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEXII DUO CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13724

_diffrn_reflns_av_R_equivalents  0.0400

_diffrn_reflns_av_sigmaI/netI    0.0430

_diffrn_reflns_theta_min         1.58

_diffrn_reflns_theta_max         27.50

_diffrn_reflns_theta_full        27.50

_diffrn_measured_fraction_theta_max 0.992

_diffrn_measured_fraction_theta_full 0.992

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       17

_reflns_number_total             4831

_reflns_number_gt                2890

_reflns_threshold_expression     I>2σ(I)

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_R_factor_all          0.0969

_refine_ls_R_factor_gt           0.0614

_refine_ls_wR_factor_gt          0.1815

_refine_ls_wR_factor_ref         0.2312

_refine_ls_goodness_of_fit_ref   1.035

_refine_ls_restrained_S_all      1.035

_refine_ls_number_reflns         4831

_refine_ls_number_parameters     290

_refine_ls_number_restraints     0

_refine_ls_hydrogen_treatment    constr

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1328P)²+0.1210P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.370

_refine_diff_density_min         -0.277

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_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 >
σ(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.
;

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'


_computing_data_collection       'APEX2 (Bruker, 2009)'

_computing_cell_refinement       'SAINT (Bruker, 2009)'

_computing_data_reduction        'SAINT (Bruker, 2009)'

_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'

_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'

_computing_publication_material  
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group

F F1 0.5226(3) -0.6774(2) -0.27438(12) 0.0963(6) Uani d . 1 1 . .
F F2 0.5484(3) -0.7593(2) -0.14756(14) 0.1015(6) Uani d . 1 1 . .
F F3 0.7645(3) -0.6755(2) -0.20656(17) 0.1229(9) Uani d . 1 1 . .
O O1 0.7623(2) 0.17853(16) 0.22070(11) 0.0530(4) Uani d . 1 1 . .
N N1 0.6121(3) -0.1679(2) -0.10374(15) 0.0627(6) Uani d . 1 1 . .
N N2 0.9415(2) -0.0424(2) 0.19566(13) 0.0506(5) Uani d . 1 1 . .
N N3 1.1662(3) 0.0381(2) 0.39233(14) 0.0602(5) Uani d . 1 1 . .
N N4 0.8354(3) 0.2779(3) 0.10041(17) 0.0738(7) Uani d . 1 1 . .
N N5 0.8316(3) 0.3860(2) 0.18536(18) 0.0745(7) Uani d . 1 1 . .
C C1 0.8270(3) -0.0818(3) 0.09901(16) 0.0487(5) Uani d . 1 1 . .
C C2 0.7750(3) -0.2268(3) 0.03114(15) 0.0493(5) Uani d . 1 1 . .
C C3 0.8327(3) -0.3329(3) 0.05590(17) 0.0580(6) Uani d . 1 1 . .
H H3A 0.9059 -0.3092 0.1204 0.070 Uiso calc R 1 1 . .
C C4 0.7844(3) -0.4679(3) -0.01160(18) 0.0606(6) Uani d . 1 1 . .
H H4A 0.8240 -0.5357 0.0066 0.073 Uiso calc R 1 1 . .
C C5 0.6736(3) -0.5050(3) -0.10978(17) 0.0555(6) Uani d . 1 1 . .
C C6 0.6166(3) -0.4057(3) -0.13745(17) 0.0585(6) Uani d . 1 1 . .
H H6A 0.5446 -0.4314 -0.2027 0.070 Uiso calc R 1 1 . .
C C7 0.6652(3) -0.2655(3) -0.06883(16) 0.0534(6) Uani d . 1 1 . .
C C8 0.6647(3) -0.0358(3) -0.04098(17) 0.0611(6) Uani d . 1 1 . .
H H8A 0.6318 0.0313 -0.0652 0.073 Uiso calc R 1 1 . .
C C9 0.7691(3) 0.0135(3) 0.06230(16) 0.0538(6) Uani d . 1 1 . .
C C10 0.7947(3) 0.1592(3) 0.12490(17) 0.0563(6) Uani d . 1 1 . .
C C11 0.7883(3) 0.3219(3) 0.25302(18) 0.0557(6) Uani d . 1 1 . .
C C12 0.7691(3) 0.3857(3) 0.35531(18) 0.0545(6) Uani d . 1 1 . .
C C13 0.7751(4) 0.5264(3) 0.3839(2) 0.0778(8) Uani d . 1 1 . .
H H13A 0.7875 0.5794 0.3371 0.093 Uiso calc R 1 1 . .
C C14 0.7628(5) 0.5883(4) 0.4819(3) 0.0946(10) Uani d . 1 1 . .
H H14A 0.7675 0.6835 0.5011 0.113 Uiso calc R 1 1 . .
C C15 0.7436(4) 0.5113(3) 0.5516(2) 0.0852(9) Uani d . 1 1 . .
H H15A 0.7351 0.5539 0.6176 0.102 Uiso calc R 1 1 . .
C C16 0.7371(5) 0.3730(4) 0.5239(2) 0.0907(10) Uani d . 1 1 . .
H H16A 0.7241 0.3206 0.5710 0.109 Uiso calc R 1 1 . .
C C17 0.7497(5) 0.3091(3) 0.4258(2) 0.0798(8) Uani d . 1 1 . .
H H17A 0.7449 0.2139 0.4074 0.096 Uiso calc R 1 1 . .
C C18 0.6293(4) -0.6518(3) -0.1835(2) 0.0661(7) Uani d . 1 1 . .
C C19 1.0295(3) -0.1042(3) 0.35015(17) 0.0603(6) Uani d . 1 1 . .
H H19A 0.9899 -0.1365 0.4063 0.072 Uiso calc R 1 1 . .
H H19B 1.0730 -0.1733 0.3137 0.072 Uiso calc R 1 1 . .
C C20 0.8802(3) -0.1007(3) 0.27605(16) 0.0568(6) Uani d . 1 1 . .
H H20A 0.7941 -0.1983 0.2446 0.068 Uiso calc R 1 1 . .
H H20B 0.8279 -0.0404 0.3138 0.068 Uiso calc R 1 1 . .
C C21 1.0767(3) 0.1013(3) 0.23898(18) 0.0585(6) Uani d . 1 1 . .
H H21A 1.0344 0.1686 0.2788 0.070 Uiso calc R 1 1 . .
H H21B 1.1149 0.1372 0.1838 0.070 Uiso calc R 1 1 . .
C C22 1.2244(3) 0.0892(3) 0.30838(18) 0.0599(6) Uani d . 1 1 . .
H H22A 1.2661 0.0216 0.2682 0.072 Uiso calc R 1 1 . .
H H22B 1.3180 0.1834 0.3369 0.072 Uiso calc R 1 1 . .
C C23 1.3087(4) 0.0320(4) 0.4630(2) 0.0857(9) Uani d . 1 1 . .
H H23A 1.2690 0.0001 0.5184 0.129 Uiso calc R 1 1 . .
H H23B 1.3982 0.1269 0.4909 0.129 Uiso calc R 1 1 . .
H H23C 1.3524 -0.0351 0.4258 0.129 Uiso calc R 1 1 . .



_geom_special_details            
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag

F1 C18 . 1.342(3) ?
F2 C18 . 1.338(3) ?
F3 C18 . 1.316(3) ?
O1 C11 . 1.356(3) ?
O1 C10 . 1.363(3) ?
N1 C8 . 1.303(3) ?
N1 C7 . 1.374(3) ?
N2 C1 . 1.404(3) ?
N2 C21 . 1.452(3) ?
N2 C20 . 1.457(3) ?
N3 C19 . 1.448(3) ?
N3 C22 . 1.459(3) ?
N3 C23 . 1.464(3) ?
N4 C10 . 1.288(3) ?
N4 N5 . 1.413(3) ?
N5 C11 . 1.288(3) ?
C1 C9 . 1.385(3) ?
C1 C2 . 1.430(3) ?
C2 C3 . 1.416(3) ?
C2 C7 . 1.424(3) ?
C3 C4 . 1.355(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.411(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.363(3) ?
C5 C18 . 1.486(4) ?
C6 C7 . 1.401(4) ?
C6 H6A . 0.9300 ?
C8 C9 . 1.429(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.457(3) ?
C11 C12 . 1.456(3) ?
C12 C13 . 1.378(4) ?
C12 C17 . 1.379(4) ?
C13 C14 . 1.376(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.372(4) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.353(5) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.383(4) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9300 ?
C19 C20 . 1.520(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C22 . 1.518(3) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag

C11 O1 C10 . . 103.18(17) ?
C8 N1 C7 . . 117.4(2) ?
C1 N2 C21 . . 120.91(17) ?
C1 N2 C20 . . 119.14(18) ?
C21 N2 C20 . . 111.94(17) ?
C19 N3 C22 . . 109.93(18) ?
C19 N3 C23 . . 110.1(2) ?
C22 N3 C23 . . 110.4(2) ?
C10 N4 N5 . . 106.5(2) ?
C11 N5 N4 . . 105.9(2) ?
C9 C1 N2 . . 124.0(2) ?
C9 C1 C2 . . 117.54(19) ?
N2 C1 C2 . . 118.30(19) ?
C3 C2 C7 . . 117.7(2) ?
C3 C2 C1 . . 123.64(19) ?
C7 C2 C1 . . 118.6(2) ?
C4 C3 C2 . . 122.0(2) ?
C4 C3 H3A . . 119.0 ?
C2 C3 H3A . . 119.0 ?
C3 C4 C5 . . 119.5(2) ?
C3 C4 H4A . . 120.3 ?
C5 C4 H4A . . 120.3 ?
C6 C5 C4 . . 120.6(2) ?
C6 C5 C18 . . 121.3(2) ?
C4 C5 C18 . . 118.0(2) ?
C5 C6 C7 . . 120.8(2) ?
C5 C6 H6A . . 119.6 ?
C7 C6 H6A . . 119.6 ?
N1 C7 C6 . . 117.9(2) ?
N1 C7 C2 . . 122.6(2) ?
C6 C7 C2 . . 119.4(2) ?
N1 C8 C9 . . 124.8(2) ?
N1 C8 H8A . . 117.6 ?
C9 C8 H8A . . 117.6 ?
C1 C9 C8 . . 119.0(2) ?
C1 C9 C10 . . 124.4(2) ?
C8 C9 C10 . . 116.4(2) ?
N4 C10 O1 . . 111.9(2) ?
N4 C10 C9 . . 128.8(2) ?
O1 C10 C9 . . 119.1(2) ?
N5 C11 O1 . . 112.5(2) ?
N5 C11 C12 . . 127.8(2) ?
O1 C11 C12 . . 119.6(2) ?
C13 C12 C17 . . 119.0(2) ?
C13 C12 C11 . . 119.9(2) ?
C17 C12 C11 . . 121.0(2) ?
C14 C13 C12 . . 119.9(3) ?
C14 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
C15 C14 C13 . . 120.7(3) ?
C15 C14 H14A . . 119.6 ?
C13 C14 H14A . . 119.6 ?
C16 C15 C14 . . 119.7(3) ?
C16 C15 H15A . . 120.2 ?
C14 C15 H15A . . 120.2 ?
C15 C16 C17 . . 120.4(3) ?
C15 C16 H16A . . 119.8 ?
C17 C16 H16A . . 119.8 ?
C12 C17 C16 . . 120.3(3) ?
C12 C17 H17A . . 119.8 ?
C16 C17 H17A . . 119.8 ?
F3 C18 F2 . . 106.3(3) ?
F3 C18 F1 . . 105.9(2) ?
F2 C18 F1 . . 104.3(2) ?
F3 C18 C5 . . 113.0(2) ?
F2 C18 C5 . . 112.9(2) ?
F1 C18 C5 . . 113.7(2) ?
N3 C19 C20 . . 111.1(2) ?
N3 C19 H19A . . 109.4 ?
C20 C19 H19A . . 109.4 ?
N3 C19 H19B . . 109.4 ?
C20 C19 H19B . . 109.4 ?
H19A C19 H19B . . 108.0 ?
N2 C20 C19 . . 109.67(19) ?
N2 C20 H20A . . 109.7 ?
C19 C20 H20A . . 109.7 ?
N2 C20 H20B . . 109.7 ?
C19 C20 H20B . . 109.7 ?
H20A C20 H20B . . 108.2 ?
N2 C21 C22 . . 108.10(19) ?
N2 C21 H21A . . 110.1 ?
C22 C21 H21A . . 110.1 ?
N2 C21 H21B . . 110.1 ?
C22 C21 H21B . . 110.1 ?
H21A C21 H21B . . 108.4 ?
N3 C22 C21 . . 109.5(2) ?
N3 C22 H22A . . 109.8 ?
C21 C22 H22A . . 109.8 ?
N3 C22 H22B . . 109.8 ?
C21 C22 H22B . . 109.8 ?
H22A C22 H22B . . 108.2 ?
N3 C23 H23A . . 109.5 ?
N3 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
N3 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag

C10 N4 N5 C11 . . . . -0.2(3) ?
C21 N2 C1 C9 . . . . -34.4(3) ?
C20 N2 C1 C9 . . . . 112.0(3) ?
C21 N2 C1 C2 . . . . 141.4(2) ?
C20 N2 C1 C2 . . . . -72.2(3) ?
C9 C1 C2 C3 . . . . 176.0(2) ?
N2 C1 C2 C3 . . . . -0.1(3) ?
C9 C1 C2 C7 . . . . -1.1(3) ?
N2 C1 C2 C7 . . . . -177.17(18) ?
C7 C2 C3 C4 . . . . -1.0(3) ?
C1 C2 C3 C4 . . . . -178.1(2) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C3 C4 C5 C6 . . . . 0.7(4) ?
C3 C4 C5 C18 . . . . 177.4(2) ?
C4 C5 C6 C7 . . . . -0.6(4) ?
C18 C5 C6 C7 . . . . -177.2(2) ?
C8 N1 C7 C6 . . . . -176.9(2) ?
C8 N1 C7 C2 . . . . -0.7(3) ?
C5 C6 C7 N1 . . . . 176.1(2) ?
C5 C6 C7 C2 . . . . -0.2(4) ?
C3 C2 C7 N1 . . . . -175.1(2) ?
C1 C2 C7 N1 . . . . 2.2(3) ?
C3 C2 C7 C6 . . . . 1.0(3) ?
C1 C2 C7 C6 . . . . 178.3(2) ?
C7 N1 C8 C9 . . . . -2.0(4) ?
N2 C1 C9 C8 . . . . 174.6(2) ?
C2 C1 C9 C8 . . . . -1.3(3) ?
N2 C1 C9 C10 . . . . -11.0(4) ?
C2 C1 C9 C10 . . . . 173.1(2) ?
N1 C8 C9 C1 . . . . 3.0(4) ?
N1 C8 C9 C10 . . . . -171.8(2) ?
N5 N4 C10 O1 . . . . 0.4(3) ?
N5 N4 C10 C9 . . . . 175.7(2) ?
C11 O1 C10 N4 . . . . -0.4(3) ?
C11 O1 C10 C9 . . . . -176.2(2) ?
C1 C9 C10 N4 . . . . 138.5(3) ?
C8 C9 C10 N4 . . . . -47.0(4) ?
C1 C9 C10 O1 . . . . -46.5(3) ?
C8 C9 C10 O1 . . . . 128.1(2) ?
N4 N5 C11 O1 . . . . -0.1(3) ?
N4 N5 C11 C12 . . . . 178.8(2) ?
C10 O1 C11 N5 . . . . 0.3(3) ?
C10 O1 C11 C12 . . . . -178.7(2) ?
N5 C11 C12 C13 . . . . 8.9(4) ?
O1 C11 C12 C13 . . . . -172.3(2) ?
N5 C11 C12 C17 . . . . -169.2(3) ?
O1 C11 C12 C17 . . . . 9.6(4) ?
C17 C12 C13 C14 . . . . 0.4(5) ?
C11 C12 C13 C14 . . . . -177.8(3) ?
C12 C13 C14 C15 . . . . -0.4(5) ?
C13 C14 C15 C16 . . . . 0.2(6) ?
C14 C15 C16 C17 . . . . 0.0(6) ?
C13 C12 C17 C16 . . . . -0.3(5) ?
C11 C12 C17 C16 . . . . 177.9(3) ?
C15 C16 C17 C12 . . . . 0.1(6) ?
C6 C5 C18 F3 . . . . 117.0(3) ?
C4 C5 C18 F3 . . . . -59.7(3) ?
C6 C5 C18 F2 . . . . -122.3(3) ?
C4 C5 C18 F2 . . . . 61.0(3) ?
C6 C5 C18 F1 . . . . -3.8(4) ?
C4 C5 C18 F1 . . . . 179.6(2) ?
C22 N3 C19 C20 . . . . -57.9(3) ?
C23 N3 C19 C20 . . . . -179.7(2) ?
C1 N2 C20 C19 . . . . 154.1(2) ?
C21 N2 C20 C19 . . . . -56.7(3) ?
N3 C19 C20 N2 . . . . 55.0(3) ?
C1 N2 C21 C22 . . . . -151.8(2) ?
C20 N2 C21 C22 . . . . 59.7(2) ?
C19 N3 C22 C21 . . . . 60.9(3) ?
C23 N3 C22 C21 . . . . -177.4(2) ?
N2 C21 C22 N3 . . . . -61.0(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag

C21 H21A O1 . 0.97 2.38 3.018(3) 123 yes
C4 H4A N4 1_545 0.93 2.56 3.426(4) 155 yes


_database_code_depnum_ccdc_archive 'CCDC 852326'
