#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:57:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178413 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023496.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_4023496
loop_
_publ_author_name
'Ivan V. Korendovych'
'Mimi Cho'
'Olga V. Makhlynets'
'Phillip L. Butler'
'Richard J. Staples'
'Elena V. Rybak-Akimova'
_publ_section_title
;
 Anion and Carboxylic Acid Binding to Monotopic and Ditopic
 Amidopyridine Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4771
_journal_page_last               4782
_journal_paper_doi               10.1021/jo800128r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C26 H42 N10 O4, 4(C7 H4 N O4), 4(C2 H6 O S)'
_chemical_formula_sum            'C62 H82 N14 O24 S4'
_chemical_formula_weight         1535.66
_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                100.467(3)
_cell_angle_beta                 101.620(4)
_cell_angle_gamma                101.649(3)
_cell_formula_units_Z            1
_cell_length_a                   10.6618(19)
_cell_length_b                   12.830(2)
_cell_length_c                   14.182(3)
_cell_measurement_reflns_used    3466
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.52
_cell_measurement_theta_min      2.79
_cell_volume                     1810.4(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0961
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13887
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.391
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         8396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0951
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2438
_refine_ls_wR_factor_ref         0.2970
_reflns_number_gt                3614
_reflns_number_total             8396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800128r-File004.cif
_cod_data_source_block           623338
_cod_database_code               4023496
loop_
_publ_contact_author_name
_publ_contact_author_address
_publ_contact_author_email
_publ_contact_author_fax
_publ_contact_author_phone
'Prof. Elena V. Rybak-Akimova'
;
Department of Chemistry
Tufts University
62 Talbot Avenue 
Medford, MA 02155
USA
;
elena.rybak-akimova@tufts.edu '1 617 627 3443' '1 617 627 3413'
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
N6 N 0.5159(3) 0.0995(4) 0.1054(3) 0.0553(9) Uani 1 1 d . . .
S1 S 0.07494(10) 0.55185(9) 0.22682(7) 0.0508(3) Uani 1 1 d . . .
N1 N 0.7046(3) 0.9763(3) 0.6135(3) 0.0453(8) Uani 1 1 d . . .
N5 N 1.0445(3) 0.7937(3) 0.4226(2) 0.0441(8) Uani 1 1 d . . .
O2 O 0.8483(3) 0.5065(3) 0.3421(2) 0.0601(8) Uani 1 1 d . . .
N3 N 0.6346(3) 0.6206(3) 0.4652(2) 0.0475(8) Uani 1 1 d . . .
N2 N 0.5786(3) 0.7604(3) 0.6056(2) 0.0481(8) Uani 1 1 d . . .
N4 N 0.8897(4) 0.6221(3) 0.4913(3) 0.0508(9) Uani 1 1 d . . .
O1 O 0.3652(3) 0.7209(3) 0.5187(2) 0.0680(9) Uani 1 1 d . . .
O1S O 0.0816(3) 0.6719(2) 0.2605(2) 0.0626(8) Uani 1 1 d . . .
C1 C 0.7577(4) 1.0904(3) 0.6100(3) 0.0484(10) Uani 1 1 d . . .
H1A H 0.7701 1.1401 0.6752 0.058 Uiso 1 1 calc R . .
H1B H 0.6962 1.1125 0.5597 0.058 Uiso 1 1 calc R . .
C5 C 0.5070(4) 0.6207(3) 0.4553(3) 0.0469(9) Uani 1 1 d . . .
C9 C 0.6654(4) 0.5514(3) 0.3975(3) 0.0467(9) Uani 1 1 d . . .
C12 C 1.0932(4) 0.7648(4) 0.5181(3) 0.0481(10) Uani 1 1 d . . .
H12A H 1.0697 0.8115 0.5721 0.058 Uiso 1 1 calc R . .
H12B H 1.1907 0.7782 0.5334 0.058 Uiso 1 1 calc R . .
C4 C 0.4786(4) 0.7052(4) 0.5289(3) 0.0510(10) Uani 1 1 d . . .
C8 C 0.5712(4) 0.4772(4) 0.3183(3) 0.0549(11) Uani 1 1 d . . .
H8 H 0.5965 0.4298 0.2699 0.066 Uiso 1 1 calc R . .
C11 C 1.0327(4) 0.6460(4) 0.5120(3) 0.0517(10) Uani 1 1 d . . .
H11A H 1.0586 0.5996 0.4592 0.062 Uiso 1 1 calc R . .
H11B H 1.0675 0.6277 0.5755 0.062 Uiso 1 1 calc R . .
C2 C 0.5832(4) 0.9564(4) 0.6505(3) 0.0504(10) Uani 1 1 d . . .
H2A H 0.5058 0.9556 0.5982 0.060 Uiso 1 1 calc R . .
H2B H 0.5914 1.0159 0.7084 0.060 Uiso 1 1 calc R . .
C3 C 0.5634(4) 0.8463(4) 0.6804(3) 0.0509(10) Uani 1 1 d . . .
H3A H 0.6286 0.8536 0.7433 0.061 Uiso 1 1 calc R . .
H3B H 0.4739 0.8262 0.6917 0.061 Uiso 1 1 calc R . .
C2S C -0.0778(4) 0.4950(4) 0.1382(3) 0.0542(11) Uani 1 1 d . . .
H2S1 H -0.1503 0.4954 0.1711 0.081 Uiso 1 1 calc R . .
H2S3 H -0.0817 0.4196 0.1063 0.081 Uiso 1 1 calc R . .
H2S2 H -0.0862 0.5385 0.0882 0.081 Uiso 1 1 calc R . .
C10 C 0.8094(4) 0.5578(4) 0.4073(3) 0.0505(10) Uani 1 1 d . . .
C6 C 0.4084(4) 0.5497(4) 0.3804(3) 0.0567(11) Uani 1 1 d . . .
H6 H 0.3190 0.5524 0.3758 0.068 Uiso 1 1 calc R . .
C13 C 1.1112(4) 0.9043(3) 0.4166(3) 0.0508(10) Uani 1 1 d . . .
H13A H 1.1257 0.9557 0.4812 0.061 Uiso 1 1 calc R . .
H13B H 1.0523 0.9287 0.3663 0.061 Uiso 1 1 calc R . .
C7 C 0.4385(4) 0.4754(4) 0.3127(3) 0.0592(12) Uani 1 1 d . . .
H7 H 0.3705 0.4232 0.2626 0.071 Uiso 1 1 calc R . .
C1S C 0.1798(4) 0.5476(4) 0.1439(3) 0.0610(12) Uani 1 1 d . . .
H1S1 H 0.1530 0.5866 0.0929 0.092 Uiso 1 1 calc R . .
H1S3 H 0.1726 0.4713 0.1125 0.092 Uiso 1 1 calc R . .
H1S2 H 0.2715 0.5825 0.1806 0.092 Uiso 1 1 calc R . .
S2 S -0.01651(12) 0.79249(10) 0.06885(9) 0.0591(4) Uani 1 1 d . . .
O2S O -0.0263(3) 0.6828(3) 0.0081(3) 0.0704(9) Uani 1 1 d . . .
C4S C -0.1067(5) 0.8584(5) -0.0114(4) 0.0763(15) Uani 1 1 d . . .
H4S2 H -0.0693 0.8615 -0.0688 0.114 Uiso 1 1 calc R . .
H4S1 H -0.1010 0.9329 0.0242 0.114 Uiso 1 1 calc R . .
H4S3 H -0.1995 0.8172 -0.0337 0.114 Uiso 1 1 calc R . .
C3S C 0.1435(5) 0.8719(4) 0.0801(4) 0.0712(13) Uani 1 1 d . . .
H3S1 H 0.2090 0.8396 0.1153 0.107 Uiso 1 1 calc R . .
H3S2 H 0.1531 0.9465 0.1173 0.107 Uiso 1 1 calc R . .
H3S3 H 0.1572 0.8737 0.0141 0.107 Uiso 1 1 calc R . .
O9 O 0.6195(3) 0.8811(2) 0.4205(2) 0.0531(7) Uani 1 1 d . . .
O10 O 0.8175(3) 0.8509(2) 0.4222(2) 0.0524(7) Uani 1 1 d . . .
O7 O 0.3857(3) 0.5966(3) -0.0646(2) 0.0683(9) Uani 1 1 d . . .
C20 C 0.6471(4) 0.7786(3) 0.2732(3) 0.0431(9) Uani 1 1 d . . .
C27 C 0.6984(4) 0.8413(3) 0.3813(3) 0.0438(9) Uani 1 1 d . . .
N7 N 0.5050(4) 0.6165(3) -0.0277(3) 0.0559(9) Uani 1 1 d . . .
C21 C 0.5194(4) 0.7709(4) 0.2246(3) 0.0495(10) Uani 1 1 d . . .
H21 H 0.4633 0.8020 0.2593 0.059 Uiso 1 1 calc R . .
O8 O 0.5839(4) 0.5897(3) -0.0727(2) 0.0738(10) Uani 1 1 d . . .
C24 C 0.6821(4) 0.6780(4) 0.1241(3) 0.0517(10) Uani 1 1 d . . .
H24 H 0.7370 0.6449 0.0896 0.062 Uiso 1 1 calc R . .
C23 C 0.5553(4) 0.6737(3) 0.0774(3) 0.0487(10) Uani 1 1 d . . .
C22 C 0.4713(4) 0.7182(4) 0.1253(3) 0.0515(10) Uani 1 1 d . . .
H22 H 0.3830 0.7130 0.0913 0.062 Uiso 1 1 calc R . .
C25 C 0.7284(4) 0.7319(3) 0.2229(3) 0.0489(10) Uani 1 1 d . . .
H25 H 0.8167 0.7369 0.2566 0.059 Uiso 1 1 calc R . .
O6 O 1.1040(3) 0.0614(3) 0.2547(2) 0.0583(8) Uani 1 1 d . . .
O5 O 1.1349(3) 0.2374(3) 0.3226(2) 0.0583(8) Uani 1 1 d . . .
O4 O 0.4405(3) 0.0101(3) 0.0933(2) 0.0661(9) Uani 1 1 d . . .
C26 C 1.0645(4) 0.1469(4) 0.2732(3) 0.0469(9) Uani 1 1 d . . .
C17 C 0.6577(4) 0.1129(4) 0.1477(3) 0.0486(10) Uani 1 1 d . . .
C16 C 0.7405(4) 0.2163(4) 0.1758(3) 0.0507(10) Uani 1 1 d . . .
H16 H 0.7082 0.2785 0.1668 0.061 Uiso 1 1 calc R . .
O3 O 0.4793(3) 0.1775(3) 0.0830(3) 0.0736(10) Uani 1 1 d . . .
C14 C 0.9202(4) 0.1363(3) 0.2290(3) 0.0470(10) Uani 1 1 d . . .
C19 C 0.8331(4) 0.0341(4) 0.2003(3) 0.0526(10) Uani 1 1 d . . .
H19 H 0.8653 -0.0281 0.2094 0.063 Uiso 1 1 calc R . .
C18 C 0.7013(4) 0.0205(4) 0.1591(3) 0.0584(11) Uani 1 1 d . . .
H18 H 0.6420 -0.0500 0.1391 0.070 Uiso 1 1 calc R . .
C15 C 0.8724(4) 0.2265(4) 0.2176(3) 0.0480(10) Uani 1 1 d . . .
H15 H 0.9314 0.2972 0.2389 0.058 Uiso 1 1 calc R . .
H4 H 0.858(4) 0.649(3) 0.528(3) 0.038(12) Uiso 1 1 d . . .
H2 H 0.664(6) 0.754(5) 0.609(4) 0.10(2) Uiso 1 1 d . . .
H5B H 1.040(4) 0.728(4) 0.364(4) 0.066(13) Uiso 1 1 d . . .
H5A H 0.959(4) 0.802(3) 0.411(3) 0.045(11) Uiso 1 1 d . . .
H3C H 0.785(5) 0.949(4) 0.665(4) 0.084(16) Uiso 1 1 d . . .
H3D H 0.681(4) 0.938(3) 0.553(3) 0.042(11) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 '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
O3 N6 O4 122.9(4) . . ?
O3 N6 C17 118.6(4) . . ?
O4 N6 C17 118.5(4) . . ?
O1S S1 C2S 105.9(2) . . ?
O1S S1 C1S 104.5(2) . . ?
C2S S1 C1S 97.8(2) . . ?
C1 N1 C2 115.4(3) . . ?
C1 N1 H3C 108(3) . . ?
C2 N1 H3C 107(3) . . ?
C1 N1 H3D 107(3) . . ?
C2 N1 H3D 105(3) . . ?
H3C N1 H3D 114(4) . . ?
C13 N5 C12 114.4(3) . . ?
C13 N5 H5B 117(3) . . ?
C12 N5 H5B 109(2) . . ?
C13 N5 H5A 98(3) . . ?
C12 N5 H5A 115(2) . . ?
H5B N5 H5A 103(3) . . ?
C9 N3 C5 118.0(3) . . ?
C4 N2 C3 121.5(3) . . ?
C4 N2 H2 122(4) . . ?
C3 N2 H2 116(4) . . ?
C10 N4 C11 123.8(4) . . ?
C10 N4 H4 117(3) . . ?
C11 N4 H4 120(3) . . ?
N1 C1 C13 106.9(3) . 2_776 ?
N1 C1 H1A 110.3 . . ?
C13 C1 H1A 110.3 2_776 . ?
N1 C1 H1B 110.3 . . ?
C13 C1 H1B 110.3 2_776 . ?
H1A C1 H1B 108.6 . . ?
N3 C5 C6 122.5(4) . . ?
N3 C5 C4 115.9(3) . . ?
C6 C5 C4 121.6(4) . . ?
N3 C9 C8 123.2(4) . . ?
N3 C9 C10 116.7(4) . . ?
C8 C9 C10 120.1(4) . . ?
N5 C12 C11 110.3(3) . . ?
N5 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N5 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O1 C4 N2 122.7(4) . . ?
O1 C4 C5 120.7(4) . . ?
N2 C4 C5 116.6(3) . . ?
C9 C8 C7 117.5(4) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
N4 C11 C12 111.9(3) . . ?
N4 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N4 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N1 C2 C3 109.6(3) . . ?
N1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 C2 112.0(3) . . ?
N2 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
S1 C2S H2S1 109.5 . . ?
S1 C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
S1 C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
H2S3 C2S H2S2 109.5 . . ?
O2 C10 N4 123.5(4) . . ?
O2 C10 C9 121.4(4) . . ?
N4 C10 C9 115.1(4) . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N5 C13 C1 113.4(3) . 2_776 ?
N5 C13 H13A 108.9 . . ?
C1 C13 H13A 108.9 2_776 . ?
N5 C13 H13B 108.9 . . ?
C1 C13 H13B 108.9 2_776 . ?
H13A C13 H13B 107.7 . . ?
C6 C7 C8 118.7(4) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
S1 C1S H1S1 109.5 . . ?
S1 C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
S1 C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
H1S3 C1S H1S2 109.5 . . ?
O2S S2 C3S 106.5(2) . . ?
O2S S2 C4S 105.7(2) . . ?
C3S S2 C4S 98.2(3) . . ?
S2 C4S H4S2 109.5 . . ?
S2 C4S H4S1 109.5 . . ?
H4S2 C4S H4S1 109.5 . . ?
S2 C4S H4S3 109.5 . . ?
H4S2 C4S H4S3 109.5 . . ?
H4S1 C4S H4S3 109.5 . . ?
S2 C3S H3S1 109.5 . . ?
S2 C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
S2 C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
C21 C20 C25 119.7(4) . . ?
C21 C20 C27 119.2(4) . . ?
C25 C20 C27 121.1(3) . . ?
O9 C27 O10 125.5(4) . . ?
O9 C27 C20 116.9(3) . . ?
O10 C27 C20 117.5(3) . . ?
O8 N7 O7 123.7(4) . . ?
O8 N7 C23 118.1(3) . . ?
O7 N7 C23 118.2(4) . . ?
C20 C21 C22 120.7(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C24 C25 118.2(4) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C24 C23 C22 122.7(4) . . ?
C24 C23 N7 118.7(4) . . ?
C22 C23 N7 118.6(3) . . ?
C23 C22 C21 118.1(4) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C24 C25 C20 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
O5 C26 O6 125.2(4) . . ?
O5 C26 C14 119.1(4) . . ?
O6 C26 C14 115.8(4) . . ?
C16 C17 C18 122.8(4) . . ?
C16 C17 N6 119.0(4) . . ?
C18 C17 N6 118.2(4) . . ?
C17 C16 C15 117.6(4) . . ?
C17 C16 H16 121.2 . . ?
C15 C16 H16 121.2 . . ?
C15 C14 C19 118.9(4) . . ?
C15 C14 C26 121.6(4) . . ?
C19 C14 C26 119.5(4) . . ?
C18 C19 C14 121.5(4) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C19 C18 C17 117.7(4) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C14 C15 C16 121.4(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
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
N6 O3 1.216(5) . ?
N6 O4 1.221(5) . ?
N6 C17 1.472(5) . ?
S1 O1S 1.510(3) . ?
S1 C2S 1.768(4) . ?
S1 C1S 1.779(5) . ?
N1 C1 1.473(5) . ?
N1 C2 1.485(5) . ?
N1 H3C 1.16(5) . ?
N1 H3D 0.87(4) . ?
N5 C13 1.479(5) . ?
N5 C12 1.490(5) . ?
N5 H5B 1.06(5) . ?
N5 H5A 0.92(4) . ?
O2 C10 1.227(5) . ?
N3 C9 1.325(5) . ?
N3 C5 1.339(5) . ?
N2 C4 1.331(5) . ?
N2 C3 1.442(5) . ?
N2 H2 0.93(6) . ?
N4 C10 1.334(6) . ?
N4 C11 1.449(5) . ?
N4 H4 0.75(4) . ?
O1 C4 1.250(5) . ?
C1 C13 1.511(6) 2_776 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C5 C6 1.369(6) . ?
C5 C4 1.485(6) . ?
C9 C8 1.395(6) . ?
C9 C10 1.498(6) . ?
C12 C11 1.509(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C8 C7 1.396(6) . ?
C8 H8 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 C3 1.533(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2S H2S1 0.9800 . ?
C2S H2S3 0.9800 . ?
C2S H2S2 0.9800 . ?
C6 C7 1.360(6) . ?
C6 H6 0.9500 . ?
C13 C1 1.511(6) 2_776 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C7 H7 0.9500 . ?
C1S H1S1 0.9800 . ?
C1S H1S3 0.9800 . ?
C1S H1S2 0.9800 . ?
S2 O2S 1.483(3) . ?
S2 C3S 1.761(5) . ?
S2 C4S 1.781(5) . ?
C4S H4S2 0.9800 . ?
C4S H4S1 0.9800 . ?
C4S H4S3 0.9800 . ?
C3S H3S1 0.9800 . ?
C3S H3S2 0.9800 . ?
C3S H3S3 0.9800 . ?
O9 C27 1.239(5) . ?
O10 C27 1.256(4) . ?
O7 N7 1.229(4) . ?
C20 C21 1.372(5) . ?
C20 C25 1.386(6) . ?
C20 C27 1.528(5) . ?
N7 O8 1.219(5) . ?
N7 C23 1.472(5) . ?
C21 C22 1.388(6) . ?
C21 H21 0.9500 . ?
C24 C23 1.365(5) . ?
C24 C25 1.384(6) . ?
C24 H24 0.9500 . ?
C23 C22 1.379(6) . ?
C22 H22 0.9500 . ?
C25 H25 0.9500 . ?
O6 C26 1.256(5) . ?
O5 C26 1.242(5) . ?
C26 C14 1.508(5) . ?
C17 C16 1.375(6) . ?
C17 C18 1.382(6) . ?
C16 C15 1.381(5) . ?
C16 H16 0.9500 . ?
C14 C15 1.378(5) . ?
C14 C19 1.381(6) . ?
C19 C18 1.371(6) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C15 H15 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 N3 0.75(4) 2.30(4) 2.667(5) 112(4) .
N5 H5A O10 0.92(4) 1.77(4) 2.666(4) 162(4) .
N1 H3D O9 0.87(4) 1.81(4) 2.672(4) 169(4) .
N4 H4 O5 0.75(4) 2.32(4) 3.005(5) 152(4) 2_766
N2 H2 O5 0.93(6) 2.14(6) 3.012(4) 157(5) 2_766
N5 H5B O1S 1.06(5) 1.70(5) 2.681(5) 153(4) 1_655
N1 H3C O6 1.16(5) 1.51(5) 2.662(4) 168(4) 2_766
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
C2 N1 C1 C13 172.8(3) . . . 2_776 ?
C9 N3 C5 C6 2.4(6) . . . . ?
C9 N3 C5 C4 -175.7(3) . . . . ?
C5 N3 C9 C8 -1.6(6) . . . . ?
C5 N3 C9 C10 176.5(4) . . . . ?
C13 N5 C12 C11 -172.5(3) . . . . ?
C3 N2 C4 O1 -2.9(6) . . . . ?
C3 N2 C4 C5 178.4(4) . . . . ?
N3 C5 C4 O1 171.0(4) . . . . ?
C6 C5 C4 O1 -7.2(6) . . . . ?
N3 C5 C4 N2 -10.2(5) . . . . ?
C6 C5 C4 N2 171.6(4) . . . . ?
N3 C9 C8 C7 -1.6(6) . . . . ?
C10 C9 C8 C7 -179.6(4) . . . . ?
C10 N4 C11 C12 113.2(4) . . . . ?
N5 C12 C11 N4 -60.2(5) . . . . ?
C1 N1 C2 C3 -162.7(3) . . . . ?
C4 N2 C3 C2 -84.7(5) . . . . ?
N1 C2 C3 N2 -47.3(4) . . . . ?
C11 N4 C10 O2 5.2(7) . . . . ?
C11 N4 C10 C9 -175.1(4) . . . . ?
N3 C9 C10 O2 -171.2(4) . . . . ?
C8 C9 C10 O2 7.0(6) . . . . ?
N3 C9 C10 N4 9.1(5) . . . . ?
C8 C9 C10 N4 -172.7(4) . . . . ?
N3 C5 C6 C7 0.1(7) . . . . ?
C4 C5 C6 C7 178.2(4) . . . . ?
C12 N5 C13 C1 81.7(4) . . . 2_776 ?
C5 C6 C7 C8 -3.4(7) . . . . ?
C9 C8 C7 C6 4.0(6) . . . . ?
C21 C20 C27 O9 1.2(6) . . . . ?
C25 C20 C27 O9 179.5(4) . . . . ?
C21 C20 C27 O10 -176.9(4) . . . . ?
C25 C20 C27 O10 1.4(6) . . . . ?
C25 C20 C21 C22 -0.9(6) . . . . ?
C27 C20 C21 C22 177.4(4) . . . . ?
C25 C24 C23 C22 -1.7(7) . . . . ?
C25 C24 C23 N7 -180.0(4) . . . . ?
O8 N7 C23 C24 -10.8(6) . . . . ?
O7 N7 C23 C24 167.8(4) . . . . ?
O8 N7 C23 C22 170.8(4) . . . . ?
O7 N7 C23 C22 -10.6(6) . . . . ?
C24 C23 C22 C21 1.0(7) . . . . ?
N7 C23 C22 C21 179.4(4) . . . . ?
C20 C21 C22 C23 0.3(6) . . . . ?
C23 C24 C25 C20 1.0(7) . . . . ?
C21 C20 C25 C24 0.3(6) . . . . ?
C27 C20 C25 C24 -178.0(4) . . . . ?
O3 N6 C17 C16 10.8(6) . . . . ?
O4 N6 C17 C16 -170.2(4) . . . . ?
O3 N6 C17 C18 -170.4(4) . . . . ?
O4 N6 C17 C18 8.6(6) . . . . ?
C18 C17 C16 C15 -0.4(6) . . . . ?
N6 C17 C16 C15 178.4(4) . . . . ?
O5 C26 C14 C15 18.4(6) . . . . ?
O6 C26 C14 C15 -160.3(4) . . . . ?
O5 C26 C14 C19 -160.6(4) . . . . ?
O6 C26 C14 C19 20.6(6) . . . . ?
C15 C14 C19 C18 1.4(6) . . . . ?
C26 C14 C19 C18 -179.5(4) . . . . ?
C14 C19 C18 C17 -0.5(6) . . . . ?
C16 C17 C18 C19 -0.1(6) . . . . ?
N6 C17 C18 C19 -178.8(4) . . . . ?
C19 C14 C15 C16 -1.8(6) . . . . ?
C26 C14 C15 C16 179.1(4) . . . . ?
C17 C16 C15 C14 1.3(6) . . . . ?
