##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-09-12
_journal_date_accepted     2006-09-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     m2625
_journal_page_last     m2626
_journal_paper_category     EM
_journal_coeditor_code     HB2145
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Bis(2-methyl-1H-indole-3-carbaldehyde
4-hydroxybenzoylhydrazonato-κ²N,O)nickel(II)
N,N-dimethylformamide disolvate dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Ali, Hapipah M.'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Najwa, Mohd Idris'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Xie, Ming-Jin'
;
     School Chemistry
     Yunnan University
     Kunming 650092
     People's Republic of China
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis(2-methyl-1H-indole-3-carbaldehyde
4-hydroxybenzoylhydrazonato-κ²N,O)nickel(II)
N,N-dimethylformamide disolvate dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C34 H28 N6 Ni O4, 2C3 H7 N O, 2H2 O'
_chemical_formula_sum     'C40 H46 N8 Ni O8'
_chemical_formula_iupac     '[Ni (C17 H14 N3 O2)2], 2C3 H7 N O, 2H2 O'
_chemical_formula_weight     825.56
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.2441(6)
_cell_length_b     12.3260(10)
_cell_length_c     12.3950(10)
_cell_angle_alpha     76.3360(10)
_cell_angle_beta     74.1200(10)
_cell_angle_gamma     86.2530(10)
_cell_volume     1034.5(2)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     3608
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     27.1
_cell_measurement_temperature     295(2)
_exptl_crystal_description     'Irregular block'
_exptl_crystal_colour     Red
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.325
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     434
_exptl_absorpt_coefficient_mu     0.529
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.801
_exptl_absorpt_correction_T_max     0.925
_diffrn_ambient_temperature     295(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     'Bruker APEX-II CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9651
_diffrn_reflns_av_R_equivalents     0.017
_diffrn_reflns_av_sigmaI/netI     0.027
_diffrn_reflns_theta_min     1.7
_diffrn_reflns_theta_max     27.1
_diffrn_reflns_theta_full     27.1
_diffrn_measured_fraction_theta_max     0.98
_diffrn_measured_fraction_theta_full     0.98
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     4495
_reflns_number_gt     3822
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.047
_refine_ls_R_factor_gt     0.038
_refine_ls_wR_factor_gt     0.100
_refine_ls_wR_factor_ref     0.107
_refine_ls_goodness_of_fit_ref     1.02
_refine_ls_restrained_S_all     1.02
_refine_ls_number_reflns     4495
_refine_ls_number_parameters     278
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0595P)²+0.185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     'difmap and 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     0.29
_refine_diff_density_min     -0.20
_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 0.0016
                         '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'
    'Ni' 'Ni' 0.3393 1.1124
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEXII (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     SHELXL97
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_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Ni Ni1 0.5000 0.5000 0.5000 0.03490(10)
                                          Uani d S 1 . .
    O O1 0.5708(2) 0.47510(10)
                             0.35410(10)
                                       0.0402(3) Uani d . 1 . .
    O O2 0.8370(3) 0.5232(2) -0.18330(10)
                                        0.0681(5) Uani d D 1 . .
    O O3 0.8506(2) 0.17390(10)
                             0.53980(10)
                                       0.0536(4) Uani d . 1 . .
    O O1W 0.9006(3) 0.3339(2) 0.33720(10)
                                        0.0652(5) Uani d D 1 . .
    N N1 0.6373(2) 0.66330(10)
                             0.30300(10)
                                       0.0399(4) Uani d . 1 . .
    N N2 0.5809(2) 0.64500(10)
                             0.42410(10)
                                       0.0370(3) Uani d . 1 . .
    N N3 0.7667(3) 1.00030(10)
                             0.4428(2) 0.0481(4) Uani d D 1 . .
    N N4 0.8494(3) 0.2488(2) 0.6909(2) 0.0590(5) Uani d . 1 . .
    C C1 0.6833(3) 0.5601(2) 0.1543(2) 0.0386(4) Uani d . 1 . .
    C C2 0.6589(3) 0.4595(2) 0.1271(2) 0.0463(5) Uani d . 1 . .
    C C3 0.7124(3) 0.4491(2) 0.0142(2) 0.0541(5) Uani d . 1 . .
    C C4 0.7904(3) 0.5381(2) -0.0739(2) 0.0485(5) Uani d . 1 . .
    C C5 0.8148(3) 0.6392(2) -0.0486(2) 0.0526(5) Uani d . 1 . .
    C C6 0.7616(3) 0.6493(2) 0.0648(2) 0.0496(5) Uani d . 1 . .
    C C7 0.6279(3) 0.56830(10)
                             0.2759(2) 0.0366(4) Uani d . 1 . .
    C C8 0.5984(3) 0.72550(10)
                             0.4719(2) 0.0385(4) Uani d . 1 . .
    C C9 0.6632(3) 0.83870(10)
                             0.4276(2) 0.0385(4) Uani d . 1 . .
    C C10 0.7043(3) 0.8969(2) 0.5019(2) 0.0413(4) Uani d . 1 . .
    C C11 0.6951(3) 0.8610(2) 0.6272(2) 0.0544(5) Uani d . 1 . .
    C C12 0.7671(3) 1.0150(2) 0.3292(2) 0.0474(5) Uani d . 1 . .
    C C13 0.8188(4) 1.1089(2) 0.2393(2) 0.0674(7) Uani d . 1 . .
    C C14 0.8003(5) 1.1028(2) 0.1338(2) 0.0880(10) Uani d . 1 . .
    C C15 0.7319(5) 1.0061(2) 0.1179(2) 0.0863(10) Uani d . 1 . .
    C C16 0.6818(4) 0.9130(2) 0.2070(2) 0.0625(6) Uani d . 1 . .
    C C17 0.7015(3) 0.9149(2) 0.3149(2) 0.0438(4) Uani d . 1 . .
    C C18 0.8306(3) 0.1669(2) 0.6431(2) 0.0547(5) Uani d . 1 . .
    C C19 0.8989(4) 0.3612(2) 0.6225(2) 0.0692(7) Uani d . 1 . .
    C C20 0.8215(6) 0.2320(3) 0.8135(2) 0.1060(12) Uani d . 1 . .
    H H2o 0.910(4) 0.5731(18) -0.232(2) 0.088(10) Uiso d D 1 . .
    H H1w1 0.798(2) 0.371(2) 0.343(2) 0.069(8) Uiso d D 1 . .
    H H1w2 0.902(4) 0.293(2) 0.4020(10)
                                      0.082(9) Uiso d D 1 . .
    H H3n 0.796(3) 1.048(2) 0.476(2) 0.066(7) Uiso d D 1 . .
    H H2 0.6059 0.3987 0.1857 0.056 Uiso calc R 1 . .
    H H3 0.6956 0.3813 -0.0024 0.065 Uiso calc R 1 . .
    H H5 0.8666 0.6999 -0.1076 0.063 Uiso calc R 1 . .
    H H6 0.7787 0.7172 0.0811 0.060 Uiso calc R 1 . .
    H H8 0.5609 0.7053 0.5520 0.046 Uiso calc R 1 . .
    H H11a 0.8227 0.8486 0.6363 0.082 Uiso calc R 1 . .
    H H11b 0.6225 0.7931 0.6601 0.082 Uiso calc R 1 . .
    H H11c 0.6341 0.9182 0.6656 0.082 Uiso calc R 1 . .
    H H13 0.8640 1.1731 0.2504 0.081 Uiso calc R 1 . .
    H H14 0.8339 1.1639 0.0719 0.106 Uiso calc R 1 . .
    H H15 0.7197 1.0043 0.0456 0.104 Uiso calc R 1 . .
    H H16 0.6353 0.8495 0.1949 0.075 Uiso calc R 1 . .
    H H18 0.7992 0.0971 0.6921 0.066 Uiso calc R 1 . .
    H H19a 0.9576 0.3585 0.5437 0.104 Uiso calc R 1 . .
    H H19b 0.9870 0.3933 0.6517 0.104 Uiso calc R 1 . .
    H H19c 0.7847 0.4060 0.6270 0.104 Uiso calc R 1 . .
    H H20a 0.7939 0.1548 0.8496 0.159 Uiso calc R 1 . .
    H H20b 0.7161 0.2771 0.8441 0.159 Uiso calc R 1 . .
    H H20c 0.9360 0.2530 0.8282 0.159 Uiso calc R 1 . .
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
    Ni1 O1 . 1.8330(10)
                      yes
    Ni1 O1 2_666 1.8330(10)
                          ?
    Ni1 N2 2_666 1.8620(10)
                          ?
    Ni1 N2 . 1.8620(10)
                      yes
    O1 C7 . 1.322(2) ?
    O2 C4 . 1.358(2) ?
    O2 H2o . 0.850(10)
                     ?
    O3 C18 . 1.231(2) ?
    O1W H1w1 . 0.840(10)
                       ?
    O1W H1w2 . 0.840(10)
                       ?
    N1 C7 . 1.302(2) ?
    N1 N2 . 1.410(2) ?
    N2 C8 . 1.299(2) ?
    N3 C10 . 1.349(2) ?
    N3 C12 . 1.376(3) ?
    N3 H3n . 0.861(10) ?
    N4 C18 . 1.316(3) ?
    N4 C20 . 1.443(3) ?
    N4 C19 . 1.453(3) ?
    C1 C6 . 1.387(3) ?
    C1 C2 . 1.394(3) ?
    C1 C7 . 1.476(2) ?
    C2 C3 . 1.381(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.375(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.388(3) ?
    C5 C6 . 1.385(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C8 C9 . 1.432(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.394(3) ?
    C9 C17 . 1.453(3) ?
    C10 C11 . 1.494(3) ?
    C11 H11a . 0.9600 ?
    C11 H11b . 0.9600 ?
    C11 H11c . 0.9600 ?
    C12 C13 . 1.393(3) ?
    C12 C17 . 1.416(3) ?
    C13 C14 . 1.369(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.395(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.380(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.390(3) ?
    C16 H16 . 0.9300 ?
    C18 H18 . 0.9300 ?
    C19 H19a . 0.9600 ?
    C19 H19b . 0.9600 ?
    C19 H19c . 0.9600 ?
    C20 H20a . 0.9600 ?
    C20 H20b . 0.9600 ?
    C20 H20c . 0.9600 ?
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
    O1 Ni1 N2 . . 83.52(6) yes
    O1 Ni1 N2 . 2_666 96.48(6) yes
    O1 Ni1 O1 . 2_666 180.0 ?
    O1 Ni1 N2 2_666 2_666 83.52(6) ?
    O1 Ni1 N2 2_666 . 96.48(6) ?
    N2 Ni1 N2 2_666 . 180.0 ?
    C7 O1 Ni1 . . 111.37(10) ?
    C4 O2 H2o . . 114(2) ?
    H1w1 O1W H1w2 . . 110(3) ?
    C7 N1 N2 . . 108.06(14) ?
    C8 N2 N1 . . 119.22(14) ?
    C8 N2 Ni1 . . 126.36(12) ?
    N1 N2 Ni1 . . 114.32(11) ?
    C10 N3 C12 . . 110.12(16) ?
    C10 N3 H3n . . 121.7(16) ?
    C12 N3 H3n . . 128.2(16) ?
    C18 N4 C20 . . 122.0(2) ?
    C18 N4 C19 . . 121.52(19) ?
    C20 N4 C19 . . 116.5(2) ?
    C6 C1 C2 . . 118.08(17) ?
    C6 C1 C7 . . 122.32(17) ?
    C2 C1 C7 . . 119.60(16) ?
    C3 C2 C1 . . 120.76(18) ?
    C3 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
    C4 C3 C2 . . 120.65(19) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    O2 C4 C3 . . 117.86(19) ?
    O2 C4 C5 . . 122.69(19) ?
    C3 C4 C5 . . 119.43(18) ?
    C6 C5 C4 . . 119.84(18) ?
    C6 C5 H5 . . 120.1 ?
    C4 C5 H5 . . 120.1 ?
    C1 C6 C5 . . 121.24(18) ?
    C1 C6 H6 . . 119.4 ?
    C5 C6 H6 . . 119.4 ?
    N1 C7 O1 . . 122.54(16) ?
    N1 C7 C1 . . 120.75(16) ?
    O1 C7 C1 . . 116.71(15) ?
    N2 C8 C9 . . 133.60(17) ?
    N2 C8 H8 . . 113.2 ?
    C9 C8 H8 . . 113.2 ?
    C10 C9 C8 . . 119.01(16) ?
    C10 C9 C17 . . 106.48(16) ?
    C8 C9 C17 . . 134.51(17) ?
    N3 C10 C9 . . 109.52(17) ?
    N3 C10 C11 . . 119.78(17) ?
    C9 C10 C11 . . 130.66(17) ?
    C10 C11 H11a . . 109.5 ?
    C10 C11 H11b . . 109.5 ?
    H11a C11 H11b . . 109.5 ?
    C10 C11 H11c . . 109.5 ?
    H11a C11 H11c . . 109.5 ?
    H11b C11 H11c . . 109.5 ?
    N3 C12 C13 . . 129.01(19) ?
    N3 C12 C17 . . 108.10(17) ?
    C13 C12 C17 . . 122.9(2) ?
    C14 C13 C12 . . 117.4(2) ?
    C14 C13 H13 . . 121.3 ?
    C12 C13 H13 . . 121.3 ?
    C13 C14 C15 . . 120.9(2) ?
    C13 C14 H14 . . 119.5 ?
    C15 C14 H14 . . 119.5 ?
    C16 C15 C14 . . 121.6(2) ?
    C16 C15 H15 . . 119.2 ?
    C14 C15 H15 . . 119.2 ?
    C15 C16 C17 . . 119.4(2) ?
    C15 C16 H16 . . 120.3 ?
    C17 C16 H16 . . 120.3 ?
    C16 C17 C12 . . 117.81(18) ?
    C16 C17 C9 . . 136.35(18) ?
    C12 C17 C9 . . 105.77(17) ?
    O3 C18 N4 . . 126.3(2) ?
    O3 C18 H18 . . 116.8 ?
    N4 C18 H18 . . 116.8 ?
    N4 C19 H19a . . 109.5 ?
    N4 C19 H19b . . 109.5 ?
    H19a C19 H19b . . 109.5 ?
    N4 C19 H19c . . 109.5 ?
    H19a C19 H19c . . 109.5 ?
    H19b C19 H19c . . 109.5 ?
    N4 C20 H20a . . 109.5 ?
    N4 C20 H20b . . 109.5 ?
    H20a C20 H20b . . 109.5 ?
    N4 C20 H20c . . 109.5 ?
    H20a C20 H20c . . 109.5 ?
    H20b C20 H20c . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N2 Ni1 O1 C7 2_666 . . . 176.52(12) ?
    N2 Ni1 O1 C7 . . . . -3.48(12) ?
    C7 N1 N2 C8 . . . . 172.68(17) ?
    C7 N1 N2 Ni1 . . . . -3.80(19) ?
    O1 Ni1 N2 C8 . . . . -172.04(17) ?
    O1 Ni1 N2 C8 2_666 . . . 7.96(17) ?
    O1 Ni1 N2 N1 . . . . 4.15(12) ?
    O1 Ni1 N2 N1 2_666 . . . -175.85(12) ?
    N2 Ni1 N2 N1 2_666 . . .  -6E1(10)
                                      ?
    C6 C1 C2 C3 . . . . 0.4(3) ?
    C7 C1 C2 C3 . . . . -178.95(19) ?
    C1 C2 C3 C4 . . . . -0.2(3) ?
    C2 C3 C4 O2 . . . . -178.8(2) ?
    C2 C3 C4 C5 . . . . -0.2(3) ?
    O2 C4 C5 C6 . . . . 179.0(2) ?
    C3 C4 C5 C6 . . . . 0.4(3) ?
    C2 C1 C6 C5 . . . . -0.2(3) ?
    C7 C1 C6 C5 . . . . 179.16(19) ?
    C4 C5 C6 C1 . . . . -0.2(4) ?
    N2 N1 C7 O1 . . . . 0.9(2) ?
    N2 N1 C7 C1 . . . . -178.49(15) ?
    Ni1 O1 C7 N1 . . . . 2.4(2) ?
    Ni1 O1 C7 C1 . . . . -178.19(13) ?
    C6 C1 C7 N1 . . . . 5.3(3) ?
    C2 C1 C7 N1 . . . . -175.40(18) ?
    C6 C1 C7 O1 . . . . -174.15(18) ?
    C2 C1 C7 O1 . . . . 5.2(3) ?
    N1 N2 C8 C9 . . . . 1.6(3) ?
    Ni1 N2 C8 C9 . . . . 177.63(17) ?
    N2 C8 C9 C10 . . . . -166.0(2) ?
    N2 C8 C9 C17 . . . . 13.5(4) ?
    C12 N3 C10 C9 . . . . 0.8(2) ?
    C12 N3 C10 C11 . . . . 178.84(19) ?
    C8 C9 C10 N3 . . . . 178.62(17) ?
    C17 C9 C10 N3 . . . . -1.1(2) ?
    C8 C9 C10 C11 . . . . 0.8(3) ?
    C17 C9 C10 C11 . . . . -178.9(2) ?
    C10 N3 C12 C13 . . . . 179.3(2) ?
    C10 N3 C12 C17 . . . . -0.1(2) ?
    N3 C12 C13 C14 . . . . -178.0(3) ?
    C17 C12 C13 C14 . . . . 1.3(4) ?
    C12 C13 C14 C15 . . . . 0.2(5) ?
    C13 C14 C15 C16 . . . . -0.5(6) ?
    C14 C15 C16 C17 . . . . -0.6(5) ?
    C15 C16 C17 C12 . . . . 2.0(4) ?
    C15 C16 C17 C9 . . . . 178.6(3) ?
    N3 C12 C17 C16 . . . . 177.0(2) ?
    C13 C12 C17 C16 . . . . -2.4(3) ?
    N3 C12 C17 C9 . . . . -0.5(2) ?
    C13 C12 C17 C9 . . . . -180.0(2) ?
    C10 C9 C17 C16 . . . . -175.9(3) ?
    C8 C9 C17 C16 . . . . 4.5(4) ?
    C10 C9 C17 C12 . . . . 1.0(2) ?
    C8 C9 C17 C12 . . . . -178.7(2) ?
    C20 N4 C18 O3 . . . . 179.6(3) ?
    C19 N4 C18 O3 . . . . -0.2(4) ?
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
    O2 H2o O1w 2_765 0.850(10)
                             1.850(10)
                                     2.688(2) 171(3) yes
    O1w H1w1 O1 . 0.840(10)
                          2.020(10)
                                  2.852(2) 173(3) yes
    O1w H1w2 O3 . 0.840(10)
                          1.940(10)
                                  2.754(2) 163(3) yes
    N3 H3n O3 1_565 0.860(10)
                            2.000(10)
                                    2.859(2) 173(2) yes
