##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-03-25
_journal_date_accepted     2012-03-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o1255
_journal_page_last     o1256
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812013190
_journal_coeditor_code     IS5101
_publ_contact_author_name     'Prof. Fun Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6533652'
_publ_section_title
;
3-Methyl-1-benzofuran-2-carbohydrazide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hatem A. Abdel-Aziz' ?
;     Department of Pharmaceutical Chemistry
      College of Pharmacy
      King Saud University
      PO Box 2457
      Riyadh 11451
      Saudi Arabia
;
    'Hazem A. Ghabbour' ?
;     Department of Pharmaceutical Chemistry
      College of Pharmacy
      King Saud University
      PO Box 2457
      Riyadh 11451
      Saudi Arabia
;
    'Suchada Chantrapromma'
;
      Thomson Reuters ResearcherID: A-5085-2009.
;
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Hoong-Kun Fun'
;
      College of Pharmacy (Visiting Professor), King Saud University,
      PO Box 2457, Riyadh 11451, Saudi Arabia.
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Methyl-1-benzofuran-2-carbohydrazide
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C10 H10 N2 O2'
_chemical_formula_sum     'C10 H10 N2 O2'
_chemical_formula_iupac     'C10 H10 N2 O2'
_chemical_formula_weight     190.20
_chemical_melting_point_gt     ?
_chemical_melting_point_lt     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     10.9391(4)
_cell_length_b     18.1257(6)
_cell_length_c     14.1818(5)
_cell_angle_alpha     90.00
_cell_angle_beta     94.157(2)
_cell_angle_gamma     90.00
_cell_volume     2804.55(17)
_cell_formula_units_Z     12
_cell_measurement_reflns_used     5217
_cell_measurement_theta_min     3.96
_cell_measurement_theta_max     69.92
_cell_measurement_temperature     296(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.59
_exptl_crystal_size_mid     0.58
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.351
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1200
_exptl_absorpt_coefficient_mu     0.796
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.6511
_exptl_absorpt_correction_T_max     0.9464
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     19906
_diffrn_reflns_av_R_equivalents     0.0480
_diffrn_reflns_av_sigmaI/netI     0.0328
_diffrn_reflns_theta_min     3.96
_diffrn_reflns_theta_max     69.92
_diffrn_reflns_theta_full     69.92
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_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 > 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     5271
_reflns_number_gt     3618
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0645
_refine_ls_R_factor_gt     0.0447
_refine_ls_wR_factor_gt     0.1215
_refine_ls_wR_factor_ref     0.1334
_refine_ls_goodness_of_fit_ref     1.001
_refine_ls_restrained_S_all     1.001
_refine_ls_number_reflns     5271
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0825P)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     0.003
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.228
_refine_diff_density_min     -0.173
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.00139(18)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1A 0.66559(14) 0.25954(9) 0.45740(10) 0.0571(4) Uani d . 1 1 . .
    N N2A 0.73238(19) 0.22213(10) 0.53133(12) 0.0631(4) Uani d . 1 1 . .
    O O1A 0.63038(14) 0.15700(7) 0.36927(10) 0.0709(4) Uani d . 1 1 . .
    O O2A 0.56996(11) 0.34643(6) 0.31969(8) 0.0561(3) Uani d . 1 1 . .
    C C1A 0.56634(15) 0.27126(9) 0.30302(11) 0.0524(4) Uani d . 1 1 . .
    C C2A 0.51543(15) 0.25509(10) 0.21547(12) 0.0562(4) Uani d . 1 1 . .
    C C3A 0.48558(15) 0.32498(10) 0.17160(12) 0.0556(4) Uani d . 1 1 . .
    C C4A 0.43569(18) 0.34786(13) 0.08226(14) 0.0717(6) Uani d . 1 1 . .
    H H4AA 0.4123 0.3136 0.0356 0.086 Uiso calc R 1 1 . .
    C C5A 0.42246(19) 0.42181(14) 0.06571(16) 0.0810(6) Uani d . 1 1 . .
    H H5AA 0.3910 0.4377 0.0065 0.097 Uiso calc R 1 1 . .
    C C6A 0.4547(2) 0.47400(13) 0.13506(18) 0.0801(6) Uani d . 1 1 . .
    H H6AA 0.4419 0.5238 0.1218 0.096 Uiso calc R 1 1 . .
    C C7A 0.50514(18) 0.45342(12) 0.22282(15) 0.0685(5) Uani d . 1 1 . .
    H H7AA 0.5279 0.4879 0.2694 0.082 Uiso calc R 1 1 . .
    C C8A 0.51987(15) 0.37872(10) 0.23764(12) 0.0550(4) Uani d . 1 1 . .
    C C9A 0.62203(16) 0.22390(10) 0.37883(12) 0.0534(4) Uani d . 1 1 . .
    C C10A 0.4931(2) 0.18129(11) 0.17137(16) 0.0808(6) Uani d . 1 1 . .
    H H10D 0.4948 0.1443 0.2198 0.121 Uiso calc R 1 1 . .
    H H10E 0.5557 0.1710 0.1291 0.121 Uiso calc R 1 1 . .
    H H10F 0.4144 0.1810 0.1367 0.121 Uiso calc R 1 1 . .
    N N1B 0.83956(14) 0.29089(8) 0.71808(11) 0.0569(4) Uani d . 1 1 . .
    N N2B 0.82765(19) 0.36857(9) 0.71889(12) 0.0633(4) Uani d . 1 1 . .
    O O1B 0.92755(12) 0.28638(7) 0.86711(9) 0.0695(4) Uani d . 1 1 . .
    O O2B 0.83348(11) 0.14361(6) 0.70444(8) 0.0566(3) Uani d . 1 1 . .
    C C1B 0.87755(15) 0.17365(9) 0.79039(11) 0.0507(4) Uani d . 1 1 . .
    C C2B 0.90239(15) 0.12155(10) 0.85708(13) 0.0560(4) Uani d . 1 1 . .
    C C3B 0.87230(16) 0.05251(10) 0.81085(14) 0.0609(5) Uani d . 1 1 . .
    C C4B 0.8743(2) -0.02149(13) 0.8389(2) 0.0897(7) Uani d . 1 1 . .
    H H4BA 0.8995 -0.0349 0.9005 0.108 Uiso calc R 1 1 . .
    C C5B 0.8378(3) -0.07389(13) 0.7722(3) 0.1080(10) Uani d . 1 1 . .
    H H5BA 0.8385 -0.1234 0.7897 0.130 Uiso calc R 1 1 . .
    C C6B 0.8001(3) -0.05510(13) 0.6802(2) 0.0974(8) Uani d . 1 1 . .
    H H6BA 0.7776 -0.0923 0.6371 0.117 Uiso calc R 1 1 . .
    C C7B 0.7950(2) 0.01714(11) 0.65068(18) 0.0770(6) Uani d . 1 1 . .
    H H7BA 0.7685 0.0302 0.5892 0.092 Uiso calc R 1 1 . .
    C C8B 0.83170(16) 0.06907(10) 0.71809(14) 0.0587(4) Uani d . 1 1 . .
    C C9B 0.88443(15) 0.25460(10) 0.79526(12) 0.0527(4) Uani d . 1 1 . .
    C C10B 0.94992(19) 0.13066(13) 0.95756(14) 0.0740(6) Uani d . 1 1 . .
    H H10A 0.9272 0.1784 0.9798 0.111 Uiso calc R 1 1 . .
    H H10B 1.0376 0.1263 0.9622 0.111 Uiso calc R 1 1 . .
    H H10C 0.9155 0.0932 0.9955 0.111 Uiso calc R 1 1 . .
    N N1C 0.69717(14) 0.46541(9) 0.57073(10) 0.0594(4) Uani d . 1 1 . .
    N N2C 0.64389(18) 0.42386(9) 0.49354(12) 0.0623(4) Uani d . 1 1 . .
    O O1C 0.64284(13) 0.57510(7) 0.50655(9) 0.0699(4) Uani d . 1 1 . .
    O O2C 0.79491(11) 0.52731(6) 0.72827(8) 0.0567(3) Uani d . 1 1 . .
    C C1C 0.75346(15) 0.57452(9) 0.65594(11) 0.0506(4) Uani d . 1 1 . .
    C C2C 0.77132(16) 0.64592(9) 0.67945(13) 0.0531(4) Uani d . 1 1 . .
    C C3C 0.82728(16) 0.64574(10) 0.77463(13) 0.0554(4) Uani d . 1 1 . .
    C C4C 0.86680(19) 0.69945(12) 0.84080(16) 0.0729(6) Uani d . 1 1 . .
    H H4CA 0.8602 0.7494 0.8261 0.088 Uiso calc R 1 1 . .
    C C5C 0.9156(2) 0.67689(15) 0.92799(16) 0.0819(7) Uani d . 1 1 . .
    H H5CA 0.9427 0.7122 0.9723 0.098 Uiso calc R 1 1 . .
    C C6C 0.92547(19) 0.60330(15) 0.95160(15) 0.0834(7) Uani d . 1 1 . .
    H H6CA 0.9585 0.5901 1.0115 0.100 Uiso calc R 1 1 . .
    C C7C 0.88740(19) 0.54871(13) 0.88830(14) 0.0730(5) Uani d . 1 1 . .
    H H7CA 0.8938 0.4989 0.9037 0.088 Uiso calc R 1 1 . .
    C C8C 0.83918(15) 0.57222(10) 0.80065(12) 0.0562(4) Uani d . 1 1 . .
    C C9C 0.69353(15) 0.53881(9) 0.57113(11) 0.0512(4) Uani d . 1 1 . .
    C C10C 0.7425(2) 0.71305(11) 0.62159(15) 0.0730(6) Uani d . 1 1 . .
    H H10G 0.7081 0.6987 0.5601 0.110 Uiso calc R 1 1 . .
    H H10H 0.8162 0.7408 0.6153 0.110 Uiso calc R 1 1 . .
    H H10I 0.6846 0.7429 0.6521 0.110 Uiso calc R 1 1 . .
    H H1N1 0.6655(17) 0.3094(11) 0.4641(14) 0.063(6) Uiso d . 1 1 . .
    H H2N1 0.8052(18) 0.2666(11) 0.6644(15) 0.069(6) Uiso d . 1 1 . .
    H H3N1 0.7349(17) 0.4363(12) 0.6145(15) 0.069(6) Uiso d . 1 1 . .
    H H1N2 0.687(2) 0.1863(14) 0.5467(18) 0.085(8) Uiso d . 1 1 . .
    H H2N2 0.792(2) 0.2002(13) 0.5072(17) 0.080(8) Uiso d . 1 1 . .
    H H3N2 0.901(2) 0.3877(13) 0.7343(17) 0.086(7) Uiso d . 1 1 . .
    H H4N2 0.777(2) 0.3793(12) 0.7671(17) 0.078(7) Uiso d . 1 1 . .
    H H5N2 0.667(2) 0.4472(13) 0.4439(18) 0.084(7) Uiso d . 1 1 . .
    H H6N2 0.560(2) 0.4227(12) 0.4966(14) 0.074(6) Uiso d . 1 1 . .
_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
    N1A C9A . 1.345(2) ?
    N1A N2A . 1.408(2) ?
    N1A H1N1 . 0.908(19) ?
    N2A H1N2 . 0.86(3) ?
    N2A H2N2 . 0.86(2) ?
    O1A C9A . 1.224(2) ?
    O2A C8A . 1.380(2) ?
    O2A C1A . 1.3829(19) ?
    C1A C2A . 1.355(2) ?
    C1A C9A . 1.473(2) ?
    C2A C3A . 1.438(3) ?
    C2A C10A . 1.489(3) ?
    C3A C8A . 1.384(2) ?
    C3A C4A . 1.405(2) ?
    C4A C5A . 1.367(3) ?
    C4A H4AA . 0.9300 ?
    C5A C6A . 1.392(3) ?
    C5A H5AA . 0.9300 ?
    C6A C7A . 1.376(3) ?
    C6A H6AA . 0.9300 ?
    C7A C8A . 1.378(3) ?
    C7A H7AA . 0.9300 ?
    C10A H10D . 0.9600 ?
    C10A H10E . 0.9600 ?
    C10A H10F . 0.9600 ?
    N1B C9B . 1.339(2) ?
    N1B N2B . 1.414(2) ?
    N1B H2N1 . 0.93(2) ?
    N2B H3N2 . 0.88(2) ?
    N2B H4N2 . 0.93(2) ?
    O1B C9B . 1.234(2) ?
    O2B C8B . 1.365(2) ?
    O2B C1B . 1.389(2) ?
    C1B C2B . 1.350(2) ?
    C1B C9B . 1.471(2) ?
    C2B C3B . 1.440(3) ?
    C2B C10B . 1.490(3) ?
    C3B C8B . 1.391(3) ?
    C3B C4B . 1.399(3) ?
    C4B C5B . 1.378(4) ?
    C4B H4BA . 0.9300 ?
    C5B C6B . 1.383(4) ?
    C5B H5BA . 0.9300 ?
    C6B C7B . 1.374(3) ?
    C6B H6BA . 0.9300 ?
    C7B C8B . 1.380(3) ?
    C7B H7BA . 0.9300 ?
    C10B H10A . 0.9600 ?
    C10B H10B . 0.9600 ?
    C10B H10C . 0.9600 ?
    N1C C9C . 1.331(2) ?
    N1C N2C . 1.419(2) ?
    N1C H3N1 . 0.89(2) ?
    N2C H5N2 . 0.87(2) ?
    N2C H6N2 . 0.92(2) ?
    O1C C9C . 1.227(2) ?
    O2C C8C . 1.371(2) ?
    O2C C1C . 1.3867(19) ?
    C1C C2C . 1.347(2) ?
    C1C C9C . 1.477(2) ?
    C2C C3C . 1.441(3) ?
    C2C C10C . 1.488(2) ?
    C3C C8C . 1.386(3) ?
    C3C C4C . 1.399(3) ?
    C4C C5C . 1.373(3) ?
    C4C H4CA . 0.9300 ?
    C5C C6C . 1.378(3) ?
    C5C H5CA . 0.9300 ?
    C6C C7C . 1.380(3) ?
    C6C H6CA . 0.9300 ?
    C7C C8C . 1.382(2) ?
    C7C H7CA . 0.9300 ?
    C10C H10G . 0.9600 ?
    C10C H10H . 0.9600 ?
    C10C H10I . 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
    C9A N1A N2A . . 121.28(16) ?
    C9A N1A H1N1 . . 124.1(13) ?
    N2A N1A H1N1 . . 113.9(13) ?
    N1A N2A H1N2 . . 105.9(16) ?
    N1A N2A H2N2 . . 107.2(16) ?
    H1N2 N2A H2N2 . . 103(2) ?
    C8A O2A C1A . . 105.61(13) ?
    C2A C1A O2A . . 111.99(15) ?
    C2A C1A C9A . . 131.56(16) ?
    O2A C1A C9A . . 116.38(13) ?
    C1A C2A C3A . . 105.73(15) ?
    C1A C2A C10A . . 128.52(18) ?
    C3A C2A C10A . . 125.75(16) ?
    C8A C3A C4A . . 118.09(18) ?
    C8A C3A C2A . . 106.57(14) ?
    C4A C3A C2A . . 135.32(18) ?
    C5A C4A C3A . . 118.3(2) ?
    C5A C4A H4AA . . 120.9 ?
    C3A C4A H4AA . . 120.9 ?
    C4A C5A C6A . . 121.81(19) ?
    C4A C5A H5AA . . 119.1 ?
    C6A C5A H5AA . . 119.1 ?
    C7A C6A C5A . . 121.3(2) ?
    C7A C6A H6AA . . 119.4 ?
    C5A C6A H6AA . . 119.4 ?
    C6A C7A C8A . . 116.1(2) ?
    C6A C7A H7AA . . 122.0 ?
    C8A C7A H7AA . . 122.0 ?
    C7A C8A O2A . . 125.48(17) ?
    C7A C8A C3A . . 124.43(17) ?
    O2A C8A C3A . . 110.09(15) ?
    O1A C9A N1A . . 122.86(16) ?
    O1A C9A C1A . . 121.78(15) ?
    N1A C9A C1A . . 115.33(15) ?
    C2A C10A H10D . . 109.5 ?
    C2A C10A H10E . . 109.5 ?
    H10D C10A H10E . . 109.5 ?
    C2A C10A H10F . . 109.5 ?
    H10D C10A H10F . . 109.5 ?
    H10E C10A H10F . . 109.5 ?
    C9B N1B N2B . . 120.72(15) ?
    C9B N1B H2N1 . . 122.5(12) ?
    N2B N1B H2N1 . . 116.3(12) ?
    N1B N2B H3N2 . . 108.1(15) ?
    N1B N2B H4N2 . . 105.9(14) ?
    H3N2 N2B H4N2 . . 108(2) ?
    C8B O2B C1B . . 105.74(13) ?
    C2B C1B O2B . . 112.32(16) ?
    C2B C1B C9B . . 131.15(16) ?
    O2B C1B C9B . . 116.47(13) ?
    C1B C2B C3B . . 105.15(16) ?
    C1B C2B C10B . . 129.11(18) ?
    C3B C2B C10B . . 125.75(17) ?
    C8B C3B C4B . . 118.2(2) ?
    C8B C3B C2B . . 106.85(16) ?
    C4B C3B C2B . . 134.9(2) ?
    C5B C4B C3B . . 117.9(2) ?
    C5B C4B H4BA . . 121.0 ?
    C3B C4B H4BA . . 121.0 ?
    C4B C5B C6B . . 122.0(2) ?
    C4B C5B H5BA . . 119.0 ?
    C6B C5B H5BA . . 119.0 ?
    C7B C6B C5B . . 121.6(2) ?
    C7B C6B H6BA . . 119.2 ?
    C5B C6B H6BA . . 119.2 ?
    C6B C7B C8B . . 115.8(2) ?
    C6B C7B H7BA . . 122.1 ?
    C8B C7B H7BA . . 122.1 ?
    O2B C8B C7B . . 125.68(18) ?
    O2B C8B C3B . . 109.94(16) ?
    C7B C8B C3B . . 124.39(18) ?
    O1B C9B N1B . . 122.75(17) ?
    O1B C9B C1B . . 121.31(15) ?
    N1B C9B C1B . . 115.92(14) ?
    C2B C10B H10A . . 109.5 ?
    C2B C10B H10B . . 109.5 ?
    H10A C10B H10B . . 109.5 ?
    C2B C10B H10C . . 109.5 ?
    H10A C10B H10C . . 109.5 ?
    H10B C10B H10C . . 109.5 ?
    C9C N1C N2C . . 121.54(14) ?
    C9C N1C H3N1 . . 126.9(13) ?
    N2C N1C H3N1 . . 111.5(13) ?
    N1C N2C H5N2 . . 103.8(16) ?
    N1C N2C H6N2 . . 109.3(13) ?
    H5N2 N2C H6N2 . . 113(2) ?
    C8C O2C C1C . . 105.44(13) ?
    C2C C1C O2C . . 112.09(15) ?
    C2C C1C C9C . . 132.11(16) ?
    O2C C1C C9C . . 115.72(14) ?
    C1C C2C C3C . . 105.88(15) ?
    C1C C2C C10C . . 128.88(17) ?
    C3C C2C C10C . . 125.23(16) ?
    C8C C3C C4C . . 118.17(18) ?
    C8C C3C C2C . . 106.07(15) ?
    C4C C3C C2C . . 135.75(18) ?
    C5C C4C C3C . . 118.6(2) ?
    C5C C4C H4CA . . 120.7 ?
    C3C C4C H4CA . . 120.7 ?
    C4C C5C C6C . . 121.7(2) ?
    C4C C5C H5CA . . 119.1 ?
    C6C C5C H5CA . . 119.1 ?
    C5C C6C C7C . . 121.4(2) ?
    C5C C6C H6CA . . 119.3 ?
    C7C C6C H6CA . . 119.3 ?
    C6C C7C C8C . . 116.2(2) ?
    C6C C7C H7CA . . 121.9 ?
    C8C C7C H7CA . . 121.9 ?
    O2C C8C C7C . . 125.56(18) ?
    O2C C8C C3C . . 110.51(15) ?
    C7C C8C C3C . . 123.92(18) ?
    O1C C9C N1C . . 123.01(16) ?
    O1C C9C C1C . . 121.52(16) ?
    N1C C9C C1C . . 115.47(14) ?
    C2C C10C H10G . . 109.5 ?
    C2C C10C H10H . . 109.5 ?
    H10G C10C H10H . . 109.5 ?
    C2C C10C H10I . . 109.5 ?
    H10G C10C H10I . . 109.5 ?
    H10H C10C H10I . . 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
    C8A O2A C1A C2A . . . . -0.71(19) ?
    C8A O2A C1A C9A . . . . 176.44(14) ?
    O2A C1A C2A C3A . . . . 0.9(2) ?
    C9A C1A C2A C3A . . . . -175.65(18) ?
    O2A C1A C2A C10A . . . . -178.90(18) ?
    C9A C1A C2A C10A . . . . 4.5(3) ?
    C1A C2A C3A C8A . . . . -0.80(19) ?
    C10A C2A C3A C8A . . . . 179.05(18) ?
    C1A C2A C3A C4A . . . . 177.5(2) ?
    C10A C2A C3A C4A . . . . -2.7(4) ?
    C8A C3A C4A C5A . . . . -0.7(3) ?
    C2A C3A C4A C5A . . . . -178.8(2) ?
    C3A C4A C5A C6A . . . . -1.2(3) ?
    C4A C5A C6A C7A . . . . 2.1(3) ?
    C5A C6A C7A C8A . . . . -0.8(3) ?
    C6A C7A C8A O2A . . . . 179.05(18) ?
    C6A C7A C8A C3A . . . . -1.2(3) ?
    C1A O2A C8A C7A . . . . 179.92(17) ?
    C1A O2A C8A C3A . . . . 0.17(18) ?
    C4A C3A C8A C7A . . . . 2.0(3) ?
    C2A C3A C8A C7A . . . . -179.37(17) ?
    C4A C3A C8A O2A . . . . -178.24(16) ?
    C2A C3A C8A O2A . . . . 0.39(19) ?
    N2A N1A C9A O1A . . . . 4.9(3) ?
    N2A N1A C9A C1A . . . . -173.31(17) ?
    C2A C1A C9A O1A . . . . 0.9(3) ?
    O2A C1A C9A O1A . . . . -175.59(16) ?
    C2A C1A C9A N1A . . . . 179.11(18) ?
    O2A C1A C9A N1A . . . . 2.6(2) ?
    C8B O2B C1B C2B . . . . -0.49(19) ?
    C8B O2B C1B C9B . . . . -178.00(14) ?
    O2B C1B C2B C3B . . . . 0.1(2) ?
    C9B C1B C2B C3B . . . . 177.12(17) ?
    O2B C1B C2B C10B . . . . -179.60(18) ?
    C9B C1B C2B C10B . . . . -2.6(3) ?
    C1B C2B C3B C8B . . . . 0.4(2) ?
    C10B C2B C3B C8B . . . . -179.95(18) ?
    C1B C2B C3B C4B . . . . -178.8(2) ?
    C10B C2B C3B C4B . . . . 0.9(3) ?
    C8B C3B C4B C5B . . . . 1.1(3) ?
    C2B C3B C4B C5B . . . . -179.9(2) ?
    C3B C4B C5B C6B . . . . 0.1(4) ?
    C4B C5B C6B C7B . . . . -1.2(4) ?
    C5B C6B C7B C8B . . . . 1.0(4) ?
    C1B O2B C8B C7B . . . . -179.46(19) ?
    C1B O2B C8B C3B . . . . 0.71(19) ?
    C6B C7B C8B O2B . . . . -179.66(19) ?
    C6B C7B C8B C3B . . . . 0.2(3) ?
    C4B C3B C8B O2B . . . . 178.62(17) ?
    C2B C3B C8B O2B . . . . -0.7(2) ?
    C4B C3B C8B C7B . . . . -1.2(3) ?
    C2B C3B C8B C7B . . . . 179.49(18) ?
    N2B N1B C9B O1B . . . . -6.8(3) ?
    N2B N1B C9B C1B . . . . 172.22(16) ?
    C2B C1B C9B O1B . . . . 6.4(3) ?
    O2B C1B C9B O1B . . . . -176.64(16) ?
    C2B C1B C9B N1B . . . . -172.58(18) ?
    O2B C1B C9B N1B . . . . 4.4(2) ?
    C8C O2C C1C C2C . . . . 0.82(19) ?
    C8C O2C C1C C9C . . . . -176.23(15) ?
    O2C C1C C2C C3C . . . . -0.7(2) ?
    C9C C1C C2C C3C . . . . 175.70(18) ?
    O2C C1C C2C C10C . . . . 178.58(17) ?
    C9C C1C C2C C10C . . . . -5.0(3) ?
    C1C C2C C3C C8C . . . . 0.3(2) ?
    C10C C2C C3C C8C . . . . -179.00(17) ?
    C1C C2C C3C C4C . . . . -178.5(2) ?
    C10C C2C C3C C4C . . . . 2.1(4) ?
    C8C C3C C4C C5C . . . . 0.2(3) ?
    C2C C3C C4C C5C . . . . 178.9(2) ?
    C3C C4C C5C C6C . . . . -0.5(3) ?
    C4C C5C C6C C7C . . . . 0.4(3) ?
    C5C C6C C7C C8C . . . . 0.0(3) ?
    C1C O2C C8C C7C . . . . 178.43(18) ?
    C1C O2C C8C C3C . . . . -0.59(19) ?
    C6C C7C C8C O2C . . . . -179.19(18) ?
    C6C C7C C8C C3C . . . . -0.3(3) ?
    C4C C3C C8C O2C . . . . 179.28(16) ?
    C2C C3C C8C O2C . . . . 0.2(2) ?
    C4C C3C C8C C7C . . . . 0.2(3) ?
    C2C C3C C8C C7C . . . . -178.86(18) ?
    N2C N1C C9C O1C . . . . 1.3(3) ?
    N2C N1C C9C C1C . . . . -179.64(17) ?
    C2C C1C C9C O1C . . . . -3.4(3) ?
    O2C C1C C9C O1C . . . . 172.87(16) ?
    C2C C1C C9C N1C . . . . 177.44(18) ?
    O2C C1C C9C N1C . . . . -6.2(2) ?
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
    N1A H1N1 N2C 1_555 0.91(2) 2.13(2) 3.034(2) 171.4(17) y
    N1B H2N1 N2A 1_555 0.93(2) 2.15(2) 3.081(2) 173.1(17) y
    N1C H3N1 N2B 1_555 0.89(2) 2.12(2) 3.016(2) 179(3) y
    N2A H2N2 O1B 4_565 0.86(2) 2.58(2) 3.275(2) 140(2) y
    N2B H4N2 O1A 4_566 0.93(2) 2.33(2) 3.176(2) 150.4(18) y
    N2C H6N2 O1C 3_666 0.92(2) 2.22(2) 3.137(2) 175.5(17) y
    C6A H6AA O1A 2_655 0.93 2.55 3.444(3) 162 y
    C5C H5CA O1B 3_767 0.93 2.59 3.333(3) 137 y
