##############################################################################
###                                                                        ###
###        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      #
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# of the IUCr Commission on Journals.                                        #
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#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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#                                                                            #
# 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     2010-05-16
_journal_date_accepted     2010-05-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1479
_journal_page_last     o1479
_journal_paper_category     QO
_journal_coeditor_code     BT5275
_publ_contact_author_name     'Y. T. Jeonga'
_publ_contact_author_address
;   Department of Image Science and Engineering,
    Pukyong National University,
    Busan, 608-739,
    Republic of Korea
;
_publ_contact_author_email     'ytjeong@pknu.ac.kr'
_publ_contact_author_fax     '+82-51-629-6408'
_publ_contact_author_phone     '+82-51-629-6411'
_publ_section_title
;
1-(2-Bromoacetyl)-3-methyl-2,6-diphenylpiperidin-4-one
;
loop_
    _publ_author_name
    _publ_author_address
    'G. Aridoss'
;
    Department of Image Science and Engineering,
    Pukyong National University,
    Busan 608-739,
    Republic of Korea
;
    'S. Sundaramoorthy'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'D. Velmurugan'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'K. S. Park'
;
    Department of Image Science and Engineering,
    Pukyong National University,
    Busan 608-739,
    Republic of Korea
;
    'Y. T. Jeong'
;
    Department of Image Science and Engineering,
    Pukyong National University,
    Busan 608-739,
    Republic of Korea
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(2-Bromoacetyl)-3-methyl-2,6-diphenylpiperidin-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H20 Br N O2'
_chemical_formula_sum     'C20 H20 Br N O2'
_chemical_formula_iupac     'C20 H20 Br N O2'
_chemical_formula_weight     386.28
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     21.4006(8)
_cell_length_b     14.5873(6)
_cell_length_c     13.8107(5)
_cell_angle_alpha     90.00
_cell_angle_beta     125.368(2)
_cell_angle_gamma     90.00
_cell_volume     3515.7(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2025
_cell_measurement_theta_min     0.499
_cell_measurement_theta_max     0.596
_cell_measurement_temperature     292(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.460
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1584
_exptl_absorpt_coefficient_mu     2.350
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.499
_exptl_absorpt_correction_T_max     0.596
_exptl_special_details
;
;
_diffrn_ambient_temperature     292(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 APEXII area-detector diffractometer'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17094
_diffrn_reflns_av_R_equivalents     0.0354
_diffrn_reflns_av_sigmaI/netI     0.0368
_diffrn_reflns_theta_min     1.82
_diffrn_reflns_theta_max     28.47
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -27
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_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 >
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     4398
_reflns_number_gt     2725
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0984
_refine_ls_R_factor_gt     0.0590
_refine_ls_wR_factor_gt     0.1835
_refine_ls_wR_factor_ref     0.2130
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     4398
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1259P)²+4.1414P] 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     0.533
_refine_diff_density_min     -0.773
_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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                            'SHELXL97 (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
    C C1 0.00908(18) 0.2545(2) 0.0494(3) 0.0355(7) Uani d . 1 . .
    H H1 0.0555 0.2317 0.1229 0.043 Uiso calc R 1 . .
    C C2 0.0317(2) 0.3418(3) 0.0168(4) 0.0517(10) Uani d . 1 . .
    H H2A 0.0432 0.3889 0.0745 0.062 Uiso calc R 1 . .
    H H2B 0.0780 0.3303 0.0214 0.062 Uiso calc R 1 . .
    C C3 -0.0287(3) 0.3764(3) -0.1039(4) 0.0581(11) Uani d . 1 . .
    C C4 -0.0933(2) 0.3111(3) -0.1867(3) 0.0463(8) Uani d . 1 . .
    H H4 -0.1307 0.3148 -0.1674 0.056 Uiso calc R 1 . .
    C C5 -0.06703(18) 0.2104(2) -0.1692(3) 0.0359(7) Uani d . 1 . .
    H H5 -0.0393 0.2039 -0.2056 0.043 Uiso calc R 1 . .
    C C6 -0.13640(19) 0.1469(2) -0.2373(3) 0.0355(7) Uani d . 1 . .
    C C7 -0.1502(2) 0.0969(3) -0.3328(3) 0.0502(9) Uani d . 1 . .
    H H7 -0.1150 0.0987 -0.3518 0.060 Uiso calc R 1 . .
    C C8 -0.2159(3) 0.0440(3) -0.4008(3) 0.0605(11) Uani d . 1 . .
    H H8 -0.2249 0.0115 -0.4657 0.073 Uiso calc R 1 . .
    C C9 -0.2672(2) 0.0396(3) -0.3726(4) 0.0622(12) Uani d . 1 . .
    H H9 -0.3110 0.0038 -0.4179 0.075 Uiso calc R 1 . .
    C C10 -0.2541(2) 0.0881(3) -0.2772(4) 0.0526(10) Uani d . 1 . .
    H H10 -0.2891 0.0848 -0.2577 0.063 Uiso calc R 1 . .
    C C11 -0.1889(2) 0.1421(2) -0.2096(3) 0.0408(8) Uani d . 1 . .
    H H11 -0.1805 0.1752 -0.1455 0.049 Uiso calc R 1 . .
    C C12 -0.05143(17) 0.2656(2) 0.0741(3) 0.0334(7) Uani d . 1 . .
    C C13 -0.0720(2) 0.3505(2) 0.0908(4) 0.0470(9) Uani d . 1 . .
    H H13 -0.0510 0.4034 0.0831 0.056 Uiso calc R 1 . .
    C C14 -0.1253(3) 0.3567(3) 0.1196(4) 0.0584(11) Uani d . 1 . .
    H H14 -0.1388 0.4140 0.1315 0.070 Uiso calc R 1 . .
    C C15 -0.1573(2) 0.2800(3) 0.1301(4) 0.0566(11) Uani d . 1 . .
    H H15 -0.1934 0.2850 0.1469 0.068 Uiso calc R 1 . .
    C C16 -0.1354(2) 0.1944(3) 0.1156(3) 0.0508(9) Uani d . 1 . .
    H H16 -0.1566 0.1417 0.1233 0.061 Uiso calc R 1 . .
    C C17 -0.0820(2) 0.1873(3) 0.0896(3) 0.0408(8) Uani d . 1 . .
    H H17 -0.0665 0.1297 0.0825 0.049 Uiso calc R 1 . .
    C C18 -0.1349(3) 0.3390(3) -0.3166(5) 0.0706(14) Uani d . 1 . .
    H H18A -0.1495 0.4023 -0.3255 0.106 Uiso calc R 1 . .
    H H18B -0.1800 0.3019 -0.3648 0.106 Uiso calc R 1 . .
    H H18C -0.1016 0.3302 -0.3412 0.106 Uiso calc R 1 . .
    C C19 0.02886(17) 0.1079(2) -0.0205(3) 0.0353(7) Uani d . 1 . .
    C C20 0.09463(19) 0.0844(3) 0.1063(3) 0.0432(8) Uani d . 1 . .
    H H20A 0.1063 0.0195 0.1125 0.052 Uiso calc R 1 . .
    H H20B 0.0803 0.0982 0.1598 0.052 Uiso calc R 1 . .
    N N1 -0.01254(14) 0.18526(19) -0.0422(2) 0.0328(6) Uani d . 1 . .
    O O1 -0.0265(3) 0.4523(2) -0.1361(4) 0.1037(15) Uani d . 1 . .
    O O2 0.01584(14) 0.05669(18) -0.1000(2) 0.0472(6) Uani d . 1 . .
    Br Br1 0.18249(2) 0.15486(4) 0.14906(5) 0.0736(3) Uani d . 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
    C1 N1 . 1.468(4) ?
    C1 C2 . 1.521(5) ?
    C1 C12 . 1.527(4) ?
    C1 H1 . 0.9800 ?
    C2 C3 . 1.486(7) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 O1 . 1.204(5) ?
    C3 C4 . 1.516(6) ?
    C4 C18 . 1.525(6) ?
    C4 C5 . 1.541(5) ?
    C4 H4 . 0.9800 ?
    C5 N1 . 1.485(4) ?
    C5 C6 . 1.527(5) ?
    C5 H5 . 0.9800 ?
    C6 C7 . 1.382(5) ?
    C6 C11 . 1.381(5) ?
    C7 C8 . 1.387(6) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.362(7) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.375(6) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.391(5) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.378(5) ?
    C12 C17 . 1.394(5) ?
    C13 C14 . 1.411(6) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.362(7) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.389(6) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.384(5) ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C19 O2 . 1.219(4) ?
    C19 N1 . 1.357(4) ?
    C19 C20 . 1.520(5) ?
    C20 Br1 . 1.912(4) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
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
    N1 C1 C2 . . 108.5(3) ?
    N1 C1 C12 . . 112.4(2) ?
    C2 C1 C12 . . 115.7(3) ?
    N1 C1 H1 . . 106.6 ?
    C2 C1 H1 . . 106.6 ?
    C12 C1 H1 . . 106.6 ?
    C3 C2 C1 . . 113.4(3) ?
    C3 C2 H2A . . 108.9 ?
    C1 C2 H2A . . 108.9 ?
    C3 C2 H2B . . 108.9 ?
    C1 C2 H2B . . 108.9 ?
    H2A C2 H2B . . 107.7 ?
    O1 C3 C2 . . 122.2(5) ?
    O1 C3 C4 . . 120.8(5) ?
    C2 C3 C4 . . 117.0(3) ?
    C3 C4 C18 . . 112.1(3) ?
    C3 C4 C5 . . 112.9(3) ?
    C18 C4 C5 . . 110.5(3) ?
    C3 C4 H4 . . 107.0 ?
    C18 C4 H4 . . 107.0 ?
    C5 C4 H4 . . 107.0 ?
    N1 C5 C6 . . 113.4(3) ?
    N1 C5 C4 . . 112.7(3) ?
    C6 C5 C4 . . 110.2(3) ?
    N1 C5 H5 . . 106.7 ?
    C6 C5 H5 . . 106.7 ?
    C4 C5 H5 . . 106.7 ?
    C7 C6 C11 . . 118.6(3) ?
    C7 C6 C5 . . 120.2(3) ?
    C11 C6 C5 . . 121.1(3) ?
    C6 C7 C8 . . 120.8(4) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C9 C8 C7 . . 120.1(4) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C8 C9 C10 . . 120.0(4) ?
    C8 C9 H9 . . 120.0 ?
    C10 C9 H9 . . 120.0 ?
    C9 C10 C11 . . 120.1(4) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C6 C11 C10 . . 120.3(3) ?
    C6 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C13 C12 C17 . . 119.2(3) ?
    C13 C12 C1 . . 121.9(3) ?
    C17 C12 C1 . . 118.8(3) ?
    C12 C13 C14 . . 119.5(4) ?
    C12 C13 H13 . . 120.2 ?
    C14 C13 H13 . . 120.2 ?
    C15 C14 C13 . . 121.0(4) ?
    C15 C14 H14 . . 119.5 ?
    C13 C14 H14 . . 119.5 ?
    C14 C15 C16 . . 119.4(4) ?
    C14 C15 H15 . . 120.3 ?
    C16 C15 H15 . . 120.3 ?
    C17 C16 C15 . . 120.2(4) ?
    C17 C16 H16 . . 119.9 ?
    C15 C16 H16 . . 119.9 ?
    C16 C17 C12 . . 120.6(4) ?
    C16 C17 H17 . . 119.7 ?
    C12 C17 H17 . . 119.7 ?
    C4 C18 H18A . . 109.5 ?
    C4 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C4 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O2 C19 N1 . . 122.1(3) ?
    O2 C19 C20 . . 118.4(3) ?
    N1 C19 C20 . . 119.5(3) ?
    C19 C20 Br1 . . 108.9(2) ?
    C19 C20 H20A . . 109.9 ?
    Br1 C20 H20A . . 109.9 ?
    C19 C20 H20B . . 109.9 ?
    Br1 C20 H20B . . 109.9 ?
    H20A C20 H20B . . 108.3 ?
    C19 N1 C1 . . 122.8(3) ?
    C19 N1 C5 . . 115.6(3) ?
    C1 N1 C5 . . 119.2(3) ?
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
    N1 C1 C2 C3 . . . . 55.3(4) ?
    C12 C1 C2 C3 . . . . -72.0(4) ?
    C1 C2 C3 O1 . . . . 166.4(5) ?
    C1 C2 C3 C4 . . . . -14.4(5) ?
    O1 C3 C4 C18 . . . . 19.2(6) ?
    C2 C3 C4 C18 . . . . -159.9(4) ?
    O1 C3 C4 C5 . . . . 144.8(5) ?
    C2 C3 C4 C5 . . . . -34.4(5) ?
    C3 C4 C5 N1 . . . . 41.5(4) ?
    C18 C4 C5 N1 . . . . 167.9(3) ?
    C3 C4 C5 C6 . . . . 169.2(3) ?
    C18 C4 C5 C6 . . . . -64.3(4) ?
    N1 C5 C6 C7 . . . . -119.1(3) ?
    C4 C5 C6 C7 . . . . 113.5(3) ?
    N1 C5 C6 C11 . . . . 64.7(4) ?
    C4 C5 C6 C11 . . . . -62.7(4) ?
    C11 C6 C7 C8 . . . . 0.9(5) ?
    C5 C6 C7 C8 . . . . -175.3(3) ?
    C6 C7 C8 C9 . . . . -1.1(6) ?
    C7 C8 C9 C10 . . . . 0.4(7) ?
    C8 C9 C10 C11 . . . . 0.4(6) ?
    C7 C6 C11 C10 . . . . -0.1(5) ?
    C5 C6 C11 C10 . . . . 176.1(3) ?
    C9 C10 C11 C6 . . . . -0.5(6) ?
    N1 C1 C12 C13 . . . . -138.6(3) ?
    C2 C1 C12 C13 . . . . -13.3(5) ?
    N1 C1 C12 C17 . . . . 46.6(4) ?
    C2 C1 C12 C17 . . . . 172.0(3) ?
    C17 C12 C13 C14 . . . . -1.9(5) ?
    C1 C12 C13 C14 . . . . -176.7(3) ?
    C12 C13 C14 C15 . . . . -0.6(7) ?
    C13 C14 C15 C16 . . . . 1.8(7) ?
    C14 C15 C16 C17 . . . . -0.5(6) ?
    C15 C16 C17 C12 . . . . -2.0(5) ?
    C13 C12 C17 C16 . . . . 3.2(5) ?
    C1 C12 C17 C16 . . . . 178.1(3) ?
    O2 C19 C20 Br1 . . . . 98.6(3) ?
    N1 C19 C20 Br1 . . . . -80.3(3) ?
    O2 C19 N1 C1 . . . . -170.7(3) ?
    C20 C19 N1 C1 . . . . 8.1(5) ?
    O2 C19 N1 C5 . . . . -8.3(5) ?
    C20 C19 N1 C5 . . . . 170.5(3) ?
    C2 C1 N1 C19 . . . . 113.0(3) ?
    C12 C1 N1 C19 . . . . -117.8(3) ?
    C2 C1 N1 C5 . . . . -48.8(4) ?
    C12 C1 N1 C5 . . . . 80.3(3) ?
    C6 C5 N1 C19 . . . . 71.5(3) ?
    C4 C5 N1 C19 . . . . -162.4(3) ?
    C6 C5 N1 C1 . . . . -125.4(3) ?
    C4 C5 N1 C1 . . . . 0.7(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
    C2 H2A O1 5_565 0.97 2.56 3.458(6) 153.5
    C13 H13 O1 5_565 0.93 2.51 3.404(5) 160.7
