#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/44/2224492.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224492
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Guanidinium quinoline-2-carboxylate
;
_journal_coeditor_code           WN2367
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3220
_journal_paper_doi               10.1107/S1600536809049733
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C H6 N3 +, C10 H6 N O2 -'
_chemical_formula_moiety         'C H6 N3 +, C10 H6 N O2 -'
_chemical_formula_sum            'C11 H12 N4 O2'
_chemical_formula_weight         232.25
_chemical_melting_point_gt       543
_chemical_melting_point_lt       544
_chemical_name_common            'guanidinium quinoline-2-carboxylate'
_chemical_name_systematic
;
Guanidinium quinoline-2-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.045(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4318(3)
_cell_length_b                   42.2105(18)
_cell_length_c                   7.3035(4)
_cell_measurement_reflns_used    4234
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.83
_cell_measurement_theta_min      2.91
_cell_volume                     2285.40(18)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S Ultra CCD-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10626
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0614P)²+2.2259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                2931
_reflns_number_total             3981
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2367.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224492
_cod_database_fobs_code          2224492
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O21A 0.8508(4) 0.09058(6) 0.2611(3) 0.0621(10) Uani . . 1.000
O O22A 0.5996(3) 0.07308(6) 0.1162(4) 0.0645(10) Uani . . 1.000
N N1A 0.9927(3) 0.03079(6) 0.2631(3) 0.0344(8) Uani . . 1.000
C C2A 0.8222(4) 0.03520(7) 0.2056(4) 0.0347(9) Uani . . 1.000
C C3A 0.7048(4) 0.01015(8) 0.1538(4) 0.0432(11) Uani . . 1.000
C C4A 0.7670(5) -0.02006(8) 0.1610(4) 0.0470(11) Uani . . 1.000
C C5A 1.0237(5) -0.05662(8) 0.2320(5) 0.0526(14) Uani . . 1.000
C C6A 1.1980(6) -0.06067(9) 0.2937(5) 0.0607(14) Uani . . 1.000
C C7A 1.3053(5) -0.03505(10) 0.3470(5) 0.0573(14) Uani . . 1.000
C C8A 1.2375(4) -0.00486(8) 0.3367(4) 0.0463(11) Uani . . 1.000
C C9A 1.0562(4) 0.00047(7) 0.2721(4) 0.0350(10) Uani . . 1.000
C C10A 0.9469(4) -0.02599(7) 0.2209(4) 0.0386(10) Uani . . 1.000
C C21A 0.7531(5) 0.06891(8) 0.1948(4) 0.0434(11) Uani . . 1.000
O O21B 0.2113(4) 0.16103(6) 0.7760(4) 0.0595(9) Uani . . 1.000
O O22B 0.4256(3) 0.17922(6) 0.6099(3) 0.0547(9) Uani . . 1.000
N N1B 0.0628(3) 0.22063(6) 0.7787(3) 0.0337(8) Uani . . 1.000
C C2B 0.2260(4) 0.21671(7) 0.7234(4) 0.0331(9) Uani . . 1.000
C C3B 0.3404(4) 0.24202(7) 0.6830(4) 0.0383(10) Uani . . 1.000
C C4B 0.2823(4) 0.27223(7) 0.7016(4) 0.0399(10) Uani . . 1.000
C C5B 0.0359(5) 0.30838(8) 0.7780(4) 0.0467(11) Uani . . 1.000
C C6B -0.1343(5) 0.31222(9) 0.8310(5) 0.0521(12) Uani . . 1.000
C C7B -0.2392(5) 0.28594(9) 0.8685(5) 0.0500(11) Uani . . 1.000
C C8B -0.1739(4) 0.25609(8) 0.8528(4) 0.0417(11) Uani . . 1.000
C C9B 0.0024(4) 0.25108(7) 0.7961(4) 0.0326(9) Uani . . 1.000
C C10B 0.1082(4) 0.27776(7) 0.7584(4) 0.0360(10) Uani . . 1.000
C C21B 0.2913(4) 0.18309(8) 0.7021(4) 0.0389(10) Uani . . 1.000
N N1C 0.1537(5) 0.11364(9) 0.4833(5) 0.0598(12) Uani . . 1.000
N N2C 0.2735(5) 0.08075(8) 0.2766(5) 0.0671(14) Uani . . 1.000
N N3C 0.4496(5) 0.11943(9) 0.4200(5) 0.0622(12) Uani . . 1.000
C C1C 0.2924(5) 0.10473(8) 0.3933(5) 0.0506(11) Uani . . 1.000
N N1D 0.6118(5) 0.13337(8) -0.0734(5) 0.0553(11) Uani . . 1.000
N N2D 0.9196(5) 0.13416(8) -0.0311(5) 0.0500(11) Uani . . 1.000
N N3D 0.7754(5) 0.17077(7) -0.2190(4) 0.0554(11) Uani . . 1.000
C C1D 0.7690(5) 0.14616(7) -0.1083(4) 0.0415(11) Uani . . 1.000
H H3A 0.58520 0.01430 0.11490 0.0520 Uiso calc R 1.000
H H4A 0.69050 -0.03680 0.12620 0.0560 Uiso calc R 1.000
H H5A 0.95370 -0.07410 0.19660 0.0630 Uiso calc R 1.000
H H6A 1.24640 -0.08100 0.30040 0.0730 Uiso calc R 1.000
H H7A 1.42460 -0.03830 0.39020 0.0680 Uiso calc R 1.000
H H8A 1.31110 0.01220 0.37240 0.0560 Uiso calc R 1.000
H H3B 0.45460 0.23800 0.64390 0.0460 Uiso calc R 1.000
H H4B 0.35710 0.28910 0.67710 0.0480 Uiso calc R 1.000
H H5B 0.10530 0.32610 0.75450 0.0560 Uiso calc R 1.000
H H6B -0.18120 0.33250 0.84230 0.0630 Uiso calc R 1.000
H H7B -0.35550 0.28890 0.90470 0.0600 Uiso calc R 1.000
H H8B -0.24530 0.23880 0.87940 0.0500 Uiso calc R 1.000
H H11C 0.165(4) 0.1267(8) 0.567(5) 0.070(10) Uiso . . 1.000
H H12C 0.046(6) 0.1036(9) 0.454(5) 0.066(12) Uiso . . 1.000
H H21C 0.376(6) 0.0750(10) 0.217(6) 0.079(13) Uiso . . 1.000
H H22C 0.173(6) 0.0684(11) 0.272(6) 0.084(14) Uiso . . 1.000
H H31C 0.448(6) 0.1394(11) 0.475(6) 0.089(15) Uiso . . 1.000
H H32C 0.540(6) 0.1136(11) 0.367(6) 0.081(15) Uiso . . 1.000
H H11D 0.611(5) 0.1156(10) -0.014(5) 0.068(13) Uiso . . 1.000
H H12D 0.514(6) 0.1421(11) -0.114(7) 0.091(17) Uiso . . 1.000
H H21D 1.022(5) 0.1409(8) -0.055(5) 0.064(10) Uiso . . 1.000
H H22D 0.908(6) 0.1206(11) 0.060(6) 0.083(15) Uiso . . 1.000
H H31D 0.882(5) 0.1819(9) -0.227(5) 0.060(11) Uiso . . 1.000
H H32D 0.670(6) 0.1793(10) -0.273(6) 0.074(13) Uiso . . 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A N1A C9A . . . 118.0(3) no
C2B N1B C9B . . . 117.5(3) no
C1C N1C H11C . . . 121(2) no
C1C N1C H12C . . . 117(3) no
H11C N1C H12C . . . 122(3) no
C1C N2C H21C . . . 116(3) no
C1C N2C H22C . . . 121(3) no
H21C N2C H22C . . . 122(4) no
C1C N3C H31C . . . 117(3) no
C1C N3C H32C . . . 122(3) no
H31C N3C H32C . . . 120(4) no
C1D N1D H11D . . . 119(2) no
C1D N1D H12D . . . 120(3) no
H11D N1D H12D . . . 121(4) no
C1D N2D H22D . . . 116(3) no
H21D N2D H22D . . . 121(4) no
C1D N2D H21D . . . 122(2) no
C1D N3D H31D . . . 120(2) no
C1D N3D H32D . . . 120(3) no
H31D N3D H32D . . . 119(4) no
N1A C2A C21A . . . 117.7(3) no
N1A C2A C3A . . . 122.9(3) no
C3A C2A C21A . . . 119.4(3) no
C2A C3A C4A . . . 119.6(3) no
C3A C4A C10A . . . 119.7(3) no
C6A C5A C10A . . . 120.6(3) no
C5A C6A C7A . . . 121.0(4) no
C6A C7A C8A . . . 120.6(3) no
C7A C8A C9A . . . 120.3(3) no
N1A C9A C10A . . . 122.5(3) no
N1A C9A C8A . . . 118.9(3) no
C8A C9A C10A . . . 118.6(3) no
C5A C10A C9A . . . 119.0(3) no
C4A C10A C9A . . . 117.3(3) no
C4A C10A C5A . . . 123.7(3) no
O21A C21A C2A . . . 119.0(3) no
O21A C21A O22A . . . 124.2(3) no
O22A C21A C2A . . . 116.8(3) no
C2A C3A H3A . . . 120.00 no
C4A C3A H3A . . . 120.00 no
C3A C4A H4A . . . 120.00 no
C10A C4A H4A . . . 120.00 no
C10A C5A H5A . . . 120.00 no
C6A C5A H5A . . . 120.00 no
C7A C6A H6A . . . 120.00 no
C5A C6A H6A . . . 119.00 no
C8A C7A H7A . . . 120.00 no
C6A C7A H7A . . . 120.00 no
C7A C8A H8A . . . 120.00 no
C9A C8A H8A . . . 120.00 no
N1B C2B C21B . . . 117.4(3) no
C3B C2B C21B . . . 119.2(3) no
N1B C2B C3B . . . 123.5(3) no
C2B C3B C4B . . . 119.4(3) no
C3B C4B C10B . . . 119.5(3) no
C6B C5B C10B . . . 120.5(3) no
C5B C6B C7B . . . 120.4(3) no
C6B C7B C8B . . . 120.9(3) no
C7B C8B C9B . . . 120.4(3) no
C8B C9B C10B . . . 118.5(3) no
N1B C9B C8B . . . 118.9(3) no
N1B C9B C10B . . . 122.7(3) no
C4B C10B C9B . . . 117.5(3) no
C5B C10B C9B . . . 119.3(3) no
C4B C10B C5B . . . 123.2(3) no
O21B C21B C2B . . . 119.3(3) no
O21B C21B O22B . . . 123.8(3) no
O22B C21B C2B . . . 116.8(3) no
C2B C3B H3B . . . 120.00 no
C4B C3B H3B . . . 120.00 no
C10B C4B H4B . . . 120.00 no
C3B C4B H4B . . . 120.00 no
C6B C5B H5B . . . 120.00 no
C10B C5B H5B . . . 120.00 no
C7B C6B H6B . . . 120.00 no
C5B C6B H6B . . . 120.00 no
C8B C7B H7B . . . 120.00 no
C6B C7B H7B . . . 120.00 no
C9B C8B H8B . . . 120.00 no
C7B C8B H8B . . . 120.00 no
N2C C1C N3C . . . 120.3(4) no
N1C C1C N2C . . . 119.3(4) no
N1C C1C N3C . . . 120.4(3) no
N2D C1D N3D . . . 119.9(3) no
N1D C1D N2D . . . 119.6(3) no
N1D C1D N3D . . . 120.5(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O21A C21A . . 1.245(4) no
O22A C21A . . 1.253(4) no
O21B C21B . . 1.248(4) no
O22B C21B . . 1.253(4) no
N1A C2A . . 1.320(4) no
N1A C9A . . 1.364(4) no
N1B C2B . . 1.316(4) no
N1B C9B . . 1.370(4) no
N1C C1C . . 1.316(5) no
N2C C1C . . 1.324(5) no
N3C C1C . . 1.325(5) no
N1C H11C . . 0.82(4) no
N1C H12C . . 0.92(4) no
N2C H21C . . 0.94(4) no
N2C H22C . . 0.91(4) no
N3C H32C . . 0.84(4) no
N3C H31C . . 0.93(5) no
N1D C1D . . 1.328(5) no
N2D C1D . . 1.318(5) no
N3D C1D . . 1.319(4) no
N1D H11D . . 0.87(4) no
N1D H12D . . 0.85(5) no
N2D H21D . . 0.84(4) no
N2D H22D . . 0.89(4) no
N3D H31D . . 0.93(4) no
N3D H32D . . 0.93(4) no
C2A C21A . . 1.513(5) no
C2A C3A . . 1.406(4) no
C3A C4A . . 1.356(5) no
C4A C10A . . 1.400(5) no
C5A C6A . . 1.352(6) no
C5A C10A . . 1.413(5) no
C6A C7A . . 1.383(6) no
C7A C8A . . 1.371(5) no
C8A C9A . . 1.414(4) no
C9A C10A . . 1.416(4) no
C3A H3A . . 0.9300 no
C4A H4A . . 0.9300 no
C5A H5A . . 0.9300 no
C6A H6A . . 0.9300 no
C7A H7A . . 0.9300 no
C8A H8A . . 0.9300 no
C2B C21B . . 1.511(4) no
C2B C3B . . 1.410(4) no
C3B C4B . . 1.356(4) no
C4B C10B . . 1.406(4) no
C5B C10B . . 1.411(5) no
C5B C6B . . 1.358(5) no
C6B C7B . . 1.394(5) no
C7B C8B . . 1.358(5) no
C8B C9B . . 1.418(4) no
C9B C10B . . 1.412(4) no
C3B H3B . . 0.9300 no
C4B H4B . . 0.9300 no
C5B H5B . . 0.9300 no
C6B H6B . . 0.9300 no
C7B H7B . . 0.9300 no
C8B H8B . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O21A N1A 2.735(4) . . no
O21A N1C 2.852(5) . 1_655 no
O21A N2C 3.163(5) . 1_655 no
O21A N2D 2.890(4) . . no
O21A C1C 3.408(5) . 1_655 no
O21B N1C 2.937(5) . . no
O21B N2D 2.899(5) . 1_456 no
O21B N1B 2.748(4) . . no
O21B N3D 3.268(5) . 1_456 no
O22A N3C 3.216(5) . . no
O22A N1D 2.902(4) . . no
O22A N2C 2.784(4) . . no
O22B N1D 3.250(4) . 1_556 no
O22B N3C 2.891(4) . . no
O22B N3D 2.826(4) . 1_556 no
O21A H12C 2.03(4) . 1_655 no
O21A H11D 2.80(4) . . no
O21A H22C 2.57(4) . 1_655 no
O21A H32C 2.67(5) . . no
O21A H22D 2.01(5) . . no
O21B H21D 2.11(4) . 1_456 no
O21B H31D 2.60(4) . 1_456 no
O21B H11C 2.12(4) . . no
O21B H12D 2.47(5) . 1_556 no
O22A H3A 2.4800 . . no
O22A H32C 2.57(5) . . no
O22A H11D 2.04(4) . . no
O22A H21C 1.87(4) . . no
O22B H12D 2.60(5) . 1_556 no
O22B H7B 2.6500 . 4_654 no
O22B H31C 1.96(5) . . no
O22B H32D 1.95(4) . 1_556 no
O22B H3B 2.5000 . . no
N1A O21A 2.735(4) . . no
N1A N2C 2.964(4) . 1_655 no
N1B O21B 2.748(4) . . no
N1B N3D 3.000(4) . 1_456 no
N1B C4B 3.403(4) . 4_555 no
N1C O21B 2.937(5) . . no
N1C O21A 2.852(5) . 1_455 no
N1D O22A 2.902(4) . . no
N1D O22B 3.250(4) . 1_554 no
N2C N1A 2.964(4) . 1_455 no
N2C O21A 3.163(5) . 1_455 no
N2C O22A 2.784(4) . . no
N2D C5B 3.384(5) . 4_654 no
N2D O21B 2.899(5) . 1_654 no
N2D O21A 2.890(4) . . no
N3C O22B 2.891(4) . . no
N3C O22A 3.216(5) . . no
N3D O22B 2.826(4) . 1_554 no
N3D O21B 3.268(5) . 1_654 no
N3D N1B 3.000(4) . 1_654 no
N1A H22C 2.08(5) . 1_655 no
N1B H31D 2.12(4) . 1_456 no
N2D H5B 2.9400 . 4_654 no
C1C O21A 3.408(5) . 1_455 no
C2A C7A 3.466(5) . 3_756 no
C2A C5A 3.586(5) . 3_755 no
C2B C10B 3.455(4) . 4_554 no
C2B C4B 3.519(4) . 4_555 no
C3B C4B 3.563(4) . 4_554 no
C3B C10B 3.541(4) . 4_554 no
C4B C2B 3.519(4) . 4_554 no
C4B C3B 3.563(4) . 4_555 no
C4B N1B 3.403(4) . 4_554 no
C5A C2A 3.586(5) . 3_755 no
C5B C21B 3.535(4) . 4_555 no
C5B N2D 3.384(5) . 4_455 no
C7A C2A 3.466(5) . 3_756 no
C8B C9B 3.419(4) . 4_555 no
C9A C9A 3.489(4) . 3_756 no
C9B C8B 3.419(4) . 4_554 no
C10B C2B 3.455(4) . 4_555 no
C10B C3B 3.541(4) . 4_555 no
C21B C5B 3.535(4) . 4_554 no
C1D H6A 3.0900 . 3_755 no
C2A H22C 2.97(5) . 1_655 no
C2B H31D 2.99(4) . 1_456 no
C3A H3A 2.9900 . 3_655 no
C4B H7B 3.0600 . 1_655 no
C9A H22C 3.00(5) . 1_655 no
C9B H31D 3.06(4) . 1_456 no
C21A H21C 2.83(4) . . no
C21A H32C 2.82(5) . . no
C21A H11D 2.66(4) . . no
C21A H22D 2.69(5) . . no
C21B H11C 2.72(3) . . no
C21B H31C 2.79(5) . . no
C21B H32D 2.81(4) . 1_556 no
C21B H12D 2.69(5) . 1_556 no
H3A O22A 2.4800 . . no
H3A C3A 2.9900 . 3_655 no
H3A H3A 2.3600 . 3_655 no
H3B H7B 2.5800 . 4_654 no
H3B O22B 2.5000 . . no
H4A H5A 2.5400 . . no
H4B H5B 2.5300 . . no
H5A H4A 2.5400 . . no
H5B H4B 2.5300 . . no
H5B N2D 2.9400 . 4_455 no
H6A C1D 3.0900 . 3_755 no
H7B H3B 2.5800 . 4_455 no
H7B C4B 3.0600 . 1_455 no
H7B O22B 2.6500 . 4_455 no
H11C C21B 2.72(3) . . no
H11C O21B 2.12(4) . . no
H11C H31C 2.32(5) . . no
H11D H22D 2.25(6) . . no
H11D C21A 2.66(4) . . no
H11D O21A 2.80(4) . . no
H11D O22A 2.04(4) . . no
H12C H22C 2.25(6) . . no
H12C O21A 2.03(4) . 1_455 no
H12D O21B 2.47(5) . 1_554 no
H12D C21B 2.69(5) . 1_554 no
H12D H32D 2.31(6) . . no
H12D O22B 2.60(5) . 1_554 no
H21C C21A 2.83(4) . . no
H21C H32C 2.27(6) . . no
H21C O22A 1.87(4) . . no
H21D O21B 2.11(4) . 1_654 no
H21D H31D 2.34(5) . . no
H22C C2A 2.97(5) . 1_455 no
H22C C9A 3.00(5) . 1_455 no
H22C H12C 2.25(6) . . no
H22C N1A 2.08(5) . 1_455 no
H22C O21A 2.57(4) . 1_455 no
H22D O21A 2.01(5) . . no
H22D C21A 2.69(5) . . no
H22D H11D 2.25(6) . . no
H31C C21B 2.79(5) . . no
H31C H11C 2.32(5) . . no
H31C O22B 1.96(5) . . no
H31D H21D 2.34(5) . . no
H31D O21B 2.60(4) . 1_654 no
H31D N1B 2.12(4) . 1_654 no
H31D C9B 3.06(4) . 1_654 no
H31D C2B 2.99(4) . 1_654 no
H32C C21A 2.82(5) . . no
H32C H21C 2.27(6) . . no
H32C O22A 2.57(5) . . no
H32C O21A 2.67(5) . . no
H32D O22B 1.95(4) . 1_554 no
H32D C21B 2.81(4) . 1_554 no
H32D H12D 2.31(6) . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1C H11C O21B . 0.82(4) 2.12(4) 2.937(5) 176(3) yes
N1C H12C O21A 1_455 0.92(4) 2.03(4) 2.852(5) 149(3) yes
N1D H11D O22A . 0.87(4) 2.04(4) 2.902(4) 177(4) yes
N1D H12D O21B 1_554 0.85(5) 2.47(5) 3.312(5) 173(4) yes
N2C H21C O22A . 0.94(4) 1.87(4) 2.784(4) 166(4) yes
N2C H22C O21A 1_455 0.91(4) 2.57(4) 3.163(5) 124(4) yes
N2C H22C N1A 1_455 0.91(4) 2.08(5) 2.964(4) 165(4) yes
N2D H21D O21B 1_654 0.84(4) 2.11(4) 2.899(5) 155(3) yes
N2D H22D O21A . 0.89(4) 2.01(5) 2.890(4) 173(4) yes
N3C H31C O22B . 0.93(5) 1.96(5) 2.891(4) 173(4) yes
N3C H32C O22A . 0.84(4) 2.57(5) 3.216(5) 135(4) yes
N3D H31D O21B 1_654 0.93(4) 2.60(4) 3.268(5) 130(3) yes
N3D H31D N1B 1_654 0.93(4) 2.12(4) 3.000(4) 159(3) yes
N3D H32D O22B 1_554 0.93(4) 1.95(4) 2.826(4) 157(4) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9A N1A C2A C3A . . . . 0.0(4) no
C9A N1A C2A C21A . . . . -179.6(2) no
C2A N1A C9A C8A . . . . -178.8(3) no
C2A N1A C9A C10A . . . . 0.6(4) no
C2B N1B C9B C8B . . . . 179.1(3) no
C2B N1B C9B C10B . . . . -0.4(4) no
C9B N1B C2B C3B . . . . 0.4(4) no
C9B N1B C2B C21B . . . . -179.3(2) no
C3A C2A C21A O21A . . . . 171.5(3) no
N1A C2A C21A O21A . . . . -8.9(4) no
N1A C2A C21A O22A . . . . 170.3(3) no
N1A C2A C3A C4A . . . . -0.5(5) no
C21A C2A C3A C4A . . . . 179.1(3) no
C3A C2A C21A O22A . . . . -9.4(4) no
C2A C3A C4A C10A . . . . 0.4(4) no
C3A C4A C10A C9A . . . . 0.1(4) no
C3A C4A C10A C5A . . . . -179.7(3) no
C6A C5A C10A C4A . . . . -179.0(3) no
C6A C5A C10A C9A . . . . 1.2(5) no
C10A C5A C6A C7A . . . . -0.1(6) no
C5A C6A C7A C8A . . . . -0.6(6) no
C6A C7A C8A C9A . . . . 0.3(5) no
C7A C8A C9A N1A . . . . -179.9(3) no
C7A C8A C9A C10A . . . . 0.8(4) no
N1A C9A C10A C5A . . . . 179.2(3) no
C8A C9A C10A C4A . . . . 178.7(3) no
C8A C9A C10A C5A . . . . -1.5(4) no
N1A C9A C10A C4A . . . . -0.6(4) no
N1B C2B C3B C4B . . . . 0.2(5) no
C21B C2B C3B C4B . . . . 179.9(3) no
N1B C2B C21B O21B . . . . -16.7(4) no
N1B C2B C21B O22B . . . . 163.6(3) no
C3B C2B C21B O21B . . . . 163.6(3) no
C3B C2B C21B O22B . . . . -16.1(4) no
C2B C3B C4B C10B . . . . -0.9(4) no
C3B C4B C10B C5B . . . . -178.8(3) no
C3B C4B C10B C9B . . . . 0.9(4) no
C10B C5B C6B C7B . . . . 0.6(5) no
C6B C5B C10B C4B . . . . 179.1(3) no
C6B C5B C10B C9B . . . . -0.6(5) no
C5B C6B C7B C8B . . . . -0.1(5) no
C6B C7B C8B C9B . . . . -0.6(5) no
C7B C8B C9B N1B . . . . -178.9(3) no
C7B C8B C9B C10B . . . . 0.6(4) no
N1B C9B C10B C4B . . . . -0.2(4) no
N1B C9B C10B C5B . . . . 179.5(3) no
C8B C9B C10B C4B . . . . -179.7(3) no
C8B C9B C10B C5B . . . . 0.0(4) no
