#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:01:11 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179551 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/20/4502089.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_4502089
loop_
_publ_author_name
'Fonari, Marina S.'
'Ganin, Eduard V.'
'Basok, Stepan S.'
'Lyssenko, Konstantin A.'
'Zaworotko, Michael J.'
'Kravtsov, Victor Ch.'
_publ_section_title
;
 Structural Study of Salicylic Acid Salts of a Series of Azacycles and
 Azacrown Ethers†
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5210
_journal_paper_doi               10.1021/cg101002x
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C12 H28 N2 O4, 2(C7 H5 O3), 3(H2 O)'
_chemical_formula_sum            'C26 H44 N2 O13'
_chemical_formula_weight         592.63
_chemical_name_common
; 
 7,16-Diazonia-18-crown-6 bis(salicylate) trihydrate
;
_chemical_name_systematic
; 
 1,4,10,13-tetraoxa-7,16-diazoniacyclooctadecane 
bis(2-hydroxybenzoate) trihydrate
;
_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                98.175(4)
_cell_angle_beta                 90.721(2)
_cell_angle_gamma                111.355(3)
_cell_formula_units_Z            2
_cell_length_a                   9.434(2)
_cell_length_b                   12.587(3)
_cell_length_c                   13.843(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1511.7(5)
_computing_cell_refinement       'Bruker SMART-APEX CCD'
_computing_data_collection       'Bruker SMART-APEX CCD'
_computing_data_reduction        'Bruker SMART-APEX CCD'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0878
_diffrn_reflns_av_sigmaI/netI    0.1606
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8062
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         5352
_refine_ls_number_restraints     276
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.1810
_refine_ls_R_factor_gt           0.0923
_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)+(0.1234P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2341
_refine_ls_wR_factor_ref         0.2700
_reflns_number_gt                2221
_reflns_number_total             5352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101002x_si_001.cif
_cod_data_source_block           vk2003c3
_cod_original_cell_volume        1511.7(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4502089
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
O1A O 0.7385(4) 0.4629(3) 0.3822(2) 0.0419(9) Uani 1 1 d . . .
C2A C 0.8530(6) 0.5692(5) 0.3761(4) 0.0439(14) Uani 1 1 d . . .
H2A1 H 0.9242 0.5588 0.3270 0.053 Uiso 1 1 calc R . .
H2A2 H 0.9115 0.6024 0.4402 0.053 Uiso 1 1 calc R . .
C3A C 0.7814(6) 0.6484(4) 0.3472(3) 0.0379(13) Uani 1 1 d . . .
H3A1 H 0.7202 0.6129 0.2843 0.045 Uiso 1 1 calc R . .
H3A2 H 0.8626 0.7215 0.3369 0.045 Uiso 1 1 calc R . .
N4A N 0.6812(5) 0.6746(4) 0.4218(3) 0.0412(11) Uani 1 1 d . . .
H4A1 H 0.6020 0.6073 0.4282 0.049 Uiso 1 1 calc R . .
H4A2 H 0.7365 0.7028 0.4813 0.049 Uiso 1 1 calc R . .
C5A C 0.6186(6) 0.7587(4) 0.3969(4) 0.0506(15) Uani 1 1 d . . .
H5A1 H 0.5450 0.7236 0.3391 0.061 Uiso 1 1 calc R . .
H5A2 H 0.7021 0.8266 0.3797 0.061 Uiso 1 1 calc R . .
C6A C 0.5406(7) 0.7972(5) 0.4797(5) 0.0588(17) Uani 1 1 d . . .
H6A1 H 0.6114 0.8278 0.5391 0.071 Uiso 1 1 calc R . .
H6A2 H 0.5081 0.8594 0.4636 0.071 Uiso 1 1 calc R . .
O7A O 0.4118(4) 0.7015(3) 0.4969(2) 0.0411(9) Uani 1 1 d . . .
C8A C 0.3358(7) 0.7265(5) 0.5800(4) 0.0512(16) Uani 1 1 d . . .
H8A1 H 0.2986 0.7887 0.5709 0.061 Uiso 1 1 calc R . .
H8A2 H 0.4072 0.7530 0.6391 0.061 Uiso 1 1 calc R . .
C9A C 0.2072(7) 0.6218(5) 0.5920(4) 0.0544(16) Uani 1 1 d . . .
H9A1 H 0.1448 0.6405 0.6438 0.065 Uiso 1 1 calc R . .
H9A2 H 0.1419 0.5909 0.5302 0.065 Uiso 1 1 calc R . .
O1B O 0.7793(5) 0.5324(3) 0.1187(2) 0.0523(11) Uani 1 1 d . . .
C2B C 0.7829(7) 0.4195(5) 0.1194(4) 0.0551(17) Uani 1 1 d . . .
H2B1 H 0.8675 0.4243 0.1650 0.066 Uiso 1 1 calc R . .
H2B2 H 0.7994 0.3865 0.0532 0.066 Uiso 1 1 calc R . .
C3B C 0.6346(6) 0.3447(5) 0.1513(4) 0.0482(15) Uani 1 1 d . . .
H3B1 H 0.6387 0.2685 0.1579 0.058 Uiso 1 1 calc R . .
H3B2 H 0.6171 0.3803 0.2163 0.058 Uiso 1 1 calc R . .
N4B N 0.5061(5) 0.3282(4) 0.0809(3) 0.0473(12) Uani 1 1 d . . .
H4B1 H 0.4924 0.3972 0.0831 0.057 Uiso 1 1 calc R . .
H4B2 H 0.5312 0.3082 0.0187 0.057 Uiso 1 1 calc R . .
C5B C 0.3615(6) 0.2390(5) 0.0998(4) 0.0484(15) Uani 1 1 d . . .
H5B1 H 0.3812 0.1703 0.1134 0.058 Uiso 1 1 calc R . .
H5B2 H 0.3207 0.2688 0.1587 0.058 Uiso 1 1 calc R . .
C6B C 0.2474(7) 0.2047(5) 0.0174(4) 0.0559(17) Uani 1 1 d . . .
H6B1 H 0.2874 0.1755 -0.0421 0.067 Uiso 1 1 calc R . .
H6B2 H 0.1539 0.1421 0.0317 0.067 Uiso 1 1 calc R . .
O7B O 0.2129(4) 0.3014(3) 0.0021(2) 0.0487(10) Uani 1 1 d . . .
C8B C 0.1097(7) 0.2806(6) -0.0780(4) 0.0643(19) Uani 1 1 d . . .
H8B1 H 0.0110 0.2201 -0.0683 0.077 Uiso 1 1 calc R . .
H8B2 H 0.1498 0.2533 -0.1384 0.077 Uiso 1 1 calc R . .
C9B C 0.0875(7) 0.3895(6) -0.0875(5) 0.0667(19) Uani 1 1 d . . .
H9B1 H 0.0006 0.3734 -0.1355 0.080 Uiso 1 1 calc R . .
H9B2 H 0.0638 0.4234 -0.0237 0.080 Uiso 1 1 calc R . .
O1M O 1.1859(5) 0.3037(4) 0.3931(4) 0.051(2) Uani 0.50 1 d PGU A 1
O2M O 1.0299(6) 0.1702(4) 0.4713(3) 0.050(2) Uani 0.50 1 d PGU A 1
O3M O 0.7750(5) 0.0270(4) 0.3910(4) 0.045(2) Uani 0.50 1 d PGU A 1
H3M H 0.8454 0.0587 0.4355 0.067 Uiso 0.50 1 calc PR A 1
C1M C 1.0653(4) 0.2163(3) 0.3951(3) 0.031(3) Uani 0.50 1 d PGU A 1
C2M C 0.9572(4) 0.1659(3) 0.3060(3) 0.025(3) Uani 0.50 1 d PGU A 1
C3M C 0.8167(4) 0.0755(4) 0.3092(3) 0.037(3) Uani 0.50 1 d PGU A 1
C4M C 0.7137(5) 0.0338(5) 0.2265(4) 0.060(5) Uani 0.50 1 d PGU A 1
H4M H 0.6180 -0.0265 0.2289 0.073 Uiso 0.50 1 calc PR A 1
C5M C 0.7506(7) 0.0800(6) 0.1414(4) 0.042(4) Uani 0.50 1 d PGU A 1
H5M H 0.6793 0.0520 0.0860 0.051 Uiso 0.50 1 calc PR A 1
C6M C 0.8906(8) 0.1667(6) 0.1360(3) 0.039(3) Uani 0.50 1 d PGU A 1
H6M H 0.9164 0.1970 0.0768 0.047 Uiso 0.50 1 calc PR A 1
C7M C 0.9922(6) 0.2088(5) 0.2176(3) 0.034(3) Uani 0.50 1 d PGU A 1
H7M H 1.0882 0.2683 0.2138 0.040 Uiso 0.50 1 calc PR A 1
O1N O 1.2051(5) 0.3185(4) 0.3236(4) 0.0483(19) Uani 0.50 1 d PGU B 2
O2N O 1.1176(5) 0.1880(4) 0.4221(3) 0.045(2) Uani 0.50 1 d PGU B 2
O3N O 0.8600(6) 0.0230(4) 0.3846(4) 0.048(2) Uani 0.50 1 d PGU B 2
H3N H 0.9433 0.0636 0.4162 0.072 Uiso 0.50 1 calc PR B 2
C1N C 1.1064(4) 0.2263(3) 0.3437(3) 0.042(3) Uani 0.50 1 d PGU B 2
C2N C 0.9689(4) 0.1603(3) 0.2749(3) 0.033(3) Uani 0.50 1 d PGU B 2
C3N C 0.8519(4) 0.0635(4) 0.2998(3) 0.029(3) Uani 0.50 1 d PGU B 2
C4N C 0.7205(5) 0.0069(5) 0.2366(4) 0.024(3) Uani 0.50 1 d PGU B 2
H4N H 0.6406 -0.0579 0.2539 0.029 Uiso 0.50 1 calc PR B 2
C5N C 0.7066(6) 0.0445(6) 0.1494(4) 0.039(3) Uani 0.50 1 d PGU B 2
H5N H 0.6163 0.0062 0.1076 0.047 Uiso 0.50 1 calc PR B 2
C6N C 0.8230(7) 0.1375(6) 0.1223(4) 0.034(3) Uani 0.50 1 d PGU B 2
H6N H 0.8139 0.1620 0.0615 0.041 Uiso 0.50 1 calc PR B 2
C7N C 0.9524(6) 0.1944(5) 0.1846(3) 0.033(3) Uani 0.50 1 d PGU B 2
H7N H 1.0322 0.2582 0.1659 0.040 Uiso 0.50 1 calc PR B 2
O1P O 0.4035(7) 0.6908(4) 0.1003(4) 0.0481(19) Uani 0.50 1 d PGU C 1
O2P O 0.4330(7) 0.8491(4) 0.0369(3) 0.046(2) Uani 0.50 1 d PGU C 1
O3P O 0.3278(9) 0.9980(4) 0.1152(4) 0.075(4) Uani 0.50 1 d PGU C 1
H3P H 0.3730 0.9685 0.0740 0.112 Uiso 0.50 1 calc PR C 1
C1P C 0.3890(5) 0.7874(3) 0.1034(3) 0.033(4) Uani 0.50 1 d PGU C 1
C2P C 0.3142(4) 0.8305(3) 0.1867(3) 0.027(3) Uani 0.50 1 d PGU C 1
C3P C 0.2852(6) 0.9323(4) 0.1871(3) 0.039(4) Uani 0.50 1 d PGU C 1
C4P C 0.2077(8) 0.9677(5) 0.2631(4) 0.049(4) Uani 0.50 1 d PGU C 1
H4P H 0.1865 1.0359 0.2629 0.058 Uiso 0.50 1 calc PR C 1
C5P C 0.1620(8) 0.9041(6) 0.3381(4) 0.047(3) Uani 0.50 1 d PGU C 1
H5P H 0.1081 0.9282 0.3887 0.056 Uiso 0.50 1 calc PR C 1
C6P C 0.1940(7) 0.8054(6) 0.3403(4) 0.043(3) Uani 0.50 1 d PGU C 1
H6P H 0.1644 0.7629 0.3930 0.051 Uiso 0.50 1 calc PR C 1
C7P C 0.2693(6) 0.7695(4) 0.2653(3) 0.041(3) Uani 0.50 1 d PGU C 1
H7P H 0.2912 0.7018 0.2670 0.049 Uiso 0.50 1 calc PR C 1
O1R O 0.3700(7) 0.6743(4) 0.1902(4) 0.056(2) Uani 0.50 1 d PGU D 2
O2R O 0.3854(6) 0.7895(4) 0.0803(3) 0.045(3) Uani 0.50 1 d PGU D 2
O3R O 0.2820(9) 0.9511(5) 0.1089(4) 0.043(2) Uani 0.50 1 d PGU D 2
H3R H 0.3241 0.9091 0.0787 0.064 Uiso 0.50 1 calc PR D 2
C1R C 0.3515(5) 0.7607(3) 0.1635(3) 0.041(3) Uani 0.50 1 d PGU D 2
C2R C 0.2838(4) 0.8311(3) 0.2303(3) 0.026(3) Uani 0.50 1 d PGU D 2
C3R C 0.2501(6) 0.9210(4) 0.1988(3) 0.034(3) Uani 0.50 1 d PGU D 2
C4R C 0.1793(7) 0.9816(5) 0.2606(4) 0.048(4) Uani 0.50 1 d PGU D 2
H4R H 0.1550 1.0417 0.2390 0.057 Uiso 0.50 1 calc PR D 2
C5R C 0.1446(8) 0.9546(5) 0.3528(4) 0.042(3) Uani 0.50 1 d PGU D 2
H5R H 0.0951 0.9954 0.3937 0.050 Uiso 0.50 1 calc PR D 2
C6R C 0.1813(8) 0.8686(6) 0.3861(3) 0.046(3) Uani 0.50 1 d PGU D 2
H6R H 0.1594 0.8515 0.4502 0.056 Uiso 0.50 1 calc PR D 2
C7R C 0.2502(6) 0.8079(5) 0.3252(3) 0.042(3) Uani 0.50 1 d PGU D 2
H7R H 0.2754 0.7489 0.3482 0.051 Uiso 0.50 1 calc PR D 2
O1W O 0.4209(8) 0.4770(6) 0.4463(5) 0.048(3) Uani 0.510(11) 1 d PU . .
O1W' O 0.442(4) 0.474(3) 0.327(3) 0.15(2) Uani 0.199(17) 1 d PU . .
O2W O 0.4897(15) 0.5387(9) 0.1007(11) 0.146(6) Uani 0.550(11) 1 d PU . .
O2W' O 0.4348(10) 0.5202(7) 0.1910(6) 0.050(3) Uani 0.450(11) 1 d PU . .
O3W O 0.1310(9) 0.4994(7) 0.2603(6) 0.081(3) Uani 0.589(10) 1 d PU . .
O3W' O 0.2402(11) 0.5103(8) 0.3435(6) 0.055(4) Uani 0.411(10) 1 d PU . .
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
C2A O1A C9A 114.3(4) . 2_666
O1A C2A C3A 108.8(4) . .
O1A C2A H2A1 109.9 . .
C3A C2A H2A1 109.9 . .
O1A C2A H2A2 109.9 . .
C3A C2A H2A2 109.9 . .
H2A1 C2A H2A2 108.3 . .
C2A C3A N4A 112.7(4) . .
C2A C3A H3A1 109.1 . .
N4A C3A H3A1 109.1 . .
C2A C3A H3A2 109.1 . .
N4A C3A H3A2 109.1 . .
H3A1 C3A H3A2 107.8 . .
C5A N4A C3A 113.0(4) . .
C5A N4A H4A1 109.0 . .
C3A N4A H4A1 109.0 . .
C5A N4A H4A2 109.0 . .
C3A N4A H4A2 109.0 . .
H4A1 N4A H4A2 107.8 . .
N4A C5A C6A 111.5(5) . .
N4A C5A H5A1 109.3 . .
C6A C5A H5A1 109.3 . .
N4A C5A H5A2 109.3 . .
C6A C5A H5A2 109.3 . .
H5A1 C5A H5A2 108.0 . .
O7A C6A C5A 108.7(4) . .
O7A C6A H6A1 110.0 . .
C5A C6A H6A1 110.0 . .
O7A C6A H6A2 110.0 . .
C5A C6A H6A2 110.0 . .
H6A1 C6A H6A2 108.3 . .
C6A O7A C8A 113.3(4) . .
O7A C8A C9A 108.8(4) . .
O7A C8A H8A1 109.9 . .
C9A C8A H8A1 109.9 . .
O7A C8A H8A2 109.9 . .
C9A C8A H8A2 109.9 . .
H8A1 C8A H8A2 108.3 . .
O1A C9A C8A 110.1(5) 2_666 .
O1A C9A H9A1 109.6 2_666 .
C8A C9A H9A1 109.6 . .
O1A C9A H9A2 109.6 2_666 .
C8A C9A H9A2 109.6 . .
H9A1 C9A H9A2 108.2 . .
C9B O1B C2B 113.7(5) 2_665 .
O1B C2B C3B 108.4(5) . .
O1B C2B H2B1 110.0 . .
C3B C2B H2B1 110.0 . .
O1B C2B H2B2 110.0 . .
C3B C2B H2B2 110.0 . .
H2B1 C2B H2B2 108.4 . .
N4B C3B C2B 111.6(5) . .
N4B C3B H3B1 109.3 . .
C2B C3B H3B1 109.3 . .
N4B C3B H3B2 109.3 . .
C2B C3B H3B2 109.3 . .
H3B1 C3B H3B2 108.0 . .
C5B N4B C3B 113.6(4) . .
C5B N4B H4B1 108.9 . .
C3B N4B H4B1 108.9 . .
C5B N4B H4B2 108.9 . .
C3B N4B H4B2 108.9 . .
H4B1 N4B H4B2 107.7 . .
C6B C5B N4B 112.3(5) . .
C6B C5B H5B1 109.1 . .
N4B C5B H5B1 109.1 . .
C6B C5B H5B2 109.1 . .
N4B C5B H5B2 109.1 . .
H5B1 C5B H5B2 107.9 . .
O7B C6B C5B 108.9(4) . .
O7B C6B H6B1 109.9 . .
C5B C6B H6B1 109.9 . .
O7B C6B H6B2 109.9 . .
C5B C6B H6B2 109.9 . .
H6B1 C6B H6B2 108.3 . .
C8B O7B C6B 114.3(4) . .
O7B C8B C9B 108.7(5) . .
O7B C8B H8B1 109.9 . .
C9B C8B H8B1 109.9 . .
O7B C8B H8B2 109.9 . .
C9B C8B H8B2 109.9 . .
H8B1 C8B H8B2 108.3 . .
O1B C9B C8B 109.4(6) 2_665 .
O1B C9B H9B1 109.8 2_665 .
C8B C9B H9B1 109.8 . .
O1B C9B H9B2 109.8 2_665 .
C8B C9B H9B2 109.8 . .
H9B1 C9B H9B2 108.2 . .
C3M O3M H3M 109.5 . .
O2M C1M O1M 122.3 . .
O2M C1M C2M 117.8 . .
O1M C1M C2M 119.9 . .
C7M C2M C3M 118.3 . .
C7M C2M C1M 121.0 . .
C3M C2M C1M 120.7 . .
O3M C3M C4M 118.0 . .
O3M C3M C2M 122.2 . .
C4M C3M C2M 119.8 . .
C5M C4M C3M 120.4 . .
C5M C4M H4M 119.8 . .
C3M C4M H4M 119.8 . .
C4M C5M C6M 120.6 . .
C4M C5M H5M 119.7 . .
C6M C5M H5M 119.7 . .
C7M C6M C5M 119.3 . .
C7M C6M H6M 120.3 . .
C5M C6M H6M 120.3 . .
C6M C7M C2M 121.6 . .
C6M C7M H7M 119.2 . .
C2M C7M H7M 119.2 . .
C3N O3N H3N 109.5 . .
O2N C1N O1N 122.3 . .
O2N C1N C2N 117.8 . .
O1N C1N C2N 119.9 . .
C7N C2N C3N 118.3 . .
C7N C2N C1N 121.0 . .
C3N C2N C1N 120.7 . .
O3N C3N C4N 118.0 . .
O3N C3N C2N 122.2 . .
C4N C3N C2N 119.8 . .
C5N C4N C3N 120.4 . .
C5N C4N H4N 119.8 . .
C3N C4N H4N 119.8 . .
C4N C5N C6N 120.6 . .
C4N C5N H5N 119.7 . .
C6N C5N H5N 119.7 . .
C7N C6N C5N 119.3 . .
C7N C6N H6N 120.3 . .
C5N C6N H6N 120.3 . .
C6N C7N C2N 121.6 . .
C6N C7N H7N 119.2 . .
C2N C7N H7N 119.2 . .
C3P O3P H3P 109.5 . .
O2P C1P O1P 122.3 . .
O2P C1P C2P 117.8 . .
O1P C1P C2P 119.9 . .
C7P C2P C3P 118.3 . .
C7P C2P C1P 121.0 . .
C3P C2P C1P 120.7 . .
O3P C3P C4P 118.0 . .
O3P C3P C2P 122.2 . .
C4P C3P C2P 119.8 . .
C5P C4P C3P 120.4 . .
C5P C4P H4P 119.8 . .
C3P C4P H4P 119.8 . .
C4P C5P C6P 120.6 . .
C4P C5P H5P 119.7 . .
C6P C5P H5P 119.7 . .
C7P C6P C5P 119.3 . .
C7P C6P H6P 120.3 . .
C5P C6P H6P 120.3 . .
C6P C7P C2P 121.6 . .
C6P C7P H7P 119.2 . .
C2P C7P H7P 119.2 . .
C3R O3R H3R 109.5 . .
O2R C1R O1R 122.3 . .
O2R C1R C2R 117.8 . .
O1R C1R C2R 119.9 . .
C7R C2R C3R 118.3 . .
C7R C2R C1R 121.0 . .
C3R C2R C1R 120.7 . .
O3R C3R C4R 118.0 . .
O3R C3R C2R 122.2 . .
C4R C3R C2R 119.8 . .
C5R C4R C3R 120.4 . .
C5R C4R H4R 119.8 . .
C3R C4R H4R 119.8 . .
C4R C5R C6R 120.6 . .
C4R C5R H5R 119.7 . .
C6R C5R H5R 119.7 . .
C7R C6R C5R 119.3 . .
C7R C6R H6R 120.3 . .
C5R C6R H6R 120.3 . .
C6R C7R C2R 121.6 . .
C6R C7R H7R 119.2 . .
C2R C7R H7R 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C2A 1.395(6) .
O1A C9A 1.424(6) 2_666
C2A C3A 1.485(7) .
C2A H2A1 0.9900 .
C2A H2A2 0.9900 .
C3A N4A 1.492(6) .
C3A H3A1 0.9900 .
C3A H3A2 0.9900 .
N4A C5A 1.464(6) .
N4A H4A1 0.9200 .
N4A H4A2 0.9200 .
C5A C6A 1.487(7) .
C5A H5A1 0.9900 .
C5A H5A2 0.9900 .
C6A O7A 1.416(6) .
C6A H6A1 0.9900 .
C6A H6A2 0.9900 .
O7A C8A 1.422(6) .
C8A C9A 1.462(8) .
C8A H8A1 0.9900 .
C8A H8A2 0.9900 .
C9A O1A 1.424(6) 2_666
C9A H9A1 0.9900 .
C9A H9A2 0.9900 .
O1B C9B 1.402(7) 2_665
O1B C2B 1.436(7) .
C2B C3B 1.487(8) .
C2B H2B1 0.9900 .
C2B H2B2 0.9900 .
C3B N4B 1.481(7) .
C3B H3B1 0.9900 .
C3B H3B2 0.9900 .
N4B C5B 1.472(6) .
N4B H4B1 0.9200 .
N4B H4B2 0.9200 .
C5B C6B 1.461(8) .
C5B H5B1 0.9900 .
C5B H5B2 0.9900 .
C6B O7B 1.412(7) .
C6B H6B1 0.9900 .
C6B H6B2 0.9900 .
O7B C8B 1.397(7) .
C8B C9B 1.483(9) .
C8B H8B1 0.9900 .
C8B H8B2 0.9900 .
C9B O1B 1.402(7) 2_665
C9B H9B1 0.9900 .
C9B H9B2 0.9900 .
O1M C1M 1.2663 .
O2M C1M 1.2660 .
O3M C3M 1.3571 .
O3M H3M 0.8400 .
C1M C2M 1.4970 .
C2M C7M 1.4015 .
C2M C3M 1.4042 .
C3M C4M 1.4003 .
C4M C5M 1.3792 .
C4M H4M 0.9500 .
C5M C6M 1.3846 .
C5M H5M 0.9500 .
C6M C7M 1.3816 .
C6M H6M 0.9500 .
C7M H7M 0.9500 .
O1N C1N 1.2663 .
O2N C1N 1.2660 .
O3N C3N 1.3571 .
O3N H3N 0.8400 .
C1N C2N 1.4969 .
C2N C7N 1.4016 .
C2N C3N 1.4043 .
C3N C4N 1.4003 .
C4N C5N 1.3792 .
C4N H4N 0.9500 .
C5N C6N 1.3846 .
C5N H5N 0.9500 .
C6N C7N 1.3816 .
C6N H6N 0.9500 .
C7N H7N 0.9500 .
O1P C1P 1.2664 .
O2P C1P 1.2660 .
O3P C3P 1.3571 .
O3P H3P 0.8400 .
C1P C2P 1.4969 .
C2P C7P 1.4016 .
C2P C3P 1.4042 .
C3P C4P 1.4003 .
C4P C5P 1.3792 .
C4P H4P 0.9500 .
C5P C6P 1.3845 .
C5P H5P 0.9500 .
C6P C7P 1.3816 .
C6P H6P 0.9500 .
C7P H7P 0.9500 .
O1R C1R 1.2663 .
O2R C1R 1.2660 .
O3R C3R 1.3571 .
O3R H3R 0.8400 .
C1R C2R 1.4969 .
C2R C7R 1.4016 .
C2R C3R 1.4042 .
C3R C4R 1.4003 .
C4R C5R 1.3791 .
C4R H4R 0.9500 .
C5R C6R 1.3846 .
C5R H5R 0.9500 .
C6R C7R 1.3816 .
C6R H6R 0.9500 .
C7R H7R 0.9500 .
O1W O1W' 1.67(4) .
O2W O2W' 1.378(13) .
O3W O3W' 1.492(12) .
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
N4A H4A1 O1W 0.92 1.94 2.853(8) 173.0 .
N4A H4A1 O1W' 0.92 2.12 2.84(4) 133.6 .
N4A H4A1 O1W 0.92 2.14 2.757(8) 124.0 2_666
N4A H4A2 O2N 0.92 1.90 2.776(17) 157.3 2_766
N4A H4A2 O1M 0.92 1.90 2.772(7) 156.7 2_766
N4A H4A2 O2M 0.92 2.22 2.938(18) 134.0 2_766
N4B H4B1 O2W 0.92 1.77 2.687(11) 171.4 .
N4B H4B1 O2W' 0.92 2.21 2.964(9) 138.2 .
N4B H4B2 O1P 0.92 1.77 2.666(7) 165.0 2_665
N4B H4B2 O2R 0.92 2.06 2.905(10) 151.4 2_665
N4B H4B2 O2P 0.92 2.16 2.809(8) 126.3 2_665
O3M H3M O2M 0.84 1.80 2.544 146.3 .
O3N H3N O2N 0.84 1.80 2.544 146.3 .
O3P H3P O2P 0.84 1.80 2.544 146.3 .
O3R H3R O2R 0.84 1.80 2.544 146.3 .
