##############################################################################
###                                                                        ###
###        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.      #
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#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-03-07
_journal_date_accepted     2011-03-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      4
_journal_page_first     o1014
_journal_page_last     o1014
_journal_paper_category     QO
_journal_coeditor_code     RZ2570
_publ_contact_author
;
 Antigoni Kotali
;
_publ_contact_author_email     ' kotali@eng.auth.gr '
_publ_contact_author_fax     ' 302310996253 '
_publ_contact_author_phone     ' 302310996253 '
_publ_section_title
;
N'-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3-\
ylidene)ethyl]thiophene-2-carbohydrazide

;
loop_
    _publ_author_name
    _publ_author_address
    ' Madeleine Helliwell '
;
The School of Chemistry
The University of Manchester
Manchester M13 9PL
England
;
    'Despina A. Nasiopoulou'
;
Laboratory of Organic Chemistry
Department of Chemical Engineering
University of Thessaloniki
Thessaloniki 54124
Greece
;
    'Philip A. Harris'
;
GlaxoSmithKline
1250 South Collegeville Road
P.O.Box 5089
Collegeville
PA 19426-0989
USA
;
    'Antigoni Kotali'
;
Laboratory of Organic Chemistry
Department of Chemical Engineering
University of Thessaloniki
Thessaloniki 54124
Greece
;
    'John A. Joule'
;
The School of Chemistry
The University of Manchester
Manchester M13 9PL
England
;

data_I
_chemical_name_systematic
;
N'-[1-(2,4-Dioxo-3,4-dihydro-2H-1-benzopyran-3-
ylidene)ethyl]thiophene-2-carbohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H12 N2 O4 S'
_chemical_formula_sum     'C16 H12 N2 O4 S'
_chemical_formula_iupac     'C16 H12 N2 O4 S'
_chemical_formula_weight     328.34
_chemical_melting_point     ?
_chemical_melting_point_gt     501
_chemical_melting_point_lt     501.5
_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     4.8631(11)
_cell_length_b     11.833(3)
_cell_length_c     13.296(3)
_cell_angle_alpha     107.106(5)
_cell_angle_beta     100.376(4)
_cell_angle_gamma     97.553(4)
_cell_volume     705.3(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     557
_cell_measurement_theta_min     3.30
_cell_measurement_theta_max     24.06
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.546
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     340
_exptl_absorpt_coefficient_mu     0.253
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(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 SMART APEX CCD'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3526
_diffrn_reflns_av_R_equivalents     0.0722
_diffrn_reflns_av_sigmaI/netI     0.1401
_diffrn_reflns_theta_min     1.84
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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     2441
_reflns_number_gt     1403
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1154
_refine_ls_R_factor_gt     0.0579
_refine_ls_wR_factor_gt     0.1000
_refine_ls_wR_factor_ref     0.1158
_refine_ls_goodness_of_fit_ref     0.873
_refine_ls_restrained_S_all     0.875
_refine_ls_number_reflns     2441
_refine_ls_number_parameters     217
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0273P)²+0.0000P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.332
_refine_diff_density_min     -0.364
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker,  2001)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    S S1 0.0444(2) 0.21501(11) 0.90847(9) 0.0263(3) Uani d . 1 . .
    O O1 -0.1997(5) 0.2309(2) 0.68338(19) 0.0196(7) Uani d . 1 . .
    O O2 -0.0262(5) 0.2667(2) 0.1854(2) 0.0191(7) Uani d . 1 . .
    O O3 0.2600(5) 0.1509(2) 0.2281(2) 0.0199(7) Uani d . 1 . .
    O O4 -0.2081(5) 0.3697(2) 0.4843(2) 0.0189(7) Uani d . 1 . .
    N N1 0.1959(7) 0.1917(3) 0.6226(3) 0.0173(8) Uani d . 1 . .
    H H1N 0.391(9) 0.201(4) 0.640(3) 0.047(15) Uiso d . 1 . .
    N N2 0.0996(7) 0.2368(3) 0.5397(3) 0.0150(8) Uani d . 1 . .
    H H2N -0.014(9) 0.302(4) 0.552(3) 0.048(15) Uiso d . 1 . .
    C C1 0.2359(8) 0.1294(4) 0.9644(3) 0.0252(11) Uani d . 1 . .
    H H1 0.2486 0.1294 1.0365 0.030 Uiso calc R 1 . .
    C C2 0.3682(8) 0.0614(4) 0.8950(3) 0.0262(11) Uani d . 1 . .
    H H2 0.4810 0.0070 0.9124 0.031 Uiso calc R 1 . .
    C C3 0.3201(8) 0.0801(4) 0.7933(3) 0.0208(10) Uani d . 1 . .
    H H3 0.3987 0.0407 0.7351 0.025 Uiso calc R 1 . .
    C C4 0.1463(8) 0.1620(4) 0.7887(3) 0.0147(10) Uani d . 1 . .
    C C5 0.0318(8) 0.1993(3) 0.6974(3) 0.0125(9) Uani d . 1 . .
    C C6 0.1535(8) 0.1983(4) 0.4433(3) 0.0133(9) Uani d U 1 . .
    C C7 0.3201(8) 0.1004(4) 0.4210(3) 0.0193(10) Uani d . 1 . .
    H H7A 0.5221 0.1358 0.4335 0.029 Uiso calc R 1 . .
    H H7B 0.2502 0.0480 0.3456 0.029 Uiso calc R 1 . .
    H H7C 0.2976 0.0528 0.4692 0.029 Uiso calc R 1 . .
    C C8 0.0388(8) 0.2517(4) 0.3664(3) 0.0141(9) Uani d . 1 . .
    C C9 0.1028(8) 0.2193(4) 0.2600(3) 0.0155(10) Uani d . 1 . .
    C C10 -0.1924(8) 0.3525(4) 0.2107(3) 0.0176(10) Uani d . 1 . .
    C C11 -0.2969(8) 0.3977(4) 0.1301(3) 0.0221(11) Uani d . 1 . .
    H H11 -0.2520 0.3710 0.0614 0.027 Uiso calc R 1 . .
    C C12 -0.4677(8) 0.4821(4) 0.1510(3) 0.0249(11) Uani d . 1 . .
    H H12 -0.5401 0.5138 0.0960 0.030 Uiso calc R 1 . .
    C C13 -0.5364(8) 0.5220(4) 0.2519(3) 0.0211(10) Uani d . 1 . .
    H H13 -0.6553 0.5797 0.2656 0.025 Uiso calc R 1 . .
    C C14 -0.4275(8) 0.4756(4) 0.3307(3) 0.0172(10) Uani d . 1 . .
    H H14 -0.4735 0.5015 0.3993 0.021 Uiso calc R 1 . .
    C C15 -0.2522(8) 0.3918(4) 0.3123(3) 0.0162(10) Uani d . 1 . .
    C C16 -0.1403(8) 0.3385(4) 0.3938(3) 0.0153(10) Uani d . 1 . .
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
    S1 0.0278(7) 0.0360(8) 0.0186(6) 0.0138(6) 0.0112(5) 0.0073(6)
    O1 0.0102(15) 0.0294(18) 0.0222(16) 0.0067(14) 0.0062(12) 0.0104(14)
    O2 0.0190(16) 0.0247(18) 0.0170(15) 0.0095(14) 0.0074(13) 0.0077(14)
    O3 0.0189(16) 0.0226(18) 0.0207(16) 0.0073(14) 0.0109(13) 0.0057(14)
    O4 0.0166(16) 0.0256(18) 0.0149(15) 0.0064(14) 0.0076(13) 0.0041(14)
    N1 0.010(2) 0.029(2) 0.0117(18) 0.0057(17) 0.0024(15) 0.0042(17)
    N2 0.0129(19) 0.019(2) 0.0143(19) 0.0045(17) 0.0017(15) 0.0067(17)
    C1 0.021(2) 0.040(3) 0.014(2) 0.005(2) 0.0002(19) 0.009(2)
    C2 0.020(2) 0.036(3) 0.026(3) 0.010(2) 0.004(2) 0.013(2)
    C3 0.019(2) 0.031(3) 0.017(2) 0.010(2) 0.0077(19) 0.010(2)
    C4 0.009(2) 0.016(2) 0.013(2) -0.0028(19) 0.0017(17) -0.0012(19)
    C5 0.011(2) 0.011(2) 0.015(2) 0.0039(18) 0.0056(17) 0.0016(18)
    C6 0.0084(16) 0.0156(17) 0.0147(16) -0.0025(13) 0.0041(13) 0.0043(14)
    C7 0.017(2) 0.019(3) 0.021(2) 0.001(2) 0.0044(19) 0.006(2)
    C8 0.010(2) 0.014(2) 0.015(2) -0.0001(18) 0.0035(17) 0.0013(19)
    C9 0.011(2) 0.014(2) 0.018(2) -0.0019(19) 0.0017(18) 0.003(2)
    C10 0.009(2) 0.023(3) 0.017(2) 0.0013(19) 0.0024(18) 0.002(2)
    C11 0.026(3) 0.027(3) 0.013(2) 0.005(2) 0.0081(19) 0.003(2)
    C12 0.021(3) 0.026(3) 0.024(3) 0.004(2) -0.002(2) 0.008(2)
    C13 0.017(2) 0.021(3) 0.022(2) 0.005(2) 0.0017(19) 0.003(2)
    C14 0.013(2) 0.019(3) 0.016(2) -0.0003(19) 0.0025(18) 0.003(2)
    C15 0.010(2) 0.016(2) 0.018(2) -0.0030(19) 0.0030(18) 0.0004(19)
    C16 0.011(2) 0.017(3) 0.016(2) -0.0026(19) 0.0025(18) 0.006(2)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    S1 C1 . 1.699(4) ?
    S1 C4 . 1.718(4) ?
    O1 C5 . 1.232(4) ?
    O2 C9 . 1.374(4) ?
    O2 C10 . 1.382(5) ?
    O3 C9 . 1.223(4) ?
    O4 C16 . 1.268(4) ?
    N1 C5 . 1.373(5) ?
    N1 N2 . 1.395(4) ?
    N1 H1N . 0.92(4) ?
    N2 C6 . 1.315(5) ?
    N2 H2N . 1.00(4) ?
    C1 C2 . 1.352(5) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.417(5) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.374(5) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.455(5) ?
    C6 C8 . 1.423(5) ?
    C6 C7 . 1.489(5) ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C8 C16 . 1.441(5) ?
    C8 C9 . 1.454(5) ?
    C10 C11 . 1.380(5) ?
    C10 C15 . 1.390(5) ?
    C11 C12 . 1.380(6) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.402(5) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.376(5) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.387(5) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.465(5) ?
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
    C1 S1 C4 . . 91.6(2) ?
    C9 O2 C10 . . 122.5(3) ?
    C5 N1 N2 . . 115.1(3) ?
    C5 N1 H1N . . 123(3) ?
    N2 N1 H1N . . 113(3) ?
    C6 N2 N1 . . 123.0(4) ?
    C6 N2 H2N . . 117(2) ?
    N1 N2 H2N . . 120(2) ?
    C2 C1 S1 . . 112.6(3) ?
    C2 C1 H1 . . 123.7 ?
    S1 C1 H1 . . 123.7 ?
    C1 C2 C3 . . 112.5(4) ?
    C1 C2 H2 . . 123.7 ?
    C3 C2 H2 . . 123.7 ?
    C4 C3 C2 . . 112.0(4) ?
    C4 C3 H3 . . 124.0 ?
    C2 C3 H3 . . 124.0 ?
    C3 C4 C5 . . 128.9(4) ?
    C3 C4 S1 . . 111.3(3) ?
    C5 C4 S1 . . 119.6(3) ?
    O1 C5 N1 . . 121.0(3) ?
    O1 C5 C4 . . 124.1(3) ?
    N1 C5 C4 . . 114.9(3) ?
    N2 C6 C8 . . 116.7(4) ?
    N2 C6 C7 . . 118.5(4) ?
    C8 C6 C7 . . 124.7(4) ?
    C6 C7 H7A . . 109.5 ?
    C6 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C6 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C6 C8 C16 . . 120.1(3) ?
    C6 C8 C9 . . 120.1(4) ?
    C16 C8 C9 . . 119.8(4) ?
    O3 C9 O2 . . 115.1(3) ?
    O3 C9 C8 . . 126.4(4) ?
    O2 C9 C8 . . 118.5(4) ?
    C11 C10 O2 . . 116.8(4) ?
    C11 C10 C15 . . 121.3(4) ?
    O2 C10 C15 . . 121.9(4) ?
    C12 C11 C10 . . 118.9(4) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C11 C12 C13 . . 121.2(4) ?
    C11 C12 H12 . . 119.4 ?
    C13 C12 H12 . . 119.4 ?
    C14 C13 C12 . . 118.4(4) ?
    C14 C13 H13 . . 120.8 ?
    C12 C13 H13 . . 120.8 ?
    C13 C14 C15 . . 121.5(4) ?
    C13 C14 H14 . . 119.2 ?
    C15 C14 H14 . . 119.2 ?
    C14 C15 C10 . . 118.6(4) ?
    C14 C15 C16 . . 122.5(4) ?
    C10 C15 C16 . . 118.8(4) ?
    O4 C16 C8 . . 123.1(4) ?
    O4 C16 C15 . . 118.6(4) ?
    C8 C16 C15 . . 118.2(4) ?
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
    C5 N1 N2 C6 . . . . -153.1(4) ?
    C4 S1 C1 C2 . . . . -1.1(3) ?
    S1 C1 C2 C3 . . . . 1.3(5) ?
    C1 C2 C3 C4 . . . . -0.9(5) ?
    C2 C3 C4 C5 . . . . -175.5(4) ?
    C2 C3 C4 S1 . . . . 0.0(5) ?
    C1 S1 C4 C3 . . . . 0.6(3) ?
    C1 S1 C4 C5 . . . . 176.6(3) ?
    N2 N1 C5 O1 . . . . 8.1(5) ?
    N2 N1 C5 C4 . . . . -174.8(3) ?
    C3 C4 C5 O1 . . . . 148.8(4) ?
    S1 C4 C5 O1 . . . . -26.4(6) ?
    C3 C4 C5 N1 . . . . -28.2(6) ?
    S1 C4 C5 N1 . . . . 156.6(3) ?
    N1 N2 C6 C8 . . . . 179.3(3) ?
    N1 N2 C6 C7 . . . . 1.2(6) ?
    N2 C6 C8 C16 . . . . -3.4(5) ?
    C7 C6 C8 C16 . . . . 174.5(4) ?
    N2 C6 C8 C9 . . . . 176.4(3) ?
    C7 C6 C8 C9 . . . . -5.7(6) ?
    C10 O2 C9 O3 . . . . -174.9(3) ?
    C10 O2 C9 C8 . . . . 6.2(5) ?
    C6 C8 C9 O3 . . . . -2.9(6) ?
    C16 C8 C9 O3 . . . . 176.9(4) ?
    C6 C8 C9 O2 . . . . 175.9(3) ?
    C16 C8 C9 O2 . . . . -4.3(5) ?
    C9 O2 C10 C11 . . . . 176.6(4) ?
    C9 O2 C10 C15 . . . . -3.5(5) ?
    O2 C10 C11 C12 . . . . 179.0(3) ?
    C15 C10 C11 C12 . . . . -1.0(6) ?
    C10 C11 C12 C13 . . . . -0.2(6) ?
    C11 C12 C13 C14 . . . . 0.5(6) ?
    C12 C13 C14 C15 . . . . 0.4(6) ?
    C13 C14 C15 C10 . . . . -1.5(6) ?
    C13 C14 C15 C16 . . . . -178.2(4) ?
    C11 C10 C15 C14 . . . . 1.8(6) ?
    O2 C10 C15 C14 . . . . -178.1(3) ?
    C11 C10 C15 C16 . . . . 178.7(4) ?
    O2 C10 C15 C16 . . . . -1.3(6) ?
    C6 C8 C16 O4 . . . . -1.3(6) ?
    C9 C8 C16 O4 . . . . 178.9(4) ?
    C6 C8 C16 C15 . . . . 179.6(3) ?
    C9 C8 C16 C15 . . . . -0.2(5) ?
    C14 C15 C16 O4 . . . . 0.5(6) ?
    C10 C15 C16 O4 . . . . -176.2(3) ?
    C14 C15 C16 C8 . . . . 179.7(4) ?
    C10 C15 C16 C8 . . . . 3.0(5) ?
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
    N2 H2N O4 . 1.00(4) 1.64(5) 2.481(4) 140(4)
    N1 H1N O1 1_655 0.92(4) 1.93(4) 2.841(4) 177(4)
