#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/65/2016581.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016581
loop_
_publ_author_name
'Neuba, Adam'
'Akin, Enver'
'Herres-Pawlis, Sonja'
'Flörke, Ulrich'
'Henkel, Gerald'
_publ_section_title
;Rare examples of base pairing via a protonated pyridine N atom in two
 salts of
 N²,N⁶-bis(1,3-dimethylimidazolin-2-ylidene)pyridine-2,6-diamine
;
_journal_coeditor_code           EM3010
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m194
_journal_page_last               m197
_journal_paper_doi               10.1107/S0108270108007567
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H24 N7 +, Cl O4 -'
_chemical_formula_moiety         'C15 H24 N7 +, Cl O4 -'
_chemical_formula_sum            'C15 H24 Cl N7 O4'
_chemical_formula_weight         401.86
_chemical_name_systematic
;
2,6-bis(1,3-dimethylimidazolin-2-ylideneamino)pyridinium perchlorate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.979(2)
_cell_angle_beta                 93.739(2)
_cell_angle_gamma                115.549(2)
_cell_formula_units_Z            4
_cell_length_a                   10.4399(11)
_cell_length_b                   12.0367(13)
_cell_length_c                   16.6200(18)
_cell_measurement_reflns_used    1687
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.37
_cell_volume                     1859.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_sigmaI/netI    0.1953
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18737
_diffrn_reflns_theta_full        28.07
_diffrn_reflns_theta_max         28.07
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         1699
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_correction_T_min  0.9196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.445
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         8994
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.835
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.0644
_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/[σ²(Fo²)+(0.0481P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                3686
_reflns_number_total             8994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            em3010.cif
_cod_data_source_block           I
_cod_database_code               2016581
_cod_database_fobs_code          2016581
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N N1 0.4193(3) 0.7986(3) 0.30531(18) 0.0298(7) Uani d . 1 . .
N N2 0.2195(3) 0.7556(3) 0.22891(18) 0.0361(8) Uani d . 1 . .
N N3 0.1938(3) 0.6525(3) 0.34145(17) 0.0257(7) Uani d . 1 . .
N N4 0.1482(3) 0.5201(3) 0.43559(17) 0.0233(7) Uani d D 1 . .
H H4 0.085(3) 0.547(3) 0.448(2) 0.031(7) Uiso d D 1 . .
N N5 0.0428(3) 0.3750(3) 0.51835(18) 0.0265(7) Uani d . 1 . .
N N7 0.1384(3) 0.2929(3) 0.61883(18) 0.0306(8) Uani d . 1 . .
N N6 -0.0726(3) 0.1735(2) 0.55170(18) 0.0279(7) Uani d . 1 . .
C C1 0.5115(4) 0.8253(3) 0.3806(2) 0.0355(10) Uani d . 1 . .
H H10D 0.4550 0.7809 0.4218 0.053 Uiso calc R 1 . .
H H10E 0.5563 0.9150 0.3997 0.053 Uiso calc R 1 . .
H H10F 0.5859 0.7979 0.3712 0.053 Uiso calc R 1 . .
C C2 0.4649(4) 0.8748(3) 0.2406(2) 0.0352(10) Uani d . 1 . .
H H10I 0.5195 0.8457 0.2046 0.042 Uiso calc R 1 . .
H H10J 0.5249 0.9633 0.2634 0.042 Uiso calc R 1 . .
C C3 0.3254(4) 0.8573(3) 0.1949(2) 0.0394(10) Uani d . 1 . .
H H10G 0.3111 0.9335 0.2049 0.047 Uiso calc R 1 . .
H H10H 0.3223 0.8350 0.1355 0.047 Uiso calc R 1 . .
C C4 0.0690(4) 0.6979(4) 0.1986(2) 0.0385(10) Uani d . 1 . .
H H10A 0.0161 0.6350 0.2323 0.058 Uiso calc R 1 . .
H H10B 0.0550 0.6582 0.1421 0.058 Uiso calc R 1 . .
H H10C 0.0336 0.7614 0.2008 0.058 Uiso calc R 1 . .
C C5 0.2768(4) 0.7299(3) 0.2956(2) 0.0264(8) Uani d . 1 . .
C C6 0.2329(4) 0.5754(3) 0.3792(2) 0.0230(8) Uani d . 1 . .
C C7 0.3394(4) 0.5383(3) 0.3625(2) 0.0257(8) Uani d . 1 . .
H H10K 0.4050 0.5766 0.3254 0.031 Uiso calc R 1 . .
C C8 0.3470(4) 0.4450(3) 0.4009(2) 0.0298(9) Uani d . 1 . .
H H10L 0.4193 0.4197 0.3897 0.036 Uiso calc R 1 . .
C C9 0.2543(4) 0.3870(3) 0.4548(2) 0.0295(9) Uani d . 1 . .
H H10M 0.2609 0.3215 0.4793 0.035 Uiso calc R 1 . .
C C10 0.1504(4) 0.4263(3) 0.4730(2) 0.0240(8) Uani d . 1 . .
C C11 0.0397(4) 0.2857(3) 0.5609(2) 0.0241(8) Uani d . 1 . .
C C12 -0.2082(4) 0.1369(3) 0.5029(2) 0.0355(10) Uani d . 1 . .
H H11D -0.2056 0.2073 0.4771 0.053 Uiso calc R 1 . .
H H11E -0.2850 0.1116 0.5379 0.053 Uiso calc R 1 . .
H H11F -0.2258 0.0669 0.4608 0.053 Uiso calc R 1 . .
C C13 -0.0588(4) 0.1033(3) 0.6152(2) 0.0304(9) Uani d . 1 . .
H H11I -0.0864 0.0155 0.5928 0.036 Uiso calc R 1 . .
H H11J -0.1176 0.1060 0.6591 0.036 Uiso calc R 1 . .
C C14 0.1006(4) 0.1726(3) 0.6458(2) 0.0361(10) Uani d . 1 . .
H H11G 0.1182 0.1810 0.7058 0.043 Uiso calc R 1 . .
H H11H 0.1544 0.1304 0.6207 0.043 Uiso calc R 1 . .
C C15 0.2695(4) 0.4028(3) 0.6505(3) 0.0434(11) Uani d . 1 . .
H H11A 0.3502 0.3961 0.6273 0.065 Uiso calc R 1 . .
H H11B 0.2845 0.4100 0.7100 0.065 Uiso calc R 1 . .
H H11C 0.2624 0.4768 0.6355 0.065 Uiso calc R 1 . .
N N1B 0.8872(3) 0.8037(2) 0.79216(17) 0.0256(7) Uani d . 1 . .
N N2B 1.0488(3) 0.7664(3) 0.73194(19) 0.0370(8) Uani d . 1 . .
N N3B 0.9617(3) 0.6540(3) 0.83672(17) 0.0241(7) Uani d . 1 . .
N N4B 0.8704(3) 0.5182(2) 0.92639(17) 0.0210(7) Uani d D 1 . .
H H4B 0.9621(14) 0.547(3) 0.9457(19) 0.031(7) Uiso d D 1 . .
N N5B 0.8266(3) 0.3693(2) 1.00946(17) 0.0247(7) Uani d . 1 . .
N N6B 0.7360(3) 0.1658(2) 1.04175(17) 0.0248(7) Uani d . 1 . .
N N7B 0.6413(3) 0.2831(2) 1.09544(17) 0.0252(7) Uani d . 1 . .
C C1B 0.8148(4) 0.8241(3) 0.8596(2) 0.0302(9) Uani d . 1 . .
H H20D 0.8269 0.7798 0.9035 0.045 Uiso calc R 1 . .
H H20E 0.7127 0.7931 0.8410 0.045 Uiso calc R 1 . .
H H20F 0.8559 0.9134 0.8798 0.045 Uiso calc R 1 . .
C C2B 0.9248(4) 0.8871(3) 0.7314(2) 0.0326(9) Uani d . 1 . .
H H20I 0.9636 0.9750 0.7571 0.039 Uiso calc R 1 . .
H H20J 0.8408 0.8677 0.6914 0.039 Uiso calc R 1 . .
C C3B 1.0391(4) 0.8621(3) 0.6907(2) 0.0341(9) Uani d . 1 . .
H H20G 1.0093 0.8329 0.6316 0.041 Uiso calc R 1 . .
H H20H 1.1317 0.9377 0.6988 0.041 Uiso calc R 1 . .
C C4B 1.1335(4) 0.7043(3) 0.7069(2) 0.0370(10) Uani d . 1 . .
H H20A 1.1239 0.6412 0.7420 0.056 Uiso calc R 1 . .
H H20B 1.2341 0.7652 0.7115 0.056 Uiso calc R 1 . .
H H20C 1.1003 0.6641 0.6502 0.056 Uiso calc R 1 . .
C C5B 0.9615(4) 0.7355(3) 0.7895(2) 0.0240(8) Uani d . 1 . .
C C6B 0.8430(4) 0.5760(3) 0.8656(2) 0.0223(8) Uani d . 1 . .
C C7B 0.7009(4) 0.5381(3) 0.8373(2) 0.0239(8) Uani d . 1 . .
H H20K 0.6752 0.5774 0.7968 0.029 Uiso calc R 1 . .
C C8B 0.5974(4) 0.4427(3) 0.8687(2) 0.0268(8) Uani d . 1 . .
H H20L 0.4999 0.4174 0.8492 0.032 Uiso calc R 1 . .
C C9B 0.6288(4) 0.3821(3) 0.9271(2) 0.0242(8) Uani d . 1 . .
H H20M 0.5549 0.3148 0.9464 0.029 Uiso calc R 1 . .
C C10B 0.7720(4) 0.4219(3) 0.9572(2) 0.0218(8) Uani d . 1 . .
C C11B 0.7369(3) 0.2783(3) 1.0469(2) 0.0222(8) Uani d . 1 . .
C C12B 0.8414(4) 0.1344(3) 1.0064(2) 0.0283(9) Uani d . 1 . .
H H21A 0.9021 0.2019 0.9780 0.043 Uiso calc R 1 . .
H H21B 0.7928 0.0573 0.9676 0.043 Uiso calc R 1 . .
H H21C 0.9007 0.1226 1.0497 0.043 Uiso calc R 1 . .
C C13B 0.6481(4) 0.0937(3) 1.0995(2) 0.0260(8) Uani d . 1 . .
H H21G 0.7075 0.0960 1.1492 0.031 Uiso calc R 1 . .
H H21H 0.5885 0.0060 1.0748 0.031 Uiso calc R 1 . .
C C14B 0.5561(4) 0.1615(3) 1.1184(2) 0.0284(9) Uani d . 1 . .
H H21I 0.4610 0.1192 1.0853 0.034 Uiso calc R 1 . .
H H21J 0.5433 0.1679 1.1769 0.034 Uiso calc R 1 . .
C C15B 0.6087(4) 0.3876(3) 1.1160(2) 0.0341(9) Uani d . 1 . .
H H21D 0.6852 0.4635 1.1023 0.051 Uiso calc R 1 . .
H H21E 0.6013 0.3984 1.1745 0.051 Uiso calc R 1 . .
H H21F 0.5178 0.3716 1.0851 0.051 Uiso calc R 1 . .
Cl Cl1 0.52136(11) 0.80821(9) 0.61828(6) 0.0374(3) Uani d D 1 . .
O O11 0.5772(7) 0.8296(7) 0.7004(4) 0.066(2) Uiso d PD 0.50 A 1
O O12 0.5313(6) 0.7574(5) 0.6928(3) 0.0422(15) Uiso d PD 0.50 A 2
O O2 0.4741(4) 0.9008(3) 0.6159(3) 0.0993(14) Uani d . 1 A .
O O3 0.4058(3) 0.6962(3) 0.5771(2) 0.0839(11) Uani d . 1 A .
O O4 0.6386(3) 0.8309(3) 0.57352(17) 0.0496(8) Uani d . 1 A .
Cl Cl2 0.21733(10) 0.18930(9) 0.90326(6) 0.0367(3) Uani d D 1 . .
O O51 0.2283(6) 0.3116(5) 0.9423(3) 0.0447(14) Uiso d PD 0.50 B 3
O O61 0.2643(6) 0.2127(6) 0.8281(3) 0.0483(15) Uiso d PD 0.50 B 3
O O52 0.2469(8) 0.3025(7) 0.8784(5) 0.092(2) Uiso d PD 0.50 B 4
O O62 0.2388(7) 0.1222(6) 0.8275(4) 0.0695(19) Uiso d PD 0.50 B 4
O O7 0.0740(3) 0.1098(3) 0.90689(19) 0.0625(9) Uani d . 1 B .
O O8 0.3122(3) 0.1735(3) 0.96106(17) 0.0539(8) Uani d . 1 B .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 124.8(3) ?
C5 N1 C2 111.4(3) ?
C1 N1 C2 121.3(3) ?
C5 N2 C4 124.9(3) ?
C5 N2 C3 111.9(3) ?
C4 N2 C3 123.0(3) ?
C5 N3 C6 122.4(3) ?
C10 N4 C6 126.0(3) ?
C10 N4 H4 118(2) ?
C6 N4 H4 116(2) ?
C11 N5 C10 119.5(3) ?
C11 N7 C15 126.0(3) ?
C11 N7 C14 111.0(3) ?
C15 N7 C14 123.0(3) ?
C11 N6 C12 125.8(3) ?
C11 N6 C13 110.6(3) ?
C12 N6 C13 121.3(3) ?
N1 C1 H10D 109.5 ?
N1 C1 H10E 109.5 ?
H10D C1 H10E 109.5 ?
N1 C1 H10F 109.5 ?
H10D C1 H10F 109.5 ?
H10E C1 H10F 109.5 ?
N1 C2 C3 103.6(3) ?
N1 C2 H10I 111.0 ?
C3 C2 H10I 111.0 ?
N1 C2 H10J 111.0 ?
C3 C2 H10J 111.0 ?
H10I C2 H10J 109.0 ?
N2 C3 C2 102.7(3) ?
N2 C3 H10G 111.2 ?
C2 C3 H10G 111.2 ?
N2 C3 H10H 111.2 ?
C2 C3 H10H 111.2 ?
H10G C3 H10H 109.1 ?
N2 C4 H10A 109.5 ?
N2 C4 H10B 109.5 ?
H10A C4 H10B 109.5 ?
N2 C4 H10C 109.5 ?
H10A C4 H10C 109.5 ?
H10B C4 H10C 109.5 ?
N3 C5 N1 130.3(3) y
N3 C5 N2 120.5(3) y
N1 C5 N2 109.1(3) y
N4 C6 N3 114.2(3) ?
N4 C6 C7 116.9(3) ?
N3 C6 C7 128.6(3) ?
C8 C7 C6 118.5(3) ?
C8 C7 H10K 120.8 ?
C6 C7 H10K 120.8 ?
C9 C8 C7 122.7(3) ?
C9 C8 H10L 118.7 ?
C7 C8 H10L 118.7 ?
C8 C9 C10 118.7(3) ?
C8 C9 H10M 120.6 ?
C10 C9 H10M 120.6 ?
N5 C10 N4 115.0(3) ?
N5 C10 C9 127.7(3) ?
N4 C10 C9 117.0(3) ?
N7 C11 N5 127.7(3) y
N7 C11 N6 109.9(3) y
N5 C11 N6 122.3(3) y
N6 C12 H11D 109.5 ?
N6 C12 H11E 109.5 ?
H11D C12 H11E 109.5 ?
N6 C12 H11F 109.5 ?
H11D C12 H11F 109.5 ?
H11E C12 H11F 109.5 ?
N6 C13 C14 102.0(3) ?
N6 C13 H11I 111.4 ?
C14 C13 H11I 111.4 ?
N6 C13 H11J 111.4 ?
C14 C13 H11J 111.4 ?
H11I C13 H11J 109.2 ?
N7 C14 C13 101.8(3) ?
N7 C14 H11G 111.4 ?
C13 C14 H11G 111.4 ?
N7 C14 H11H 111.4 ?
C13 C14 H11H 111.4 ?
H11G C14 H11H 109.3 ?
N7 C15 H11A 109.5 ?
N7 C15 H11B 109.5 ?
H11A C15 H11B 109.5 ?
N7 C15 H11C 109.5 ?
H11A C15 H11C 109.5 ?
H11B C15 H11C 109.5 ?
C5B N1B C1B 126.0(3) ?
C5B N1B C2B 110.9(3) ?
C1B N1B C2B 120.4(3) ?
C5B N2B C3B 112.4(3) ?
C5B N2B C4B 125.0(3) ?
C3B N2B C4B 122.3(3) ?
C5B N3B C6B 122.7(3) ?
C10B N4B C6B 125.9(3) ?
C10B N4B H4B 119(2) ?
C6B N4B H4B 115(2) ?
C11B N5B C10B 119.1(3) ?
C11B N6B C12B 124.9(3) ?
C11B N6B C13B 110.5(3) ?
C12B N6B C13B 121.5(3) ?
C11B N7B C15B 127.0(3) ?
C11B N7B C14B 110.9(3) ?
C15B N7B C14B 121.7(3) ?
N1B C1B H20D 109.5 ?
N1B C1B H20E 109.5 ?
H20D C1B H20E 109.5 ?
N1B C1B H20F 109.5 ?
H20D C1B H20F 109.5 ?
H20E C1B H20F 109.5 ?
N1B C2B C3B 103.5(3) ?
N1B C2B H20I 111.1 ?
C3B C2B H20I 111.1 ?
N1B C2B H20J 111.1 ?
C3B C2B H20J 111.1 ?
H20I C2B H20J 109.0 ?
N2B C3B C2B 103.2(3) ?
N2B C3B H20G 111.1 ?
C2B C3B H20G 111.1 ?
N2B C3B H20H 111.1 ?
C2B C3B H20H 111.1 ?
H20G C3B H20H 109.1 ?
N2B C4B H20A 109.5 ?
N2B C4B H20B 109.5 ?
H20A C4B H20B 109.5 ?
N2B C4B H20C 109.5 ?
H20A C4B H20C 109.5 ?
H20B C4B H20C 109.5 ?
N3B C5B N2B 120.9(3) y
N3B C5B N1B 129.1(3) y
N2B C5B N1B 109.9(3) y
N3B C6B N4B 113.5(3) ?
N3B C6B C7B 129.4(3) ?
N4B C6B C7B 116.8(3) ?
C8B C7B C6B 119.0(3) ?
C8B C7B H20K 120.5 ?
C6B C7B H20K 120.5 ?
C7B C8B C9B 122.8(3) ?
C7B C8B H20L 118.6 ?
C9B C8B H20L 118.6 ?
C8B C9B C10B 118.4(3) ?
C8B C9B H20M 120.8 ?
C10B C9B H20M 120.8 ?
N4B C10B N5B 115.0(3) ?
N4B C10B C9B 117.0(3) ?
N5B C10B C9B 127.7(3) ?
N7B C11B N5B 127.9(3) y
N7B C11B N6B 109.9(3) y
N5B C11B N6B 122.2(3) y
N6B C12B H21A 109.5 ?
N6B C12B H21B 109.5 ?
H21A C12B H21B 109.5 ?
N6B C12B H21C 109.5 ?
H21A C12B H21C 109.5 ?
H21B C12B H21C 109.5 ?
N6B C13B C14B 102.0(3) ?
N6B C13B H21G 111.4 ?
C14B C13B H21G 111.4 ?
N6B C13B H21H 111.4 ?
C14B C13B H21H 111.4 ?
H21G C13B H21H 109.2 ?
N7B C14B C13B 101.8(3) ?
N7B C14B H21I 111.4 ?
C13B C14B H21I 111.4 ?
N7B C14B H21J 111.4 ?
C13B C14B H21J 111.4 ?
H21I C14B H21J 109.3 ?
N7B C15B H21D 109.5 ?
N7B C15B H21E 109.5 ?
H21D C15B H21E 109.5 ?
N7B C15B H21F 109.5 ?
H21D C15B H21F 109.5 ?
H21E C15B H21F 109.5 ?
O11 Cl1 O2 101.5(3) ?
O11 Cl1 O4 105.7(3) ?
O2 Cl1 O4 111.7(2) ?
O11 Cl1 O3 125.7(3) ?
O2 Cl1 O3 105.6(2) ?
O4 Cl1 O3 106.4(2) ?
O2 Cl1 O12 121.6(3) ?
O4 Cl1 O12 113.7(2) ?
O3 Cl1 O12 94.8(3) ?
O52 Cl2 O7 117.1(3) ?
O61 Cl2 O7 119.3(3) ?
O52 Cl2 O8 122.3(4) ?
O61 Cl2 O8 115.7(3) ?
O7 Cl2 O8 112.83(18) ?
O61 Cl2 O51 104.1(3) ?
O7 Cl2 O51 101.8(2) ?
O8 Cl2 O51 99.4(3) ?
O52 Cl2 O62 100.0(4) ?
O7 Cl2 O62 98.5(3) ?
O8 Cl2 O62 99.3(3) ?
O51 Cl2 O62 144.4(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.342(4) y
N1 C1 1.445(4) ?
N1 C2 1.455(4) ?
N2 C5 1.352(4) y
N2 C4 1.445(4) ?
N2 C3 1.449(4) ?
N3 C5 1.318(4) y
N3 C6 1.355(4) y
N4 C10 1.352(4) y
N4 C6 1.354(4) y
N4 H4 0.881(10) ?
N5 C11 1.337(4) y
N5 C10 1.350(4) y
N7 C11 1.331(4) y
N7 C15 1.449(4) ?
N7 C14 1.456(4) ?
N6 C11 1.338(4) y
N6 C12 1.447(4) ?
N6 C13 1.456(4) ?
C1 H10D 0.9800 ?
C1 H10E 0.9800 ?
C1 H10F 0.9800 ?
C2 C3 1.517(5) ?
C2 H10I 0.9900 ?
C2 H10J 0.9900 ?
C3 H10G 0.9900 ?
C3 H10H 0.9900 ?
C4 H10A 0.9800 ?
C4 H10B 0.9800 ?
C4 H10C 0.9800 ?
C6 C7 1.398(4) ?
C7 C8 1.377(5) ?
C7 H10K 0.9500 ?
C8 C9 1.373(5) ?
C8 H10L 0.9500 ?
C9 C10 1.395(4) ?
C9 H10M 0.9500 ?
C12 H11D 0.9800 ?
C12 H11E 0.9800 ?
C12 H11F 0.9800 ?
C13 C14 1.525(5) ?
C13 H11I 0.9900 ?
C13 H11J 0.9900 ?
C14 H11G 0.9900 ?
C14 H11H 0.9900 ?
C15 H11A 0.9800 ?
C15 H11B 0.9800 ?
C15 H11C 0.9800 ?
N1B C5B 1.350(4) y
N1B C1B 1.449(4) ?
N1B C2B 1.451(4) ?
N2B C5B 1.334(4) y
N2B C3B 1.436(4) ?
N2B C4B 1.438(4) ?
N3B C5B 1.319(4) y
N3B C6B 1.348(4) y
N4B C10B 1.352(4) y
N4B C6B 1.366(4) y
N4B H4B 0.888(10) ?
N5B C11B 1.341(4) y
N5B C10B 1.357(4) y
N6B C11B 1.344(4) y
N6B C12B 1.448(4) ?
N6B C13B 1.455(4) ?
N7B C11B 1.340(4) y
N7B C15B 1.452(4) ?
N7B C14B 1.455(4) ?
C1B H20D 0.9800 ?
C1B H20E 0.9800 ?
C1B H20F 0.9800 ?
C2B C3B 1.530(5) ?
C2B H20I 0.9900 ?
C2B H20J 0.9900 ?
C3B H20G 0.9900 ?
C3B H20H 0.9900 ?
C4B H20A 0.9800 ?
C4B H20B 0.9800 ?
C4B H20C 0.9800 ?
C6B C7B 1.383(4) ?
C7B C8B 1.373(4) ?
C7B H20K 0.9500 ?
C8B C9B 1.377(5) ?
C8B H20L 0.9500 ?
C9B C10B 1.397(4) ?
C9B H20M 0.9500 ?
C12B H21A 0.9800 ?
C12B H21B 0.9800 ?
C12B H21C 0.9800 ?
C13B C14B 1.532(4) ?
C13B H21G 0.9900 ?
C13B H21H 0.9900 ?
C14B H21I 0.9900 ?
C14B H21J 0.9900 ?
C15B H21D 0.9800 ?
C15B H21E 0.9800 ?
C15B H21F 0.9800 ?
Cl1 O11 1.400(6) ?
Cl1 O2 1.403(3) ?
Cl1 O4 1.414(3) ?
Cl1 O3 1.428(3) ?
Cl1 O12 1.454(5) ?
Cl2 O52 1.376(7) ?
Cl2 O61 1.384(5) ?
Cl2 O7 1.395(3) ?
Cl2 O8 1.420(3) ?
Cl2 O51 1.499(5) ?
Cl2 O62 1.507(6) ?
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
N4 H4 N5 2_566 0.881(10) 2.007(11) 2.885(4) 175(3)
N4B H4B N5B 2_767 0.888(10) 2.037(11) 2.922(4) 174(3)
C1 H10E O2 2_676 0.98 2.41 3.229(5) 141.0
C2 H10J O2 2_676 0.99 2.45 3.219(5) 134.3
C1B H20F O7 1_665 0.98 2.44 3.301(4) 145.7
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
C5 N1 C2 C3 8.0(4)
C1 N1 C2 C3 -154.7(3)
C5 N2 C3 C2 11.0(4)
C4 N2 C3 C2 -174.4(3)
N1 C2 C3 N2 -10.8(4)
C6 N3 C5 N1 -38.5(5)
C6 N3 C5 N2 145.3(3)
C1 N1 C5 N3 -15.9(6)
C2 N1 C5 N3 -177.9(3)
C1 N1 C5 N2 160.6(3)
C2 N1 C5 N2 -1.4(4)
C4 N2 C5 N3 -4.1(5)
C3 N2 C5 N3 170.4(3)
C4 N2 C5 N1 179.0(3)
C3 N2 C5 N1 -6.5(4)
C10 N4 C6 N3 169.6(3)
C10 N4 C6 C7 -5.0(5)
C5 N3 C6 N4 168.0(3)
C5 N3 C6 C7 -18.1(5)
N4 C6 C7 C8 3.1(5)
N3 C6 C7 C8 -170.7(3)
C6 C7 C8 C9 0.0(5)
C7 C8 C9 C10 -1.6(5)
C11 N5 C10 N4 -176.7(3)
C11 N5 C10 C9 9.3(5)
C6 N4 C10 N5 -171.1(3)
C6 N4 C10 C9 3.5(5)
C8 C9 C10 N5 173.8(3)
C8 C9 C10 N4 0.0(5)
C15 N7 C11 N5 2.7(6)
C14 N7 C11 N5 -175.3(3)
C15 N7 C11 N6 -174.8(3)
C14 N7 C11 N6 7.2(4)
C10 N5 C11 N7 59.1(5)
C10 N5 C11 N6 -123.7(4)
C12 N6 C11 N7 170.9(3)
C13 N6 C11 N7 8.0(4)
C12 N6 C11 N5 -6.8(5)
C13 N6 C11 N5 -169.6(3)
C11 N6 C13 C14 -18.6(4)
C12 N6 C13 C14 177.6(3)
C11 N7 C14 C13 -18.1(4)
C15 N7 C14 C13 163.8(3)
N6 C13 C14 N7 20.9(4)
C5B N1B C2B C3B -1.3(4)
C1B N1B C2B C3B 161.4(3)
C5B N2B C3B C2B -1.2(4)
C4B N2B C3B C2B 173.1(3)
N1B C2B C3B N2B 1.4(4)
C6B N3B C5B N2B -147.1(3)
C6B N3B C5B N1B 37.0(5)
C3B N2B C5B N3B -176.2(3)
C4B N2B C5B N3B 9.7(5)
C3B N2B C5B N1B 0.4(4)
C4B N2B C5B N1B -173.7(3)
C1B N1B C5B N3B 15.3(6)
C2B N1B C5B N3B 176.9(3)
C1B N1B C5B N2B -160.9(3)
C2B N1B C5B N2B 0.6(4)
C5B N3B C6B N4B -166.9(3)
C5B N3B C6B C7B 20.3(5)
C10B N4B C6B N3B -168.9(3)
C10B N4B C6B C7B 4.8(5)
N3B C6B C7B C8B 169.9(3)
N4B C6B C7B C8B -2.7(5)
C6B C7B C8B C9B -0.4(5)
C7B C8B C9B C10B 1.8(5)
C6B N4B C10B N5B 171.5(3)
C6B N4B C10B C9B -3.4(5)
C11B N5B C10B N4B 175.9(3)
C11B N5B C10B C9B -9.9(5)
C8B C9B C10B N4B 0.0(5)
C8B C9B C10B N5B -174.2(3)
C15B N7B C11B N5B 2.7(6)
C14B N7B C11B N5B 175.1(3)
C15B N7B C11B N6B -179.4(3)
C14B N7B C11B N6B -7.0(4)
C10B N5B C11B N7B -58.2(5)
C10B N5B C11B N6B 124.1(3)
C12B N6B C11B N7B -168.8(3)
C13B N6B C11B N7B -8.5(4)
C12B N6B C11B N5B 9.2(5)
C13B N6B C11B N5B 169.6(3)
C11B N6B C13B C14B 19.0(4)
C12B N6B C13B C14B -179.8(3)
C11B N7B C14B C13B 18.2(4)
C15B N7B C14B C13B -169.0(3)
N6B C13B C14B N7B -21.3(3)
