##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# 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.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-12-27
_journal_date_accepted     2011-01-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     o403
_journal_page_last     o404
_journal_paper_category     QO
_journal_coeditor_code     IS2655
_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     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
5-Ethyl-4-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wan-Sin Loh'
;
      Thomson Reuters ResearcherID: C-7581-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'R. Venkat Ragavan' ?
;
      Organic Chemistry Division
      School of Advanced Sciences
      VIT University
      Vellore 632 014, India
;
    'V. Vijayakumar' ?
;
      Organic Chemistry Division
      School of Advanced Sciences
      VIT University
      Vellore 632 014, India
;
    'M. Venkatesh' ?
;
      Organic Chemistry Division
      School of Advanced Sciences
      VIT University
      Vellore 632 014, India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-Ethyl-4-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H12 N2 O'
_chemical_formula_sum     'C11 H12 N2 O'
_chemical_formula_iupac     'C11 H12 N2 O'
_chemical_formula_weight     188.23
_chemical_melting_point     ?
_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     11.0898(3)
_cell_length_b     13.2171(4)
_cell_length_c     15.0265(5)
_cell_angle_alpha     90.00
_cell_angle_beta     114.539(2)
_cell_angle_gamma     90.00
_cell_volume     2003.58(11)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4628
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     30.04
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.248
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     800
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(<i>SADABS</i>; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9527
_exptl_absorpt_correction_T_max     0.9891
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K.
;
_diffrn_ambient_temperature     100.00(10)
_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 APEXII CCD area-detector
;
_diffrn_measurement_method     '\f and \w'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     22130
_diffrn_reflns_av_R_equivalents     0.0628
_diffrn_reflns_av_sigmaI/netI     0.0683
_diffrn_reflns_theta_min     2.14
_diffrn_reflns_theta_max     30.09
_diffrn_reflns_theta_full     30.09
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     5845
_reflns_number_gt     3654
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1053
_refine_ls_R_factor_gt     0.0645
_refine_ls_wR_factor_gt     0.1464
_refine_ls_wR_factor_ref     0.1662
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     5845
_refine_ls_number_parameters     284
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.5295P] where P=(Fo^2^+2Fc^2^)/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     0.378
_refine_diff_density_min     -0.301
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0163(19)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-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' 0.0033 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'
_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_disorder_assembly
    _atom_site_disorder_group
    O O1A 0.59450(13) 0.07629(9) 0.94578(11) 0.0314(3) Uani d . 1 . .
    N N1A 0.29084(17) 0.16378(11) 0.92423(13) 0.0288(4) Uani d . 1 . .
    N N2A 0.38633(15) 0.09048(11) 0.94491(12) 0.0271(4) Uani d . 1 . .
    C C1A 0.32664(18) 0.24453(13) 0.88567(14) 0.0246(4) Uani d . 1 . .
    C C2A 0.48806(18) 0.12736(13) 0.92718(14) 0.0244(4) Uani d . 1 . .
    C C3A 0.44982(17) 0.22608(12) 0.88657(14) 0.0239(4) Uani d . 1 . .
    C C4A 0.53044(18) 0.29233(13) 0.85342(16) 0.0298(4) Uani d . 1 . .
    C C5A 0.6668(2) 0.30005(15) 0.90864(18) 0.0396(5) Uani d . 1 . .
    H H5AA 0.7066 0.2645 0.9671 0.047 Uiso calc R 1 . .
    C C6A 0.7438(2) 0.36080(18) 0.8767(3) 0.0602(8) Uani d . 1 . .
    H H6AA 0.8348 0.3652 0.9137 0.072 Uiso calc R 1 . .
    C C7A 0.6861(3) 0.41400(18) 0.7910(3) 0.0685(10) Uani d . 1 . .
    H H7AA 0.7379 0.4549 0.7704 0.082 Uiso calc R 1 . .
    C C8A 0.5513(3) 0.40705(19) 0.7351(2) 0.0604(8) Uani d . 1 . .
    H H8AA 0.5124 0.4430 0.6768 0.072 Uiso calc R 1 . .
    C C9A 0.4736(2) 0.34624(16) 0.76586(18) 0.0401(5) Uani d . 1 . .
    H H9AA 0.3829 0.3415 0.7278 0.048 Uiso calc R 1 . .
    C C10A 0.23852(19) 0.33569(14) 0.85216(16) 0.0306(4) Uani d . 1 . .
    H H10C 0.1769 0.3258 0.7845 0.037 Uiso calc R 1 . .
    H H10D 0.2927 0.3942 0.8546 0.037 Uiso calc R 1 . .
    C C11A 0.1600(2) 0.35798(17) 0.91215(19) 0.0450(6) Uani d . 1 . .
    H H11D 0.1092 0.4187 0.8884 0.068 Uiso calc R 1 . .
    H H11E 0.2199 0.3668 0.9795 0.068 Uiso calc R 1 . .
    H H11F 0.1013 0.3025 0.9064 0.068 Uiso calc R 1 . .
    O O1B 1.07863(12) 0.06616(9) 0.92558(9) 0.0254(3) Uani d . 1 . .
    N N1B 0.73764(15) 0.06391(11) 0.83821(12) 0.0275(4) Uani d . 1 . .
    N N2B 0.86312(14) 0.04445(11) 0.90754(12) 0.0228(3) Uani d . 1 . .
    C C1B 0.74826(19) 0.11417(14) 0.76342(15) 0.0303(4) Uani d . 1 A .
    C C2B 0.95360(17) 0.07674(12) 0.87492(13) 0.0215(4) Uani d . 1 . .
    C C3B 0.88097(18) 0.12138(13) 0.78120(14) 0.0251(4) Uani d . 1 . .
    C C4B 0.9388(2) 0.16679(13) 0.71837(14) 0.0291(4) Uani d . 1 . .
    C C5B 1.0386(2) 0.11721(15) 0.70194(16) 0.0361(5) Uani d . 1 . .
    H H5BA 1.0694 0.0549 0.7315 0.043 Uiso calc R 1 . .
    C C6B 1.0928(3) 0.15955(16) 0.64204(18) 0.0505(7) Uani d . 1 . .
    H H6BA 1.1588 0.1253 0.6312 0.061 Uiso calc R 1 . .
    C C7B 1.0483(3) 0.25308(17) 0.59830(17) 0.0541(7) Uani d . 1 . .
    H H7BA 1.0840 0.2814 0.5579 0.065 Uiso calc R 1 . .
    C C8B 0.9506(3) 0.30381(16) 0.61513(16) 0.0459(6) Uani d . 1 . .
    H H8BA 0.9209 0.3665 0.5862 0.055 Uiso calc R 1 . .
    C C9B 0.8973(2) 0.26163(15) 0.67475(15) 0.0360(5) Uani d . 1 . .
    H H9BA 0.8326 0.2969 0.6862 0.043 Uiso calc R 1 . .
    C C10B 0.6280(2) 0.14952(18) 0.67717(18) 0.0499(6) Uani d D 1 . .
    H H10A 0.5568 0.1581 0.6980 0.060 Uiso calc PR 0.508(5) A 1
    H H10B 0.6473 0.2157 0.6583 0.060 Uiso calc PR 0.508(5) A 1
    H H10E 0.6172 0.2209 0.6868 0.060 Uiso calc PR 0.492(5) A 2
    H H10F 0.6477 0.1442 0.6202 0.060 Uiso calc PR 0.492(5) A 2
    C C11B 0.5811(4) 0.0874(3) 0.5935(3) 0.0427(13) Uani d PD 0.508(5) A 1
    H H11A 0.5027 0.1168 0.5442 0.064 Uiso calc PR 0.508(5) A 1
    H H11B 0.5608 0.0215 0.6104 0.064 Uiso calc PR 0.508(5) A 1
    H H11C 0.6481 0.0816 0.5689 0.064 Uiso calc PR 0.508(5) A 1
    C C11C 0.5046(3) 0.1031(3) 0.6533(4) 0.0395(13) Uani d PD 0.492(5) A 2
    H H11G 0.4387 0.1358 0.5970 0.059 Uiso calc PR 0.492(5) A 2
    H H11H 0.4805 0.1090 0.7075 0.059 Uiso calc PR 0.492(5) A 2
    H H11I 0.5101 0.0329 0.6390 0.059 Uiso calc PR 0.492(5) A 2
    H H1NB 0.669(2) 0.0719(16) 0.8648(17) 0.043(6) Uiso d . 1 . .
    H H2NB 0.881(2) 0.0033(18) 0.9694(18) 0.053(7) Uiso d . 1 . .
    H H2NA 0.384(2) 0.029(2) 0.9802(19) 0.060(8) Uiso d . 1 . .
    H H1NA 0.204(3) 0.1404(18) 0.9184(19) 0.052(7) Uiso 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
    O1A 0.0284(7) 0.0292(7) 0.0398(9) 0.0114(5) 0.0174(7) 0.0106(6)
    N1A 0.0297(9) 0.0254(8) 0.0368(10) 0.0094(6) 0.0193(8) 0.0101(6)
    N2A 0.0286(8) 0.0247(8) 0.0325(9) 0.0087(6) 0.0172(7) 0.0083(6)
    C1A 0.0265(9) 0.0235(8) 0.0255(10) 0.0036(7) 0.0125(8) 0.0027(7)
    C2A 0.0246(9) 0.0250(8) 0.0234(10) 0.0043(7) 0.0097(7) 0.0020(7)
    C3A 0.0234(9) 0.0223(8) 0.0256(10) 0.0022(6) 0.0097(7) 0.0024(7)
    C4A 0.0229(9) 0.0237(9) 0.0442(13) 0.0030(7) 0.0153(9) 0.0036(8)
    C5A 0.0263(10) 0.0321(10) 0.0574(15) 0.0007(8) 0.0144(10) -0.0018(10)
    C6A 0.0270(12) 0.0389(13) 0.116(3) -0.0031(9) 0.0309(15) -0.0020(14)
    C7A 0.0510(16) 0.0381(13) 0.141(3) 0.0047(11) 0.064(2) 0.0232(16)
    C8A 0.0510(15) 0.0508(14) 0.100(2) 0.0200(11) 0.0524(16) 0.0411(14)
    C9A 0.0293(11) 0.0391(11) 0.0591(16) 0.0110(8) 0.0255(11) 0.0210(10)
    C10A 0.0316(10) 0.0290(9) 0.0372(12) 0.0101(7) 0.0203(9) 0.0095(8)
    C11A 0.0548(15) 0.0391(12) 0.0558(16) 0.0228(10) 0.0375(13) 0.0147(10)
    O1B 0.0221(6) 0.0288(6) 0.0264(7) 0.0022(5) 0.0111(6) 0.0067(5)
    N1B 0.0201(8) 0.0305(8) 0.0294(9) 0.0028(6) 0.0076(7) 0.0030(6)
    N2B 0.0189(7) 0.0276(7) 0.0221(8) 0.0029(5) 0.0087(6) 0.0017(6)
    C1B 0.0321(10) 0.0248(9) 0.0266(10) 0.0025(7) 0.0049(8) 0.0028(7)
    C2B 0.0249(9) 0.0212(8) 0.0217(9) 0.0026(6) 0.0129(7) 0.0004(6)
    C3B 0.0307(10) 0.0229(8) 0.0213(9) 0.0022(7) 0.0104(8) 0.0019(7)
    C4B 0.0410(11) 0.0255(9) 0.0186(9) -0.0031(7) 0.0102(8) 0.0008(7)
    C5B 0.0589(14) 0.0258(9) 0.0337(12) -0.0007(9) 0.0294(11) 0.0013(8)
    C6B 0.092(2) 0.0353(11) 0.0465(15) -0.0071(11) 0.0504(15) -0.0031(10)
    C7B 0.104(2) 0.0381(12) 0.0357(13) -0.0155(13) 0.0448(15) -0.0001(10)
    C8B 0.0787(18) 0.0286(10) 0.0245(11) -0.0093(10) 0.0156(12) 0.0046(8)
    C9B 0.0488(13) 0.0281(10) 0.0239(10) -0.0020(8) 0.0081(9) 0.0042(7)
    C10B 0.0427(13) 0.0442(13) 0.0400(14) 0.0094(10) -0.0054(11) 0.0093(10)
    C11B 0.032(2) 0.053(3) 0.033(3) 0.0001(18) 0.0032(19) 0.0136(19)
    C11C 0.021(2) 0.047(3) 0.047(3) -0.0040(17) 0.0109(19) 0.014(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
    O1A C2A . 1.286(2) ?
    N1A C1A . 1.350(2) ?
    N1A N2A . 1.372(2) ?
    N1A H1NA . 0.98(2) ?
    N2A C2A . 1.353(2) ?
    N2A H2NA . 0.98(3) ?
    C1A C3A . 1.382(2) ?
    C1A C10A . 1.500(2) ?
    C2A C3A . 1.428(2) ?
    C3A C4A . 1.478(2) ?
    C4A C5A . 1.394(3) ?
    C4A C9A . 1.396(3) ?
    C5A C6A . 1.395(3) ?
    C5A H5AA . 0.9300 ?
    C6A C7A . 1.371(4) ?
    C6A H6AA . 0.9300 ?
    C7A C8A . 1.381(4) ?
    C7A H7AA . 0.9300 ?
    C8A C9A . 1.391(3) ?
    C8A H8AA . 0.9300 ?
    C9A H9AA . 0.9300 ?
    C10A C11A . 1.520(3) ?
    C10A H10C . 0.9700 ?
    C10A H10D . 0.9700 ?
    C11A H11D . 0.9600 ?
    C11A H11E . 0.9600 ?
    C11A H11F . 0.9600 ?
    O1B C2B . 1.283(2) ?
    N1B C1B . 1.352(2) ?
    N1B N2B . 1.372(2) ?
    N1B H1NB . 1.00(2) ?
    N2B C2B . 1.356(2) ?
    N2B H2NB . 1.02(3) ?
    C1B C3B . 1.386(3) ?
    C1B C10B . 1.497(3) ?
    C2B C3B . 1.427(2) ?
    C3B C4B . 1.471(3) ?
    C4B C5B . 1.394(3) ?
    C4B C9B . 1.401(3) ?
    C5B C6B . 1.391(3) ?
    C5B H5BA . 0.9300 ?
    C6B C7B . 1.391(3) ?
    C6B H6BA . 0.9300 ?
    C7B C8B . 1.383(4) ?
    C7B H7BA . 0.9300 ?
    C8B C9B . 1.379(3) ?
    C8B H8BA . 0.9300 ?
    C9B H9BA . 0.9300 ?
    C10B C11C . 1.403(3) ?
    C10B C11B . 1.408(3) ?
    C10B H10A . 0.9700 ?
    C10B H10B . 0.9700 ?
    C10B H10E . 0.9700 ?
    C10B H10F . 0.9700 ?
    C11B H11A . 0.9600 ?
    C11B H11B . 0.9600 ?
    C11B H11C . 0.9600 ?
    C11C H11G . 0.9600 ?
    C11C H11H . 0.9600 ?
    C11C H11I . 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
    C1A N1A N2A . . 108.56(15) ?
    C1A N1A H1NA . . 131.6(14) ?
    N2A N1A H1NA . . 115.8(14) ?
    C2A N2A N1A . . 109.22(15) ?
    C2A N2A H2NA . . 128.0(15) ?
    N1A N2A H2NA . . 121.5(15) ?
    N1A C1A C3A . . 108.78(15) ?
    N1A C1A C10A . . 120.80(16) ?
    C3A C1A C10A . . 130.40(16) ?
    O1A C2A N2A . . 122.23(16) ?
    O1A C2A C3A . . 130.95(17) ?
    N2A C2A C3A . . 106.82(15) ?
    C1A C3A C2A . . 106.39(15) ?
    C1A C3A C4A . . 128.76(15) ?
    C2A C3A C4A . . 124.86(16) ?
    C5A C4A C9A . . 118.53(19) ?
    C5A C4A C3A . . 120.08(18) ?
    C9A C4A C3A . . 121.37(17) ?
    C4A C5A C6A . . 120.4(2) ?
    C4A C5A H5AA . . 119.8 ?
    C6A C5A H5AA . . 119.8 ?
    C7A C6A C5A . . 120.3(2) ?
    C7A C6A H6AA . . 119.8 ?
    C5A C6A H6AA . . 119.8 ?
    C6A C7A C8A . . 120.2(2) ?
    C6A C7A H7AA . . 119.9 ?
    C8A C7A H7AA . . 119.9 ?
    C7A C8A C9A . . 120.0(2) ?
    C7A C8A H8AA . . 120.0 ?
    C9A C8A H8AA . . 120.0 ?
    C8A C9A C4A . . 120.6(2) ?
    C8A C9A H9AA . . 119.7 ?
    C4A C9A H9AA . . 119.7 ?
    C1A C10A C11A . . 114.22(16) ?
    C1A C10A H10C . . 108.7 ?
    C11A C10A H10C . . 108.7 ?
    C1A C10A H10D . . 108.7 ?
    C11A C10A H10D . . 108.7 ?
    H10C C10A H10D . . 107.6 ?
    C10A C11A H11D . . 109.5 ?
    C10A C11A H11E . . 109.5 ?
    H11D C11A H11E . . 109.5 ?
    C10A C11A H11F . . 109.5 ?
    H11D C11A H11F . . 109.5 ?
    H11E C11A H11F . . 109.5 ?
    C1B N1B N2B . . 108.18(15) ?
    C1B N1B H1NB . . 128.5(13) ?
    N2B N1B H1NB . . 114.6(14) ?
    C2B N2B N1B . . 109.63(15) ?
    C2B N2B H2NB . . 126.9(14) ?
    N1B N2B H2NB . . 123.0(14) ?
    N1B C1B C3B . . 109.01(16) ?
    N1B C1B C10B . . 121.27(19) ?
    C3B C1B C10B . . 129.69(19) ?
    O1B C2B N2B . . 122.08(16) ?
    O1B C2B C3B . . 131.19(16) ?
    N2B C2B C3B . . 106.72(16) ?
    C1B C3B C2B . . 106.31(16) ?
    C1B C3B C4B . . 127.96(17) ?
    C2B C3B C4B . . 125.72(17) ?
    C5B C4B C9B . . 117.91(18) ?
    C5B C4B C3B . . 120.77(16) ?
    C9B C4B C3B . . 121.31(18) ?
    C6B C5B C4B . . 120.9(2) ?
    C6B C5B H5BA . . 119.5 ?
    C4B C5B H5BA . . 119.5 ?
    C5B C6B C7B . . 120.0(2) ?
    C5B C6B H6BA . . 120.0 ?
    C7B C6B H6BA . . 120.0 ?
    C8B C7B C6B . . 119.7(2) ?
    C8B C7B H7BA . . 120.1 ?
    C6B C7B H7BA . . 120.1 ?
    C9B C8B C7B . . 120.1(2) ?
    C9B C8B H8BA . . 119.9 ?
    C7B C8B H8BA . . 119.9 ?
    C8B C9B C4B . . 121.3(2) ?
    C8B C9B H9BA . . 119.3 ?
    C4B C9B H9BA . . 119.3 ?
    C11C C10B C1B . . 120.6(3) ?
    C11B C10B C1B . . 117.2(2) ?
    C11B C10B H10A . . 108.0 ?
    C1B C10B H10A . . 108.0 ?
    C11B C10B H10B . . 108.0 ?
    C1B C10B H10B . . 108.0 ?
    H10A C10B H10B . . 107.2 ?
    C11C C10B H10E . . 107.2 ?
    C1B C10B H10E . . 107.2 ?
    C11C C10B H10F . . 107.2 ?
    C1B C10B H10F . . 107.2 ?
    H10E C10B H10F . . 106.8 ?
    C10B C11B H11A . . 109.5 ?
    C10B C11B H11B . . 109.5 ?
    C10B C11B H11C . . 109.5 ?
    C10B C11C H11G . . 109.5 ?
    C10B C11C H11H . . 109.5 ?
    H11G C11C H11H . . 109.5 ?
    C10B C11C H11I . . 109.5 ?
    H11G C11C H11I . . 109.5 ?
    H11H C11C H11I . . 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
    C1A N1A N2A C2A . . . . 5.0(2) ?
    N2A N1A C1A C3A . . . . -3.5(2) ?
    N2A N1A C1A C10A . . . . 177.71(17) ?
    N1A N2A C2A O1A . . . . 175.93(17) ?
    N1A N2A C2A C3A . . . . -4.4(2) ?
    N1A C1A C3A C2A . . . . 0.8(2) ?
    C10A C1A C3A C2A . . . . 179.43(19) ?
    N1A C1A C3A C4A . . . . -179.05(19) ?
    C10A C1A C3A C4A . . . . -0.4(3) ?
    O1A C2A C3A C1A . . . . -178.1(2) ?
    N2A C2A C3A C1A . . . . 2.2(2) ?
    O1A C2A C3A C4A . . . . 1.7(3) ?
    N2A C2A C3A C4A . . . . -177.92(18) ?
    C1A C3A C4A C5A . . . . 138.1(2) ?
    C2A C3A C4A C5A . . . . -41.7(3) ?
    C1A C3A C4A C9A . . . . -43.5(3) ?
    C2A C3A C4A C9A . . . . 136.7(2) ?
    C9A C4A C5A C6A . . . . 0.2(3) ?
    C3A C4A C5A C6A . . . . 178.6(2) ?
    C4A C5A C6A C7A . . . . 0.4(4) ?
    C5A C6A C7A C8A . . . . -0.6(4) ?
    C6A C7A C8A C9A . . . . 0.2(4) ?
    C7A C8A C9A C4A . . . . 0.4(4) ?
    C5A C4A C9A C8A . . . . -0.6(3) ?
    C3A C4A C9A C8A . . . . -179.0(2) ?
    N1A C1A C10A C11A . . . . 33.3(3) ?
    C3A C1A C10A C11A . . . . -145.2(2) ?
    C1B N1B N2B C2B . . . . -3.53(19) ?
    N2B N1B C1B C3B . . . . 4.0(2) ?
    N2B N1B C1B C10B . . . . -177.96(18) ?
    N1B N2B C2B O1B . . . . -179.06(15) ?
    N1B N2B C2B C3B . . . . 1.65(18) ?
    N1B C1B C3B C2B . . . . -2.9(2) ?
    C10B C1B C3B C2B . . . . 179.2(2) ?
    N1B C1B C3B C4B . . . . 177.89(17) ?
    C10B C1B C3B C4B . . . . 0.1(3) ?
    O1B C2B C3B C1B . . . . -178.43(18) ?
    N2B C2B C3B C1B . . . . 0.77(19) ?
    O1B C2B C3B C4B . . . . 0.8(3) ?
    N2B C2B C3B C4B . . . . 179.96(16) ?
    C1B C3B C4B C5B . . . . -134.8(2) ?
    C2B C3B C4B C5B . . . . 46.2(3) ?
    C1B C3B C4B C9B . . . . 46.4(3) ?
    C2B C3B C4B C9B . . . . -132.6(2) ?
    C9B C4B C5B C6B . . . . -1.6(3) ?
    C3B C4B C5B C6B . . . . 179.5(2) ?
    C4B C5B C6B C7B . . . . 0.6(4) ?
    C5B C6B C7B C8B . . . . 0.4(4) ?
    C6B C7B C8B C9B . . . . -0.2(4) ?
    C7B C8B C9B C4B . . . . -0.8(3) ?
    C5B C4B C9B C8B . . . . 1.8(3) ?
    C3B C4B C9B C8B . . . . -179.4(2) ?
    N1B C1B C10B C11C . . . . -22.8(4) ?
    C3B C1B C10B C11C . . . . 154.8(3) ?
    N1B C1B C10B C11B . . . . -96.9(3) ?
    C3B C1B C10B C11B . . . . 80.7(3) ?
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
    N1B H1NB O1A . 1.00(2) 1.73(2) 2.700(2) 161(2) yes
    N2B H2NB O1B 3_757 1.02(2) 1.72(2) 2.738(2) 176(2) yes
    N2A H2NA O1A 3_657 0.98(3) 1.74(3) 2.704(2) 171(2) yes
    N1A H1NA O1B 1_455 0.98(3) 1.74(3) 2.691(2) 162(2) yes
    C8A H8AA O1A 2_656 0.93 2.47 3.370(3) 163 yes
    C10A H10C Cg1 1_455 0.97 2.61 3.464(2) 147 yes
    C10B H10E Cg2 1_555 0.97 2.71 3.524(3) 142 yes