# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#  This CIF contains data from an original supplementary publication 
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#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_duangj0916
_database_code_depnum_ccdc_archive 'CCDC 915787'
#TrackingRef 'duangj0916.cif'
_audit_creation_date             2012-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C24 H22 Br N5 O4'
_chemical_formula_sum            'C24 H22 Br N5 O4'
_chemical_formula_weight         524.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
_cell_length_a                   5.6126(3)
_cell_length_b                   16.8138(9)
_cell_length_c                   25.1126(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2369.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1060
_cell_measurement_temperature    291.98(10)
_cell_measurement_theta_max      28.5098
_cell_measurement_theta_min      2.9100
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.1134
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6731
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.92
_diffrn_ambient_temperature      291.98(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9681
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -4.00 24.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -19.3492 -99.0000 60.0000 28
#__ type_ start__ end____ width___ exp.time_
2 omega 59.00 92.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 -150.0000 33
#__ type_ start__ end____ width___ exp.time_
3 omega -19.00 93.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 0.0000 0.0000 112
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0008416000
_diffrn_orient_matrix_UB_12      0.0200504000
_diffrn_orient_matrix_UB_13      -0.0248606000
_diffrn_orient_matrix_UB_21      0.0652826000
_diffrn_orient_matrix_UB_22      0.0317140000
_diffrn_orient_matrix_UB_23      0.0115714000
_diffrn_orient_matrix_UB_31      0.1081413000
_diffrn_orient_matrix_UB_32      -0.0193153000
_diffrn_orient_matrix_UB_33      -0.0067798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2219
_reflns_number_total             4294
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.2118
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N3 N -0.0320(12) 0.2756(3) 0.3860(2) 0.0484(15) Uani 1 1 d . . .
H3 H 0.0663 0.2765 0.4122 0.058 Uiso 1 1 calc R . .
C16 C 0.4769(14) 0.3920(4) 0.2181(3) 0.0439(18) Uani 1 1 d . . .
C14 C -0.4600(15) 0.1172(4) 0.4246(3) 0.050(2) Uani 1 1 d . . .
H14 H -0.4929 0.0829 0.4527 0.060 Uiso 1 1 calc R . .
C11 C -0.3642(13) 0.2171(4) 0.3394(3) 0.0433(18) Uani 1 1 d . . .
H11 H -0.3347 0.2500 0.3104 0.052 Uiso 1 1 calc R . .
N2 N -0.0067(11) 0.3282(3) 0.3432(2) 0.0439(15) Uani 1 1 d . . .
C7 C 0.4624(13) 0.4281(4) 0.2721(3) 0.0444(17) Uani 1 1 d . . .
H7 H 0.5868 0.4053 0.2949 0.053 Uiso 1 1 calc R . .
N5 N -0.1394(14) 0.1719(4) 0.4770(3) 0.0554(18) Uani 1 1 d . . .
C10 C -0.2164(13) 0.2229(4) 0.3850(3) 0.0402(17) Uani 1 1 d . . .
C9 C 0.1767(15) 0.3723(4) 0.3451(3) 0.0447(19) Uani 1 1 d . . .
H9 H 0.2834 0.3664 0.3732 0.054 Uiso 1 1 calc R . .
C12 C -0.5470(15) 0.1648(4) 0.3370(3) 0.051(2) Uani 1 1 d . . .
H12 H -0.6416 0.1621 0.3067 0.061 Uiso 1 1 calc R . .
C13 C -0.5926(13) 0.1157(4) 0.3798(3) 0.0464(19) Uani 1 1 d . . .
C19 C 0.5194(17) 0.3323(5) 0.1165(3) 0.057(2) Uani 1 1 d . . .
O4 O 0.0518(12) 0.2082(4) 0.4786(2) 0.0728(16) Uani 1 1 d . . .
C3 C 0.0409(16) 0.6339(4) 0.2848(3) 0.058(2) Uani 1 1 d . . .
H3A H 0.1000 0.6363 0.2503 0.070 Uiso 1 1 calc R . .
C21 C 0.6629(14) 0.3413(4) 0.2041(3) 0.049(2) Uani 1 1 d . . .
H21 H 0.7753 0.3274 0.2297 0.059 Uiso 1 1 calc R . .
C20 C 0.6841(15) 0.3110(5) 0.1529(3) 0.056(2) Uani 1 1 d . . .
H20 H 0.8084 0.2770 0.1439 0.068 Uiso 1 1 calc R . .
C6 C 0.4737(15) 0.5212(4) 0.2751(3) 0.060(2) Uani 1 1 d . . .
H6A H 0.6294 0.5418 0.2847 0.072 Uiso 1 1 calc R . .
H6B H 0.4119 0.5477 0.2437 0.072 Uiso 1 1 calc R . .
N4 N -0.7891(15) 0.0591(4) 0.3757(4) 0.069(2) Uani 1 1 d . . .
O3 O -0.2200(12) 0.1361(4) 0.5158(2) 0.0740(18) Uani 1 1 d . . .
O1 O -0.9064(14) 0.0590(5) 0.3353(4) 0.111(3) Uani 1 1 d . . .
C8 C 0.2247(13) 0.4328(4) 0.3037(3) 0.0392(17) Uani 1 1 d . . .
H8 H 0.0901 0.4356 0.2789 0.047 Uiso 1 1 calc R . .
C15 C -0.2735(14) 0.1711(4) 0.4278(3) 0.0463(19) Uani 1 1 d . . .
C4 C 0.1139(14) 0.5830(4) 0.3244(3) 0.051(2) Uani 1 1 d . . .
C18 C 0.3268(17) 0.3819(5) 0.1280(3) 0.063(2) Uani 1 1 d . . .
H18 H 0.2151 0.3947 0.1020 0.075 Uiso 1 1 calc R . .
C5 C 0.2957(13) 0.5185(4) 0.3222(3) 0.0448(18) Uani 1 1 d . . .
H5 H 0.3825 0.5158 0.3560 0.054 Uiso 1 1 calc R . .
O2 O -0.8361(14) 0.0176(5) 0.4138(3) 0.112(3) Uani 1 1 d . . .
C17 C 0.3077(15) 0.4112(5) 0.1789(3) 0.057(2) Uani 1 1 d . . .
H17 H 0.1808 0.4444 0.1875 0.069 Uiso 1 1 calc R . .
Br35 Br 0.5459(3) 0.28963(7) 0.04599(4) 0.1041(5) Uani 1 1 d . . .
C1 C -0.1764(19) 0.6592(6) 0.3576(5) 0.082(3) Uani 1 1 d . . .
H1 H -0.2879 0.6805 0.3810 0.099 Uiso 1 1 calc R . .
C2 C -0.1399(18) 0.6815(5) 0.3065(5) 0.073(3) Uani 1 1 d . . .
H2 H -0.2211 0.7217 0.2887 0.088 Uiso 1 1 calc R . .
N1 N -0.0177(15) 0.5993(4) 0.3683(3) 0.075(2) Uani 1 1 d . . .
C22 C 0.014(2) 0.5620(8) 0.4212(5) 0.108(4) Uani 1 1 d U . .
H22A H 0.0157 0.6026 0.4486 0.130 Uiso 1 1 calc R . .
H22B H 0.1641 0.5336 0.4224 0.130 Uiso 1 1 calc R . .
C23 C -0.186(3) 0.5058(10) 0.4310(6) 0.132(5) Uani 1 1 d U . .
H23 H -0.2008 0.4608 0.4097 0.159 Uiso 1 1 calc R . .
C24 C -0.337(3) 0.5181(11) 0.4678(7) 0.172(7) Uani 1 1 d U . .
H24A H -0.3242 0.5630 0.4893 0.206 Uiso 1 1 calc R . .
H24B H -0.4610 0.4822 0.4733 0.206 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
N3 0.052(4) 0.050(3) 0.043(3) 0.009(3) -0.006(3) -0.008(4)
C16 0.050(5) 0.038(3) 0.044(4) 0.006(3) -0.003(4) -0.011(4)
C14 0.063(5) 0.039(4) 0.049(4) 0.003(3) 0.017(5) 0.003(5)
C11 0.048(5) 0.044(4) 0.037(4) 0.003(4) 0.006(4) -0.007(4)
N2 0.049(4) 0.036(3) 0.046(3) 0.003(3) 0.003(3) -0.002(4)
C7 0.038(4) 0.053(4) 0.042(4) -0.003(3) 0.004(4) 0.000(4)
N5 0.063(5) 0.056(4) 0.047(4) 0.003(3) 0.003(4) 0.007(4)
C10 0.045(4) 0.038(4) 0.038(4) 0.005(3) 0.012(4) 0.000(4)
C9 0.045(4) 0.048(4) 0.041(4) -0.001(4) -0.011(4) 0.008(4)
C12 0.055(5) 0.049(4) 0.049(5) -0.005(4) 0.001(4) 0.003(5)
C13 0.046(5) 0.042(4) 0.051(5) -0.005(4) 0.009(4) -0.007(4)
C19 0.069(6) 0.061(4) 0.040(4) 0.006(4) 0.008(5) -0.017(5)
O4 0.080(4) 0.081(4) 0.057(3) 0.006(3) -0.014(3) -0.002(5)
C3 0.062(5) 0.048(4) 0.066(5) 0.004(4) 0.000(5) -0.007(5)
C21 0.051(5) 0.052(4) 0.045(5) -0.003(4) -0.001(4) 0.015(4)
C20 0.060(5) 0.056(5) 0.054(5) 0.002(4) 0.016(5) 0.004(5)
C6 0.058(5) 0.041(4) 0.081(6) -0.011(4) 0.027(5) -0.004(5)
N4 0.066(5) 0.059(5) 0.082(6) 0.004(4) 0.006(5) -0.016(5)
O3 0.095(5) 0.085(4) 0.043(3) 0.020(3) 0.003(3) -0.002(4)
O1 0.101(6) 0.114(6) 0.118(6) 0.015(5) -0.040(5) -0.055(5)
C8 0.040(4) 0.038(4) 0.039(4) -0.005(3) -0.001(3) -0.004(4)
C15 0.048(4) 0.044(4) 0.047(5) 0.000(4) 0.003(4) 0.005(4)
C4 0.054(5) 0.037(4) 0.062(5) -0.012(4) 0.001(4) 0.000(4)
C18 0.070(6) 0.066(5) 0.052(5) 0.016(4) -0.013(5) 0.008(5)
C5 0.041(4) 0.045(4) 0.048(4) -0.009(4) 0.009(4) -0.002(4)
O2 0.127(6) 0.102(6) 0.108(6) 0.013(5) 0.012(5) -0.056(5)
C17 0.055(5) 0.058(5) 0.058(5) 0.008(4) -0.010(5) 0.010(5)
Br35 0.1639(12) 0.1048(8) 0.0435(5) -0.0070(5) 0.0180(7) -0.0180(9)
C1 0.069(6) 0.066(6) 0.112(9) -0.022(6) 0.010(7) 0.010(6)
C2 0.070(6) 0.035(4) 0.114(9) -0.005(5) -0.015(6) 0.001(5)
N1 0.091(6) 0.073(5) 0.061(5) -0.008(4) 0.013(5) 0.016(5)
C22 0.095(7) 0.141(8) 0.088(6) -0.020(6) 0.006(6) 0.029(7)
C23 0.144(9) 0.135(8) 0.117(8) 0.008(7) 0.010(7) 0.015(8)
C24 0.165(12) 0.181(13) 0.170(13) 0.042(11) -0.043(11) -0.017(12)
_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
N3 N2 1.397(7) . ?
N3 C10 1.363(9) . ?
C16 C7 1.489(9) . ?
C16 C21 1.392(10) . ?
C16 C17 1.406(10) . ?
C14 C13 1.349(10) . ?
C14 C15 1.386(10) . ?
C11 C10 1.417(10) . ?
C11 C12 1.352(10) . ?
N2 C9 1.269(9) . ?
C7 C6 1.569(9) . ?
C7 C8 1.555(10) . ?
N5 O4 1.235(8) . ?
N5 O3 1.231(8) . ?
N5 C15 1.447(10) . ?
C10 C15 1.420(10) . ?
C9 C8 1.479(10) . ?
C12 C13 1.379(10) . ?
C13 N4 1.460(10) . ?
C19 C20 1.347(11) . ?
C19 C18 1.395(12) . ?
C19 Br35 1.917(8) . ?
C3 C4 1.373(10) . ?
C3 C2 1.402(12) . ?
C21 C20 1.390(10) . ?
C6 C5 1.548(10) . ?
N4 O1 1.208(9) . ?
N4 O2 1.215(9) . ?
C8 C5 1.565(9) . ?
C4 C5 1.491(10) . ?
C4 N1 1.355(10) . ?
C18 C17 1.374(11) . ?
C1 C2 1.352(13) . ?
C1 N1 1.371(12) . ?
N1 C22 1.480(13) . ?
C22 C23 1.486(18) . ?
C23 C24 1.273(19) . ?
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
C10 N3 N2 118.4(6) . . ?
C21 C16 C7 121.3(7) . . ?
C21 C16 C17 118.1(7) . . ?
C17 C16 C7 120.5(7) . . ?
C13 C14 C15 118.5(7) . . ?
C12 C11 C10 121.7(6) . . ?
C9 N2 N3 115.1(6) . . ?
C16 C7 C6 116.7(6) . . ?
C16 C7 C8 122.2(6) . . ?
C8 C7 C6 87.7(5) . . ?
O4 N5 C15 119.0(7) . . ?
O3 N5 O4 122.3(7) . . ?
O3 N5 C15 118.7(8) . . ?
N3 C10 C11 120.2(6) . . ?
N3 C10 C15 123.9(7) . . ?
C11 C10 C15 115.9(7) . . ?
N2 C9 C8 121.5(7) . . ?
C11 C12 C13 119.7(7) . . ?
C14 C13 C12 122.4(7) . . ?
C14 C13 N4 119.3(8) . . ?
C12 C13 N4 118.4(8) . . ?
C20 C19 C18 123.4(8) . . ?
C20 C19 Br35 118.2(7) . . ?
C18 C19 Br35 118.3(7) . . ?
C4 C3 C2 106.9(8) . . ?
C20 C21 C16 121.5(7) . . ?
C19 C20 C21 118.1(8) . . ?
C5 C6 C7 88.9(5) . . ?
O1 N4 C13 118.2(8) . . ?
O1 N4 O2 122.8(9) . . ?
O2 N4 C13 118.8(9) . . ?
C7 C8 C5 88.8(5) . . ?
C9 C8 C7 118.7(6) . . ?
C9 C8 C5 118.1(6) . . ?
C14 C15 N5 116.6(7) . . ?
C14 C15 C10 121.8(7) . . ?
C10 C15 N5 121.6(7) . . ?
C3 C4 C5 129.2(8) . . ?
N1 C4 C3 107.4(7) . . ?
N1 C4 C5 123.4(8) . . ?
C17 C18 C19 117.8(8) . . ?
C6 C5 C8 88.0(5) . . ?
C4 C5 C6 116.6(6) . . ?
C4 C5 C8 120.5(6) . . ?
C18 C17 C16 121.1(8) . . ?
C2 C1 N1 106.9(9) . . ?
C1 C2 C3 108.7(9) . . ?
C4 N1 C1 110.1(8) . . ?
C4 N1 C22 125.4(8) . . ?
C1 N1 C22 124.4(9) . . ?
N1 C22 C23 109.2(10) . . ?
C24 C23 C22 121.3(16) . . ?