#------------------------------------------------------------------------------
#$Date: 2016-03-23 04:07:30 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179277 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/97/4319754.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4319754
loop_
_publ_author_name
'Gilles Muller'
'Jean-Claude G. Bünzli'
'Kurt J. Schenk'
'Claude Piguet'
'Gérard Hopfgartner'
_publ_section_title
;
 Influence of Bulky N-Substituents on the Formation of Lanthanide Triple
 Helical Complexes with a Ligand Derived from Bis(benzimidazole)pyridine:
 Structural and Thermodynamic Evidence
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2642
_journal_page_last               2651
_journal_paper_doi               10.1021/ic001289o
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C29 H33 N5'
_chemical_formula_weight         451.60
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.71(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.435(3)
_cell_length_b                   11.973(2)
_cell_length_c                   16.352(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2555.4(9)
_computing_cell_refinement       KM4CCD
_computing_data_collection       KM4CCD
_computing_data_reduction        KM4CCD
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18681
_diffrn_reflns_theta_full        20.81
_diffrn_reflns_theta_max         20.81
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0565P)²+0.2746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                3679
_reflns_number_total             5308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic001289o_1.cif
_cod_data_source_block           Ligand_II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.2746P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.2746P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2555.5(9)
_cod_database_code               4319754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.6652(3) 0.2753(3) 0.1675(2) 0.0551(11) Uani 1 d . . .
N2A N 0.6967(3) 0.2476(4) -0.0437(3) 0.0599(11) Uani 1 d . . .
N3A N 0.5484(3) 0.2210(3) -0.0040(2) 0.0531(11) Uani 1 d . . .
N4A N 0.6125(3) 0.2011(4) 0.3260(2) 0.0625(12) Uani 1 d . . .
N5A N 0.6772(4) 0.3666(4) 0.3776(3) 0.0705(13) Uani 1 d . . .
C1A C 0.6996(4) 0.3044(4) 0.1003(3) 0.0492(12) Uani 1 d . . .
C2A C 0.7812(4) 0.3782(5) 0.1059(3) 0.0621(15) Uani 1 d . . .
H2A H 0.8038 0.3972 0.0582 0.075 Uiso 1 calc R . .
C4A C 0.7917(4) 0.3925(5) 0.2526(3) 0.0708(16) Uani 1 d . . .
H4A H 0.8215 0.4215 0.3055 0.085 Uiso 1 calc R . .
C3A C 0.8279(4) 0.4229(5) 0.1837(4) 0.0717(16) Uani 1 d . . .
H3A H 0.8826 0.4723 0.1892 0.086 Uiso 1 calc R . .
C5A C 0.7106(4) 0.3185(4) 0.2426(3) 0.0558(14) Uani 1 d . . .
C6A C 0.6479(4) 0.2590(4) 0.0172(3) 0.0497(13) Uani 1 d . . .
C7A C 0.6241(4) 0.1995(4) -0.1104(3) 0.0598(14) Uani 1 d . . .
C8A C 0.6342(6) 0.1696(5) -0.1902(4) 0.0815(18) Uani 1 d . . .
H8A H 0.6952 0.1805 -0.2067 0.098 Uiso 1 calc R . .
C9A C 0.5502(7) 0.1235(6) -0.2431(4) 0.093(2) Uani 1 d . . .
H9A H 0.5543 0.1033 -0.2971 0.111 Uiso 1 calc R . .
C10A C 0.4581(6) 0.1056(6) -0.2192(4) 0.0857(18) Uani 1 d . . .
H10A H 0.4036 0.0722 -0.2570 0.103 Uiso 1 calc R . .
C11A C 0.4462(5) 0.1363(5) -0.1406(3) 0.0694(15) Uani 1 d . . .
H11A H 0.3847 0.1262 -0.1248 0.083 Uiso 1 calc R . .
C12A C 0.5316(4) 0.1832(4) -0.0866(3) 0.0580(14) Uani 1 d . . .
C14A C 0.6681(4) 0.2944(5) 0.3157(3) 0.0596(14) Uani 1 d . . .
C15A C 0.5818(4) 0.2186(5) 0.3996(3) 0.0627(15) Uani 1 d . . .
C16A C 0.5205(4) 0.1530(6) 0.4398(3) 0.0831(18) Uani 1 d . . .
H16A H 0.4932 0.0846 0.4186 0.100 Uiso 1 calc R . .
C17A C 0.5038(5) 0.1987(7) 0.5138(4) 0.089(2) Uani 1 d . . .
H17A H 0.4622 0.1599 0.5420 0.106 Uiso 1 calc R . .
C18A C 0.5455(5) 0.2973(8) 0.5468(4) 0.104(2) Uani 1 d . . .
H18A H 0.5346 0.3220 0.5979 0.124 Uiso 1 calc R . .
C19A C 0.6036(5) 0.3610(6) 0.5053(4) 0.095(2) Uani 1 d . . .
H19A H 0.6302 0.4296 0.5268 0.114 Uiso 1 calc R . .
C20A C 0.6215(5) 0.3201(6) 0.4303(3) 0.0738(16) Uani 1 d . . .
C13A C 0.4687(3) 0.2352(4) 0.0426(3) 0.0538(13) Uani 1 d . . .
H13A H 0.4923 0.2034 0.0984 0.065 Uiso 1 calc R . .
H13B H 0.4079 0.1946 0.0141 0.065 Uiso 1 calc R . .
C23A C 0.4408(4) 0.3586(4) 0.0507(3) 0.0554(13) Uani 1 d . . .
H23A H 0.5025 0.3981 0.0810 0.066 Uiso 1 calc R . .
C33A C 0.4029(4) 0.4140(5) -0.0358(3) 0.0788(16) Uani 1 d . . .
H33A H 0.3448 0.3736 -0.0678 0.118 Uiso 1 calc R . .
H33B H 0.4567 0.4132 -0.0653 0.118 Uiso 1 calc R . .
H33C H 0.3834 0.4898 -0.0285 0.118 Uiso 1 calc R . .
C43A C 0.3605(4) 0.3674(4) 0.1019(3) 0.0703(14) Uani 1 d . . .
H43A H 0.3005 0.3255 0.0732 0.084 Uiso 1 calc R . .
H43B H 0.3403 0.4451 0.1029 0.084 Uiso 1 calc R . .
C53A C 0.3932(4) 0.3258(5) 0.1921(3) 0.0873(17) Uani 1 d . . .
H53A H 0.4018 0.2461 0.1921 0.131 Uiso 1 calc R . .
H53B H 0.3417 0.3446 0.2216 0.131 Uiso 1 calc R . .
H53C H 0.4569 0.3602 0.2195 0.131 Uiso 1 calc R . .
C21A C 0.6008(4) 0.0941(5) 0.2804(3) 0.0699(16) Uani 1 d . . .
H21A H 0.6199 0.1045 0.2273 0.084 Uiso 1 calc R . .
H21B H 0.5293 0.0722 0.2679 0.084 Uiso 1 calc R . .
C31A C 0.6637(5) 0.0023(5) 0.3277(3) 0.0841(17) Uani 1 d . . .
H31A H 0.6453 -0.0044 0.3820 0.101 Uiso 1 calc R . .
C41A C 0.6382(6) -0.1071(6) 0.2823(5) 0.141(3) Uani 1 d . . .
H41A H 0.5655 -0.1192 0.2704 0.211 Uiso 1 calc R . .
H41B H 0.6727 -0.1667 0.3170 0.211 Uiso 1 calc R . .
H41C H 0.6601 -0.1052 0.2305 0.211 Uiso 1 calc R . .
C51A C 0.7764(5) 0.0316(6) 0.3457(4) 0.118(2) Uani 1 d . . .
H51A H 0.7959 0.0415 0.2927 0.141 Uiso 1 calc R . .
H51B H 0.7872 0.1022 0.3756 0.141 Uiso 1 calc R . .
C61A C 0.8443(6) -0.0544(7) 0.3964(5) 0.165(3) Uani 1 d . . .
H61A H 0.8249 -0.0656 0.4487 0.248 Uiso 1 calc R . .
H61B H 0.9141 -0.0295 0.4075 0.248 Uiso 1 calc R . .
H61C H 0.8375 -0.1234 0.3657 0.248 Uiso 1 calc R . .
N1B N 0.8311(3) -0.3694(3) -0.1726(2) 0.0537(11) Uani 1 d . . .
N2B N 0.8191(4) -0.4726(4) -0.3801(3) 0.0819(15) Uani 1 d . . .
N3B N 0.8841(3) -0.3042(4) -0.3314(2) 0.0597(11) Uani 1 d . . .
N4B N 0.9522(3) -0.3117(3) -0.0052(2) 0.0485(10) Uani 1 d . . .
N5B N 0.8102(3) -0.3409(4) 0.0426(3) 0.0618(12) Uani 1 d . . .
C1B C 0.7841(4) -0.4176(5) -0.2456(3) 0.0567(14) Uani 1 d . . .
C2B C 0.7041(4) -0.4928(4) -0.2531(3) 0.0626(14) Uani 1 d . . .
H2B H 0.6742 -0.5255 -0.3046 0.075 Uiso 1 calc R . .
C3B C 0.6701(4) -0.5178(5) -0.1824(4) 0.0659(15) Uani 1 d . . .
H3B H 0.6152 -0.5663 -0.1860 0.079 Uiso 1 calc R . .
C4B C 0.7171(4) -0.4711(4) -0.1065(3) 0.0584(14) Uani 1 d . . .
H4B H 0.6951 -0.4881 -0.0582 0.070 Uiso 1 calc R . .
C5B C 0.7978(4) -0.3984(4) -0.1031(3) 0.0520(13) Uani 1 d . . .
C6B C 0.8262(4) -0.3941(5) -0.3205(3) 0.0610(15) Uani 1 d . . .
C7B C 0.8730(4) -0.4267(6) -0.4354(3) 0.0752(17) Uani 1 d . . .
C8B C 0.8882(5) -0.4717(6) -0.5106(4) 0.099(2) Uani 1 d . . .
H8B H 0.8591 -0.5393 -0.5320 0.119 Uiso 1 calc R . .
C9B C 0.9486(5) -0.4100(8) -0.5511(4) 0.104(2) Uani 1 d . . .
H9B H 0.9598 -0.4370 -0.6015 0.125 Uiso 1 calc R . .
C10B C 0.9936(5) -0.3092(7) -0.5202(4) 0.095(2) Uani 1 d . . .
H10B H 1.0352 -0.2719 -0.5493 0.114 Uiso 1 calc R . .
C11B C 0.9772(4) -0.2633(5) -0.4459(3) 0.0767(17) Uani 1 d . . .
H11B H 1.0060 -0.1954 -0.4250 0.092 Uiso 1 calc R . .
C12B C 0.9164(4) -0.3238(5) -0.4053(3) 0.0652(16) Uani 1 d . . .
C14B C 0.8526(4) -0.3497(4) -0.0221(3) 0.0507(13) Uani 1 d . . .
C15B C 0.9736(4) -0.2748(4) 0.0769(3) 0.0521(13) Uani 1 d . . .
C16B C 1.0621(4) -0.2280(4) 0.1278(3) 0.0652(15) Uani 1 d . . .
H16B H 1.1207 -0.2163 0.1082 0.078 Uiso 1 calc R . .
C17B C 1.0578(5) -0.1999(5) 0.2094(3) 0.0793(16) Uani 1 d . . .
H17B H 1.1150 -0.1683 0.2454 0.095 Uiso 1 calc R . .
C18B C 0.9697(6) -0.2180(5) 0.2381(3) 0.0852(18) Uani 1 d . . .
H18B H 0.9695 -0.1977 0.2930 0.102 Uiso 1 calc R . .
C19B C 0.8828(5) -0.2648(5) 0.1882(3) 0.0754(17) Uani 1 d . . .
H19B H 0.8247 -0.2769 0.2086 0.090 Uiso 1 calc R . .
C20B C 0.8848(4) -0.2938(4) 0.1054(3) 0.0601(14) Uani 1 d . . .
C13B C 0.8838(4) -0.1922(5) -0.2942(3) 0.0645(15) Uani 1 d . . .
H13C H 0.9540 -0.1670 -0.2741 0.077 Uiso 1 calc R . .
H13D H 0.8534 -0.1968 -0.2461 0.077 Uiso 1 calc R . .
C23B C 0.8245(4) -0.1062(5) -0.3567(3) 0.0636(14) Uani 1 d . . .
H23B H 0.8609 -0.0962 -0.4014 0.076 Uiso 1 calc R . .
C33B C 0.7161(4) -0.1475(5) -0.3974(3) 0.0902(17) Uani 1 d . . .
H33D H 0.6791 -0.1591 -0.3546 0.135 Uiso 1 calc R . .
H33E H 0.7201 -0.2165 -0.4263 0.135 Uiso 1 calc R . .
H33F H 0.6813 -0.0927 -0.4368 0.135 Uiso 1 calc R . .
C43B C 0.8241(4) 0.0050(5) -0.3127(3) 0.0840(17) Uani 1 d . . .
H43C H 0.8938 0.0231 -0.2834 0.101 Uiso 1 calc R . .
H43D H 0.7842 -0.0025 -0.2707 0.101 Uiso 1 calc R . .
C53B C 0.7807(3) 0.1018(3) -0.3709(2) 0.0899(16) Uani 1 d . . .
H53D H 0.8205 0.1113 -0.4120 0.135 Uiso 1 calc R . .
H53E H 0.7835 0.1691 -0.3384 0.135 Uiso 1 calc R . .
H53F H 0.7109 0.0861 -0.3988 0.135 Uiso 1 calc R . .
C21B C 1.0282(3) -0.3207(3) -0.0566(2) 0.0567(13) Uani 1 d R . .
H21C H 1.0900 -0.2820 -0.0278 0.068 Uiso 1 calc R . .
H21D H 1.0016 -0.2824 -0.1096 0.068 Uiso 1 calc R . .
C31B C 1.0566(4) -0.4389(4) -0.0755(3) 0.0582(14) Uani 1 d . . .
H31B H 0.9930 -0.4812 -0.0956 0.070 Uiso 1 calc R . .
C41B C 1.1132(4) -0.4346(5) -0.1478(3) 0.0893(19) Uani 1 d . . .
H41D H 1.1731 -0.3885 -0.1312 0.134 Uiso 1 calc R . .
H41E H 1.0685 -0.4038 -0.1973 0.134 Uiso 1 calc R . .
H41F H 1.1331 -0.5087 -0.1596 0.134 Uiso 1 calc R . .
C51B C 1.1209(4) -0.4998(5) -0.0015(3) 0.0769(15) Uani 1 d . . .
H51C H 1.1786 -0.4527 0.0240 0.092 Uiso 1 calc R . .
H51D H 1.1481 -0.5665 -0.0219 0.092 Uiso 1 calc R . .
C61B C 1.0666(5) -0.5339(5) 0.0664(3) 0.0975(19) Uani 1 d . . .
H61D H 1.0560 -0.4692 0.0979 0.146 Uiso 1 calc R . .
H61E H 1.1080 -0.5871 0.1034 0.146 Uiso 1 calc R . .
H61F H 1.0017 -0.5670 0.0406 0.146 Uiso 1 calc R . .
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'
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
C1A N1A C5A 118.8(4) . . ?
C6A N2A C7A 104.5(4) . . ?
C6A N3A C12A 106.1(4) . . ?
C6A N3A C13A 128.0(4) . . ?
C12A N3A C13A 124.9(4) . . ?
C14A N4A C15A 105.4(4) . . ?
C14A N4A C21A 129.8(4) . . ?
C15A N4A C21A 123.9(5) . . ?
C14A N5A C20A 104.4(5) . . ?
N1A C1A C2A 122.1(4) . . ?
N1A C1A C6A 118.8(5) . . ?
C2A C1A C6A 119.1(4) . . ?
C3A C2A C1A 118.9(5) . . ?
C3A C2A H2A 120.6 . . ?
C1A C2A H2A 120.6 . . ?
C3A C4A C5A 119.5(5) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A H4A 120.2 . . ?
C4A C3A C2A 118.5(5) . . ?
C4A C3A H3A 120.7 . . ?
C2A C3A H3A 120.7 . . ?
N1A C5A C4A 122.1(4) . . ?
N1A C5A C14A 119.3(5) . . ?
C4A C5A C14A 118.4(5) . . ?
N2A C6A N3A 113.6(4) . . ?
N2A C6A C1A 121.5(5) . . ?
N3A C6A C1A 124.9(4) . . ?
C8A C7A C12A 121.0(5) . . ?
C8A C7A N2A 129.1(6) . . ?
C12A C7A N2A 109.9(4) . . ?
C9A C8A C7A 116.7(6) . . ?
C9A C8A H8A 121.7 . . ?
C7A C8A H8A 121.7 . . ?
C8A C9A C10A 122.5(6) . . ?
C8A C9A H9A 118.8 . . ?
C10A C9A H9A 118.8 . . ?
C11A C10A C9A 121.6(6) . . ?
C11A C10A H10A 119.2 . . ?
C9A C10A H10A 119.2 . . ?
C10A C11A C12A 116.0(5) . . ?
C10A C11A H11A 122.0 . . ?
C12A C11A H11A 122.0 . . ?
C11A C12A N3A 131.9(5) . . ?
C11A C12A C7A 122.2(5) . . ?
N3A C12A C7A 105.9(5) . . ?
N5A C14A N4A 113.2(4) . . ?
N5A C14A C5A 120.9(5) . . ?
N4A C14A C5A 125.8(5) . . ?
C20A C15A N4A 106.5(5) . . ?
C20A C15A C16A 122.8(5) . . ?
N4A C15A C16A 130.7(6) . . ?
C17A C16A C15A 114.8(6) . . ?
C17A C16A H16A 122.6 . . ?
C15A C16A H16A 122.6 . . ?
C18A C17A C16A 123.3(6) . . ?
C18A C17A H17A 118.3 . . ?
C16A C17A H17A 118.3 . . ?
C17A C18A C19A 120.7(6) . . ?
C17A C18A H18A 119.6 . . ?
C19A C18A H18A 119.6 . . ?
C18A C19A C20A 118.3(6) . . ?
C18A C19A H19A 120.8 . . ?
C20A C19A H19A 120.8 . . ?
C15A C20A N5A 110.4(4) . . ?
C15A C20A C19A 120.0(6) . . ?
N5A C20A C19A 129.6(6) . . ?
N3A C13A C23A 112.3(4) . . ?
N3A C13A H13A 109.2 . . ?
C23A C13A H13A 109.2 . . ?
N3A C13A H13B 109.2 . . ?
C23A C13A H13B 109.2 . . ?
H13A C13A H13B 107.9 . . ?
C43A C23A C33A 110.7(4) . . ?
C43A C23A C13A 109.5(4) . . ?
C33A C23A C13A 111.7(4) . . ?
C43A C23A H23A 108.3 . . ?
C33A C23A H23A 108.3 . . ?
C13A C23A H23A 108.3 . . ?
C23A C33A H33A 109.5 . . ?
C23A C33A H33B 109.5 . . ?
H33A C33A H33B 109.5 . . ?
C23A C33A H33C 109.5 . . ?
H33A C33A H33C 109.5 . . ?
H33B C33A H33C 109.5 . . ?
C23A C43A C53A 115.6(4) . . ?
C23A C43A H43A 108.4 . . ?
C53A C43A H43A 108.4 . . ?
C23A C43A H43B 108.4 . . ?
C53A C43A H43B 108.4 . . ?
H43A C43A H43B 107.4 . . ?
C43A C53A H53A 109.5 . . ?
C43A C53A H53B 109.5 . . ?
H53A C53A H53B 109.5 . . ?
C43A C53A H53C 109.5 . . ?
H53A C53A H53C 109.5 . . ?
H53B C53A H53C 109.5 . . ?
N4A C21A C31A 113.6(4) . . ?
N4A C21A H21A 108.8 . . ?
C31A C21A H21A 108.8 . . ?
N4A C21A H21B 108.8 . . ?
C31A C21A H21B 108.8 . . ?
H21A C21A H21B 107.7 . . ?
C21A C31A C41A 110.6(5) . . ?
C21A C31A C51A 110.5(5) . . ?
C41A C31A C51A 113.4(6) . . ?
C21A C31A H31A 107.4 . . ?
C41A C31A H31A 107.4 . . ?
C51A C31A H31A 107.4 . . ?
C31A C41A H41A 109.5 . . ?
C31A C41A H41B 109.5 . . ?
H41A C41A H41B 109.5 . . ?
C31A C41A H41C 109.5 . . ?
H41A C41A H41C 109.5 . . ?
H41B C41A H41C 109.5 . . ?
C61A C51A C31A 113.6(6) . . ?
C61A C51A H51A 108.8 . . ?
C31A C51A H51A 108.8 . . ?
C61A C51A H51B 108.8 . . ?
C31A C51A H51B 108.8 . . ?
H51A C51A H51B 107.7 . . ?
C51A C61A H61A 109.5 . . ?
C51A C61A H61B 109.5 . . ?
H61A C61A H61B 109.5 . . ?
C51A C61A H61C 109.5 . . ?
H61A C61A H61C 109.5 . . ?
H61B C61A H61C 109.5 . . ?
C1B N1B C5B 117.0(4) . . ?
C6B N2B C7B 103.6(5) . . ?
C6B N3B C12B 106.5(4) . . ?
C6B N3B C13B 127.4(4) . . ?
C12B N3B C13B 122.8(4) . . ?
C15B N4B C14B 105.6(4) . . ?
C15B N4B C21B 124.6(4) . . ?
C14B N4B C21B 129.3(4) . . ?
C14B N5B C20B 104.8(4) . . ?
N1B C1B C2B 123.4(4) . . ?
N1B C1B C6B 117.3(5) . . ?
C2B C1B C6B 119.2(5) . . ?
C3B C2B C1B 118.2(5) . . ?
C3B C2B H2B 120.9 . . ?
C1B C2B H2B 120.9 . . ?
C4B C3B C2B 120.0(5) . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B C5B 118.9(5) . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B H4B 120.6 . . ?
N1B C5B C4B 122.5(4) . . ?
N1B C5B C14B 117.1(5) . . ?
C4B C5B C14B 120.4(4) . . ?
N2B C6B N3B 113.8(4) . . ?
N2B C6B C1B 119.2(6) . . ?
N3B C6B C1B 126.5(5) . . ?
N2B C7B C12B 110.8(5) . . ?
N2B C7B C8B 128.4(6) . . ?
C12B C7B C8B 120.8(6) . . ?
C9B C8B C7B 116.1(6) . . ?
C9B C8B H8B 121.9 . . ?
C7B C8B H8B 121.9 . . ?
C8B C9B C10B 123.1(6) . . ?
C8B C9B H9B 118.5 . . ?
C10B C9B H9B 118.5 . . ?
C9B C10B C11B 120.9(6) . . ?
C9B C10B H10B 119.6 . . ?
C11B C10B H10B 119.6 . . ?
C12B C11B C10B 116.6(6) . . ?
C12B C11B H11B 121.7 . . ?
C10B C11B H11B 121.7 . . ?
C11B C12B N3B 132.2(6) . . ?
C11B C12B C7B 122.6(5) . . ?
N3B C12B C7B 105.2(5) . . ?
N5B C14B N4B 113.3(4) . . ?
N5B C14B C5B 122.2(5) . . ?
N4B C14B C5B 124.5(4) . . ?
N4B C15B C16B 131.4(5) . . ?
N4B C15B C20B 106.0(4) . . ?
C16B C15B C20B 122.6(5) . . ?
C17B C16B C15B 116.5(5) . . ?
C17B C16B H16B 121.7 . . ?
C15B C16B H16B 121.7 . . ?
C16B C17B C18B 121.2(5) . . ?
C16B C17B H17B 119.4 . . ?
C18B C17B H17B 119.4 . . ?
C19B C18B C17B 122.2(5) . . ?
C19B C18B H18B 118.9 . . ?
C17B C18B H18B 118.9 . . ?
C18B C19B C20B 117.8(5) . . ?
C18B C19B H19B 121.1 . . ?
C20B C19B H19B 121.1 . . ?
N5B C20B C15B 110.2(4) . . ?
N5B C20B C19B 130.2(5) . . ?
C15B C20B C19B 119.6(5) . . ?
N3B C13B C23B 112.8(4) . . ?
N3B C13B H13C 109.0 . . ?
C23B C13B H13C 109.0 . . ?
N3B C13B H13D 109.0 . . ?
C23B C13B H13D 109.0 . . ?
H13C C13B H13D 107.8 . . ?
C43B C23B C33B 112.3(4) . . ?
C43B C23B C13B 109.5(4) . . ?
C33B C23B C13B 111.3(4) . . ?
C43B C23B H23B 107.8 . . ?
C33B C23B H23B 107.8 . . ?
C13B C23B H23B 107.8 . . ?
C23B C33B H33D 109.5 . . ?
C23B C33B H33E 109.5 . . ?
H33D C33B H33E 109.5 . . ?
C23B C33B H33F 109.5 . . ?
H33D C33B H33F 109.5 . . ?
H33E C33B H33F 109.5 . . ?
C23B C43B C53B 114.6(4) . . ?
C23B C43B H43C 108.6 . . ?
C53B C43B H43C 108.6 . . ?
C23B C43B H43D 108.6 . . ?
C53B C43B H43D 108.6 . . ?
H43C C43B H43D 107.6 . . ?
C43B C53B H53D 109.5 . . ?
C43B C53B H53E 109.5 . . ?
H53D C53B H53E 109.5 . . ?
C43B C53B H53F 109.5 . . ?
H53D C53B H53F 109.5 . . ?
H53E C53B H53F 109.5 . . ?
N4B C21B C31B 115.3(3) . . ?
N4B C21B H21C 108.5 . . ?
C31B C21B H21C 108.5 . . ?
N4B C21B H21D 108.5 . . ?
C31B C21B H21D 108.5 . . ?
H21C C21B H21D 107.5 . . ?
C51B C31B C21B 114.4(4) . . ?
C51B C31B C41B 109.8(4) . . ?
C21B C31B C41B 108.5(4) . . ?
C51B C31B H31B 108.0 . . ?
C21B C31B H31B 108.0 . . ?
C41B C31B H31B 108.0 . . ?
C31B C41B H41D 109.5 . . ?
C31B C41B H41E 109.5 . . ?
H41D C41B H41E 109.5 . . ?
C31B C41B H41F 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
C31B C51B C61B 115.8(4) . . ?
C31B C51B H51C 108.3 . . ?
C61B C51B H51C 108.3 . . ?
C31B C51B H51D 108.3 . . ?
C61B C51B H51D 108.3 . . ?
H51C C51B H51D 107.4 . . ?
C51B C61B H61D 109.5 . . ?
C51B C61B H61E 109.5 . . ?
H61D C61B H61E 109.5 . . ?
C51B C61B H61F 109.5 . . ?
H61D C61B H61F 109.5 . . ?
H61E C61B H61F 109.5 . . ?
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
N1A C1A 1.336(5) . ?
N1A C5A 1.339(6) . ?
N2A C6A 1.323(5) . ?
N2A C7A 1.403(6) . ?
N3A C6A 1.377(6) . ?
N3A C12A 1.391(6) . ?
N3A C13A 1.465(5) . ?
N4A C14A 1.377(6) . ?
N4A C15A 1.377(6) . ?
N4A C21A 1.471(7) . ?
N5A C14A 1.315(6) . ?
N5A C20A 1.385(7) . ?
C1A C2A 1.393(6) . ?
C1A C6A 1.474(6) . ?
C2A C3A 1.386(7) . ?
C2A H2A 0.9300 . ?
C4A C3A 1.379(6) . ?
C4A C5A 1.383(7) . ?
C4A H4A 0.9300 . ?
C3A H3A 0.9300 . ?
C5A C14A 1.470(6) . ?
C7A C8A 1.391(7) . ?
C7A C12A 1.401(7) . ?
C8A C9A 1.365(9) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.400(8) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.381(7) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.390(7) . ?
C11A H11A 0.9300 . ?
C15A C20A 1.374(8) . ?
C15A C16A 1.409(7) . ?
C16A C17A 1.393(8) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.363(9) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.380(9) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.394(7) . ?
C19A H19A 0.9300 . ?
C13A C23A 1.538(6) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C23A C43A 1.518(6) . ?
C23A C33A 1.536(7) . ?
C23A H23A 0.9800 . ?
C33A H33A 0.9600 . ?
C33A H33B 0.9600 . ?
C33A H33C 0.9600 . ?
C43A C53A 1.520(6) . ?
C43A H43A 0.9700 . ?
C43A H43B 0.9700 . ?
C53A H53A 0.9600 . ?
C53A H53B 0.9600 . ?
C53A H53C 0.9600 . ?
C21A C31A 1.487(8) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C31A C41A 1.505(8) . ?
C31A C51A 1.514(8) . ?
C31A H31A 0.9800 . ?
C41A H41A 0.9600 . ?
C41A H41B 0.9600 . ?
C41A H41C 0.9600 . ?
C51A C61A 1.489(8) . ?
C51A H51A 0.9700 . ?
C51A H51B 0.9700 . ?
C61A H61A 0.9600 . ?
C61A H61B 0.9600 . ?
C61A H61C 0.9600 . ?
N1B C1B 1.342(6) . ?
N1B C5B 1.362(5) . ?
N2B C6B 1.341(7) . ?
N2B C7B 1.398(7) . ?
N3B C6B 1.364(7) . ?
N3B C12B 1.397(6) . ?
N3B C13B 1.472(7) . ?
N4B C15B 1.377(5) . ?
N4B C14B 1.378(6) . ?
N4B C21B 1.472(5) . ?
N5B C14B 1.319(5) . ?
N5B C20B 1.374(6) . ?
C1B C2B 1.385(6) . ?
C1B C6B 1.492(7) . ?
C2B C3B 1.373(6) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.371(7) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.380(6) . ?
C4B H4B 0.9300 . ?
C5B C14B 1.475(7) . ?
C7B C12B 1.401(8) . ?
C7B C8B 1.402(7) . ?
C8B C9B 1.378(9) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.390(9) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.397(7) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.375(7) . ?
C11B H11B 0.9300 . ?
C15B C16B 1.397(7) . ?
C15B C20B 1.398(6) . ?
C16B C17B 1.390(6) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.391(7) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.375(7) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.405(7) . ?
C19B H19B 0.9300 . ?
C13B C23B 1.534(7) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C23B C43B 1.514(7) . ?
C23B C33B 1.532(6) . ?
C23B H23B 0.9800 . ?
C33B H33D 0.9600 . ?
C33B H33E 0.9600 . ?
C33B H33F 0.9600 . ?
C43B C53B 1.525(6) . ?
C43B H43C 0.9700 . ?
C43B H43D 0.9700 . ?
C53B H53D 0.9600 . ?
C53B H53E 0.9600 . ?
C53B H53F 0.9600 . ?
C21B C31B 1.516(6) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C31B C51B 1.499(6) . ?
C31B C41B 1.550(6) . ?
C31B H31B 0.9800 . ?
C41B H41D 0.9600 . ?
C41B H41E 0.9600 . ?
C41B H41F 0.9600 . ?
C51B C61B 1.521(7) . ?
C51B H51C 0.9700 . ?
C51B H51D 0.9700 . ?
C61B H61D 0.9600 . ?
C61B H61E 0.9600 . ?
C61B H61F 0.9600 . ?
