#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023994.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_4023994
loop_
_publ_author_name
'Zhidong Ma'
'Cynthia S. Day'
'Ulrich Bierbach'
_publ_contact_author_address
; 
Department of Chemistry 
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
_publ_contact_author_email       bierbau@wfu.edu
_publ_contact_author_fax         '336 758 4656'
_publ_contact_author_name        'Ulrich Bierbach'
_publ_contact_author_phone       '336 758 3507'
_publ_section_title
;
 Unexpected Reactivity of the 9-Aminoacridine Chromophore
 in Guanidylation Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5387
_journal_page_last               5390
_journal_paper_doi               10.1021/jo0705972
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C37 H50 N14 O13'
_chemical_formula_weight         898.91
_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           SHELXTL
_cell_angle_alpha                109.081(4)
_cell_angle_beta                 100.725(4)
_cell_angle_gamma                94.547(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1233(17)
_cell_length_b                   16.267(4)
_cell_length_c                   17.002(4)
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.022
_cell_measurement_theta_min      3.840
_cell_volume                     2062.3(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0652
_diffrn_reflns_av_sigmaI/netI    0.1124
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15189
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.79
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular-parallelepiped
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         7216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0242P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                4018
_reflns_number_total             7216
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705972si20070322_112545.cif
_cod_data_source_block           a29k2f
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023994
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
N1 N -0.7336(3) 0.16044(17) 0.01995(15) 0.0290(7) Uani 1 1 d . . .
H1N H -0.773(4) 0.1180(18) 0.0263(17) 0.030(10) Uiso 1 1 d . . .
N2 N -0.5175(3) 0.36530(16) 0.24321(16) 0.0281(6) Uani 1 1 d . . .
H2N H -0.463(3) 0.4044(17) 0.2913(17) 0.028(9) Uiso 1 1 d . . .
N3 N -0.8959(3) 0.05022(15) -0.21410(14) 0.0271(6) Uani 1 1 d . . .
N4 N -0.6288(3) 0.02958(17) -0.23907(18) 0.0316(7) Uani 1 1 d . . .
H4N H -0.585(4) 0.034(2) -0.189(2) 0.064(13) Uiso 1 1 d . . .
N5 N -0.8417(4) 0.03176(18) -0.34646(16) 0.0350(7) Uani 1 1 d . . .
H5N1 H -0.765(4) 0.0323(18) -0.3808(18) 0.043(10) Uiso 1 1 d . . .
H5N2 H -0.953(4) 0.0259(19) -0.3706(19) 0.047(10) Uiso 1 1 d . . .
C1 C -0.6712(4) 0.23143(18) 0.08885(18) 0.0252(7) Uani 1 1 d . . .
C2 C -0.5748(4) 0.30976(18) 0.08908(18) 0.0255(7) Uani 1 1 d . . .
C3 C -0.4948(4) 0.37509(18) 0.16924(18) 0.0250(7) Uani 1 1 d . . .
C4 C -0.6202(4) 0.29630(18) 0.24576(18) 0.0260(7) Uani 1 1 d . . .
C5 C -0.7009(3) 0.22809(18) 0.16919(17) 0.0236(7) Uani 1 1 d . . .
C6 C -0.5455(4) 0.32714(19) 0.01546(18) 0.0300(7) Uani 1 1 d . . .
H6 H -0.5979 0.2860 -0.0396 0.036 Uiso 1 1 calc R . .
C7 C -0.4442(4) 0.40130(19) 0.0220(2) 0.0376(8) Uani 1 1 d . . .
H7 H -0.4272 0.4111 -0.0282 0.045 Uiso 1 1 calc R . .
C8 C -0.3657(4) 0.4626(2) 0.1019(2) 0.0363(8) Uani 1 1 d . . .
H8 H -0.2940 0.5134 0.1057 0.044 Uiso 1 1 calc R . .
C9 C -0.3902(4) 0.45075(19) 0.17471(19) 0.0319(8) Uani 1 1 d . . .
H9 H -0.3370 0.4934 0.2289 0.038 Uiso 1 1 calc R . .
C10 C -0.6430(4) 0.2943(2) 0.32477(18) 0.0314(8) Uani 1 1 d . . .
H10 H -0.5865 0.3404 0.3761 0.038 Uiso 1 1 calc R . .
C11 C -0.7470(4) 0.22577(19) 0.32758(19) 0.0332(8) Uani 1 1 d . . .
H11 H -0.7615 0.2239 0.3812 0.040 Uiso 1 1 calc R . .
C12 C -0.8325(4) 0.15830(19) 0.25250(19) 0.0329(8) Uani 1 1 d . . .
H12 H -0.9063 0.1115 0.2552 0.040 Uiso 1 1 calc R . .
C13 C -0.8101(4) 0.15941(18) 0.17509(18) 0.0293(7) Uani 1 1 d . . .
H13 H -0.8690 0.1132 0.1244 0.035 Uiso 1 1 calc R . .
C14 C -0.7881(4) 0.03829(18) -0.26598(18) 0.0270(7) Uani 1 1 d . . .
C15 C -0.8412(4) 0.05672(18) -0.12506(16) 0.0281(7) Uani 1 1 d . . .
H15A H -0.7657 0.0125 -0.1216 0.034 Uiso 1 1 calc R . .
H15B H -0.9413 0.0437 -0.1033 0.034 Uiso 1 1 calc R . .
C16 C -0.7483(4) 0.14758(18) -0.07019(16) 0.0272(7) Uani 1 1 d . . .
H16A H -0.6338 0.1548 -0.0816 0.033 Uiso 1 1 calc R . .
H16B H -0.8105 0.1925 -0.0847 0.033 Uiso 1 1 calc R . .
C17 C -1.0548(4) 0.0827(2) -0.23681(19) 0.0421(9) Uani 1 1 d . . .
H17A H -1.0513 0.1035 -0.2845 0.063 Uiso 0.50 1 calc PR . .
H17B H -1.0693 0.1313 -0.1875 0.063 Uiso 0.50 1 calc PR . .
H17C H -1.1500 0.0349 -0.2536 0.063 Uiso 0.50 1 calc PR . .
H17D H -1.1291 0.0763 -0.1992 0.063 Uiso 0.50 1 calc PR . .
H17E H -1.1111 0.0485 -0.2963 0.063 Uiso 0.50 1 calc PR . .
H17F H -1.0304 0.1449 -0.2301 0.063 Uiso 0.50 1 calc PR . .
C18 C -0.5112(4) 0.0038(2) -0.29515(19) 0.0395(8) Uani 1 1 d . . .
H18A H -0.4139 -0.0149 -0.2656 0.059 Uiso 1 1 calc R . .
H18B H -0.4719 0.0539 -0.3103 0.059 Uiso 1 1 calc R . .
H18C H -0.5690 -0.0450 -0.3472 0.059 Uiso 1 1 calc R . .
N1A N 0.1185(3) 0.45567(16) 0.31016(18) 0.0326(7) Uani 1 1 d . . .
H1NA H 0.111(3) 0.4459(17) 0.3531(17) 0.022(9) Uiso 1 1 d . . .
N2A N -0.1419(3) 0.25486(17) 0.09229(17) 0.0310(7) Uani 1 1 d . . .
H2NA H -0.200(4) 0.2110(19) 0.0443(19) 0.043(10) Uiso 1 1 d . . .
N3A N 0.3321(3) 0.68291(15) 0.44224(15) 0.0325(6) Uani 1 1 d . . .
N4A N 0.0688(3) 0.72816(19) 0.44672(18) 0.0383(7) Uani 1 1 d . . .
H4NA H 0.025(4) 0.673(2) 0.428(2) 0.058(12) Uiso 1 1 d . . .
N5A N 0.3030(4) 0.82902(18) 0.4714(2) 0.0436(8) Uani 1 1 d . . .
H5N3 H 0.231(4) 0.872(2) 0.4732(19) 0.057(11) Uiso 1 1 d . . .
H5N4 H 0.409(4) 0.841(2) 0.470(2) 0.056(12) Uiso 1 1 d . . .
C1A C 0.0311(3) 0.39517(18) 0.23762(18) 0.0258(7) Uani 1 1 d . . .
C2A C 0.0413(4) 0.39487(18) 0.15384(18) 0.0258(7) Uani 1 1 d . . .
C3A C -0.0463(4) 0.32212(18) 0.08259(19) 0.0280(7) Uani 1 1 d . . .
C4A C -0.1630(4) 0.25546(18) 0.16982(19) 0.0268(7) Uani 1 1 d . . .
C5A C -0.0784(3) 0.32407(18) 0.24441(18) 0.0243(7) Uani 1 1 d . . .
C6A C 0.1348(4) 0.46185(19) 0.13539(19) 0.0325(8) Uani 1 1 d . . .
H6A H 0.1947 0.5128 0.1811 0.039 Uiso 1 1 calc R . .
C7A C 0.1402(4) 0.4543(2) 0.0541(2) 0.0373(8) Uani 1 1 d . . .
H7A H 0.2043 0.4998 0.0441 0.045 Uiso 1 1 calc R . .
C8A C 0.0530(4) 0.3807(2) -0.0154(2) 0.0370(8) Uani 1 1 d . . .
H8A H 0.0582 0.3763 -0.0720 0.044 Uiso 1 1 calc R . .
C9A C -0.0393(4) 0.3154(2) -0.00130(19) 0.0350(8) Uani 1 1 d . . .
H9A H -0.0990 0.2654 -0.0481 0.042 Uiso 1 1 calc R . .
C10A C -0.2749(4) 0.18630(18) 0.1730(2) 0.0322(8) Uani 1 1 d . . .
H10A H -0.3319 0.1400 0.1220 0.039 Uiso 1 1 calc R . .
C11A C -0.3004(4) 0.18655(19) 0.2502(2) 0.0350(8) Uani 1 1 d . . .
H11A H -0.3763 0.1404 0.2527 0.042 Uiso 1 1 calc R . .
C12A C -0.2159(4) 0.2539(2) 0.3254(2) 0.0358(8) Uani 1 1 d . . .
H12A H -0.2334 0.2530 0.3789 0.043 Uiso 1 1 calc R . .
C13A C -0.1088(4) 0.32064(19) 0.32233(19) 0.0317(8) Uani 1 1 d . . .
H13A H -0.0529 0.3663 0.3741 0.038 Uiso 1 1 calc R . .
C14A C 0.2344(4) 0.7459(2) 0.45170(18) 0.0307(8) Uani 1 1 d . . .
C15A C 0.2621(4) 0.59102(18) 0.42272(19) 0.0351(8) Uani 1 1 d . . .
H15C H 0.1632 0.5884 0.4487 0.042 Uiso 1 1 calc R . .
H15D H 0.3485 0.5614 0.4476 0.042 Uiso 1 1 calc R . .
C16A C 0.2084(4) 0.54397(18) 0.32769(18) 0.0328(8) Uani 1 1 d . . .
H16C H 0.1331 0.5776 0.3016 0.039 Uiso 1 1 calc R . .
H16D H 0.3092 0.5393 0.3025 0.039 Uiso 1 1 calc R . .
C17A C 0.5078(4) 0.7002(2) 0.4363(2) 0.0431(9) Uani 1 1 d . . .
H17G H 0.5599 0.7587 0.4768 0.065 Uiso 0.50 1 calc PR . .
H17H H 0.5107 0.6975 0.3782 0.065 Uiso 0.50 1 calc PR . .
H17I H 0.5708 0.6558 0.4499 0.065 Uiso 0.50 1 calc PR . .
H17J H 0.5343 0.6493 0.3931 0.065 Uiso 0.50 1 calc PR . .
H17K H 0.5836 0.7105 0.4918 0.065 Uiso 0.50 1 calc PR . .
H17L H 0.5234 0.7523 0.4200 0.065 Uiso 0.50 1 calc PR . .
C18A C -0.0401(4) 0.7950(2) 0.4602(3) 0.0623(11) Uani 1 1 d . . .
H18D H -0.1552 0.7681 0.4560 0.093 Uiso 1 1 calc R . .
H18E H -0.0420 0.8225 0.4167 0.093 Uiso 1 1 calc R . .
H18F H 0.0029 0.8398 0.5170 0.093 Uiso 1 1 calc R . .
N6 N -0.6824(3) -0.04456(17) 0.05779(15) 0.0304(6) Uani 1 1 d . . .
O1 O -0.8141(3) -0.03205(13) 0.01534(12) 0.0397(6) Uani 1 1 d . . .
O2 O -0.6681(3) -0.11950(13) 0.06158(13) 0.0478(6) Uani 1 1 d . . .
O3 O -0.5634(3) 0.01661(14) 0.09745(14) 0.0472(6) Uani 1 1 d . . .
N7 N -0.7185(3) 0.04839(16) -0.52523(16) 0.0303(6) Uani 1 1 d . . .
O4 O -0.8341(2) -0.01566(13) -0.54215(13) 0.0365(5) Uani 1 1 d . . .
O5 O -0.7088(3) 0.08508(13) -0.57786(13) 0.0443(6) Uani 1 1 d . . .
O6 O -0.6164(3) 0.07441(15) -0.45460(13) 0.0471(6) Uani 1 1 d . . .
N8 N 0.2366(4) 0.46541(17) 0.56336(18) 0.0385(7) Uani 1 1 d . . .
O7 O 0.3756(3) 0.51489(14) 0.58912(13) 0.0491(6) Uani 1 1 d . . .
O8 O 0.1869(3) 0.42161(17) 0.48584(15) 0.0756(9) Uani 1 1 d . . .
O9 O 0.1553(3) 0.45610(17) 0.61479(16) 0.0697(8) Uani 1 1 d . . .
N9 N -0.1587(6) 0.6966(2) 0.2349(2) 0.0651(10) Uani 1 1 d . . .
O10 O -0.2385(5) 0.6593(2) 0.2724(2) 0.1130(13) Uani 1 1 d . . .
O11 O -0.0067(5) 0.6983(3) 0.2453(2) 0.1419(17) Uani 1 1 d . . .
O12 O -0.2332(4) 0.7337(2) 0.19091(19) 0.1001(11) Uani 1 1 d . . .
O1S O -0.5909(5) 0.6494(2) 0.2092(2) 0.0866(10) Uani 1 1 d . . .
H1S H -0.472(8) 0.652(4) 0.220(4) 0.17(3) Uiso 1 1 d . . .
C1S C -0.6273(6) 0.7341(3) 0.2158(3) 0.0889(14) Uani 1 1 d . . .
H1SA H -0.5979 0.7491 0.1682 0.133 Uiso 1 1 calc R . .
H1SB H -0.5610 0.7769 0.2700 0.133 Uiso 1 1 calc R . .
H1SC H -0.7484 0.7355 0.2137 0.133 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'
O O 0.0106 0.0060 '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
C1 N1 C16 130.1(3) . . ?
C1 N1 H1N 118(2) . . ?
C16 N1 H1N 112(2) . . ?
C3 N2 C4 123.4(3) . . ?
C3 N2 H2N 118.6(18) . . ?
C4 N2 H2N 118.0(17) . . ?
C14 N3 C15 121.3(2) . . ?
C14 N3 C17 119.7(2) . . ?
C15 N3 C17 116.7(2) . . ?
C14 N4 C18 123.9(3) . . ?
C14 N4 H4N 125(2) . . ?
C18 N4 H4N 111(2) . . ?
C14 N5 H5N1 120.4(18) . . ?
C14 N5 H5N2 121.9(19) . . ?
H5N1 N5 H5N2 118(3) . . ?
N1 C1 C2 124.7(3) . . ?
N1 C1 C5 116.8(3) . . ?
C2 C1 C5 118.4(3) . . ?
C3 C2 C6 115.9(3) . . ?
C3 C2 C1 118.2(3) . . ?
C6 C2 C1 125.9(3) . . ?
N2 C3 C9 118.2(3) . . ?
N2 C3 C2 120.3(3) . . ?
C9 C3 C2 121.5(3) . . ?
N2 C4 C10 119.3(3) . . ?
N2 C4 C5 119.6(3) . . ?
C10 C4 C5 121.1(3) . . ?
C4 C5 C13 117.4(3) . . ?
C4 C5 C1 119.5(3) . . ?
C13 C5 C1 123.1(3) . . ?
C7 C6 C2 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C2 C6 H6 119.1 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C3 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C3 C9 H9 120.2 . . ?
C11 C10 C4 119.5(3) . . ?
C11 C10 H10 120.2 . . ?
C4 C10 H10 120.2 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C5 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C5 C13 H13 119.4 . . ?
N5 C14 N4 119.0(3) . . ?
N5 C14 N3 119.9(3) . . ?
N4 C14 N3 121.0(3) . . ?
N3 C15 C16 111.0(2) . . ?
N3 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N1 C16 C15 110.2(2) . . ?
N1 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
N3 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
N3 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1A N1A C16A 131.0(3) . . ?
C1A N1A H1NA 115(2) . . ?
C16A N1A H1NA 113(2) . . ?
C4A N2A C3A 122.4(3) . . ?
C4A N2A H2NA 119.9(18) . . ?
C3A N2A H2NA 117.4(18) . . ?
C14A N3A C17A 120.9(2) . . ?
C14A N3A C15A 121.7(3) . . ?
C17A N3A C15A 116.6(2) . . ?
C14A N4A C18A 122.9(3) . . ?
C14A N4A H4NA 117(2) . . ?
C18A N4A H4NA 120(2) . . ?
C14A N5A H5N3 119(2) . . ?
C14A N5A H5N4 120(2) . . ?
H5N3 N5A H5N4 120(3) . . ?
N1A C1A C2A 124.4(3) . . ?
N1A C1A C5A 117.0(3) . . ?
C2A C1A C5A 118.6(3) . . ?
C3A C2A C6A 115.8(3) . . ?
C3A C2A C1A 118.2(3) . . ?
C6A C2A C1A 126.0(3) . . ?
N2A C3A C2A 121.1(3) . . ?
N2A C3A C9A 117.1(3) . . ?
C2A C3A C9A 121.8(3) . . ?
N2A C4A C5A 120.6(3) . . ?
N2A C4A C10A 118.4(3) . . ?
C5A C4A C10A 121.0(3) . . ?
C4A C5A C13A 117.2(3) . . ?
C4A C5A C1A 119.0(3) . . ?
C13A C5A C1A 123.8(3) . . ?
C7A C6A C2A 121.5(3) . . ?
C7A C6A H6A 119.2 . . ?
C2A C6A H6A 119.2 . . ?
C6A C7A C8A 121.2(3) . . ?
C6A C7A H7A 119.4 . . ?
C8A C7A H7A 119.4 . . ?
C9A C8A C7A 119.5(3) . . ?
C9A C8A H8A 120.2 . . ?
C7A C8A H8A 120.2 . . ?
C8A C9A C3A 120.0(3) . . ?
C8A C9A H9A 120.0 . . ?
C3A C9A H9A 120.0 . . ?
C11A C10A C4A 119.3(3) . . ?
C11A C10A H10A 120.3 . . ?
C4A C10A H10A 120.3 . . ?
C10A C11A C12A 120.6(3) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A H11A 119.7 . . ?
C13A C12A C11A 120.1(3) . . ?
C13A C12A H12A 119.9 . . ?
C11A C12A H12A 119.9 . . ?
C12A C13A C5A 121.8(3) . . ?
C12A C13A H13A 119.1 . . ?
C5A C13A H13A 119.1 . . ?
N5A C14A N3A 120.1(3) . . ?
N5A C14A N4A 118.7(3) . . ?
N3A C14A N4A 121.2(3) . . ?
N3A C15A C16A 110.5(2) . . ?
N3A C15A H15C 109.5 . . ?
C16A C15A H15C 109.5 . . ?
N3A C15A H15D 109.5 . . ?
C16A C15A H15D 109.5 . . ?
H15C C15A H15D 108.1 . . ?
N1A C16A C15A 109.2(2) . . ?
N1A C16A H16C 109.8 . . ?
C15A C16A H16C 109.8 . . ?
N1A C16A H16D 109.8 . . ?
C15A C16A H16D 109.8 . . ?
H16C C16A H16D 108.3 . . ?
N3A C17A H17G 109.5 . . ?
N3A C17A H17H 109.5 . . ?
H17G C17A H17H 109.5 . . ?
N3A C17A H17I 109.5 . . ?
H17G C17A H17I 109.5 . . ?
H17H C17A H17I 109.5 . . ?
N3A C17A H17J 109.5 . . ?
H17G C17A H17J 141.1 . . ?
H17H C17A H17J 56.3 . . ?
H17I C17A H17J 56.3 . . ?
N3A C17A H17K 109.5 . . ?
H17G C17A H17K 56.3 . . ?
H17H C17A H17K 141.1 . . ?
H17I C17A H17K 56.3 . . ?
H17J C17A H17K 109.5 . . ?
N3A C17A H17L 109.5 . . ?
H17G C17A H17L 56.3 . . ?
H17H C17A H17L 56.3 . . ?
H17I C17A H17L 141.1 . . ?
H17J C17A H17L 109.5 . . ?
H17K C17A H17L 109.5 . . ?
N4A C18A H18D 109.5 . . ?
N4A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
N4A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
O3 N6 O1 120.9(3) . . ?
O3 N6 O2 118.8(3) . . ?
O1 N6 O2 120.2(2) . . ?
O5 N7 O6 120.8(3) . . ?
O5 N7 O4 120.3(3) . . ?
O6 N7 O4 119.0(2) . . ?
O9 N8 O7 120.0(3) . . ?
O9 N8 O8 120.6(3) . . ?
O7 N8 O8 119.2(3) . . ?
O11 N9 O12 121.0(4) . . ?
O11 N9 O10 119.4(5) . . ?
O12 N9 O10 119.5(5) . . ?
C1S O1S H1S 108(3) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 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
N1 C1 1.328(3) . ?
N1 C16 1.458(3) . ?
N1 H1N 0.79(3) . ?
N2 C3 1.361(3) . ?
N2 C4 1.362(3) . ?
N2 H2N 0.87(3) . ?
N3 C14 1.336(3) . ?
N3 C15 1.462(3) . ?
N3 C17 1.466(3) . ?
N4 C14 1.325(4) . ?
N4 C18 1.462(4) . ?
N4 H4N 0.84(3) . ?
N5 C14 1.322(4) . ?
N5 H5N1 0.93(3) . ?
N5 H5N2 0.91(3) . ?
C1 C2 1.440(4) . ?
C1 C5 1.448(4) . ?
C2 C3 1.423(4) . ?
C2 C6 1.427(4) . ?
C3 C9 1.405(4) . ?
C4 C10 1.400(4) . ?
C4 C5 1.407(4) . ?
C5 C13 1.412(4) . ?
C6 C7 1.366(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.360(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.364(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.511(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1A C1A 1.328(3) . ?
N1A C16A 1.469(3) . ?
N1A H1NA 0.81(2) . ?
N2A C4A 1.358(4) . ?
N2A C3A 1.363(3) . ?
N2A H2NA 0.91(3) . ?
N3A C14A 1.333(4) . ?
N3A C17A 1.461(4) . ?
N3A C15A 1.463(3) . ?
N4A C14A 1.334(4) . ?
N4A C18A 1.443(4) . ?
N4A H4NA 0.87(3) . ?
N5A C14A 1.328(4) . ?
N5A H5N3 0.94(3) . ?
N5A H5N4 0.87(3) . ?
C1A C2A 1.441(4) . ?
C1A C5A 1.451(4) . ?
C2A C3A 1.408(4) . ?
C2A C6A 1.430(4) . ?
C3A C9A 1.407(4) . ?
C4A C5A 1.398(4) . ?
C4A C10A 1.411(4) . ?
C5A C13A 1.410(4) . ?
C6A C7A 1.356(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.401(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.361(4) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.365(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.394(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.358(4) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C15A C16A 1.504(4) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A H17G 0.9800 . ?
C17A H17H 0.9800 . ?
C17A H17I 0.9800 . ?
C17A H17J 0.9800 . ?
C17A H17K 0.9800 . ?
C17A H17L 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
N6 O3 1.243(3) . ?
N6 O1 1.245(3) . ?
N6 O2 1.255(3) . ?
N7 O5 1.237(3) . ?
N7 O6 1.245(3) . ?
N7 O4 1.264(3) . ?
N8 O9 1.228(3) . ?
N8 O7 1.248(3) . ?
N8 O8 1.245(3) . ?
N9 O11 1.211(4) . ?
N9 O12 1.213(4) . ?
N9 O10 1.241(4) . ?
O1S C1S 1.405(5) . ?
O1S H1S 0.95(6) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
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
N1 H1N O1 0.79(3) 2.38(3) 3.120(3) 158(3) .
N2 H2N O7 0.87(3) 1.98(3) 2.836(3) 168(2) 2_566
N4 H4N O3 0.84(3) 2.20(3) 2.961(4) 151(3) 2_455
N5 H5N1 O6 0.93(3) 2.12(3) 3.016(4) 161(2) .
N5 H5N1 O4 0.93(3) 2.53(3) 3.174(3) 126(2) .
N5 H5N2 O4 0.91(3) 2.01(3) 2.881(4) 160(3) 2_354
N1A H1NA O8 0.81(2) 2.39(3) 3.170(4) 161(3) .
N2A H2NA O2 0.91(3) 1.97(3) 2.875(3) 177(3) 2_455
N4A H4NA O9 0.87(3) 2.28(3) 3.126(4) 164(3) 2_566
N5A H5N3 O4 0.94(3) 2.03(3) 2.899(4) 153(3) 1_666
N5A H5N4 O6 0.87(3) 2.20(3) 2.993(4) 151(3) 2_565
O1S H1S O10 0.95(6) 1.91(6) 2.836(5) 165(5) .
O1S H1S O12 0.95(6) 2.48(6) 3.225(5) 136(5) .
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
C16 N1 C1 C2 -11.5(5) . . . . ?
C16 N1 C1 C5 169.6(3) . . . . ?
N1 C1 C2 C3 -170.7(3) . . . . ?
C5 C1 C2 C3 8.2(4) . . . . ?
N1 C1 C2 C6 6.6(5) . . . . ?
C5 C1 C2 C6 -174.5(3) . . . . ?
C4 N2 C3 C9 177.8(3) . . . . ?
C4 N2 C3 C2 -2.5(4) . . . . ?
C6 C2 C3 N2 178.8(2) . . . . ?
C1 C2 C3 N2 -3.6(4) . . . . ?
C6 C2 C3 C9 -1.5(4) . . . . ?
C1 C2 C3 C9 176.1(3) . . . . ?
C3 N2 C4 C10 -176.4(3) . . . . ?
C3 N2 C4 C5 3.8(4) . . . . ?
N2 C4 C5 C13 -178.1(2) . . . . ?
C10 C4 C5 C13 2.1(4) . . . . ?
N2 C4 C5 C1 1.2(4) . . . . ?
C10 C4 C5 C1 -178.6(3) . . . . ?
N1 C1 C5 C4 171.9(3) . . . . ?
C2 C1 C5 C4 -7.1(4) . . . . ?
N1 C1 C5 C13 -8.8(4) . . . . ?
C2 C1 C5 C13 172.2(3) . . . . ?
C3 C2 C6 C7 1.1(4) . . . . ?
C1 C2 C6 C7 -176.2(3) . . . . ?
C2 C6 C7 C8 0.1(5) . . . . ?
C6 C7 C8 C9 -1.1(5) . . . . ?
C7 C8 C9 C3 0.7(4) . . . . ?
N2 C3 C9 C8 -179.7(3) . . . . ?
C2 C3 C9 C8 0.6(4) . . . . ?
N2 C4 C10 C11 179.4(3) . . . . ?
C5 C4 C10 C11 -0.9(4) . . . . ?
C4 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C11 C12 C13 C5 0.1(4) . . . . ?
C4 C5 C13 C12 -1.7(4) . . . . ?
C1 C5 C13 C12 179.0(3) . . . . ?
C18 N4 C14 N5 -6.8(4) . . . . ?
C18 N4 C14 N3 170.8(3) . . . . ?
C15 N3 C14 N5 179.3(3) . . . . ?
C17 N3 C14 N5 -18.7(4) . . . . ?
C15 N3 C14 N4 1.8(4) . . . . ?
C17 N3 C14 N4 163.8(3) . . . . ?
C14 N3 C15 C16 79.5(3) . . . . ?
C17 N3 C15 C16 -83.0(3) . . . . ?
C1 N1 C16 C15 -175.5(3) . . . . ?
N3 C15 C16 N1 165.3(2) . . . . ?
C16A N1A C1A C2A 16.8(5) . . . . ?
C16A N1A C1A C5A -164.5(3) . . . . ?
N1A C1A C2A C3A 174.0(3) . . . . ?
C5A C1A C2A C3A -4.5(4) . . . . ?
N1A C1A C2A C6A -5.1(5) . . . . ?
C5A C1A C2A C6A 176.3(3) . . . . ?
C4A N2A C3A C2A 2.4(4) . . . . ?
C4A N2A C3A C9A -177.6(3) . . . . ?
C6A C2A C3A N2A -179.0(3) . . . . ?
C1A C2A C3A N2A 1.8(4) . . . . ?
C6A C2A C3A C9A 1.0(4) . . . . ?
C1A C2A C3A C9A -178.2(3) . . . . ?
C3A N2A C4A C5A -3.6(4) . . . . ?
C3A N2A C4A C10A 175.1(3) . . . . ?
N2A C4A C5A C13A 179.1(3) . . . . ?
C10A C4A C5A C13A 0.4(4) . . . . ?
N2A C4A C5A C1A 0.6(4) . . . . ?
C10A C4A C5A C1A -178.0(3) . . . . ?
N1A C1A C5A C4A -175.3(3) . . . . ?
C2A C1A C5A C4A 3.4(4) . . . . ?
N1A C1A C5A C13A 6.4(4) . . . . ?
C2A C1A C5A C13A -175.0(3) . . . . ?
C3A C2A C6A C7A -1.0(4) . . . . ?
C1A C2A C6A C7A 178.1(3) . . . . ?
C2A C6A C7A C8A 0.5(5) . . . . ?
C6A C7A C8A C9A 0.2(5) . . . . ?
C7A C8A C9A C3A -0.2(4) . . . . ?
N2A C3A C9A C8A 179.5(3) . . . . ?
C2A C3A C9A C8A -0.5(4) . . . . ?
N2A C4A C10A C11A -178.8(3) . . . . ?
C5A C4A C10A C11A -0.1(4) . . . . ?
C4A C10A C11A C12A -0.6(4) . . . . ?
C10A C11A C12A C13A 0.9(5) . . . . ?
C11A C12A C13A C5A -0.5(4) . . . . ?
C4A C5A C13A C12A -0.1(4) . . . . ?
C1A C5A C13A C12A 178.2(3) . . . . ?
C17A N3A C14A N5A -12.3(4) . . . . ?
C15A N3A C14A N5A 178.4(3) . . . . ?
C17A N3A C14A N4A 171.7(3) . . . . ?
C15A N3A C14A N4A 2.4(4) . . . . ?
C18A N4A C14A N5A 1.2(5) . . . . ?
C18A N4A C14A N3A 177.3(3) . . . . ?
C14A N3A C15A C16A 89.5(3) . . . . ?
C17A N3A C15A C16A -80.2(3) . . . . ?
C1A N1A C16A C15A 170.7(3) . . . . ?
N3A C15A C16A N1A -172.6(2) . . . . ?
