# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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
_chemical_name_systematic        ?
_chemical_name_common            t2-132
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 F N5 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         443.50
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.5092(5)
_cell_length_b                   8.1592(3)
_cell_length_c                   19.6436(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2165.20(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8890
_cell_measurement_theta_min      2.7032
_cell_measurement_theta_max      30.1300
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       
'slightly irregular, but more or less box shaped'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.260
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            29337
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         30.18
_diffrn_reflns_theta_full        30.18
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_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.
;

_reflns_number_total             6400
_reflns_number_gt                5712
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0879
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_number_reflns         6400
_refine_ls_number_parameters     300
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    noref
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.2127P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?

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       'Bruker Instrument Service v2011.2.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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_disorder_assembly
_atom_site_disorder_group
F F1 0.80783(7) -0.15558(11) 0.33455(5) 0.0342(2) Uani d . 1 . .
O O1 1.07911(7) 0.62640(12) 0.09821(5) 0.02075(19) Uani d . 1 . .
O O2 1.02099(8) 0.70016(14) 0.27531(5) 0.0295(2) Uani d . 1 . .
N N5 0.93374(8) 0.52968(14) 0.20702(5) 0.0176(2) Uani d . 1 . .
N N1 0.99727(8) 0.19426(13) 0.08579(5) 0.0155(2) Uani d . 1 . .
N N4 1.08186(8) 0.29780(15) 0.16898(6) 0.0192(2) Uani d . 1 . .
N N3 1.13087(9) 0.16719(14) 0.14125(6) 0.0212(2) Uani d . 1 . .
N N2 1.08111(8) 0.10361(14) 0.09154(6) 0.0191(2) Uani d . 1 . .
C C15 0.82083(11) 0.00468(17) 0.31822(7) 0.0236(3) Uani d . 1 . .
C C16 0.73847(10) 0.09629(18) 0.30318(7) 0.0225(3) Uani d . 1 . .
H H2 0.674 0.0501 0.3055 0.027 Uiso calc R 1 . .
C C17 0.75256(10) 0.25883(17) 0.28437(6) 0.0200(3) Uani d . 1 . .
H H3 0.6967 0.3245 0.2734 0.024 Uiso calc R 1 . .
C C12 0.84661(10) 0.32717(16) 0.28129(6) 0.0182(2) Uani d . 1 . .
C C11 0.85855(10) 0.50326(17) 0.26014(7) 0.0211(3) Uani d . 1 . .
H H5A 0.7941 0.5443 0.2433 0.025 Uiso calc R 1 . .
H H5B 0.8766 0.5689 0.3007 0.025 Uiso calc R 1 . .
C C2 0.91964(9) 0.43990(15) 0.14294(6) 0.0163(2) Uani d . 1 . .
H H6 0.8556 0.3794 0.1471 0.02 Uiso calc R 1 . .
C C1 0.99969(9) 0.31229(15) 0.13379(6) 0.0158(2) Uani d . 1 . .
C C18 0.92126(9) 0.15583(15) 0.03668(6) 0.0146(2) Uani d . 1 . .
C C19 0.93689(9) 0.20429(15) -0.03080(6) 0.0163(2) Uani d . 1 . .
C C20 0.86235(10) 0.17100(16) -0.07749(7) 0.0185(2) Uani d . 1 . .
H H10 0.8704 0.2012 -0.1239 0.022 Uiso calc R 1 . .
C C21 0.77587(10) 0.09345(17) -0.05648(7) 0.0204(3) Uani d . 1 . .
H H11 0.7247 0.0733 -0.0886 0.024 Uiso calc R 1 . .
C C6 0.91109(10) 0.54868(15) 0.08078(6) 0.0172(2) Uani d . 1 . .
C C7 0.82596(10) 0.55225(17) 0.04100(7) 0.0210(3) Uani d . 1 . .
H H13 0.769 0.4919 0.0543 0.025 Uiso calc R 1 . .
C C8 0.82474(12) 0.64475(18) -0.01842(8) 0.0268(3) Uani d . 1 . .
H H14 0.7667 0.6472 -0.0457 0.032 Uiso calc R 1 . .
C C9 0.90706(12) 0.73311(18) -0.03814(7) 0.0278(3) Uani d . 1 . .
H H15 0.9057 0.7938 -0.0794 0.033 Uiso calc R 1 . .
C C10 0.99182(12) 0.73394(18) 0.00196(7) 0.0245(3) Uani d . 1 . .
H H16 1.0479 0.797 -0.0109 0.029 Uiso calc R 1 . .
C C5 0.99291(10) 0.64080(17) 0.06115(7) 0.0194(2) Uani d . 1 . .
C C4 1.07810(10) 0.69871(18) 0.16406(7) 0.0216(3) Uani d . 1 . .
H H18A 1.0646 0.817 0.1578 0.026 Uiso calc R 1 . .
H H18B 1.1461 0.6898 0.1825 0.026 Uiso calc R 1 . .
C C3 1.00808(10) 0.63772(17) 0.21929(7) 0.0196(3) Uani d . 1 . .
C C23 0.83715(9) 0.07381(15) 0.05881(6) 0.0164(2) Uani d . 1 . .
C C22 0.76323(10) 0.04536(17) 0.01031(7) 0.0198(2) Uani d . 1 . .
H H21 0.7037 -0.0077 0.0235 0.024 Uiso calc R 1 . .
C C25 1.03060(11) 0.28972(18) -0.05209(7) 0.0221(3) Uani d . 1 . .
H H22A 1.0275 0.3153 -0.1008 0.033 Uiso calc R 1 . .
H H22B 1.0874 0.2181 -0.0433 0.033 Uiso calc R 1 . .
H H22C 1.038 0.3915 -0.0261 0.033 Uiso calc R 1 . .
C C24 0.82499(10) 0.01115(17) 0.13040(7) 0.0204(3) Uani d . 1 . .
H H23A 0.8823 0.044 0.1578 0.031 Uiso calc R 1 . .
H H23B 0.8201 -0.1087 0.1297 0.031 Uiso calc R 1 . .
H H23C 0.7646 0.0574 0.1503 0.031 Uiso calc R 1 . .
C C13 0.92775(10) 0.22992(19) 0.29822(7) 0.0231(3) Uani d . 1 . .
H H24 0.9923 0.2761 0.2972 0.028 Uiso calc R 1 . .
C C14 0.91587(10) 0.06643(19) 0.31653(8) 0.0258(3) Uani d . 1 . .
H H25 0.9712 -0.0003 0.3275 0.031 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.0368(5) 0.0240(5) 0.0419(5) -0.0005(4) 0.0067(4) 0.0133(4)
O1 0.0207(5) 0.0219(5) 0.0196(4) 0.0005(4) 0.0028(4) -0.0021(4)
O2 0.0334(6) 0.0331(6) 0.0218(5) -0.0054(4) -0.0018(4) -0.0108(4)
N5 0.0218(5) 0.0165(5) 0.0144(5) -0.0009(4) 0.0020(4) -0.0026(4)
N1 0.0161(5) 0.0152(5) 0.0151(4) 0.0002(4) 0.0000(4) -0.0008(4)
N4 0.0208(5) 0.0175(5) 0.0192(5) 0.0017(4) -0.0026(4) -0.0016(4)
N3 0.0220(6) 0.0204(5) 0.0213(5) 0.0027(4) -0.0029(4) -0.0003(4)
N2 0.0171(5) 0.0183(5) 0.0220(5) 0.0021(4) -0.0013(4) -0.0002(4)
C15 0.0285(7) 0.0228(7) 0.0194(6) -0.0011(5) 0.0024(5) 0.0057(5)
C16 0.0223(6) 0.0273(7) 0.0179(6) -0.0035(5) 0.0010(5) 0.0007(5)
C17 0.0205(6) 0.0251(7) 0.0144(5) 0.0018(5) -0.0002(4) -0.0004(5)
C12 0.0221(6) 0.0210(6) 0.0115(5) -0.0002(5) 0.0000(4) -0.0011(4)
C11 0.0234(7) 0.0219(6) 0.0181(6) -0.0003(5) 0.0065(5) -0.0028(5)
C2 0.0187(6) 0.0160(6) 0.0143(5) -0.0007(4) -0.0001(4) -0.0016(4)
C1 0.0187(6) 0.0140(5) 0.0148(5) -0.0011(4) 0.0012(4) -0.0004(4)
C18 0.0145(5) 0.0144(6) 0.0149(5) 0.0016(4) -0.0014(4) -0.0025(4)
C19 0.0178(6) 0.0155(6) 0.0157(5) 0.0001(4) 0.0026(4) -0.0012(4)
C20 0.0206(6) 0.0189(6) 0.0160(5) 0.0035(5) -0.0004(5) -0.0007(4)
C21 0.0171(6) 0.0239(6) 0.0202(6) 0.0013(5) -0.0038(5) -0.0024(5)
C6 0.0232(6) 0.0142(6) 0.0144(5) 0.0031(5) 0.0010(4) -0.0015(4)
C7 0.0231(7) 0.0193(6) 0.0205(6) 0.0045(5) -0.0016(5) -0.0018(5)
C8 0.0326(8) 0.0265(7) 0.0211(6) 0.0094(6) -0.0060(6) -0.0014(5)
C9 0.0423(9) 0.0231(7) 0.0181(6) 0.0095(6) 0.0030(6) 0.0034(5)
C10 0.0322(7) 0.0193(7) 0.0219(6) 0.0044(6) 0.0071(5) 0.0021(5)
C5 0.0241(6) 0.0163(6) 0.0178(5) 0.0035(5) 0.0016(5) -0.0023(5)
C4 0.0228(6) 0.0205(7) 0.0214(6) -0.0034(5) -0.0002(5) -0.0027(5)
C3 0.0212(6) 0.0187(6) 0.0189(6) 0.0022(5) -0.0008(5) -0.0025(5)
C23 0.0191(6) 0.0148(5) 0.0153(5) 0.0020(5) 0.0020(4) -0.0004(4)
C22 0.0170(6) 0.0213(6) 0.0211(6) -0.0004(5) 0.0019(5) -0.0012(5)
C25 0.0239(7) 0.0242(7) 0.0182(6) -0.0055(5) 0.0052(5) -0.0015(5)
C24 0.0226(6) 0.0214(6) 0.0174(6) -0.0010(5) 0.0028(5) 0.0020(5)
C13 0.0198(6) 0.0288(7) 0.0208(6) -0.0024(5) -0.0008(5) 0.0030(5)
C14 0.0226(7) 0.0301(8) 0.0248(6) 0.0034(5) 0.0003(5) 0.0067(6)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C15 . 1.3578(16) ?
O1 C5 . 1.3783(16) ?
O1 C4 . 1.4218(17) ?
O2 C3 . 1.2252(17) ?
N5 C3 . 1.3579(18) ?
N5 C2 . 1.4687(15) ?
N5 C11 . 1.4721(16) ?
N1 C1 . 1.3482(15) ?
N1 N2 . 1.3575(15) ?
N1 C18 . 1.4434(15) ?
N4 C1 . 1.3130(16) ?
N4 N3 . 1.3677(16) ?
N3 N2 . 1.2940(16) ?
C15 C16 . 1.3726(19) ?
C15 C14 . 1.380(2) ?
C16 C17 . 1.390(2) ?
C16 H2 . 0.95 ?
C17 C12 . 1.3888(19) ?
C17 H3 . 0.95 ?
C12 C13 . 1.3935(19) ?
C12 C11 . 1.5042(19) ?
C11 H5A . 0.99 ?
C11 H5B . 0.99 ?
C2 C1 . 1.5119(17) ?
C2 C6 . 1.5140(16) ?
C2 H6 . 1.0 ?
C18 C23 . 1.3885(17) ?
C18 C19 . 1.3992(17) ?
C19 C20 . 1.3888(18) ?
C19 C25 . 1.5045(18) ?
C20 C21 . 1.3912(19) ?
C20 H10 . 0.95 ?
C21 C22 . 1.3800(18) ?
C21 H11 . 0.95 ?
C6 C7 . 1.3906(18) ?
C6 C5 . 1.3911(19) ?
C7 C8 . 1.390(2) ?
C7 H13 . 0.95 ?
C8 C9 . 1.381(2) ?
C8 H14 . 0.95 ?
C9 C10 . 1.390(2) ?
C9 H15 . 0.95 ?
C10 C5 . 1.3892(18) ?
C10 H16 . 0.95 ?
C4 C3 . 1.5229(19) ?
C4 H18A . 0.99 ?
C4 H18B . 0.99 ?
C23 C22 . 1.3996(18) ?
C23 C24 . 1.5053(17) ?
C22 H21 . 0.95 ?
C25 H22A . 0.98 ?
C25 H22B . 0.98 ?
C25 H22C . 0.98 ?
C24 H23A . 0.98 ?
C24 H23B . 0.98 ?
C24 H23C . 0.98 ?
C13 C14 . 1.391(2) ?
C13 H24 . 0.95 ?
C14 H25 . 0.95 ?

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
C5 O1 C4 . . 115.92(10) ?
C3 N5 C2 . . 124.88(10) ?
C3 N5 C11 . . 118.66(11) ?
C2 N5 C11 . . 116.42(10) ?
C1 N1 N2 . . 108.10(10) ?
C1 N1 C18 . . 129.79(11) ?
N2 N1 C18 . . 122.06(10) ?
C1 N4 N3 . . 105.65(10) ?
N2 N3 N4 . . 111.19(10) ?
N3 N2 N1 . . 106.13(10) ?
F1 C15 C16 . . 118.06(13) ?
F1 C15 C14 . . 118.55(13) ?
C16 C15 C14 . . 123.39(13) ?
C15 C16 C17 . . 117.76(13) ?
C15 C16 H2 . . 121.1 ?
C17 C16 H2 . . 121.1 ?
C12 C17 C16 . . 121.34(12) ?
C12 C17 H3 . . 119.3 ?
C16 C17 H3 . . 119.3 ?
C17 C12 C13 . . 118.72(12) ?
C17 C12 C11 . . 119.58(12) ?
C13 C12 C11 . . 121.70(12) ?
N5 C11 C12 . . 114.18(11) ?
N5 C11 H5A . . 108.7 ?
C12 C11 H5A . . 108.7 ?
N5 C11 H5B . . 108.7 ?
C12 C11 H5B . . 108.7 ?
H5A C11 H5B . . 107.6 ?
N5 C2 C1 . . 110.65(10) ?
N5 C2 C6 . . 114.13(10) ?
C1 C2 C6 . . 111.25(10) ?
N5 C2 H6 . . 106.8 ?
C1 C2 H6 . . 106.8 ?
C6 C2 H6 . . 106.8 ?
N4 C1 N1 . . 108.93(11) ?
N4 C1 C2 . . 127.17(11) ?
N1 C1 C2 . . 123.89(11) ?
C23 C18 C19 . . 123.80(11) ?
C23 C18 N1 . . 118.53(11) ?
C19 C18 N1 . . 117.67(11) ?
C20 C19 C18 . . 117.44(11) ?
C20 C19 C25 . . 121.14(12) ?
C18 C19 C25 . . 121.42(11) ?
C19 C20 C21 . . 120.13(12) ?
C19 C20 H10 . . 119.9 ?
C21 C20 H10 . . 119.9 ?
C22 C21 C20 . . 121.01(12) ?
C22 C21 H11 . . 119.5 ?
C20 C21 H11 . . 119.5 ?
C7 C6 C5 . . 119.35(12) ?
C7 C6 C2 . . 121.91(12) ?
C5 C6 C2 . . 118.66(11) ?
C8 C7 C6 . . 119.53(13) ?
C8 C7 H13 . . 120.2 ?
C6 C7 H13 . . 120.2 ?
C9 C8 C7 . . 120.63(14) ?
C9 C8 H14 . . 119.7 ?
C7 C8 H14 . . 119.7 ?
C8 C9 C10 . . 120.47(13) ?
C8 C9 H15 . . 119.8 ?
C10 C9 H15 . . 119.8 ?
C5 C10 C9 . . 118.72(14) ?
C5 C10 H16 . . 120.6 ?
C9 C10 H16 . . 120.6 ?
O1 C5 C10 . . 119.85(12) ?
O1 C5 C6 . . 118.61(11) ?
C10 C5 C6 . . 121.27(13) ?
O1 C4 C3 . . 121.23(11) ?
O1 C4 H18A . . 107.0 ?
C3 C4 H18A . . 107.0 ?
O1 C4 H18B . . 107.0 ?
C3 C4 H18B . . 107.0 ?
H18A C4 H18B . . 106.8 ?
O2 C3 N5 . . 122.32(13) ?
O2 C3 C4 . . 114.55(12) ?
N5 C3 C4 . . 123.03(12) ?
C18 C23 C22 . . 116.79(11) ?
C18 C23 C24 . . 123.06(11) ?
C22 C23 C24 . . 120.12(11) ?
C21 C22 C23 . . 120.78(12) ?
C21 C22 H21 . . 119.6 ?
C23 C22 H21 . . 119.6 ?
C19 C25 H22A . . 109.5 ?
C19 C25 H22B . . 109.5 ?
H22A C25 H22B . . 109.5 ?
C19 C25 H22C . . 109.5 ?
H22A C25 H22C . . 109.5 ?
H22B C25 H22C . . 109.5 ?
C23 C24 H23A . . 109.5 ?
C23 C24 H23B . . 109.5 ?
H23A C24 H23B . . 109.5 ?
C23 C24 H23C . . 109.5 ?
H23A C24 H23C . . 109.5 ?
H23B C24 H23C . . 109.5 ?
C14 C13 C12 . . 121.14(13) ?
C14 C13 H24 . . 119.4 ?
C12 C13 H24 . . 119.4 ?
C15 C14 C13 . . 117.64(13) ?
C15 C14 H25 . . 121.2 ?
C13 C14 H25 . . 121.2 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N4 N3 N2 . . . . -0.29(15) ?
N4 N3 N2 N1 . . . . 0.27(14) ?
C1 N1 N2 N3 . . . . -0.14(13) ?
C18 N1 N2 N3 . . . . -177.83(11) ?
F1 C15 C16 C17 . . . . -177.96(12) ?
C14 C15 C16 C17 . . . . 1.0(2) ?
C15 C16 C17 C12 . . . . -0.44(19) ?
C16 C17 C12 C13 . . . . -0.68(19) ?
C16 C17 C12 C11 . . . . 179.51(12) ?
C3 N5 C11 C12 . . . . -124.54(13) ?
C2 N5 C11 C12 . . . . 57.76(16) ?
C17 C12 C11 N5 . . . . -130.83(13) ?
C13 C12 C11 N5 . . . . 49.36(17) ?
C3 N5 C2 C1 . . . . 70.01(16) ?
C11 N5 C2 C1 . . . . -112.45(12) ?
C3 N5 C2 C6 . . . . -56.37(17) ?
C11 N5 C2 C6 . . . . 121.17(12) ?
N3 N4 C1 N1 . . . . 0.19(14) ?
N3 N4 C1 C2 . . . . -178.86(12) ?
N2 N1 C1 N4 . . . . -0.04(14) ?
C18 N1 C1 N4 . . . . 177.41(12) ?
N2 N1 C1 C2 . . . . 179.06(11) ?
C18 N1 C1 C2 . . . . -3.5(2) ?
N5 C2 C1 N4 . . . . -12.20(18) ?
C6 C2 C1 N4 . . . . 115.77(14) ?
N5 C2 C1 N1 . . . . 168.88(11) ?
C6 C2 C1 N1 . . . . -63.16(15) ?
C1 N1 C18 C23 . . . . -76.26(17) ?
N2 N1 C18 C23 . . . . 100.88(14) ?
C1 N1 C18 C19 . . . . 103.58(15) ?
N2 N1 C18 C19 . . . . -79.28(15) ?
C23 C18 C19 C20 . . . . 1.54(19) ?
N1 C18 C19 C20 . . . . -178.29(11) ?
C23 C18 C19 C25 . . . . -178.66(12) ?
N1 C18 C19 C25 . . . . 1.51(17) ?
C18 C19 C20 C21 . . . . 0.49(18) ?
C25 C19 C20 C21 . . . . -179.30(12) ?
C19 C20 C21 C22 . . . . -1.3(2) ?
N5 C2 C6 C7 . . . . -117.87(13) ?
C1 C2 C6 C7 . . . . 116.06(13) ?
N5 C2 C6 C5 . . . . 65.59(15) ?
C1 C2 C6 C5 . . . . -60.48(14) ?
C5 C6 C7 C8 . . . . 1.42(19) ?
C2 C6 C7 C8 . . . . -175.09(12) ?
C6 C7 C8 C9 . . . . -0.1(2) ?
C7 C8 C9 C10 . . . . -1.5(2) ?
C8 C9 C10 C5 . . . . 1.7(2) ?
C4 O1 C5 C10 . . . . 113.97(14) ?
C4 O1 C5 C6 . . . . -71.94(15) ?
C9 C10 C5 O1 . . . . 173.54(12) ?
C9 C10 C5 C6 . . . . -0.4(2) ?
C7 C6 C5 O1 . . . . -175.17(12) ?
C2 C6 C5 O1 . . . . 1.45(17) ?
C7 C6 C5 C10 . . . . -1.17(19) ?
C2 C6 C5 C10 . . . . 175.46(12) ?
C5 O1 C4 C3 . . . . 63.16(16) ?
C2 N5 C3 O2 . . . . -174.35(13) ?
C11 N5 C3 O2 . . . . 8.2(2) ?
C2 N5 C3 C4 . . . . 9.4(2) ?
C11 N5 C3 C4 . . . . -168.13(12) ?
O1 C4 C3 O2 . . . . 173.61(13) ?
O1 C4 C3 N5 . . . . -9.8(2) ?
C19 C18 C23 C22 . . . . -2.63(19) ?
N1 C18 C23 C22 . . . . 177.20(11) ?
C19 C18 C23 C24 . . . . 175.14(12) ?
N1 C18 C23 C24 . . . . -5.03(18) ?
C20 C21 C22 C23 . . . . 0.2(2) ?
C18 C23 C22 C21 . . . . 1.72(19) ?
C24 C23 C22 C21 . . . . -176.12(12) ?
C17 C12 C13 C14 . . . . 1.35(19) ?
C11 C12 C13 C14 . . . . -178.84(13) ?
F1 C15 C14 C13 . . . . 178.60(13) ?
C16 C15 C14 C13 . . . . -0.3(2) ?
C12 C13 C14 C15 . . . . -0.9(2) ?

_database_code_depnum_ccdc_archive 'CCDC 936637'