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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-02-28
_journal_date_accepted     2009-04-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o996
_journal_page_last     o997
_journal_paper_category     QO
_journal_coeditor_code     BT2890
_publ_contact_author_name     ' M.N. Ponnuswamy '
_publ_contact_author_address
;   Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai - 600 025
    India
;
_publ_contact_author_email     'mnpsy2004@yahoo.com'
_publ_contact_author_fax     '+9144 22352494'
_publ_contact_author_phone     '+9144 22300122'
_publ_section_title
;
4-(2, 4-Dichlorophenyl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Ramesh'
;     Department of Physics
      Presidency College (Autonomous)
      Chennai 600 005
      India
;
    'S. S. Sundaresan'
;   Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'P. Thirumurugan'
;
      Organic Chemistry Division
      Central Leather Research Institute
      Adyar
      Chennai 600 020
      India
;
    'Paramasivan T. Perumal '
;
      Organic Chemistry Division
      Central Leather Research Institute
      Adyar
      Chennai 600 020
      India
;
    'M. N. Ponnuswamy'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-(2, 4-Dichlorophenyl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile
;
_chemical_name_common
;
4-(2, 4-Dichlorophenyl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile
;
_chemical_formula_moiety     'C25 H14 Cl2 N4'
_chemical_formula_sum     'C25 H14 Cl2 N4'
_chemical_formula_weight     441.30
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P21/c
_symmetry_space_group_name_Hall     '-P 2ybc '
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     10.0307(12)
_cell_length_b     22.446(3)
_cell_length_c     17.932(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.991(4)
_cell_angle_gamma     90.00
_cell_volume     4036.7(10)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4532
_cell_measurement_theta_min     1.45
_cell_measurement_theta_max     26.01
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.452
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1808
_exptl_absorpt_coefficient_mu     0.343
_exptl_absorpt_correction_type     'Multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.902
_exptl_absorpt_correction_T_max     0.934
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 Kappa APEXII area-detector diffractometer'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     38628
_diffrn_reflns_av_R_equivalents     0.0384
_diffrn_reflns_av_sigmaI/netI     0.0301
_diffrn_reflns_theta_min     1.45
_diffrn_reflns_theta_max     26.01
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     7874
_reflns_number_gt     5586
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0716
_refine_ls_R_factor_gt     0.0426
_refine_ls_wR_factor_gt     0.1135
_refine_ls_wR_factor_ref     0.1410
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     7874
_refine_ls_number_parameters     567
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0749P)²+1.1730P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.517
_refine_diff_density_min     -0.414
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP3 (Farrugia, 1997)'
_computing_publication_material
                            'SHELXL97 (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_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.45103(8) 0.83228(3) -0.01221(4) 0.0625(2) Uani d . 1 . .
    Cl Cl1' 1.02167(6) 0.57914(3) 0.01576(4) 0.04880(18) Uani d . 1 . .
    Cl Cl2 0.36009(7) 0.60707(3) 0.06685(5) 0.0571(2) Uani d . 1 . .
    Cl Cl2' 0.83340(8) 0.80040(3) 0.03850(6) 0.0715(3) Uani d . 1 . .
    N N1 0.20249(18) 0.98708(8) 0.13679(11) 0.0348(4) Uani d . 1 . .
    N N1' 0.74187(17) 0.42415(8) 0.15496(11) 0.0344(4) Uani d . 1 . .
    C C2 0.3239(2) 0.96455(10) 0.15411(12) 0.0341(5) Uani d . 1 . .
    C C2' 0.8626(2) 0.44706(10) 0.17186(12) 0.0324(5) Uani d . 1 . .
    C C3 0.3509(2) 0.90381(10) 0.14152(13) 0.0356(5) Uani d . 1 . .
    C C3' 0.8898(2) 0.50742(10) 0.15868(13) 0.0344(5) Uani d . 1 . .
    C C4 0.2523(2) 0.86696(10) 0.11020(13) 0.0346(5) Uani d . 1 . .
    C C4' 0.7929(2) 0.54340(10) 0.12346(13) 0.0331(5) Uani d . 1 . .
    C C5 0.1296(2) 0.89156(10) 0.09365(14) 0.0379(5) Uani d . 1 . .
    H H5 0.0617 0.8682 0.0733 0.046 Uiso calc R 1 . .
    C C5' 0.6708(2) 0.51797(10) 0.10687(13) 0.0360(5) Uani d . 1 . .
    H H5' 0.6040 0.5404 0.0837 0.043 Uiso calc R 1 . .
    C C6 0.1082(2) 0.95146(10) 0.10757(13) 0.0338(5) Uani d . 1 . .
    C C6' 0.6482(2) 0.45913(10) 0.12483(13) 0.0336(5) Uani d . 1 . .
    C C7 0.4203(2) 1.00692(11) 0.18467(13) 0.0363(5) Uani d . 1 . .
    C C7' 0.9576(2) 0.40339(10) 0.20169(13) 0.0341(5) Uani d . 1 . .
    C C8 0.4100(2) 1.07118(10) 0.18173(13) 0.0361(5) Uani d . 1 . .
    C C8' 0.9477(2) 0.33985(11) 0.19115(14) 0.0379(5) Uani d . 1 . .
    C C9 0.3196(2) 1.11211(11) 0.15114(14) 0.0422(6) Uani d . 1 . .
    H H9 0.2435 1.0990 0.1258 0.051 Uiso calc R 1 . .
    C C9' 0.8629(3) 0.30236(12) 0.15088(17) 0.0496(7) Uani d . 1 . .
    H H9' 0.7916 0.3179 0.1233 0.060 Uiso calc R 1 . .
    C C10 0.3444(3) 1.17177(12) 0.15879(16) 0.0486(6) Uani d . 1 . .
    H H10 0.2842 1.1990 0.1383 0.058 Uiso calc R 1 . .
    C C10' 0.8856(3) 0.24218(13) 0.1523(2) 0.0661(9) Uani d . 1 . .
    H H10' 0.8289 0.2171 0.1253 0.079 Uiso calc R 1 . .
    C C11 0.4577(3) 1.19271(12) 0.19653(16) 0.0526(7) Uani d . 1 . .
    H H11 0.4711 1.2335 0.2016 0.063 Uiso calc R 1 . .
    C C11' 0.9914(3) 0.21783(13) 0.1930(2) 0.0681(9) Uani d . 1 . .
    H H11' 1.0034 0.1767 0.1937 0.082 Uiso calc R 1 . .
    C C12 0.5494(3) 1.15379(12) 0.22616(15) 0.0489(7) Uani d . 1 . .
    H H12 0.6263 1.1674 0.2504 0.059 Uiso calc R 1 . .
    C C12' 1.0781(3) 0.25361(13) 0.23219(18) 0.0573(8) Uani d . 1 . .
    H H12' 1.1499 0.2375 0.2588 0.069 Uiso calc R 1 . .
    C C13 0.5240(2) 1.09366(11) 0.21879(14) 0.0399(6) Uani d . 1 . .
    C C13' 1.0555(2) 0.31442(12) 0.23096(14) 0.0422(6) Uani d . 1 . .
    N N14 0.5971(2) 1.04600(10) 0.24325(13) 0.0462(6) Uani d . 1 . .
    H H14 0.662(3) 1.0477(14) 0.2631(17) 0.057(10) Uiso d . 1 . .
    N N14' 1.1256(2) 0.35976(10) 0.26389(12) 0.0447(5) Uani d . 1 . .
    H H14' 1.197(3) 0.3551(13) 0.2910(16) 0.056(9) Uiso d . 1 . .
    C C15 0.5373(2) 0.99500(12) 0.22312(14) 0.0432(6) Uani d . 1 . .
    H H15 0.5699 0.9571 0.2336 0.052 Uiso calc R 1 . .
    C C15' 1.0688(2) 0.41225(12) 0.24621(13) 0.0398(6) Uani d . 1 . .
    H H15' 1.1002 0.4493 0.2619 0.048 Uiso calc R 1 . .
    C C16 0.4777(3) 0.87749(11) 0.15980(15) 0.0437(6) Uani d . 1 . .
    C C16' 1.0143(2) 0.53357(11) 0.18177(14) 0.0405(6) Uani d . 1 . .
    N N17 0.5778(2) 0.85535(11) 0.17464(15) 0.0609(7) Uani d . 1 . .
    N N17' 1.1115(2) 0.55515(11) 0.20191(14) 0.0582(6) Uani d . 1 . .
    C C18 0.2769(2) 0.80267(10) 0.09598(13) 0.0352(5) Uani d . 1 . .
    C C18' 0.8131(2) 0.60717(10) 0.10453(13) 0.0345(5) Uani d . 1 . .
    C C19 0.3670(2) 0.78254(11) 0.04386(14) 0.0385(5) Uani d . 1 . .
    C C19' 0.9112(2) 0.62789(10) 0.05739(14) 0.0374(5) Uani d . 1 . .
    C C20 0.3917(2) 0.72262(11) 0.03353(15) 0.0443(6) Uani d . 1 . .
    H H20 0.4535 0.7100 -0.0012 0.053 Uiso calc R 1 . .
    C C20' 0.9179(2) 0.68721(11) 0.03654(15) 0.0431(6) Uani d . 1 . .
    H H20' 0.9843 0.7005 0.0050 0.052 Uiso calc R 1 . .
    C C21 0.3230(2) 0.68196(11) 0.07557(14) 0.0408(6) Uani d . 1 . .
    C C21' 0.8242(3) 0.72612(11) 0.06352(16) 0.0452(6) Uani d . 1 . .
    C C22 0.2279(2) 0.70021(11) 0.12538(15) 0.0435(6) Uani d . 1 . .
    H H22 0.1788 0.6723 0.1517 0.052 Uiso calc R 1 . .
    C C22' 0.7246(3) 0.70747(11) 0.11006(16) 0.0491(7) Uani d . 1 . .
    H H22' 0.6617 0.7343 0.1274 0.059 Uiso calc R 1 . .
    C C23 0.2068(2) 0.76007(11) 0.13554(14) 0.0407(6) Uani d . 1 . .
    H H23 0.1439 0.7724 0.1698 0.049 Uiso calc R 1 . .
    C C23' 0.7198(3) 0.64864(11) 0.13038(15) 0.0447(6) Uani d . 1 . .
    H H23' 0.6531 0.6359 0.1621 0.054 Uiso calc R 1 . .
    C C24 -0.0246(2) 0.97866(10) 0.09155(13) 0.0354(5) Uani d . 1 . .
    C C24' 0.5145(2) 0.43164(10) 0.11345(13) 0.0326(5) Uani d . 1 . .
    C C25 -0.0512(3) 1.03740(11) 0.10704(16) 0.0472(6) Uani d . 1 . .
    H H25 0.0152 1.0620 0.1267 0.057 Uiso calc R 1 . .
    C C25' 0.4913(2) 0.37279(11) 0.13089(15) 0.0437(6) Uani d . 1 . .
    H H25' 0.5606 0.3483 0.1472 0.052 Uiso calc R 1 . .
    C C26 -0.1781(3) 1.05944(13) 0.09294(17) 0.0558(7) Uani d . 1 . .
    H H26 -0.1982 1.0990 0.1031 0.067 Uiso calc R 1 . .
    C C26' 0.3625(3) 0.35088(12) 0.12371(16) 0.0500(7) Uani d . 1 . .
    H H26' 0.3439 0.3114 0.1352 0.060 Uiso calc R 1 . .
    C C27 -0.2730(3) 1.02249(13) 0.06407(17) 0.0531(7) Uani d . 1 . .
    H H27 -0.3592 1.0361 0.0544 0.064 Uiso calc R 1 . .
    C C27' 0.2636(2) 0.38809(12) 0.09957(14) 0.0432(6) Uani d . 1 . .
    H H27' 0.1761 0.3747 0.0950 0.052 Uiso calc R 1 . .
    C C28 -0.2384(3) 0.96470(13) 0.04952(17) 0.0515(7) Uani d . 1 . .
    H H28 -0.3034 0.9396 0.0294 0.062 Uiso calc R 1 . .
    C C28' 0.2955(2) 0.44533(12) 0.08230(15) 0.0438(6) Uani d . 1 . .
    H H28' 0.2275 0.4702 0.0651 0.053 Uiso calc R 1 . .
    N N29 -0.1168(2) 0.94216(9) 0.06248(13) 0.0453(5) Uani d . 1 . .
    N N29' 0.41791(19) 0.46807(9) 0.08843(12) 0.0402(5) Uani d . 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
    Cl1 C19 . 1.731(3) ?
    Cl1' C19' . 1.735(2) ?
    Cl2 C21 . 1.729(2) ?
    Cl2' C21' . 1.729(3) ?
    N1 C6 . 1.338(3) ?
    N1 C2 . 1.350(3) ?
    N1' C6' . 1.332(3) ?
    N1' C2' . 1.346(3) ?
    C2 C3 . 1.409(3) ?
    C2 C7 . 1.457(3) ?
    C2' C3' . 1.403(3) ?
    C2' C7' . 1.462(3) ?
    C3 C4 . 1.400(3) ?
    C3 C16 . 1.435(3) ?
    C3' C4' . 1.406(3) ?
    C3' C16' . 1.434(3) ?
    C4 C5 . 1.377(3) ?
    C4 C18 . 1.487(3) ?
    C4' C5' . 1.379(3) ?
    C4' C18' . 1.486(3) ?
    C5 C6 . 1.385(3) ?
    C5 H5 . 0.9300 ?
    C5' C6' . 1.379(3) ?
    C5' H5' . 0.9300 ?
    C6 C24 . 1.489(3) ?
    C6' C24' . 1.487(3) ?
    C7 C15 . 1.376(3) ?
    C7 C8 . 1.447(3) ?
    C7' C15' . 1.375(3) ?
    C7' C8' . 1.442(3) ?
    C8 C9 . 1.396(3) ?
    C8 C13 . 1.406(3) ?
    C8' C9' . 1.390(4) ?
    C8' C13' . 1.406(3) ?
    C9 C10 . 1.368(4) ?
    C9 H9 . 0.9300 ?
    C9' C10' . 1.370(4) ?
    C9' H9' . 0.9300 ?
    C10 C11 . 1.394(4) ?
    C10 H10 . 0.9300 ?
    C10' C11' . 1.390(4) ?
    C10' H10' . 0.9300 ?
    C11 C12 . 1.370(4) ?
    C11 H11 . 0.9300 ?
    C11' C12' . 1.369(4) ?
    C11' H11' . 0.9300 ?
    C12 C13 . 1.380(4) ?
    C12 H12 . 0.9300 ?
    C12' C13' . 1.384(4) ?
    C12' H12' . 0.9300 ?
    C13 N14 . 1.365(3) ?
    C13' N14' . 1.365(3) ?
    N14 C15 . 1.339(3) ?
    N14 H14 . 0.73(3) ?
    N14' C15' . 1.344(3) ?
    N14' H14' . 0.86(3) ?
    C15 H15 . 0.9300 ?
    C15' H15' . 0.9300 ?
    C16 N17 . 1.147(3) ?
    C16' N17' . 1.142(3) ?
    C18 C19 . 1.387(3) ?
    C18 C23 . 1.389(3) ?
    C18' C19' . 1.389(3) ?
    C18' C23' . 1.404(3) ?
    C19 C20 . 1.380(3) ?
    C19' C20' . 1.385(3) ?
    C20 C21 . 1.376(4) ?
    C20 H20 . 0.9300 ?
    C20' C21' . 1.377(4) ?
    C20' H20' . 0.9300 ?
    C21 C22 . 1.380(4) ?
    C21' C22' . 1.378(4) ?
    C22 C23 . 1.373(3) ?
    C22 H22 . 0.9300 ?
    C22' C23' . 1.371(4) ?
    C22' H22' . 0.9300 ?
    C23 H23 . 0.9300 ?
    C23' H23' . 0.9300 ?
    C24 N29 . 1.335(3) ?
    C24 C25 . 1.374(3) ?
    C24' N29' . 1.339(3) ?
    C24' C25' . 1.378(3) ?
    C25 C26 . 1.386(4) ?
    C25 H25 . 0.9300 ?
    C25' C26' . 1.386(3) ?
    C25' H25' . 0.9300 ?
    C26 C27 . 1.358(4) ?
    C26 H26 . 0.9300 ?
    C26' C27' . 1.361(4) ?
    C26' H26' . 0.9300 ?
    C27 C28 . 1.369(4) ?
    C27 H27 . 0.9300 ?
    C27' C28' . 1.361(4) ?
    C27' H27' . 0.9300 ?
    C28 N29 . 1.337(3) ?
    C28 H28 . 0.9300 ?
    C28' N29' . 1.332(3) ?
    C28' H28' . 0.9300 ?
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
    C6 N1 C2 . . 119.67(19) ?
    C6' N1' C2' . . 119.48(19) ?
    N1 C2 C3 . . 120.1(2) ?
    N1 C2 C7 . . 115.6(2) ?
    C3 C2 C7 . . 124.3(2) ?
    N1' C2' C3' . . 120.5(2) ?
    N1' C2' C7' . . 113.9(2) ?
    C3' C2' C7' . . 125.6(2) ?
    C4 C3 C2 . . 120.0(2) ?
    C4 C3 C16 . . 117.8(2) ?
    C2 C3 C16 . . 122.3(2) ?
    C2' C3' C4' . . 119.7(2) ?
    C2' C3' C16' . . 121.2(2) ?
    C4' C3' C16' . . 119.1(2) ?
    C5 C4 C3 . . 118.2(2) ?
    C5 C4 C18 . . 120.2(2) ?
    C3 C4 C18 . . 121.6(2) ?
    C5' C4' C3' . . 117.7(2) ?
    C5' C4' C18' . . 118.3(2) ?
    C3' C4' C18' . . 124.0(2) ?
    C4 C5 C6 . . 119.4(2) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C4' C5' C6' . . 119.7(2) ?
    C4' C5' H5' . . 120.2 ?
    C6' C5' H5' . . 120.2 ?
    N1 C6 C5 . . 122.7(2) ?
    N1 C6 C24 . . 117.0(2) ?
    C5 C6 C24 . . 120.3(2) ?
    N1' C6' C5' . . 122.8(2) ?
    N1' C6' C24' . . 116.1(2) ?
    C5' C6' C24' . . 121.1(2) ?
    C15 C7 C8 . . 105.8(2) ?
    C15 C7 C2 . . 128.0(2) ?
    C8 C7 C2 . . 126.2(2) ?
    C15' C7' C8' . . 105.8(2) ?
    C15' C7' C2' . . 129.2(2) ?
    C8' C7' C2' . . 124.9(2) ?
    C9 C8 C13 . . 117.8(2) ?
    C9 C8 C7 . . 135.7(2) ?
    C13 C8 C7 . . 106.4(2) ?
    C9' C8' C13' . . 118.4(2) ?
    C9' C8' C7' . . 135.0(2) ?
    C13' C8' C7' . . 106.5(2) ?
    C10 C9 C8 . . 119.3(2) ?
    C10 C9 H9 . . 120.3 ?
    C8 C9 H9 . . 120.3 ?
    C10' C9' C8' . . 119.2(3) ?
    C10' C9' H9' . . 120.4 ?
    C8' C9' H9' . . 120.4 ?
    C9 C10 C11 . . 121.6(3) ?
    C9 C10 H10 . . 119.2 ?
    C11 C10 H10 . . 119.2 ?
    C9' C10' C11' . . 121.5(3) ?
    C9' C10' H10' . . 119.3 ?
    C11' C10' H10' . . 119.3 ?
    C12 C11 C10 . . 120.7(2) ?
    C12 C11 H11 . . 119.7 ?
    C10 C11 H11 . . 119.7 ?
    C12' C11' C10' . . 120.8(3) ?
    C12' C11' H11' . . 119.6 ?
    C10' C11' H11' . . 119.6 ?
    C11 C12 C13 . . 117.7(2) ?
    C11 C12 H12 . . 121.1 ?
    C13 C12 H12 . . 121.1 ?
    C11' C12' C13' . . 117.9(3) ?
    C11' C12' H12' . . 121.0 ?
    C13' C12' H12' . . 121.0 ?
    N14 C13 C12 . . 129.7(2) ?
    N14 C13 C8 . . 107.4(2) ?
    C12 C13 C8 . . 123.0(2) ?
    N14' C13' C12' . . 130.2(2) ?
    N14' C13' C8' . . 107.6(2) ?
    C12' C13' C8' . . 122.2(3) ?
    C15 N14 C13 . . 110.3(2) ?
    C15 N14 H14 . . 124(2) ?
    C13 N14 H14 . . 125(2) ?
    C15' N14' C13' . . 109.8(2) ?
    C15' N14' H14' . . 126(2) ?
    C13' N14' H14' . . 124.5(19) ?
    N14 C15 C7 . . 110.1(2) ?
    N14 C15 H15 . . 125.0 ?
    C7 C15 H15 . . 125.0 ?
    N14' C15' C7' . . 110.3(2) ?
    N14' C15' H15' . . 124.9 ?
    C7' C15' H15' . . 124.9 ?
    N17 C16 C3 . . 178.6(3) ?
    N17' C16' C3' . . 178.0(3) ?
    C19 C18 C23 . . 117.5(2) ?
    C19 C18 C4 . . 122.9(2) ?
    C23 C18 C4 . . 119.6(2) ?
    C19' C18' C23' . . 117.5(2) ?
    C19' C18' C4' . . 124.2(2) ?
    C23' C18' C4' . . 118.0(2) ?
    C20 C19 C18 . . 121.9(2) ?
    C20 C19 Cl1 . . 117.41(19) ?
    C18 C19 Cl1 . . 120.71(19) ?
    C20' C19' C18' . . 121.6(2) ?
    C20' C19' Cl1' . . 117.12(19) ?
    C18' C19' Cl1' . . 121.02(18) ?
    C21 C20 C19 . . 118.7(2) ?
    C21 C20 H20 . . 120.7 ?
    C19 C20 H20 . . 120.7 ?
    C21' C20' C19' . . 118.6(2) ?
    C21' C20' H20' . . 120.7 ?
    C19' C20' H20' . . 120.7 ?
    C20 C21 C22 . . 121.0(2) ?
    C20 C21 Cl2 . . 119.0(2) ?
    C22 C21 Cl2 . . 119.9(2) ?
    C20' C21' C22' . . 121.8(2) ?
    C20' C21' Cl2' . . 118.7(2) ?
    C22' C21' Cl2' . . 119.5(2) ?
    C23 C22 C21 . . 119.1(2) ?
    C23 C22 H22 . . 120.5 ?
    C21 C22 H22 . . 120.5 ?
    C23' C22' C21' . . 118.9(2) ?
    C23' C22' H22' . . 120.6 ?
    C21' C22' H22' . . 120.6 ?
    C22 C23 C18 . . 121.7(2) ?
    C22 C23 H23 . . 119.2 ?
    C18 C23 H23 . . 119.2 ?
    C22' C23' C18' . . 121.6(3) ?
    C22' C23' H23' . . 119.2 ?
    C18' C23' H23' . . 119.2 ?
    N29 C24 C25 . . 122.1(2) ?
    N29 C24 C6 . . 115.8(2) ?
    C25 C24 C6 . . 122.0(2) ?
    N29' C24' C25' . . 122.5(2) ?
    N29' C24' C6' . . 115.98(19) ?
    C25' C24' C6' . . 121.5(2) ?
    C24 C25 C26 . . 119.1(2) ?
    C24 C25 H25 . . 120.4 ?
    C26 C25 H25 . . 120.4 ?
    C24' C25' C26' . . 118.7(2) ?
    C24' C25' H25' . . 120.7 ?
    C26' C25' H25' . . 120.7 ?
    C27 C26 C25 . . 119.2(3) ?
    C27 C26 H26 . . 120.4 ?
    C25 C26 H26 . . 120.4 ?
    C27' C26' C25' . . 119.0(2) ?
    C27' C26' H26' . . 120.5 ?
    C25' C26' H26' . . 120.5 ?
    C26 C27 C28 . . 118.2(2) ?
    C26 C27 H27 . . 120.9 ?
    C28 C27 H27 . . 120.9 ?
    C28' C27' C26' . . 118.6(2) ?
    C28' C27' H27' . . 120.7 ?
    C26' C27' H27' . . 120.7 ?
    N29 C28 C27 . . 124.0(3) ?
    N29 C28 H28 . . 118.0 ?
    C27 C28 H28 . . 118.0 ?
    N29' C28' C27' . . 124.2(2) ?
    N29' C28' H28' . . 117.9 ?
    C27' C28' H28' . . 117.9 ?
    C24 N29 C28 . . 117.4(2) ?
    C28' N29' C24' . . 117.0(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
    C6 N1 C2 C3 . . . . -0.1(3) ?
    C6 N1 C2 C7 . . . . 179.2(2) ?
    C6' N1' C2' C3' . . . . 0.6(3) ?
    C6' N1' C2' C7' . . . . -177.6(2) ?
    N1 C2 C3 C4 . . . . 0.8(3) ?
    C7 C2 C3 C4 . . . . -178.5(2) ?
    N1 C2 C3 C16 . . . . -179.2(2) ?
    C7 C2 C3 C16 . . . . 1.6(4) ?
    N1' C2' C3' C4' . . . . -3.8(3) ?
    C7' C2' C3' C4' . . . . 174.2(2) ?
    N1' C2' C3' C16' . . . . 175.0(2) ?
    C7' C2' C3' C16' . . . . -7.0(4) ?
    C2 C3 C4 C5 . . . . -1.1(3) ?
    C16 C3 C4 C5 . . . . 178.9(2) ?
    C2 C3 C4 C18 . . . . 180.0(2) ?
    C16 C3 C4 C18 . . . . -0.1(3) ?
    C2' C3' C4' C5' . . . . 3.5(3) ?
    C16' C3' C4' C5' . . . . -175.4(2) ?
    C2' C3' C4' C18' . . . . -177.8(2) ?
    C16' C3' C4' C18' . . . . 3.4(4) ?
    C3 C4 C5 C6 . . . . 0.7(3) ?
    C18 C4 C5 C6 . . . . 179.7(2) ?
    C3' C4' C5' C6' . . . . -0.2(3) ?
    C18' C4' C5' C6' . . . . -179.0(2) ?
    C2 N1 C6 C5 . . . . -0.3(3) ?
    C2 N1 C6 C24 . . . . 178.4(2) ?
    C4 C5 C6 N1 . . . . 0.0(4) ?
    C4 C5 C6 C24 . . . . -178.7(2) ?
    C2' N1' C6' C5' . . . . 2.9(3) ?
    C2' N1' C6' C24' . . . . -175.3(2) ?
    C4' C5' C6' N1' . . . . -3.1(4) ?
    C4' C5' C6' C24' . . . . 175.0(2) ?
    N1 C2 C7 C15 . . . . 163.0(2) ?
    C3 C2 C7 C15 . . . . -17.8(4) ?
    N1 C2 C7 C8 . . . . -15.6(3) ?
    C3 C2 C7 C8 . . . . 163.7(2) ?
    N1' C2' C7' C15' . . . . -156.2(2) ?
    C3' C2' C7' C15' . . . . 25.6(4) ?
    N1' C2' C7' C8' . . . . 21.3(3) ?
    C3' C2' C7' C8' . . . . -156.9(2) ?
    C15 C7 C8 C9 . . . . 179.0(3) ?
    C2 C7 C8 C9 . . . . -2.2(4) ?
    C15 C7 C8 C13 . . . . 0.5(3) ?
    C2 C7 C8 C13 . . . . 179.3(2) ?
    C15' C7' C8' C9' . . . . -177.3(3) ?
    C2' C7' C8' C9' . . . . 4.7(4) ?
    C15' C7' C8' C13' . . . . 0.1(3) ?
    C2' C7' C8' C13' . . . . -177.9(2) ?
    C13 C8 C9 C10 . . . . -0.6(4) ?
    C7 C8 C9 C10 . . . . -179.0(3) ?
    C13' C8' C9' C10' . . . . 1.1(4) ?
    C7' C8' C9' C10' . . . . 178.3(3) ?
    C8 C9 C10 C11 . . . . -0.1(4) ?
    C8' C9' C10' C11' . . . . 0.0(5) ?
    C9 C10 C11 C12 . . . . 1.2(4) ?
    C9' C10' C11' C12' . . . . -1.2(5) ?
    C10 C11 C12 C13 . . . . -1.5(4) ?
    C10' C11' C12' C13' . . . . 1.2(5) ?
    C11 C12 C13 N14 . . . . -179.4(3) ?
    C11 C12 C13 C8 . . . . 0.8(4) ?
    C9 C8 C13 N14 . . . . -179.6(2) ?
    C7 C8 C13 N14 . . . . -0.8(3) ?
    C9 C8 C13 C12 . . . . 0.2(4) ?
    C7 C8 C13 C12 . . . . 179.0(2) ?
    C11' C12' C13' N14' . . . . -179.3(3) ?
    C11' C12' C13' C8' . . . . 0.0(4) ?
    C9' C8' C13' N14' . . . . 178.4(2) ?
    C7' C8' C13' N14' . . . . 0.4(3) ?
    C9' C8' C13' C12' . . . . -1.1(4) ?
    C7' C8' C13' C12' . . . . -179.1(2) ?
    C12 C13 N14 C15 . . . . -179.0(3) ?
    C8 C13 N14 C15 . . . . 0.8(3) ?
    C12' C13' N14' C15' . . . . 178.6(3) ?
    C8' C13' N14' C15' . . . . -0.8(3) ?
    C13 N14 C15 C7 . . . . -0.5(3) ?
    C8 C7 C15 N14 . . . . 0.0(3) ?
    C2 C7 C15 N14 . . . . -178.8(2) ?
    C13' N14' C15' C7' . . . . 0.9(3) ?
    C8' C7' C15' N14' . . . . -0.6(3) ?
    C2' C7' C15' N14' . . . . 177.3(2) ?
    C4 C3 C16 N17 . . . . -28(12) ?
    C2 C3 C16 N17 . . . . 152(12) ?
    C2' C3' C16' N17' . . . . -103(8) ?
    C4' C3' C16' N17' . . . . 76(8) ?
    C5 C4 C18 C19 . . . . 114.7(3) ?
    C3 C4 C18 C19 . . . . -66.4(3) ?
    C5 C4 C18 C23 . . . . -64.7(3) ?
    C3 C4 C18 C23 . . . . 114.2(3) ?
    C5' C4' C18' C19' . . . . -121.2(3) ?
    C3' C4' C18' C19' . . . . 60.1(3) ?
    C5' C4' C18' C23' . . . . 52.8(3) ?
    C3' C4' C18' C23' . . . . -126.0(3) ?
    C23 C18 C19 C20 . . . . -3.0(4) ?
    C4 C18 C19 C20 . . . . 177.6(2) ?
    C23 C18 C19 Cl1 . . . . 175.85(18) ?
    C4 C18 C19 Cl1 . . . . -3.6(3) ?
    C23' C18' C19' C20' . . . . 0.2(3) ?
    C4' C18' C19' C20' . . . . 174.2(2) ?
    C23' C18' C19' Cl1' . . . . -174.10(18) ?
    C4' C18' C19' Cl1' . . . . -0.1(3) ?
    C18 C19 C20 C21 . . . . 1.0(4) ?
    Cl1 C19 C20 C21 . . . . -177.85(19) ?
    C18' C19' C20' C21' . . . . -0.1(4) ?
    Cl1' C19' C20' C21' . . . . 174.42(19) ?
    C19 C20 C21 C22 . . . . 2.2(4) ?
    C19 C20 C21 Cl2 . . . . -176.34(19) ?
    C19' C20' C21' C22' . . . . -0.3(4) ?
    C19' C20' C21' Cl2' . . . . 179.25(19) ?
    C20 C21 C22 C23 . . . . -3.3(4) ?
    Cl2 C21 C22 C23 . . . . 175.3(2) ?
    C20' C21' C22' C23' . . . . 0.6(4) ?
    Cl2' C21' C22' C23' . . . . -179.0(2) ?
    C21 C22 C23 C18 . . . . 1.2(4) ?
    C19 C18 C23 C22 . . . . 1.8(4) ?
    C4 C18 C23 C22 . . . . -178.7(2) ?
    C21' C22' C23' C18' . . . . -0.5(4) ?
    C19' C18' C23' C22' . . . . 0.1(4) ?
    C4' C18' C23' C22' . . . . -174.3(2) ?
    N1 C6 C24 N29 . . . . -180.0(2) ?
    C5 C6 C24 N29 . . . . -1.2(3) ?
    N1 C6 C24 C25 . . . . -1.1(3) ?
    C5 C6 C24 C25 . . . . 177.7(2) ?
    N1' C6' C24' N29' . . . . 175.1(2) ?
    C5' C6' C24' N29' . . . . -3.0(3) ?
    N1' C6' C24' C25' . . . . -2.1(3) ?
    C5' C6' C24' C25' . . . . 179.7(2) ?
    N29 C24 C25 C26 . . . . 0.8(4) ?
    C6 C24 C25 C26 . . . . -178.0(2) ?
    N29' C24' C25' C26' . . . . -1.4(4) ?
    C6' C24' C25' C26' . . . . 175.7(2) ?
    C24 C25 C26 C27 . . . . -0.1(4) ?
    C24' C25' C26' C27' . . . . 0.1(4) ?
    C25 C26 C27 C28 . . . . -0.5(4) ?
    C25' C26' C27' C28' . . . . 1.0(4) ?
    C26 C27 C28 N29 . . . . 0.5(5) ?
    C26' C27' C28' N29' . . . . -1.0(4) ?
    C25 C24 N29 C28 . . . . -0.8(4) ?
    C6 C24 N29 C28 . . . . 178.0(2) ?
    C27 C28 N29 C24 . . . . 0.2(4) ?
    C27' C28' N29' C24' . . . . -0.2(4) ?
    C25' C24' N29' C28' . . . . 1.4(4) ?
    C6' C24' N29' C28' . . . . -175.9(2) ?
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
    C9 H9 N1 1 0.93 2.55 3.052(3) 114.0
    C9' H9' N1' 1 0.93 2.50 2.993(3) 113.1
    C15 H15 N17 1 0.93 2.52 3.280(4) 139.4
    C15' H15' N17' 1 0.93 2.61 3.334(3) 134.9
    C5 H5 Cl2' 1_455 0.93 2.81 3.727(3) 169.0
    N14 H14 N17' 2_755 0.73(3) 2.36(3) 3.075(3) 166(3)
    N14' H14' N17 2_745 0.86(3) 2.33(3) 3.157(3) 160(3)
    C15' H15' Cg5 1_555 0.93 3.1253 3.798(3) 130.75
    C23 H23 Cg8 1_555 0.93 2.7553 3.620(3) 154.99
    C23' H23' Cg7 1_555 0.93 2.8284 3.633(3) 145.42

