#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:12:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178425 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024696.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_4024696
loop_
_publ_author_name
'Bo Yao'
'De-Xian Wang'
'Han-Yuan Gong'
'Zhi-Tang Huang'
'Mei-Xiang Wang'
_publ_section_title
;
Synthesis, Structure, and Reactions of NH-Bridged Calix[m]arene[n]pyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5361
_journal_page_last               5368
_journal_paper_doi               10.1021/jo900826n
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H18 N6'
_chemical_formula_sum            'C22 H18 N6'
_chemical_formula_weight         366.42
_chemical_name_systematic
; 
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.76(3)
_cell_angle_beta                 101.25(3)
_cell_angle_gamma                97.86(3)
_cell_formula_units_Z            4
_cell_length_a                   8.3972(17)
_cell_length_b                   10.175(2)
_cell_length_c                   21.221(4)
_cell_measurement_reflns_used    6720
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.99
_cell_volume                     1731.5(6)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP'
_diffrn_measurement_method       oscillation
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11252
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         6071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0627
_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)+(0.0658P)²+1.2864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                5015
_reflns_number_total             6071
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900826n_si_002.cif
_cod_data_source_block           sx2323
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024696
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.0818(3) 0.7760(2) 0.43737(11) 0.0282(5) Uani 1 1 d . . .
N1B N -0.2683(3) 0.8521(2) 0.15476(11) 0.0329(5) Uani 1 1 d . . .
N2A N -0.0432(3) 0.5506(2) 0.39113(11) 0.0319(5) Uani 1 1 d . . .
H2AA H -0.0090 0.4810 0.3712 0.038 Uiso 1 1 calc R . .
N2B N -0.5266(3) 0.7490(2) 0.17153(12) 0.0349(6) Uani 1 1 d . . .
H2BA H -0.5724 0.7190 0.2017 0.042 Uiso 1 1 calc R . .
N3A N -0.5133(3) 0.7844(2) 0.39211(11) 0.0316(5) Uani 1 1 d . . .
H3AA H -0.5560 0.7951 0.4269 0.038 Uiso 1 1 calc R . .
N3B N -0.7052(3) 1.0222(2) 0.01176(11) 0.0315(5) Uani 1 1 d . . .
H3BA H -0.7570 1.0110 -0.0295 0.038 Uiso 1 1 calc R . .
N4A N -0.3560(3) 0.9280(2) 0.34230(10) 0.0271(5) Uani 1 1 d . . .
N4B N -0.4926(3) 1.1783(2) 0.09007(11) 0.0328(5) Uani 1 1 d . . .
N5B N -0.2798(3) 1.3398(2) 0.16599(12) 0.0357(6) Uani 1 1 d . . .
H5BA H -0.2826 1.3955 0.2016 0.043 Uiso 1 1 calc R . .
N5A N -0.1897(3) 1.0715(2) 0.29517(11) 0.0306(5) Uani 1 1 d . . .
H5AA H -0.1848 1.0836 0.2554 0.037 Uiso 1 1 calc R . .
N6A N 0.2099(3) 1.0015(2) 0.48425(10) 0.0290(5) Uani 1 1 d . . .
H6AA H 0.2638 1.0522 0.5217 0.035 Uiso 1 1 calc R . .
N6B N -0.0103(3) 0.9514(2) 0.13773(11) 0.0334(6) Uani 1 1 d . . .
H6BA H 0.0458 0.9173 0.1102 0.040 Uiso 1 1 calc R . .
C1A C 0.1978(3) 0.8635(3) 0.48275(12) 0.0269(6) Uani 1 1 d . . .
C1B C -0.1016(3) 0.8620(3) 0.16803(13) 0.0282(6) Uani 1 1 d . . .
C2A C 0.3140(3) 0.8213(3) 0.52867(13) 0.0302(6) Uani 1 1 d . . .
H2AB H 0.3958 0.8854 0.5598 0.036 Uiso 1 1 calc R . .
C2B C -0.0184(4) 0.7882(3) 0.20868(13) 0.0347(7) Uani 1 1 d . . .
H2BB H 0.0976 0.7939 0.2150 0.042 Uiso 1 1 calc R . .
C3A C 0.3075(4) 0.6856(3) 0.52774(13) 0.0331(6) Uani 1 1 d . . .
H3AB H 0.3868 0.6545 0.5578 0.040 Uiso 1 1 calc R . .
C3B C -0.1084(4) 0.7060(3) 0.23987(14) 0.0378(7) Uani 1 1 d . . .
H3BB H -0.0535 0.6572 0.2696 0.045 Uiso 1 1 calc R . .
C4B C -0.2765(4) 0.6943(3) 0.22823(13) 0.0335(7) Uani 1 1 d . . .
H4BB H -0.3388 0.6374 0.2495 0.040 Uiso 1 1 calc R . .
C4A C 0.1853(4) 0.5941(3) 0.48298(13) 0.0318(6) Uani 1 1 d . . .
H4AB H 0.1766 0.4999 0.4827 0.038 Uiso 1 1 calc R . .
C5B C -0.3547(4) 0.7675(2) 0.18445(13) 0.0293(6) Uani 1 1 d . . .
C5A C 0.0763(3) 0.6433(3) 0.43866(13) 0.0271(6) Uani 1 1 d . . .
C6A C -0.2112(3) 0.5568(3) 0.37184(13) 0.0290(6) Uani 1 1 d . . .
C6B C -0.6363(4) 0.7719(3) 0.11695(13) 0.0308(6) Uani 1 1 d . . .
C7A C -0.3142(4) 0.4423(3) 0.33191(13) 0.0327(6) Uani 1 1 d . . .
H7AA H -0.2688 0.3657 0.3174 0.039 Uiso 1 1 calc R . .
C7B C -0.7758(4) 0.6739(3) 0.08963(15) 0.0358(7) Uani 1 1 d . . .
H7BA H -0.7947 0.5950 0.1078 0.043 Uiso 1 1 calc R . .
C8B C -0.8866(4) 0.6929(3) 0.03568(15) 0.0386(7) Uani 1 1 d . . .
H8BA H -0.9817 0.6264 0.0166 0.046 Uiso 1 1 calc R . .
C8A C -0.4816(4) 0.4405(3) 0.31354(14) 0.0369(7) Uani 1 1 d . . .
H8AA H -0.5510 0.3621 0.2869 0.044 Uiso 1 1 calc R . .
C9B C -0.8600(4) 0.8074(3) 0.00952(14) 0.0327(6) Uani 1 1 d . . .
H9BA H -0.9352 0.8197 -0.0279 0.039 Uiso 1 1 calc R . .
C9A C -0.5492(4) 0.5524(3) 0.33366(14) 0.0336(6) Uani 1 1 d . . .
H9AA H -0.6643 0.5513 0.3210 0.040 Uiso 1 1 calc R . .
C10A C -0.4462(3) 0.6657(3) 0.37255(13) 0.0289(6) Uani 1 1 d . . .
C10B C -0.7208(3) 0.9056(3) 0.03871(13) 0.0277(6) Uani 1 1 d . . .
C11A C -0.2790(3) 0.6688(3) 0.39206(12) 0.0260(6) Uani 1 1 d . . .
H11A H -0.2105 0.7471 0.4192 0.031 Uiso 1 1 calc R . .
C11B C -0.6106(3) 0.8877(2) 0.09199(12) 0.0233(5) Uani 1 1 d . . .
H11B H -0.5167 0.9551 0.1116 0.028 Uiso 1 1 calc R . .
C12A C -0.5060(3) 0.8827(3) 0.35190(12) 0.0261(6) Uani 1 1 d . . .
C12B C -0.6227(3) 1.1529(3) 0.03828(12) 0.0267(6) Uani 1 1 d . . .
C13B C -0.6832(4) 1.2557(3) 0.00935(14) 0.0325(6) Uani 1 1 d . . .
H13A H -0.7736 1.2349 -0.0274 0.039 Uiso 1 1 calc R . .
C13A C -0.6474(3) 0.9290(3) 0.32574(13) 0.0319(6) Uani 1 1 d . . .
H13B H -0.7507 0.8971 0.3349 0.038 Uiso 1 1 calc R . .
C14A C -0.6326(4) 1.0233(3) 0.28580(14) 0.0354(7) Uani 1 1 d . . .
H14A H -0.7272 1.0571 0.2669 0.043 Uiso 1 1 calc R . .
C14B C -0.6104(4) 1.3869(3) 0.03467(14) 0.0363(7) Uani 1 1 d . . .
H14B H -0.6516 1.4582 0.0162 0.044 Uiso 1 1 calc R . .
C15A C -0.4823(4) 1.0685(3) 0.27323(13) 0.0333(7) Uani 1 1 d . . .
H15A H -0.4720 1.1306 0.2445 0.040 Uiso 1 1 calc R . .
C15B C -0.4763(4) 1.4155(3) 0.08731(14) 0.0361(7) Uani 1 1 d . . .
H15B H -0.4249 1.5061 0.1053 0.043 Uiso 1 1 calc R . .
C16A C -0.3441(3) 1.0201(2) 0.30415(12) 0.0264(6) Uani 1 1 d . . .
C16B C -0.4189(3) 1.3095(3) 0.11316(13) 0.0302(6) Uani 1 1 d . . .
C17B C -0.1361(4) 1.2827(3) 0.16298(13) 0.0302(6) Uani 1 1 d . . .
C17A C -0.0403(3) 1.1065(3) 0.34225(12) 0.0258(6) Uani 1 1 d . . .
C18A C 0.0625(3) 1.2255(3) 0.34085(13) 0.0311(6) Uani 1 1 d . . .
H18A H 0.0344 1.2757 0.3073 0.037 Uiso 1 1 calc R . .
C18B C 0.0133(4) 1.3685(3) 0.17053(14) 0.0362(7) Uani 1 1 d . . .
H18B H 0.0191 1.4636 0.1785 0.043 Uiso 1 1 calc R . .
C19A C 0.2049(4) 1.2696(3) 0.38855(14) 0.0345(7) Uani 1 1 d . . .
H19A H 0.2743 1.3514 0.3881 0.041 Uiso 1 1 calc R . .
C19B C 0.1532(4) 1.3127(3) 0.16618(14) 0.0383(7) Uani 1 1 d . . .
H19B H 0.2554 1.3701 0.1706 0.046 Uiso 1 1 calc R . .
C20A C 0.2478(3) 1.1961(3) 0.43692(14) 0.0311(6) Uani 1 1 d . . .
H20A H 0.3435 1.2291 0.4708 0.037 Uiso 1 1 calc R . .
C20B C 0.1456(4) 1.1749(3) 0.15561(13) 0.0327(6) Uani 1 1 d . . .
H20B H 0.2418 1.1370 0.1526 0.039 Uiso 1 1 calc R . .
C21A C 0.1503(3) 1.0733(2) 0.43596(12) 0.0244(6) Uani 1 1 d . . .
C21B C -0.0048(3) 1.0919(3) 0.14936(12) 0.0269(6) Uani 1 1 d . . .
C22B C -0.1440(3) 1.1456(2) 0.15309(12) 0.0216(5) Uani 1 1 d . . .
H22A H -0.2460 1.0880 0.1488 0.026 Uiso 1 1 calc R . .
C22A C 0.0057(3) 1.0290(3) 0.38900(12) 0.0240(5) Uani 1 1 d . . .
H22B H -0.0618 0.9459 0.3887 0.029 Uiso 1 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 117.5(2) . . ?
C5B N1B C1B 117.6(2) . . ?
C6A N2A C5A 127.1(2) . . ?
C6A N2A H2AA 116.4 . . ?
C5A N2A H2AA 116.4 . . ?
C5B N2B C6B 128.7(2) . . ?
C5B N2B H2BA 115.6 . . ?
C6B N2B H2BA 115.6 . . ?
C12A N3A C10A 115.7(2) . . ?
C12A N3A H3AA 122.2 . . ?
C10A N3A H3AA 122.2 . . ?
C12B N3B C10B 131.6(2) . . ?
C12B N3B H3BA 114.2 . . ?
C10B N3B H3BA 114.2 . . ?
C16A N4A C12A 118.1(2) . . ?
C12B N4B C16B 117.7(2) . . ?
C16B N5B C17B 121.7(2) . . ?
C16B N5B H5BA 119.1 . . ?
C17B N5B H5BA 119.1 . . ?
C16A N5A C17A 127.6(2) . . ?
C16A N5A H5AA 116.2 . . ?
C17A N5A H5AA 116.2 . . ?
C1A N6A C21A 130.7(2) . . ?
C1A N6A H6AA 114.7 . . ?
C21A N6A H6AA 114.7 . . ?
C21B N6B C1B 123.4(2) . . ?
C21B N6B H6BA 118.3 . . ?
C1B N6B H6BA 118.3 . . ?
N1A C1A N6A 120.4(2) . . ?
N1A C1A C2A 122.4(2) . . ?
N6A C1A C2A 117.1(2) . . ?
N1B C1B C2B 123.1(3) . . ?
N1B C1B N6B 118.0(2) . . ?
C2B C1B N6B 118.9(2) . . ?
C3A C2A C1A 118.6(3) . . ?
C3A C2A H2AB 120.7 . . ?
C1A C2A H2AB 120.7 . . ?
C3B C2B C1B 118.1(3) . . ?
C3B C2B H2BB 120.9 . . ?
C1B C2B H2BB 120.9 . . ?
C2A C3A C4A 119.8(3) . . ?
C2A C3A H3AB 120.1 . . ?
C4A C3A H3AB 120.1 . . ?
C4B C3B C2B 120.4(3) . . ?
C4B C3B H3BB 119.8 . . ?
C2B C3B H3BB 119.8 . . ?
C3B C4B C5B 118.9(3) . . ?
C3B C4B H4BB 120.6 . . ?
C5B C4B H4BB 120.6 . . ?
C5A C4A C3A 118.2(3) . . ?
C5A C4A H4AB 120.9 . . ?
C3A C4A H4AB 120.9 . . ?
N1B C5B N2B 120.8(2) . . ?
N1B C5B C4B 121.8(3) . . ?
N2B C5B C4B 117.5(2) . . ?
N1A C5A C4A 123.4(2) . . ?
N1A C5A N2A 118.2(2) . . ?
C4A C5A N2A 118.4(2) . . ?
C11A C6A C7A 119.3(3) . . ?
C11A C6A N2A 123.1(2) . . ?
C7A C6A N2A 117.6(2) . . ?
C11B C6B C7B 120.7(3) . . ?
C11B C6B N2B 121.7(3) . . ?
C7B C6B N2B 117.6(2) . . ?
C8A C7A C6A 120.2(3) . . ?
C8A C7A H7AA 119.9 . . ?
C6A C7A H7AA 119.9 . . ?
C8B C7B C6B 119.2(3) . . ?
C8B C7B H7BA 120.4 . . ?
C6B C7B H7BA 120.4 . . ?
C9B C8B C7B 120.4(3) . . ?
C9B C8B H8BA 119.8 . . ?
C7B C8B H8BA 119.8 . . ?
C7A C8A C9A 120.5(3) . . ?
C7A C8A H8AA 119.8 . . ?
C9A C8A H8AA 119.8 . . ?
C8B C9B C10B 119.2(3) . . ?
C8B C9B H9BA 120.4 . . ?
C10B C9B H9BA 120.4 . . ?
C10A C9A C8A 119.0(3) . . ?
C10A C9A H9AA 120.5 . . ?
C8A C9A H9AA 120.5 . . ?
C11A C10A C9A 121.4(3) . . ?
C11A C10A N3A 118.8(2) . . ?
C9A C10A N3A 119.8(3) . . ?
C11B C10B N3B 122.9(2) . . ?
C11B C10B C9B 120.7(2) . . ?
N3B C10B C9B 116.3(2) . . ?
C10A C11A C6A 119.6(3) . . ?
C10A C11A H11A 120.2 . . ?
C6A C11A H11A 120.2 . . ?
C10B C11B C6B 119.7(3) . . ?
C10B C11B H11B 120.2 . . ?
C6B C11B H11B 120.2 . . ?
N4A C12A C13A 123.5(3) . . ?
N4A C12A N3A 116.2(2) . . ?
C13A C12A N3A 120.3(2) . . ?
N4B C12B N3B 121.4(2) . . ?
N4B C12B C13B 122.3(2) . . ?
N3B C12B C13B 116.3(2) . . ?
C14B C13B C12B 119.0(3) . . ?
C14B C13B H13A 120.5 . . ?
C12B C13B H13A 120.5 . . ?
C14A C13A C12A 117.4(3) . . ?
C14A C13A H13B 121.3 . . ?
C12A C13A H13B 121.3 . . ?
C15A C14A C13A 120.5(3) . . ?
C15A C14A H14A 119.7 . . ?
C13A C14A H14A 119.7 . . ?
C13B C14B C15B 119.8(3) . . ?
C13B C14B H14B 120.1 . . ?
C15B C14B H14B 120.1 . . ?
C14A C15A C16A 118.1(3) . . ?
C14A C15A H15A 121.0 . . ?
C16A C15A H15A 121.0 . . ?
C16B C15B C14B 118.8(3) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N4A C16A N5A 119.1(2) . . ?
N4A C16A C15A 122.3(3) . . ?
N5A C16A C15A 118.7(2) . . ?
N4B C16B C15B 122.4(3) . . ?
N4B C16B N5B 119.4(2) . . ?
C15B C16B N5B 118.2(2) . . ?
C22B C17B C18B 120.6(3) . . ?
C22B C17B N5B 120.5(2) . . ?
C18B C17B N5B 118.9(2) . . ?
C22A C17A C18A 120.2(2) . . ?
C22A C17A N5A 122.9(2) . . ?
C18A C17A N5A 117.0(2) . . ?
C19A C18A C17A 119.5(3) . . ?
C19A C18A H18A 120.2 . . ?
C17A C18A H18A 120.2 . . ?
C19B C18B C17B 118.9(3) . . ?
C19B C18B H18B 120.6 . . ?
C17B C18B H18B 120.6 . . ?
C18A C19A C20A 120.6(3) . . ?
C18A C19A H19A 119.7 . . ?
C20A C19A H19A 119.7 . . ?
C20B C19B C18B 120.7(3) . . ?
C20B C19B H19B 119.6 . . ?
C18B C19B H19B 119.6 . . ?
C19A C20A C21A 119.8(3) . . ?
C19A C20A H20A 120.1 . . ?
C21A C20A H20A 120.1 . . ?
C19B C20B C21B 119.1(3) . . ?
C19B C20B H20B 120.5 . . ?
C21B C20B H20B 120.5 . . ?
C22A C21A C20A 120.1(2) . . ?
C22A C21A N6A 124.3(2) . . ?
C20A C21A N6A 115.7(2) . . ?
C22B C21B C20B 120.8(2) . . ?
C22B C21B N6B 121.0(2) . . ?
C20B C21B N6B 118.2(2) . . ?
C21B C22B C17B 119.9(2) . . ?
C21B C22B H22A 120.1 . . ?
C17B C22B H22A 120.1 . . ?
C21A C22A C17A 119.7(2) . . ?
C21A C22A H22B 120.1 . . ?
C17A C22A H22B 120.1 . . ?
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 1.343(3) . ?
N1A C5A 1.349(3) . ?
N1B C5B 1.356(4) . ?
N1B C1B 1.359(4) . ?
N2A C6A 1.403(4) . ?
N2A C5A 1.404(4) . ?
N2A H2AA 0.8800 . ?
N2B C5B 1.397(4) . ?
N2B C6B 1.403(4) . ?
N2B H2BA 0.8800 . ?
N3A C12A 1.412(4) . ?
N3A C10A 1.440(3) . ?
N3A H3AA 0.8800 . ?
N3B C12B 1.391(3) . ?
N3B C10B 1.394(3) . ?
N3B H3BA 0.8800 . ?
N4A C16A 1.334(3) . ?
N4A C12A 1.346(3) . ?
N4B C12B 1.355(3) . ?
N4B C16B 1.364(3) . ?
N5B C16B 1.415(4) . ?
N5B C17B 1.417(4) . ?
N5B H5BA 0.8800 . ?
N5A C16A 1.390(4) . ?
N5A C17A 1.407(3) . ?
N5A H5AA 0.8800 . ?
N6A C1A 1.389(3) . ?
N6A C21A 1.401(3) . ?
N6A H6AA 0.8800 . ?
N6B C21B 1.405(3) . ?
N6B C1B 1.417(4) . ?
N6B H6BA 0.8800 . ?
C1A C2A 1.399(4) . ?
C1B C2B 1.379(4) . ?
C2A C3A 1.372(4) . ?
C2A H2AB 0.9500 . ?
C2B C3B 1.378(4) . ?
C2B H2BB 0.9500 . ?
C3A C4A 1.382(4) . ?
C3A H3AB 0.9500 . ?
C3B C4B 1.369(4) . ?
C3B H3BB 0.9500 . ?
C4B C5B 1.398(4) . ?
C4B H4BB 0.9500 . ?
C4A C5A 1.381(4) . ?
C4A H4AB 0.9500 . ?
C6A C11A 1.389(4) . ?
C6A C7A 1.401(4) . ?
C6B C11B 1.372(4) . ?
C6B C7B 1.393(4) . ?
C7A C8A 1.380(4) . ?
C7A H7AA 0.9500 . ?
C7B C8B 1.384(4) . ?
C7B H7BA 0.9500 . ?
C8B C9B 1.375(4) . ?
C8B H8BA 0.9500 . ?
C8A C9A 1.387(4) . ?
C8A H8AA 0.9500 . ?
C9B C10B 1.399(4) . ?
C9B H9BA 0.9500 . ?
C9A C10A 1.384(4) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.379(4) . ?
C10B C11B 1.367(4) . ?
C11A H11A 0.9500 . ?
C11B H11B 0.9500 . ?
C12A C13A 1.384(4) . ?
C12B C13B 1.395(4) . ?
C13B C14B 1.370(4) . ?
C13B H13A 0.9500 . ?
C13A C14A 1.383(4) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.373(4) . ?
C14A H14A 0.9500 . ?
C14B C15B 1.386(4) . ?
C14B H14B 0.9500 . ?
C15A C16A 1.406(4) . ?
C15A H15A 0.9500 . ?
C15B C16B 1.384(4) . ?
C15B H15B 0.9500 . ?
C17B C22B 1.369(4) . ?
C17B C18B 1.393(4) . ?
C17A C22A 1.388(4) . ?
C17A C18A 1.395(4) . ?
C18A C19A 1.378(4) . ?
C18A H18A 0.9500 . ?
C18B C19B 1.386(4) . ?
C18B H18B 0.9500 . ?
C19A C20A 1.381(4) . ?
C19A H19A 0.9500 . ?
C19B C20B 1.376(4) . ?
C19B H19B 0.9500 . ?
C20A C21A 1.392(4) . ?
C20A H20A 0.9500 . ?
C20B C21B 1.391(4) . ?
C20B H20B 0.9500 . ?
C21A C22A 1.382(4) . ?
C21B C22B 1.368(4) . ?
C22B H22A 0.9500 . ?
C22A H22B 0.9500 . ?
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
C5A N1A C1A N6A -179.8(2) . . . . ?
C5A N1A C1A C2A 2.4(4) . . . . ?
C21A N6A C1A N1A -19.5(4) . . . . ?
C21A N6A C1A C2A 158.4(3) . . . . ?
C5B N1B C1B C2B 1.5(4) . . . . ?
C5B N1B C1B N6B -179.3(2) . . . . ?
C21B N6B C1B N1B 63.7(3) . . . . ?
C21B N6B C1B C2B -117.1(3) . . . . ?
N1A C1A C2A C3A -0.9(4) . . . . ?
N6A C1A C2A C3A -178.8(2) . . . . ?
N1B C1B C2B C3B -3.5(4) . . . . ?
N6B C1B C2B C3B 177.3(2) . . . . ?
C1A C2A C3A C4A -1.5(4) . . . . ?
C1B C2B C3B C4B 2.8(4) . . . . ?
C2B C3B C4B C5B -0.3(4) . . . . ?
C2A C3A C4A C5A 2.3(4) . . . . ?
C1B N1B C5B N2B -178.0(2) . . . . ?
C1B N1B C5B C4B 1.2(4) . . . . ?
C6B N2B C5B N1B 22.0(4) . . . . ?
C6B N2B C5B C4B -157.2(3) . . . . ?
C3B C4B C5B N1B -1.8(4) . . . . ?
C3B C4B C5B N2B 177.4(2) . . . . ?
C1A N1A C5A C4A -1.5(4) . . . . ?
C1A N1A C5A N2A -179.4(2) . . . . ?
C3A C4A C5A N1A -0.8(4) . . . . ?
C3A C4A C5A N2A 177.0(2) . . . . ?
C6A N2A C5A N1A -46.8(4) . . . . ?
C6A N2A C5A C4A 135.2(3) . . . . ?
C5A N2A C6A C11A 9.0(4) . . . . ?
C5A N2A C6A C7A -169.1(3) . . . . ?
C5B N2B C6B C11B -46.0(4) . . . . ?
C5B N2B C6B C7B 135.7(3) . . . . ?
C11A C6A C7A C8A -0.7(4) . . . . ?
N2A C6A C7A C8A 177.4(2) . . . . ?
C11B C6B C7B C8B 1.8(4) . . . . ?
N2B C6B C7B C8B -179.9(2) . . . . ?
C6B C7B C8B C9B -0.4(4) . . . . ?
C6A C7A C8A C9A 0.8(4) . . . . ?
C7B C8B C9B C10B -1.0(4) . . . . ?
C7A C8A C9A C10A -0.1(4) . . . . ?
C8A C9A C10A C11A -0.7(4) . . . . ?
C8A C9A C10A N3A 177.9(2) . . . . ?
C12A N3A C10A C11A 84.5(3) . . . . ?
C12A N3A C10A C9A -94.1(3) . . . . ?
C12B N3B C10B C11B -22.7(4) . . . . ?
C12B N3B C10B C9B 155.2(3) . . . . ?
C8B C9B C10B C11B 1.0(4) . . . . ?
C8B C9B C10B N3B -177.0(2) . . . . ?
C9A C10A C11A C6A 0.8(4) . . . . ?
N3A C10A C11A C6A -177.8(2) . . . . ?
C7A C6A C11A C10A -0.1(4) . . . . ?
N2A C6A C11A C10A -178.1(2) . . . . ?
N3B C10B C11B C6B 178.2(2) . . . . ?
C9B C10B C11B C6B 0.3(4) . . . . ?
C7B C6B C11B C10B -1.7(4) . . . . ?
N2B C6B C11B C10B 180.0(2) . . . . ?
C16A N4A C12A C13A -1.7(4) . . . . ?
C16A N4A C12A N3A 179.4(2) . . . . ?
C10A N3A C12A N4A -55.1(3) . . . . ?
C10A N3A C12A C13A 126.0(3) . . . . ?
C16B N4B C12B N3B -179.8(2) . . . . ?
C16B N4B C12B C13B -1.0(4) . . . . ?
C10B N3B C12B N4B 24.4(4) . . . . ?
C10B N3B C12B C13B -154.5(3) . . . . ?
N4B C12B C13B C14B -1.0(4) . . . . ?
N3B C12B C13B C14B 177.9(2) . . . . ?
N4A C12A C13A C14A 2.4(4) . . . . ?
N3A C12A C13A C14A -178.8(2) . . . . ?
C12A C13A C14A C15A -0.2(4) . . . . ?
C12B C13B C14B C15B 1.4(4) . . . . ?
C13A C14A C15A C16A -2.5(4) . . . . ?
C13B C14B C15B C16B 0.1(4) . . . . ?
C12A N4A C16A N5A 178.0(2) . . . . ?
C12A N4A C16A C15A -1.2(4) . . . . ?
C17A N5A C16A N4A -40.2(4) . . . . ?
C17A N5A C16A C15A 139.0(3) . . . . ?
C14A C15A C16A N4A 3.2(4) . . . . ?
C14A C15A C16A N5A -175.9(2) . . . . ?
C12B N4B C16B C15B 2.6(4) . . . . ?
C12B N4B C16B N5B -178.2(2) . . . . ?
C14B C15B C16B N4B -2.1(4) . . . . ?
C14B C15B C16B N5B 178.6(3) . . . . ?
C17B N5B C16B N4B 57.0(4) . . . . ?
C17B N5B C16B C15B -123.8(3) . . . . ?
C16B N5B C17B C22B -59.4(4) . . . . ?
C16B N5B C17B C18B 120.9(3) . . . . ?
C16A N5A C17A C22A 41.1(4) . . . . ?
C16A N5A C17A C18A -138.3(3) . . . . ?
C22A C17A C18A C19A -3.9(4) . . . . ?
N5A C17A C18A C19A 175.5(2) . . . . ?
C22B C17B C18B C19B 1.6(4) . . . . ?
N5B C17B C18B C19B -178.6(3) . . . . ?
C17A C18A C19A C20A 1.0(4) . . . . ?
C17B C18B C19B C20B -1.0(4) . . . . ?
C18A C19A C20A C21A 2.8(4) . . . . ?
C18B C19B C20B C21B -0.1(4) . . . . ?
C19A C20A C21A C22A -3.9(4) . . . . ?
C19A C20A C21A N6A 175.6(2) . . . . ?
C1A N6A C21A C22A 33.0(4) . . . . ?
C1A N6A C21A C20A -146.4(3) . . . . ?
C19B C20B C21B C22B 0.5(4) . . . . ?
C19B C20B C21B N6B 179.2(2) . . . . ?
C1B N6B C21B C22B -42.3(4) . . . . ?
C1B N6B C21B C20B 139.1(3) . . . . ?
C20B C21B C22B C17B 0.1(4) . . . . ?
N6B C21B C22B C17B -178.5(2) . . . . ?
C18B C17B C22B C21B -1.2(4) . . . . ?
N5B C17B C22B C21B 179.1(2) . . . . ?
C20A C21A C22A C17A 1.0(4) . . . . ?
N6A C21A C22A C17A -178.4(2) . . . . ?
C18A C17A C22A C21A 2.9(4) . . . . ?
N5A C17A C22A C21A -176.5(2) . . . . ?
