##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2005-11-07
_journal_date_accepted     2005-12-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     m72
_journal_page_last     m73
_journal_paper_category     EM
_journal_coeditor_code     XU6086
_publ_contact_author_name     'Jin-Hua Cai'
_publ_contact_author_address
;
Department of Chemistry and life Science
Hechi Normal College
Yizhou,GuangXi,546300
P. R. China
;
_publ_contact_author_email     cjhzse@163.com
_publ_contact_author_fax     '86 773 5845973 '
_publ_contact_author_phone     '86 773 5856134 '
_publ_section_title
;\
catena-Poly[[[bis(2-aminoethanesulfonato-κ²N,O)\
copper(II)]-μ-4,4'- bipyridine-κ²N:N'] 4,4'-bipyridine
monohydrate]]
;
loop_
    _publ_author_name
    _publ_author_address
    'Jin-Hua Cai'
;
Department of Chemistry and Life Sciences
Hechi Normal College
Yizhou
Guangxi 546300
People's Republic of China
;
    'Yi-Min Jiang'
;
College of Chemistry and Chemical Engineering
Guangxi Normal University
Guilin
Guangxi 541004
People's Republic of China
;
    'Xiu-Ju Yin'
;
Department of Chemistry and Life Sciences
Hechi Normal College
Yizhou
Guangxi 546300
People's Republic of China
;
    'Xu-Hui Liu'
;
Department of Chemistry and Life Sciences
Hechi Normal College
Yizhou
Guangxi 546300
People's Republic of China
;
    'Xiu-Jian Wang'
;
College of Chemistry and Chemical Engineering
Guangxi Normal University
Guilin
Guangxi 541004
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
catena-Poly[[[bis(2-aminoethanesulfonato-κ²N,O)copper(II)]-μ-4,4'-
bipyridine-κ²N:N'] 4,4'-bipyridine monohydrate]]
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H20 Cu N4 O6 S2, C10 H8 N2, H2 O'
_chemical_formula_sum     'C24 H30 Cu N6 O7 S2'
_chemical_formula_iupac     '[Cu (C2 H6 N O3 S)2 (C10 H8 N2)], C10 H8 N2, H2 O'
_chemical_formula_weight     642.2
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 2/c'
_symmetry_space_group_name_Hall     '-P 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
_cell_length_a     9.8647(11)
_cell_length_b     11.3846(9)
_cell_length_c     12.9516(14)
_cell_angle_alpha     90.00
_cell_angle_beta     107.446(5)
_cell_angle_gamma     90.00
_cell_volume     1387.6(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2887
_cell_measurement_theta_min     3.3
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Blue
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.537
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     666
_exptl_absorpt_coefficient_mu     0.992
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.775
_exptl_absorpt_correction_T_max     0.860
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku Mercury CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10598
_diffrn_reflns_av_R_equivalents     0.039
_diffrn_reflns_av_sigmaI/netI     0.038
_diffrn_reflns_theta_min     3.3
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3176
_reflns_number_gt     2681
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.060
_refine_ls_R_factor_gt     0.047
_refine_ls_wR_factor_gt     0.093
_refine_ls_wR_factor_ref     0.099
_refine_ls_goodness_of_fit_ref     1.083
_refine_ls_restrained_S_all     1.083
_refine_ls_number_reflns     3176
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.031P)²+1.3917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.42
_refine_diff_density_min     -0.40
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cu' 'Cu' 0.3201 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrystalClear (Rigaku, 2000)'
_computing_cell_refinement     'CrystalClear'
_computing_data_reduction     'CrystalClear'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Cu 0.0000 0.37558(3) 0.2500 0.02478(14) Uani d S 1 . . Cu
    S 0.25875(8) 0.39859(6) 0.49274(6) 0.03598(18) Uani d . 1 . . S
    N1 0.0000 0.1853(2) 0.2500 0.0332(7) Uani d S 1 . . N
    N2 0.1844(2) 0.37126(19) 0.21701(18) 0.0325(5) Uani d . 1 . . N
    H2A 0.1791 0.4239 0.1658 0.039 Uiso d R 1 A . H
    H2B 0.1885 0.3042 0.1896 0.039 Uiso d R 1 . . H
    N3 0.0000 0.5624(2) 0.2500 0.0280(7) Uani d S 1 . . N
    N4 0.7300(4) 0.1558(3) 0.3845(3) 0.0790(11) Uani d . 1 . . N
    O1 0.3188(3) 0.3010(2) 0.5593(2) 0.0904(10) Uani d . 1 . . O
    O2 0.2828(3) 0.5085(2) 0.5489(2) 0.0729(8) Uani d . 1 . . O
    O3 0.1092(2) 0.37865(16) 0.43436(15) 0.0370(4) Uani d . 1 . . O
    O1W 0.5829(8) 0.2895(8) 0.7232(5) 0.134(3) Uani d P 0.50 . . O
    H1C 0.4958 0.2944 0.6791 0.161 Uiso d PR 0.50 . . H
    H1D 0.5936 0.2934 0.7961 0.161 Uiso d PR 0.50 . . H
    C1A 0.3188(5) 0.3414(5) 0.3031(4) 0.0278(11) Uani d P 0.50 A 1 C
    H1A1 0.3974 0.3384 0.2727 0.033 Uiso calc PR 0.50 A 1 H
    H1A2 0.3101 0.2652 0.3340 0.033 Uiso calc PR 0.50 A 1 H
    C2A 0.3459(7) 0.4380(6) 0.3919(6) 0.0350(15) Uani d P 0.50 A 1 C
    H2A1 0.3093 0.5126 0.3591 0.042 Uiso calc PR 0.50 A 1 H
    H2A2 0.4472 0.4464 0.4265 0.042 Uiso calc PR 0.50 A 1 H
    C1B 0.3085(7) 0.4331(8) 0.2996(6) 0.0589(19) Uani d P 0.50 A 2 C
    H1B1 0.3880 0.4387 0.2703 0.071 Uiso calc PR 0.50 A 2 H
    H1B2 0.2799 0.5123 0.3113 0.071 Uiso calc PR 0.50 A 2 H
    C2B 0.3536(8) 0.3728(8) 0.4012(7) 0.053(2) Uani d P 0.50 A 2 C
    H2B1 0.4521 0.3932 0.4364 0.063 Uiso calc PR 0.50 A 2 H
    H2B2 0.3505 0.2891 0.3866 0.063 Uiso calc PR 0.50 A 2 H
    C3 0.0111(3) 0.6237(2) 0.1647(2) 0.0328(6) Uani d . 1 A . C
    H3 0.0175 0.5827 0.1043 0.039 Uiso calc R 1 . . H
    C4 0.0134(3) 0.7442(2) 0.1622(2) 0.0359(6) Uani d . 1 . . C
    H4 0.0239 0.7830 0.1018 0.043 Uiso calc R 1 A . H
    C5 0.0000 0.8084(3) 0.2500 0.0302(8) Uani d S 1 . . C
    C6 -0.0586(3) 0.1244(2) 0.1593(2) 0.0395(7) Uani d . 1 . . C
    H6 -0.0997 0.1655 0.0956 0.047 Uiso calc R 1 . . H
    C7 -0.0606(3) 0.0027(2) 0.1561(3) 0.0424(7) Uani d . 1 . . C
    H7 -0.1025 -0.0361 0.0912 0.051 Uiso calc R 1 . . H
    C8 0.0000 -0.0610(3) 0.2500 0.0358(9) Uani d S 1 . . C
    C9 0.5482(3) 0.0322(2) 0.4758(3) 0.0414(7) Uani d . 1 . . C
    C10 0.5921(4) 0.1457(3) 0.5069(3) 0.0540(9) Uani d . 1 . . C
    H10 0.5626 0.1830 0.5602 0.065 Uiso calc R 1 . . H
    C11 0.6802(4) 0.2032(3) 0.4582(4) 0.0678(12) Uani d . 1 . . C
    H11 0.7058 0.2802 0.4790 0.081 Uiso calc R 1 . . H
    C12 0.6910(5) 0.0463(4) 0.3565(4) 0.0864(15) Uani d . 1 . . C
    H12 0.7262 0.0102 0.3054 0.104 Uiso calc R 1 . . H
    C13 0.6007(4) -0.0176(3) 0.3989(3) 0.0671(11) Uani d . 1 . . C
    H13 0.5756 -0.0939 0.3754 0.081 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cu 0.0296(2) 0.0165(2) 0.0310(3) 0.000 0.01326(19) 0.000
    S 0.0381(4) 0.0362(4) 0.0315(4) 0.0053(3) 0.0072(3) -0.0069(3)
    N1 0.0352(18) 0.0186(14) 0.046(2) 0.000 0.0124(15) 0.000
    N2 0.0344(12) 0.0353(11) 0.0311(12) 0.0008(9) 0.0149(10) -0.0025(10)
    N3 0.0365(17) 0.0196(13) 0.0311(16) 0.000 0.0150(14) 0.000
    N4 0.086(2) 0.0542(19) 0.122(3) -0.0166(17) 0.070(2) 0.006(2)
    O1 0.084(2) 0.0679(18) 0.093(2) 0.0237(15) -0.0139(17) 0.0292(16)
    O2 0.0695(17) 0.0516(14) 0.106(2) -0.0207(12) 0.0397(16) -0.0400(14)
    O3 0.0366(11) 0.0424(11) 0.0327(11) 0.0007(8) 0.0114(9) 0.0010(8)
    O1W 0.126(6) 0.192(8) 0.057(4) 0.038(6) -0.015(4) -0.033(5)
    C1A 0.026(3) 0.031(3) 0.030(3) 0.005(2) 0.013(2) -0.010(2)
    C2A 0.034(3) 0.036(3) 0.037(4) -0.009(3) 0.014(3) -0.013(3)
    C1B 0.037(4) 0.080(6) 0.068(5) -0.009(4) 0.029(4) -0.010(4)
    C2B 0.030(3) 0.067(5) 0.058(5) 0.007(4) 0.009(3) -0.008(5)
    C3 0.0472(16) 0.0235(12) 0.0312(14) -0.0006(11) 0.0170(13) -0.0008(10)
    C4 0.0530(18) 0.0242(12) 0.0330(15) -0.0001(11) 0.0167(13) 0.0047(11)
    C5 0.0309(19) 0.0196(16) 0.039(2) 0.000 0.0092(17) 0.000
    C6 0.0476(17) 0.0238(12) 0.0429(17) 0.0017(12) 0.0073(14) 0.0014(12)
    C7 0.0531(19) 0.0247(13) 0.0440(17) -0.0009(12) 0.0062(15) -0.0031(12)
    C8 0.038(2) 0.0234(18) 0.047(2) 0.000 0.0141(19) 0.000
    C9 0.0352(15) 0.0318(14) 0.059(2) -0.0020(12) 0.0173(14) 0.0101(14)
    C10 0.053(2) 0.0329(16) 0.088(3) -0.0010(14) 0.0392(19) 0.0029(16)
    C11 0.067(2) 0.0331(16) 0.119(4) -0.0088(16) 0.051(3) 0.006(2)
    C12 0.109(4) 0.069(3) 0.112(4) -0.022(3) 0.080(3) -0.012(3)
    C13 0.083(3) 0.047(2) 0.089(3) -0.0233(19) 0.053(2) -0.009(2)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cu N1 . 2.166(3) y
    Cu N2 . 1.990(2) y
    Cu N2 2 1.990(2) ?
    Cu N3 . 2.127(3) y
    Cu O3 2 2.3067(19) ?
    Cu O3 . 2.3067(19) y
    S O1 . 1.422(3) ?
    S O2 . 1.431(2) ?
    S O3 . 1.460(2) ?
    S C2B . 1.741(8) ?
    S C2A . 1.822(7) ?
    N1 C6 . 1.336(3) ?
    N1 C6 2 1.336(3) ?
    N2 C1A . 1.493(6) ?
    N2 C1B . 1.534(8) ?
    N2 H2A . 0.8838 ?
    N2 H2B . 0.8482 ?
    N3 C3 2 1.338(3) ?
    N3 C3 . 1.338(3) ?
    N4 C11 . 1.313(5) ?
    N4 C12 . 1.323(5) ?
    O1W H1C . 0.8790 ?
    O1W H1D . 0.9192 ?
    C1A C2A . 1.556(8) ?
    C1A H1A1 . 0.9700 ?
    C1A H1A2 . 0.9700 ?
    C2A H2A1 . 0.9700 ?
    C2A H2A2 . 0.9700 ?
    C1B C2B . 1.432(11) ?
    C1B H1B1 . 0.9700 ?
    C1B H1B2 . 0.9700 ?
    C2B H2B1 . 0.9700 ?
    C2B H2B2 . 0.9700 ?
    C3 C4 . 1.373(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.391(3) ?
    C4 H4 . 0.9300 ?
    C5 C4 2 1.391(3) ?
    C5 C8 1_565 1.487(5) ?
    C6 C7 . 1.386(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.388(3) ?
    C7 H7 . 0.9300 ?
    C8 C7 2 1.388(3) ?
    C8 C5 1_545 1.487(5) ?
    C9 C13 . 1.375(5) ?
    C9 C10 . 1.384(4) ?
    C9 C9 3_656 1.482(6) ?
    C10 C11 . 1.381(5) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.384(5) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    N2 Cu N2 . 2 177.17(13) y
    N2 Cu N3 . . 91.42(6) y
    N2 Cu N3 2 . 91.42(6) ?
    N2 Cu N1 . . 88.58(6) ?
    N2 Cu N1 2 . 88.58(6) ?
    N3 Cu N1 . . 180.0 ?
    N2 Cu O3 . 2 87.22(8) ?
    N2 Cu O3 2 2 92.83(8) ?
    N3 Cu O3 . 2 89.13(5) ?
    N1 Cu O3 . 2 90.87(5) ?
    N2 Cu O3 . . 92.83(8) ?
    N2 Cu O3 2 . 87.22(8) ?
    N3 Cu O3 . . 89.13(5) ?
    N1 Cu O3 . . 90.87(5) ?
    O3 Cu O3 2 . 178.27(9) ?
    O1 S O2 . . 113.56(19) ?
    O1 S O3 . . 111.42(15) ?
    O2 S O3 . . 112.77(14) ?
    O1 S C2B . . 94.0(3) ?
    O2 S C2B . . 116.9(3) ?
    O3 S C2B . . 106.7(3) ?
    O1 S C2A . . 115.3(3) ?
    O2 S C2A . . 96.1(2) ?
    O3 S C2A . . 106.7(2) ?
    C6 N1 C6 . 2 117.5(3) ?
    C6 N1 Cu . . 121.25(16) ?
    C6 N1 Cu 2 . 121.25(16) ?
    C1A N2 Cu . . 120.6(2) ?
    C1B N2 Cu . . 115.4(3) ?
    C1A N2 H2A . . 123.7 ?
    C1B N2 H2A . . 93.9 ?
    Cu N2 H2A . . 107.0 ?
    C1A N2 H2B . . 88.0 ?
    C1B N2 H2B . . 125.2 ?
    Cu N2 H2B . . 105.9 ?
    H2A N2 H2B . . 107.2 ?
    C3 N3 C3 2 . 117.2(3) ?
    C3 N3 Cu 2 . 121.42(15) ?
    C3 N3 Cu . . 121.42(15) ?
    C11 N4 C12 . . 116.4(3) ?
    S O3 Cu . . 128.64(12) ?
    H1C O1W H1D . . 117.0 ?
    N2 C1A C2A . . 107.9(4) ?
    N2 C1A H1A1 . . 110.1 ?
    C2A C1A H1A1 . . 110.1 ?
    N2 C1A H1A2 . . 110.1 ?
    C2A C1A H1A2 . . 110.1 ?
    H1A1 C1A H1A2 . . 108.4 ?
    C1A C2A S . . 110.0(4) ?
    C1A C2A H2A1 . . 109.7 ?
    S C2A H2A1 . . 109.7 ?
    C1A C2A H2A2 . . 109.7 ?
    S C2A H2A2 . . 109.7 ?
    H2A1 C2A H2A2 . . 108.2 ?
    C2B C1B N2 . . 112.6(6) ?
    C2B C1B H1B1 . . 109.1 ?
    N2 C1B H1B1 . . 109.1 ?
    C2B C1B H1B2 . . 109.1 ?
    N2 C1B H1B2 . . 109.1 ?
    H1B1 C1B H1B2 . . 107.8 ?
    C1B C2B S . . 117.5(6) ?
    C1B C2B H2B1 . . 107.9 ?
    S C2B H2B1 . . 107.9 ?
    C1B C2B H2B2 . . 107.9 ?
    S C2B H2B2 . . 107.9 ?
    H2B1 C2B H2B2 . . 107.2 ?
    N3 C3 C4 . . 123.1(3) ?
    N3 C3 H3 . . 118.4 ?
    C4 C3 H3 . . 118.4 ?
    C3 C4 C5 . . 119.9(3) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C4 C5 C4 . 2 116.7(3) ?
    C4 C5 C8 . 1_565 121.67(16) ?
    C4 C5 C8 2 1_565 121.67(16) ?
    N1 C6 C7 . . 122.9(3) ?
    N1 C6 H6 . . 118.5 ?
    C7 C6 H6 . . 118.5 ?
    C6 C7 C8 . . 119.8(3) ?
    C6 C7 H7 . . 120.1 ?
    C8 C7 H7 . . 120.1 ?
    C7 C8 C7 2 . 117.0(3) ?
    C7 C8 C5 2 1_545 121.51(17) ?
    C7 C8 C5 . 1_545 121.51(17) ?
    C13 C9 C10 . . 116.3(3) ?
    C13 C9 C9 . 3_656 122.1(3) ?
    C10 C9 C9 . 3_656 121.6(4) ?
    C11 C10 C9 . . 119.6(3) ?
    C11 C10 H10 . . 120.2 ?
    C9 C10 H10 . . 120.2 ?
    N4 C11 C10 . . 124.1(3) ?
    N4 C11 H11 . . 118.0 ?
    C10 C11 H11 . . 118.0 ?
    N4 C12 C13 . . 123.7(4) ?
    N4 C12 H12 . . 118.2 ?
    C13 C12 H12 . . 118.2 ?
    C9 C13 C12 . . 119.8(3) ?
    C9 C13 H13 . . 120.1 ?
    C12 C13 H13 . . 120.1 ?
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
    O1W H1C O1 . 0.88 1.96 2.827(8) 169 y
    O1W H1D O1 2_656 0.92 1.81 2.693(7) 159 y
    N2 H2A O2 4_565 0.88 2.20 2.971(3) 145 y
    N2 H2B N4 2_655 0.85 2.21 3.021(4) 160 y
