# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Toshiaki Murai'
_publ_contact_author_email       MTOSHI@GIFU-U.AC.JP

_publ_section_title              
;
Iodine-mediated cyclization of N-thioacyl
1-(2-pyridyl)-1,2-aminoalcohols and their subsequent condensation
leading to formation of novel bis(1-imidazo[1,5-a]pyridyl)
arylmethanes
;
loop_
_publ_author_name
'Toshiaki Murai'
'Toshifumi Maruyama'
'Fumitoshi Shibahara'
'Shinsuke Tahara'

# Attachment 'B90172A.cif'

data_crystalclear
_database_code_depnum_ccdc_archive 'CCDC 733497'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            bis(1-imidazo(1,5-a)pyridyl)arylmethanes
_chemical_melting_point          81-82
_chemical_formula_moiety         'C31 H21 Cl N6'
_chemical_formula_sum            'C31 H21 Cl N6'
_chemical_formula_weight         512.99

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_Int_Tables_number      14

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                   11.262(6)
_cell_length_b                   10.562(6)
_cell_length_c                   20.766(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.078(7)
_cell_angle_gamma                90.00
_cell_volume                     2456(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4250
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.989

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.62
_diffrn_reflns_number            19735
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5616
_reflns_number_gt                4376
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CRYSTALCLEAR
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 2.0'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.1000P)^2^+9.0500P] 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         5616
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.1074
_refine_ls_wR_factor_ref         0.2600
_refine_ls_wR_factor_gt          0.2353
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C1 C 0.6811(5) -0.0909(4) 0.5864(2) 0.0344(10) Uani 1 1 d . . .
C2 C 0.5740(5) -0.1430(5) 0.5617(2) 0.0399(12) Uani 1 1 d . . .
H1 H 0.5085 -0.0901 0.5468 0.048 Uiso 1 1 calc R . .
C3 C 0.5629(4) -0.2739(5) 0.5588(2) 0.0336(10) Uani 1 1 d . . .
H2 H 0.4891 -0.3105 0.5419 0.040 Uiso 1 1 calc R . .
C4 C 0.6579(4) -0.3521(4) 0.58018(19) 0.0264(9) Uani 1 1 d . . .
C5 C 0.7643(4) -0.2964(4) 0.6056(2) 0.0300(10) Uani 1 1 d . . .
H3 H 0.8299 -0.3487 0.6210 0.036 Uiso 1 1 calc R . .
C6 C 0.7767(4) -0.1664(5) 0.6090(2) 0.0365(11) Uani 1 1 d . . .
H4 H 0.8499 -0.1294 0.6266 0.044 Uiso 1 1 calc R . .
C7 C 0.6444(4) -0.4965(4) 0.57626(19) 0.0247(9) Uani 1 1 d . . .
H5 H 0.5651 -0.5133 0.5514 0.030 Uiso 1 1 calc R . .
C8 C 0.6381(4) -0.5510(4) 0.64350(19) 0.0256(9) Uani 1 1 d . . .
C9 C 0.5494(4) -0.6288(4) 0.6629(2) 0.0253(9) Uani 1 1 d . . .
C10 C 0.4470(4) -0.6904(4) 0.6317(2) 0.0338(10) Uani 1 1 d . . .
H6 H 0.4285 -0.6837 0.5862 0.041 Uiso 1 1 calc R . .
C11 C 0.3760(4) -0.7588(5) 0.6673(2) 0.0395(11) Uani 1 1 d . . .
H7 H 0.3083 -0.8015 0.6465 0.047 Uiso 1 1 calc R . .
C12 C 0.4028(5) -0.7666(5) 0.7358(3) 0.0416(12) Uani 1 1 d . . .
H8 H 0.3507 -0.8122 0.7605 0.050 Uiso 1 1 calc R . .
C13 C 0.5001(4) -0.7109(5) 0.7659(2) 0.0358(11) Uani 1 1 d . . .
H9 H 0.5171 -0.7177 0.8116 0.043 Uiso 1 1 calc R . .
C14 C 0.6800(4) -0.5781(4) 0.7468(2) 0.0274(9) Uani 1 1 d . . .
C15 C 0.7435(4) -0.5647(4) 0.8119(2) 0.0288(9) Uani 1 1 d . . .
C16 C 0.8551(4) -0.5079(4) 0.8198(2) 0.0349(10) Uani 1 1 d . . .
H10 H 0.8918 -0.4799 0.7832 0.042 Uiso 1 1 calc R . .
C17 C 0.9123(5) -0.4925(5) 0.8813(3) 0.0418(12) Uani 1 1 d . . .
H11 H 0.9888 -0.4536 0.8878 0.050 Uiso 1 1 calc R . .
C18 C 0.8569(5) -0.5343(5) 0.9331(2) 0.0426(12) Uani 1 1 d . . .
H12 H 0.8941 -0.5250 0.9761 0.051 Uiso 1 1 calc R . .
C19 C 0.7463(5) -0.5901(5) 0.9214(2) 0.0437(12) Uani 1 1 d . . .
H13 H 0.7087 -0.6191 0.9575 0.052 Uiso 1 1 calc R . .
C20 C 0.7367(4) -0.5548(4) 0.53777(19) 0.0257(9) Uani 1 1 d . . .
C21 C 0.8506(4) -0.6013(4) 0.5564(2) 0.0246(9) Uani 1 1 d . . .
C22 C 0.9249(4) -0.6201(4) 0.6153(2) 0.0320(10) Uani 1 1 d . . .
H14 H 0.8956 -0.6015 0.6555 0.038 Uiso 1 1 calc R . .
C23 C 1.0374(4) -0.6644(5) 0.6142(2) 0.0385(11) Uani 1 1 d . . .
H15 H 1.0876 -0.6749 0.6536 0.046 Uiso 1 1 calc R . .
C24 C 1.0806(4) -0.6954(4) 0.5542(2) 0.0368(11) Uani 1 1 d . . .
H16 H 1.1596 -0.7268 0.5541 0.044 Uiso 1 1 calc R . .
C25 C 1.0118(4) -0.6811(4) 0.4976(2) 0.0313(10) Uani 1 1 d . . .
H17 H 1.0413 -0.7035 0.4579 0.038 Uiso 1 1 calc R . .
C26 C 0.8103(4) -0.6039(4) 0.4485(2) 0.0254(9) Uani 1 1 d . . .
C27 C 0.8218(4) -0.6164(4) 0.37926(19) 0.0279(9) Uani 1 1 d . . .
C28 C 0.7277(4) -0.5762(5) 0.3346(2) 0.0357(11) Uani 1 1 d . . .
H18 H 0.6564 -0.5439 0.3491 0.043 Uiso 1 1 calc R . .
C29 C 0.7395(5) -0.5838(5) 0.2692(2) 0.0441(13) Uani 1 1 d . . .
H19 H 0.6772 -0.5558 0.2380 0.053 Uiso 1 1 calc R . .
C30 C 0.8438(5) -0.6331(5) 0.2500(2) 0.0444(13) Uani 1 1 d . . .
H20 H 0.8549 -0.6394 0.2054 0.053 Uiso 1 1 calc R . .
C31 C 0.9306(5) -0.6726(5) 0.2966(2) 0.0407(12) Uani 1 1 d . . .
H21 H 1.0015 -0.7076 0.2829 0.049 Uiso 1 1 calc R . .
N1 N 0.7179(3) -0.5221(3) 0.69530(16) 0.0273(8) Uani 1 1 d . . .
N2 N 0.5758(3) -0.6431(3) 0.73010(16) 0.0260(8) Uani 1 1 d . . .
N3 N 0.6883(4) -0.6061(4) 0.86232(17) 0.0355(9) Uani 1 1 d . . .
N4 N 0.7142(3) -0.5570(3) 0.47202(16) 0.0263(8) Uani 1 1 d . . .
N5 N 0.8970(3) -0.6330(3) 0.49800(16) 0.0252(8) Uani 1 1 d . . .
N6 N 0.9225(3) -0.6654(4) 0.36043(18) 0.0323(8) Uani 1 1 d . . .
Cl1 Cl 0.69482(15) 0.07437(12) 0.59056(6) 0.0515(4) Uani 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
C1 0.048(3) 0.031(2) 0.024(2) 0.0015(18) 0.004(2) 0.000(2)
C2 0.038(3) 0.042(3) 0.038(3) 0.006(2) -0.001(2) 0.011(2)
C3 0.026(2) 0.043(3) 0.031(2) 0.002(2) -0.0002(18) 0.002(2)
C4 0.027(2) 0.034(2) 0.0185(19) 0.0017(17) 0.0057(16) -0.0003(18)
C5 0.025(2) 0.032(2) 0.032(2) 0.0032(18) 0.0002(18) -0.0015(18)
C6 0.038(3) 0.036(2) 0.035(2) 0.002(2) 0.001(2) -0.004(2)
C7 0.0210(19) 0.033(2) 0.0194(19) 0.0017(17) 0.0002(15) -0.0019(17)
C8 0.027(2) 0.027(2) 0.0226(19) -0.0023(16) 0.0037(16) -0.0015(17)
C9 0.026(2) 0.026(2) 0.025(2) 0.0019(16) 0.0070(16) 0.0009(17)
C10 0.033(2) 0.036(2) 0.031(2) -0.0008(19) -0.0027(19) -0.005(2)
C11 0.037(3) 0.038(3) 0.044(3) 0.003(2) 0.001(2) -0.009(2)
C12 0.037(3) 0.040(3) 0.048(3) 0.012(2) 0.008(2) -0.011(2)
C13 0.042(3) 0.039(3) 0.027(2) 0.0065(19) 0.009(2) -0.007(2)
C14 0.030(2) 0.028(2) 0.025(2) -0.0039(17) 0.0066(17) -0.0019(18)
C15 0.034(2) 0.027(2) 0.025(2) 0.0000(17) 0.0056(18) -0.0012(18)
C16 0.038(3) 0.035(2) 0.032(2) -0.0015(19) 0.005(2) -0.001(2)
C17 0.035(3) 0.037(3) 0.051(3) -0.012(2) -0.004(2) -0.002(2)
C18 0.045(3) 0.051(3) 0.029(2) -0.008(2) -0.009(2) 0.002(2)
C19 0.057(3) 0.047(3) 0.027(2) 0.005(2) 0.004(2) 0.004(3)
C20 0.029(2) 0.029(2) 0.0196(19) -0.0003(16) 0.0018(16) -0.0053(17)
C21 0.026(2) 0.0207(19) 0.027(2) -0.0051(16) 0.0025(17) -0.0050(16)
C22 0.033(2) 0.035(2) 0.027(2) 0.0023(18) 0.0007(18) -0.0001(19)
C23 0.040(3) 0.041(3) 0.032(2) 0.002(2) -0.009(2) 0.005(2)
C24 0.034(2) 0.034(2) 0.042(3) 0.000(2) 0.000(2) 0.009(2)
C25 0.031(2) 0.031(2) 0.032(2) 0.0018(19) 0.0075(19) 0.0009(19)
C26 0.028(2) 0.023(2) 0.024(2) -0.0012(16) -0.0015(17) -0.0058(17)
C27 0.037(2) 0.026(2) 0.0207(19) -0.0011(16) 0.0037(17) -0.0011(18)
C28 0.039(3) 0.042(3) 0.026(2) -0.002(2) 0.0027(19) 0.003(2)
C29 0.051(3) 0.053(3) 0.027(2) 0.004(2) -0.003(2) 0.008(3)
C30 0.058(3) 0.051(3) 0.025(2) -0.002(2) 0.009(2) 0.000(3)
C31 0.047(3) 0.046(3) 0.030(2) -0.002(2) 0.010(2) 0.004(2)
N1 0.0287(19) 0.0325(19) 0.0210(17) 0.0014(14) 0.0032(14) -0.0013(15)
N2 0.0270(18) 0.0268(18) 0.0248(17) 0.0015(14) 0.0064(14) -0.0011(15)
N3 0.041(2) 0.043(2) 0.0224(18) 0.0012(16) 0.0031(16) -0.0006(18)
N4 0.0246(18) 0.0309(19) 0.0238(17) -0.0039(15) 0.0036(14) -0.0041(15)
N5 0.0296(19) 0.0216(17) 0.0245(17) -0.0003(13) 0.0033(14) -0.0005(14)
N6 0.034(2) 0.035(2) 0.0284(19) -0.0039(16) 0.0047(16) 0.0008(17)
Cl1 0.0876(11) 0.0319(6) 0.0331(6) -0.0011(5) -0.0026(6) -0.0002(7)

_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
C1 C2 1.374(7) . ?
C1 C6 1.381(7) . ?
C1 Cl1 1.754(5) . ?
C2 C3 1.390(7) . ?
C2 H1 0.9500 . ?
C3 C4 1.386(6) . ?
C3 H2 0.9500 . ?
C4 C5 1.389(6) . ?
C4 C7 1.533(6) . ?
C5 C6 1.381(6) . ?
C5 H3 0.9500 . ?
C6 H4 0.9500 . ?
C7 C20 1.508(6) . ?
C7 C8 1.519(6) . ?
C7 H5 1.0000 . ?
C8 N1 1.361(5) . ?
C8 C9 1.386(6) . ?
C9 N2 1.404(5) . ?
C9 C10 1.419(6) . ?
C10 C11 1.353(7) . ?
C10 H6 0.9500 . ?
C11 C12 1.425(7) . ?
C11 H7 0.9500 . ?
C12 C13 1.340(7) . ?
C12 H8 0.9500 . ?
C13 N2 1.388(6) . ?
C13 H9 0.9500 . ?
C14 N1 1.332(5) . ?
C14 N2 1.373(5) . ?
C14 C15 1.468(6) . ?
C15 N3 1.345(6) . ?
C15 C16 1.387(6) . ?
C16 C17 1.378(7) . ?
C16 H10 0.9500 . ?
C17 C18 1.372(8) . ?
C17 H11 0.9500 . ?
C18 C19 1.377(7) . ?
C18 H12 0.9500 . ?
C19 N3 1.337(6) . ?
C19 H13 0.9500 . ?
C20 N4 1.362(5) . ?
C20 C21 1.390(6) . ?
C21 N5 1.410(5) . ?
C21 C22 1.421(6) . ?
C22 C23 1.352(7) . ?
C22 H14 0.9500 . ?
C23 C24 1.423(7) . ?
C23 H15 0.9500 . ?
C24 C25 1.347(6) . ?
C24 H16 0.9500 . ?
C25 N5 1.390(6) . ?
C25 H17 0.9500 . ?
C26 N4 1.329(6) . ?
C26 N5 1.375(5) . ?
C26 C27 1.464(6) . ?
C27 N6 1.342(6) . ?
C27 C28 1.398(6) . ?
C28 C29 1.381(6) . ?
C28 H18 0.9500 . ?
C29 C30 1.382(8) . ?
C29 H19 0.9500 . ?
C30 C31 1.367(7) . ?
C30 H20 0.9500 . ?
C31 N6 1.340(6) . ?
C31 H21 0.9500 . ?

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
C2 C1 C6 121.2(4) . . ?
C2 C1 Cl1 119.1(4) . . ?
C6 C1 Cl1 119.7(4) . . ?
C1 C2 C3 119.0(4) . . ?
C1 C2 H1 120.5 . . ?
C3 C2 H1 120.5 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H2 119.4 . . ?
C2 C3 H2 119.4 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 C7 120.5(4) . . ?
C5 C4 C7 121.2(4) . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H3 119.4 . . ?
C4 C5 H3 119.4 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 H4 120.5 . . ?
C5 C6 H4 120.5 . . ?
C20 C7 C8 115.8(3) . . ?
C20 C7 C4 111.4(3) . . ?
C8 C7 C4 110.0(3) . . ?
C20 C7 H5 106.4 . . ?
C8 C7 H5 106.4 . . ?
C4 C7 H5 106.4 . . ?
N1 C8 C9 109.8(4) . . ?
N1 C8 C7 123.4(4) . . ?
C9 C8 C7 126.7(4) . . ?
C8 C9 N2 105.7(4) . . ?
C8 C9 C10 135.6(4) . . ?
N2 C9 C10 118.7(4) . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H6 120.2 . . ?
C9 C10 H6 120.2 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H7 120.0 . . ?
C12 C11 H7 120.0 . . ?
C13 C12 C11 121.2(5) . . ?
C13 C12 H8 119.4 . . ?
C11 C12 H8 119.4 . . ?
C12 C13 N2 119.6(4) . . ?
C12 C13 H9 120.2 . . ?
N2 C13 H9 120.2 . . ?
N1 C14 N2 110.9(4) . . ?
N1 C14 C15 122.1(4) . . ?
N2 C14 C15 127.0(4) . . ?
N3 C15 C16 122.4(4) . . ?
N3 C15 C14 117.7(4) . . ?
C16 C15 C14 119.9(4) . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H10 120.3 . . ?
C15 C16 H10 120.3 . . ?
C18 C17 C16 118.8(5) . . ?
C18 C17 H11 120.6 . . ?
C16 C17 H11 120.6 . . ?
C19 C18 C17 118.5(4) . . ?
C19 C18 H12 120.7 . . ?
C17 C18 H12 120.7 . . ?
N3 C19 C18 124.1(5) . . ?
N3 C19 H13 117.9 . . ?
C18 C19 H13 117.9 . . ?
N4 C20 C21 109.9(4) . . ?
N4 C20 C7 118.2(4) . . ?
C21 C20 C7 131.7(4) . . ?
C20 C21 N5 105.1(3) . . ?
C20 C21 C22 136.9(4) . . ?
N5 C21 C22 118.0(4) . . ?
C23 C22 C21 120.0(4) . . ?
C23 C22 H14 120.0 . . ?
C21 C22 H14 120.0 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H15 119.9 . . ?
C24 C23 H15 119.9 . . ?
C25 C24 C23 121.4(4) . . ?
C25 C24 H16 119.3 . . ?
C23 C24 H16 119.3 . . ?
C24 C25 N5 119.0(4) . . ?
C24 C25 H17 120.5 . . ?
N5 C25 H17 120.5 . . ?
N4 C26 N5 110.6(4) . . ?
N4 C26 C27 123.7(4) . . ?
N5 C26 C27 125.7(4) . . ?
N6 C27 C28 121.9(4) . . ?
N6 C27 C26 119.1(4) . . ?
C28 C27 C26 119.0(4) . . ?
C29 C28 C27 119.3(5) . . ?
C29 C28 H18 120.3 . . ?
C27 C28 H18 120.3 . . ?
C30 C29 C28 118.6(5) . . ?
C30 C29 H19 120.7 . . ?
C28 C29 H19 120.7 . . ?
C31 C30 C29 118.5(5) . . ?
C31 C30 H20 120.8 . . ?
C29 C30 H20 120.8 . . ?
N6 C31 C30 124.4(5) . . ?
N6 C31 H21 117.8 . . ?
C30 C31 H21 117.8 . . ?
C14 N1 C8 107.1(4) . . ?
C14 N2 C13 132.8(4) . . ?
C14 N2 C9 106.4(3) . . ?
C13 N2 C9 120.7(4) . . ?
C19 N3 C15 116.8(4) . . ?
C26 N4 C20 107.6(3) . . ?
C26 N5 C25 131.6(4) . . ?
C26 N5 C21 106.9(3) . . ?
C25 N5 C21 121.5(4) . . ?
C31 N6 C27 117.3(4) . . ?

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
C6 C1 C2 C3 -0.9(7) . . . . ?
Cl1 C1 C2 C3 -179.6(4) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C2 C3 C4 C7 -179.6(4) . . . . ?
C3 C4 C5 C6 -0.8(7) . . . . ?
C7 C4 C5 C6 179.8(4) . . . . ?
C2 C1 C6 C5 1.1(7) . . . . ?
Cl1 C1 C6 C5 179.7(4) . . . . ?
C4 C5 C6 C1 -0.2(7) . . . . ?
C3 C4 C7 C20 123.3(4) . . . . ?
C5 C4 C7 C20 -57.4(5) . . . . ?
C3 C4 C7 C8 -107.0(4) . . . . ?
C5 C4 C7 C8 72.4(5) . . . . ?
C20 C7 C8 N1 77.5(5) . . . . ?
C4 C7 C8 N1 -49.8(5) . . . . ?
C20 C7 C8 C9 -107.0(5) . . . . ?
C4 C7 C8 C9 125.7(4) . . . . ?
N1 C8 C9 N2 2.1(5) . . . . ?
C7 C8 C9 N2 -174.0(4) . . . . ?
N1 C8 C9 C10 -178.2(5) . . . . ?
C7 C8 C9 C10 5.7(8) . . . . ?
C8 C9 C10 C11 -178.2(5) . . . . ?
N2 C9 C10 C11 1.5(7) . . . . ?
C9 C10 C11 C12 1.2(7) . . . . ?
C10 C11 C12 C13 -2.3(8) . . . . ?
C11 C12 C13 N2 0.6(8) . . . . ?
N1 C14 C15 N3 168.8(4) . . . . ?
N2 C14 C15 N3 -9.0(7) . . . . ?
N1 C14 C15 C16 -9.5(7) . . . . ?
N2 C14 C15 C16 172.7(4) . . . . ?
N3 C15 C16 C17 -0.1(7) . . . . ?
C14 C15 C16 C17 178.1(4) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C16 C17 C18 C19 0.0(8) . . . . ?
C17 C18 C19 N3 -0.2(8) . . . . ?
C8 C7 C20 N4 150.0(4) . . . . ?
C4 C7 C20 N4 -83.3(4) . . . . ?
C8 C7 C20 C21 -35.7(6) . . . . ?
C4 C7 C20 C21 90.9(5) . . . . ?
N4 C20 C21 N5 -0.3(5) . . . . ?
C7 C20 C21 N5 -174.9(4) . . . . ?
N4 C20 C21 C22 178.3(5) . . . . ?
C7 C20 C21 C22 3.7(9) . . . . ?
C20 C21 C22 C23 -177.0(5) . . . . ?
N5 C21 C22 C23 1.5(6) . . . . ?
C21 C22 C23 C24 -1.6(7) . . . . ?
C22 C23 C24 C25 0.3(8) . . . . ?
C23 C24 C25 N5 1.1(7) . . . . ?
N4 C26 C27 N6 -179.8(4) . . . . ?
N5 C26 C27 N6 3.1(6) . . . . ?
N4 C26 C27 C28 0.6(6) . . . . ?
N5 C26 C27 C28 -176.4(4) . . . . ?
N6 C27 C28 C29 -1.6(7) . . . . ?
C26 C27 C28 C29 177.9(4) . . . . ?
C27 C28 C29 C30 1.0(8) . . . . ?
C28 C29 C30 C31 0.2(8) . . . . ?
C29 C30 C31 N6 -1.0(8) . . . . ?
N2 C14 N1 C8 -0.4(5) . . . . ?
C15 C14 N1 C8 -178.5(4) . . . . ?
C9 C8 N1 C14 -1.1(5) . . . . ?
C7 C8 N1 C14 175.1(4) . . . . ?
N1 C14 N2 C13 -176.8(4) . . . . ?
C15 C14 N2 C13 1.2(8) . . . . ?
N1 C14 N2 C9 1.7(5) . . . . ?
C15 C14 N2 C9 179.7(4) . . . . ?
C12 C13 N2 C14 -179.4(5) . . . . ?
C12 C13 N2 C9 2.2(7) . . . . ?
C8 C9 N2 C14 -2.3(4) . . . . ?
C10 C9 N2 C14 178.0(4) . . . . ?
C8 C9 N2 C13 176.5(4) . . . . ?
C10 C9 N2 C13 -3.3(6) . . . . ?
C18 C19 N3 C15 0.2(8) . . . . ?
C16 C15 N3 C19 -0.1(7) . . . . ?
C14 C15 N3 C19 -178.3(4) . . . . ?
N5 C26 N4 C20 -0.1(5) . . . . ?
C27 C26 N4 C20 -177.5(4) . . . . ?
C21 C20 N4 C26 0.2(5) . . . . ?
C7 C20 N4 C26 175.7(4) . . . . ?
N4 C26 N5 C25 -178.5(4) . . . . ?
C27 C26 N5 C25 -1.1(7) . . . . ?
N4 C26 N5 C21 -0.1(4) . . . . ?
C27 C26 N5 C21 177.3(4) . . . . ?
C24 C25 N5 C26 177.1(4) . . . . ?
C24 C25 N5 C21 -1.2(6) . . . . ?
C20 C21 N5 C26 0.2(4) . . . . ?
C22 C21 N5 C26 -178.7(4) . . . . ?
C20 C21 N5 C25 178.8(4) . . . . ?
C22 C21 N5 C25 -0.1(6) . . . . ?
C30 C31 N6 C27 0.4(8) . . . . ?
C28 C27 N6 C31 1.0(7) . . . . ?
C26 C27 N6 C31 -178.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.053