#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226893.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226893
loop_
_publ_author_name
'Rajesh, K.'
'Vijayakumar, V.'
'Sarveswari, S.'
'Narasimhamurthy, T.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1-{3-[(4-Oxopiperidin-1-yl)carbonyl]benzoyl}piperidin-4-one
;
_journal_coeditor_code           HB5532
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1988
_journal_paper_doi               10.1107/S1600536810026681
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H20 N2 O4'
_chemical_formula_moiety         'C18 H20 N2 O4'
_chemical_formula_sum            'C18 H20 N2 O4'
_chemical_formula_weight         328.36
_chemical_name_systematic
;
1-{3-[(4-Oxopiperidin-1-yl)carbonyl]benzoyl}piperidin-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.500(5)
_cell_angle_beta                 92.279(5)
_cell_angle_gamma                90.009(5)
_cell_formula_units_Z            4
_cell_length_a                   10.777(5)
_cell_length_b                   11.244(5)
_cell_length_c                   13.665(5)
_cell_measurement_reflns_used    5023
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.5
_cell_measurement_theta_min      1.2
_cell_volume                     1621.3(12)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.047
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33080
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.4
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0747P)²+0.149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1566
_reflns_number_gt                4023
_reflns_number_total             6729
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5532.cif
_cod_data_source_block           I
_cod_database_code               2226893
_cod_database_fobs_code          2226893
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 O1 0.0517(2) 0.05185(19) 0.37691(15) 0.0823(6) Uani d . 1 . .
O O2 0.15121(18) 0.57298(16) 0.53412(13) 0.0638(5) Uani d . 1 . .
O O3 -0.17857(18) 0.34740(19) 0.82228(18) 0.0876(7) Uani d . 1 . .
O O4 -0.55985(18) 0.7338(2) 0.87389(15) 0.0817(6) Uani d . 1 . .
N N1 0.17700(18) 0.37391(18) 0.53706(13) 0.0467(5) Uani d . 1 . .
N N2 -0.25096(19) 0.53525(19) 0.86990(16) 0.0571(6) Uani d . 1 . .
C C1 0.2050(2) 0.3415(2) 0.43153(17) 0.0558(7) Uani d . 1 . .
H H1A 0.2861 0.3040 0.4247 0.067 Uiso calc R 1 . .
H H1B 0.2069 0.4141 0.4034 0.067 Uiso calc R 1 . .
C C2 0.1071(3) 0.2538(2) 0.37500(18) 0.0587(7) Uani d . 1 . .
H H2A 0.0317 0.2985 0.3668 0.070 Uiso calc R 1 . .
H H2B 0.1360 0.2207 0.3089 0.070 Uiso calc R 1 . .
C C3 0.0769(2) 0.1518(2) 0.4244(2) 0.0539(6) Uani d . 1 . .
C C4 0.0729(3) 0.1818(2) 0.53700(18) 0.0604(7) Uani d . 1 . .
H H4A -0.0073 0.2165 0.5557 0.072 Uiso calc R 1 . .
H H4B 0.0813 0.1076 0.5626 0.072 Uiso calc R 1 . .
C C5 0.1739(2) 0.2699(2) 0.58474(18) 0.0524(6) Uani d . 1 . .
H H5A 0.1592 0.2969 0.6552 0.063 Uiso calc R 1 . .
H H5B 0.2536 0.2295 0.5789 0.063 Uiso calc R 1 . .
C C6 0.1487(2) 0.4878(2) 0.57888(17) 0.0441(6) Uani d . 1 . .
C C7 0.1117(2) 0.5125(2) 0.68628(16) 0.0403(5) Uani d . 1 . .
C C8 -0.0031(2) 0.4751(2) 0.71243(16) 0.0421(5) Uani d . 1 . .
H H8 -0.0558 0.4292 0.6637 0.050 Uiso calc R 1 . .
C C9 -0.0401(2) 0.5051(2) 0.80980(16) 0.0408(5) Uani d . 1 . .
C C10 0.0404(2) 0.5695(2) 0.88251(17) 0.0465(6) Uani d . 1 . .
H H10 0.0166 0.5893 0.9484 0.056 Uiso calc R 1 . .
C C11 0.1561(2) 0.6045(2) 0.85785(18) 0.0485(6) Uani d . 1 . .
H H11 0.2106 0.6462 0.9074 0.058 Uiso calc R 1 . .
C C12 0.1907(2) 0.5776(2) 0.75993(17) 0.0452(6) Uani d . 1 . .
H H12 0.2677 0.6035 0.7433 0.054 Uiso calc R 1 . .
C C13 -0.1622(2) 0.4571(2) 0.83514(17) 0.0469(6) Uani d . 1 . .
C C14 -0.2436(2) 0.6670(2) 0.8809(2) 0.0612(7) Uani d . 1 . .
H H14A -0.1656 0.6890 0.8559 0.073 Uiso calc R 1 . .
H H14B -0.2453 0.7046 0.9512 0.073 Uiso calc R 1 . .
C C15 -0.3504(2) 0.7144(3) 0.8245(2) 0.0665(8) Uani d . 1 . .
H H15A -0.3500 0.8024 0.8411 0.080 Uiso calc R 1 . .
H H15B -0.3393 0.6898 0.7533 0.080 Uiso calc R 1 . .
C C16 -0.4735(2) 0.6676(3) 0.84948(19) 0.0586(7) Uani d . 1 . .
C C17 -0.4781(2) 0.5332(3) 0.8422(2) 0.0632(7) Uani d . 1 . .
H H17A -0.4755 0.4926 0.7726 0.076 Uiso calc R 1 . .
H H17B -0.5554 0.5108 0.8681 0.076 Uiso calc R 1 . .
C C18 -0.3685(2) 0.4922(3) 0.9015(2) 0.0671(8) Uani d . 1 . .
H H18A -0.3772 0.5240 0.9722 0.081 Uiso calc R 1 . .
H H18B -0.3681 0.4043 0.8910 0.081 Uiso calc R 1 . .
O O5 0.5437(2) 0.38661(19) 0.38183(15) 0.0794(6) Uani d . 1 . .
O O6 0.64560(18) -0.05160(16) 0.54295(13) 0.0646(5) Uani d . 1 . .
O O7 0.2983(2) 0.31306(19) 0.8416(2) 0.1035(8) Uani d . 1 A .
O O8 -0.08234(17) -0.06160(18) 0.88350(15) 0.0737(6) Uani d . 1 . .
N N3 0.67154(18) 0.14907(18) 0.54821(13) 0.0481(5) Uani d . 1 . .
C C19 0.7071(3) 0.1321(3) 0.44466(18) 0.0589(7) Uani d . 1 . .
H H19A 0.7131 0.0461 0.4167 0.071 Uiso calc R 1 . .
H H19B 0.7880 0.1689 0.4420 0.071 Uiso calc R 1 . .
C C20 0.6126(3) 0.1891(2) 0.38345(18) 0.0578(7) Uani d . 1 . .
H H20A 0.6475 0.1930 0.3198 0.069 Uiso calc R 1 . .
H H20B 0.5399 0.1367 0.3699 0.069 Uiso calc R 1 . .
C C21 0.5730(2) 0.3124(2) 0.43124(18) 0.0510(6) Uani d . 1 . .
C C22 0.5636(3) 0.3373(2) 0.54298(18) 0.0599(7) Uani d . 1 . .
H H22A 0.4829 0.3101 0.5591 0.072 Uiso calc R 1 . .
H H22B 0.5693 0.4242 0.5681 0.072 Uiso calc R 1 . .
C C23 0.6631(2) 0.2758(2) 0.59541(18) 0.0539(6) Uani d . 1 . .
H H23A 0.7424 0.3157 0.5930 0.065 Uiso calc R 1 . .
H H23B 0.6438 0.2826 0.6650 0.065 Uiso calc R 1 . .
C C24 0.6393(2) 0.0544(2) 0.58790(17) 0.0446(6) Uani d . 1 . .
C C25 0.5937(2) 0.0812(2) 0.69292(16) 0.0402(5) Uani d . 1 . .
C C26 0.4768(2) 0.1274(2) 0.71318(16) 0.0413(5) Uani d . 1 . .
H H26 0.4265 0.1460 0.6615 0.050 Uiso calc R 1 . .
C C27 0.4329(2) 0.1466(2) 0.80919(16) 0.0419(5) Uani d . 1 A .
C C28 0.5098(3) 0.1197(3) 0.88504(18) 0.0594(7) Uani d . 1 . .
H H28 0.4825 0.1326 0.9500 0.071 Uiso calc R 1 . .
C C29 0.6268(3) 0.0741(3) 0.86509(19) 0.0660(8) Uani d . 1 . .
H H29 0.6780 0.0568 0.9167 0.079 Uiso calc R 1 . .
C C30 0.6685(2) 0.0539(2) 0.76915(19) 0.0545(6) Uani d . 1 . .
H H30 0.7470 0.0219 0.7560 0.065 Uiso calc R 1 . .
C C31 0.3084(2) 0.2047(2) 0.82956(16) 0.0462(6) Uani d . 1 . .
N N4 0.2093(2) 0.13604(18) 0.8326(2) 0.0849(9) Uani d PD 0.651(5) A 1
C C32 0.2036(4) 0.0042(3) 0.7921(3) 0.0601(13) Uani d PD 0.651(5) A 1
H H32A 0.2866 -0.0286 0.7838 0.072 Uiso calc PR 0.651(5) A 1
H H32B 0.1590 -0.0125 0.7278 0.072 Uiso calc PR 0.651(5) A 1
C C33 0.1364(4) -0.0516(4) 0.8672(5) 0.0654(15) Uani d PD 0.651(5) A 1
H H33A 0.1330 -0.1392 0.8461 0.078 Uiso calc PR 0.651(5) A 1
H H33B 0.1795 -0.0318 0.9322 0.078 Uiso calc PR 0.651(5) A 1
C C34 0.0071(2) -0.0008(2) 0.8733(3) 0.0783(9) Uani d PD 0.651(5) A 1
C C35 0.0043(3) 0.1382(3) 0.9018(3) 0.0468(10) Uani d PD 0.651(5) A 1
H H35A -0.0805 0.1664 0.8990 0.056 Uiso calc PR 0.651(5) A 1
H H35B 0.0385 0.1654 0.9693 0.056 Uiso calc PR 0.651(5) A 1
C C36 0.0810(3) 0.1890(3) 0.8286(4) 0.0525(11) Uani d PD 0.651(5) A 1
H H36A 0.0439 0.1667 0.7616 0.063 Uiso calc PR 0.651(5) A 1
H H36B 0.0852 0.2769 0.8471 0.063 Uiso calc PR 0.651(5) A 1
N N4' 0.2093(2) 0.13604(18) 0.8326(2) 0.0849(9) Uani d P 0.349(5) A 2
C C32' 0.2315(6) 0.0198(5) 0.8719(6) 0.051(2) Uiso d PD 0.349(5) A 2
H H32C 0.2297 0.0347 0.9442 0.061 Uiso calc PR 0.349(5) A 2
H H32D 0.3102 -0.0165 0.8511 0.061 Uiso calc PR 0.349(5) A 2
C C33' 0.1227(5) -0.0600(9) 0.8235(7) 0.059(3) Uiso d PD 0.349(5) A 2
H H33C 0.1322 -0.1420 0.8350 0.071 Uiso calc PR 0.349(5) A 2
H H33D 0.1171 -0.0629 0.7520 0.071 Uiso calc PR 0.349(5) A 2
C C34' 0.0071(2) -0.0008(2) 0.8733(3) 0.0783(9) Uani d P 0.349(5) A 2
C C35' -0.0040(7) 0.1174(5) 0.8348(6) 0.061(2) Uiso d PD 0.349(5) A 2
H H35C 0.0037 0.1031 0.7630 0.073 Uiso calc PR 0.349(5) A 2
H H35D -0.0827 0.1566 0.8517 0.073 Uiso calc PR 0.349(5) A 2
C C36' 0.1034(5) 0.1925(7) 0.8885(6) 0.059(3) Uiso d PD 0.349(5) A 2
H H36C 0.0953 0.2772 0.8841 0.071 Uiso calc PR 0.349(5) A 2
H H36D 0.1109 0.1861 0.9582 0.071 Uiso calc PR 0.349(5) A 2
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'
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
C6 N1 C5 . . 126.11(19) ?
C6 N1 C1 . . 120.8(2) ?
C5 N1 C1 . . 112.87(19) ?
C13 N2 C14 . . 125.6(2) ?
C13 N2 C18 . . 120.7(2) ?
C14 N2 C18 . . 113.6(2) ?
N1 C1 C2 . . 110.16(19) ?
N1 C1 H1A . . 109.6 ?
C2 C1 H1A . . 109.6 ?
N1 C1 H1B . . 109.6 ?
C2 C1 H1B . . 109.6 ?
H1A C1 H1B . . 108.1 ?
C3 C2 C1 . . 114.2(2) ?
C3 C2 H2A . . 108.7 ?
C1 C2 H2A . . 108.7 ?
C3 C2 H2B . . 108.7 ?
C1 C2 H2B . . 108.7 ?
H2A C2 H2B . . 107.6 ?
O1 C3 C2 . . 121.7(2) ?
O1 C3 C4 . . 122.0(2) ?
C2 C3 C4 . . 116.3(2) ?
C5 C4 C3 . . 112.7(2) ?
C5 C4 H4A . . 109.1 ?
C3 C4 H4A . . 109.1 ?
C5 C4 H4B . . 109.1 ?
C3 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
N1 C5 C4 . . 110.7(2) ?
N1 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
O2 C6 N1 . . 123.4(2) ?
O2 C6 C7 . . 118.9(2) ?
N1 C6 C7 . . 117.74(19) ?
C12 C7 C8 . . 119.0(2) ?
C12 C7 C6 . . 119.9(2) ?
C8 C7 C6 . . 121.05(19) ?
C9 C8 C7 . . 120.9(2) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 119.2(2) ?
C8 C9 C13 . . 118.8(2) ?
C10 C9 C13 . . 121.8(2) ?
C9 C10 C11 . . 120.4(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 120.1(2) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C12 C7 . . 120.4(2) ?
C11 C12 H12 . . 119.8 ?
C7 C12 H12 . . 119.8 ?
O3 C13 N2 . . 121.6(2) ?
O3 C13 C9 . . 119.2(2) ?
N2 C13 C9 . . 119.2(2) ?
N2 C14 C15 . . 111.3(2) ?
N2 C14 H14A . . 109.4 ?
C15 C14 H14A . . 109.4 ?
N2 C14 H14B . . 109.4 ?
C15 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
C16 C15 C14 . . 111.7(2) ?
C16 C15 H15A . . 109.3 ?
C14 C15 H15A . . 109.3 ?
C16 C15 H15B . . 109.3 ?
C14 C15 H15B . . 109.3 ?
H15A C15 H15B . . 107.9 ?
O4 C16 C17 . . 123.7(3) ?
O4 C16 C15 . . 122.3(3) ?
C17 C16 C15 . . 114.0(2) ?
C16 C17 C18 . . 110.4(2) ?
C16 C17 H17A . . 109.6 ?
C18 C17 H17A . . 109.6 ?
C16 C17 H17B . . 109.6 ?
C18 C17 H17B . . 109.6 ?
H17A C17 H17B . . 108.1 ?
N2 C18 C17 . . 110.5(2) ?
N2 C18 H18A . . 109.6 ?
C17 C18 H18A . . 109.6 ?
N2 C18 H18B . . 109.6 ?
C17 C18 H18B . . 109.6 ?
H18A C18 H18B . . 108.1 ?
C24 N3 C23 . . 126.11(19) ?
C24 N3 C19 . . 121.0(2) ?
C23 N3 C19 . . 112.53(19) ?
N3 C19 C20 . . 110.6(2) ?
N3 C19 H19A . . 109.5 ?
C20 C19 H19A . . 109.5 ?
N3 C19 H19B . . 109.5 ?
C20 C19 H19B . . 109.5 ?
H19A C19 H19B . . 108.1 ?
C21 C20 C19 . . 114.7(2) ?
C21 C20 H20A . . 108.6 ?
C19 C20 H20A . . 108.6 ?
C21 C20 H20B . . 108.6 ?
C19 C20 H20B . . 108.6 ?
H20A C20 H20B . . 107.6 ?
O5 C21 C20 . . 121.2(2) ?
O5 C21 C22 . . 122.1(2) ?
C20 C21 C22 . . 116.6(2) ?
C21 C22 C23 . . 113.4(2) ?
C21 C22 H22A . . 108.9 ?
C23 C22 H22A . . 108.9 ?
C21 C22 H22B . . 108.9 ?
C23 C22 H22B . . 108.9 ?
H22A C22 H22B . . 107.7 ?
N3 C23 C22 . . 110.4(2) ?
N3 C23 H23A . . 109.6 ?
C22 C23 H23A . . 109.6 ?
N3 C23 H23B . . 109.6 ?
C22 C23 H23B . . 109.6 ?
H23A C23 H23B . . 108.1 ?
O6 C24 N3 . . 123.1(2) ?
O6 C24 C25 . . 119.5(2) ?
N3 C24 C25 . . 117.4(2) ?
C30 C25 C26 . . 119.5(2) ?
C30 C25 C24 . . 119.0(2) ?
C26 C25 C24 . . 121.44(19) ?
C25 C26 C27 . . 121.3(2) ?
C25 C26 H26 . . 119.4 ?
C27 C26 H26 . . 119.4 ?
C28 C27 C26 . . 118.4(2) ?
C28 C27 C31 . . 121.8(2) ?
C26 C27 C31 . . 119.7(2) ?
C29 C28 C27 . . 120.4(2) ?
C29 C28 H28 . . 119.8 ?
C27 C28 H28 . . 119.8 ?
C28 C29 C30 . . 120.5(2) ?
C28 C29 H29 . . 119.7 ?
C30 C29 H29 . . 119.7 ?
C25 C30 C29 . . 119.9(2) ?
C25 C30 H30 . . 120.1 ?
C29 C30 H30 . . 120.1 ?
O7 C31 N4' . . 119.9(2) ?
O7 C31 N4 . . 119.9(2) ?
O7 C31 C27 . . 120.2(2) ?
N4' C31 C27 . . 119.9(2) ?
N4 C31 C27 . . 119.9(2) ?
C31 N4 C32 . . 123.9(2) ?
C31 N4 C36 . . 120.1(2) ?
C32 N4 C36 . . 109.7(3) ?
N4 C32 C33 . . 106.3(3) ?
N4 C32 H32A . . 110.5 ?
C33 C32 H32A . . 110.5 ?
N4 C32 H32B . . 110.5 ?
C33 C32 H32B . . 110.5 ?
H32A C32 H32B . . 108.7 ?
C34 C33 C32 . . 107.6(3) ?
C34 C33 H33A . . 110.2 ?
C32 C33 H33A . . 110.2 ?
C34 C33 H33B . . 110.2 ?
C32 C33 H33B . . 110.2 ?
H33A C33 H33B . . 108.5 ?
O8 C34 C33 . . 122.2(3) ?
O8 C34 C35 . . 121.2(3) ?
C33 C34 C35 . . 113.4(3) ?
C36 C35 C34 . . 108.4(3) ?
C36 C35 H35A . . 110.0 ?
C34 C35 H35A . . 110.0 ?
C36 C35 H35B . . 110.0 ?
C34 C35 H35B . . 110.0 ?
H35A C35 H35B . . 108.4 ?
N4 C36 C35 . . 107.2(3) ?
N4 C36 H36A . . 110.3 ?
C35 C36 H36A . . 110.3 ?
N4 C36 H36B . . 110.3 ?
C35 C36 H36B . . 110.3 ?
H36A C36 H36B . . 108.5 ?
C31 N4' C36' . . 117.8(3) ?
C31 N4' C32' . . 116.2(3) ?
C36' N4' C32' . . 104.0(5) ?
N4' C32' C33' . . 102.3(6) ?
N4' C32' H32C . . 111.3 ?
C33' C32' H32C . . 111.3 ?
N4' C32' H32D . . 111.3 ?
C33' C32' H32D . . 111.3 ?
H32C C32' H32D . . 109.2 ?
C32' C33' C34' . . 105.5(5) ?
C32' C33' H33C . . 110.6 ?
C34' C33' H33C . . 110.6 ?
C32' C33' H33D . . 110.6 ?
C34' C33' H33D . . 110.6 ?
H33C C33' H33D . . 108.8 ?
O8 C34' C35' . . 122.6(4) ?
O8 C34' C33' . . 120.7(4) ?
C35' C34' C33' . . 103.4(6) ?
C36' C35' C34' . . 103.0(5) ?
C36' C35' H35C . . 111.2 ?
C34' C35' H35C . . 111.2 ?
C36' C35' H35D . . 111.2 ?
C34' C35' H35D . . 111.2 ?
H35C C35' H35D . . 109.1 ?
N4' C36' C35' . . 101.6(5) ?
N4' C36' H36C . . 111.4 ?
C35' C36' H36C . . 111.4 ?
N4' C36' H36D . . 111.4 ?
C35' C36' H36D . . 111.4 ?
H36C C36' H36D . . 109.3 ?
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
O1 C3 . 1.205(3) ?
O2 C6 . 1.236(3) ?
O3 C13 . 1.222(3) ?
O4 C16 . 1.207(3) ?
N1 C6 . 1.335(3) ?
N1 C5 . 1.449(3) ?
N1 C1 . 1.459(3) ?
N2 C13 . 1.335(3) ?
N2 C14 . 1.461(3) ?
N2 C18 . 1.467(3) ?
C1 C2 . 1.521(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.484(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.510(4) ?
C4 C5 . 1.509(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.508(3) ?
C7 C12 . 1.382(3) ?
C7 C8 . 1.390(3) ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.381(3) ?
C9 C13 . 1.501(3) ?
C10 C11 . 1.381(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C14 C15 . 1.516(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.504(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.495(4) ?
C17 C18 . 1.530(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
O5 C21 . 1.208(3) ?
O6 C24 . 1.230(3) ?
O7 C31 . 1.202(3) ?
O8 C34' . 1.210(3) ?
O8 C34 . 1.210(3) ?
N3 C24 . 1.339(3) ?
N3 C23 . 1.446(3) ?
N3 C19 . 1.456(3) ?
C19 C20 . 1.514(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 C21 . 1.481(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C22 . 1.504(3) ?
C22 C23 . 1.510(4) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 C25 . 1.509(3) ?
C25 C30 . 1.375(3) ?
C25 C26 . 1.379(3) ?
C26 C27 . 1.389(3) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.382(3) ?
C27 C31 . 1.504(3) ?
C28 C29 . 1.377(4) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.379(3) ?
C29 H29 . 0.9300 ?
C30 H30 . 0.9300 ?
C31 N4' . 1.324(3) ?
C31 N4 . 1.324(3) ?
N4 C32 . 1.476(3) ?
N4 C36 . 1.509(3) ?
C32 C33 . 1.513(4) ?
C32 H32A . 0.9700 ?
C32 H32B . 0.9700 ?
C33 C34 . 1.505(4) ?
C33 H33A . 0.9700 ?
C33 H33B . 0.9700 ?
C34 C35 . 1.534(4) ?
C35 C36 . 1.517(4) ?
C35 H35A . 0.9700 ?
C35 H35B . 0.9700 ?
C36 H36A . 0.9700 ?
C36 H36B . 0.9700 ?
N4' C36' . 1.471(5) ?
N4' C32' . 1.524(4) ?
C32' C33' . 1.522(5) ?
C32' H32C . 0.9700 ?
C32' H32D . 0.9700 ?
C33' C34' . 1.532(5) ?
C33' H33C . 0.9700 ?
C33' H33D . 0.9700 ?
C34' C35' . 1.526(5) ?
C35' C36' . 1.509(5) ?
C35' H35C . 0.9700 ?
C35' H35D . 0.9700 ?
C36' H36C . 0.9700 ?
C36' H36D . 0.9700 ?
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
C4 H4b O1 2_556 0.97 2.58 3.383(4) 141
C22 H22b O5 2_666 0.97 2.44 3.295(4) 146
C35 H35b O8 2_557 0.97 2.55 3.297(5) 134
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
C6 N1 C1 C2 . . . . -115.3(2) ?
C5 N1 C1 C2 . . . . 60.0(3) ?
N1 C1 C2 C3 . . . . -46.9(3) ?
C1 C2 C3 O1 . . . . -145.0(3) ?
C1 C2 C3 C4 . . . . 38.2(3) ?
O1 C3 C4 C5 . . . . 144.0(3) ?
C2 C3 C4 C5 . . . . -39.2(3) ?
C6 N1 C5 C4 . . . . 112.9(3) ?
C1 N1 C5 C4 . . . . -62.0(3) ?
C3 C4 C5 N1 . . . . 49.6(3) ?
C5 N1 C6 O2 . . . . -178.9(2) ?
C1 N1 C6 O2 . . . . -4.4(3) ?
C5 N1 C6 C7 . . . . 1.0(3) ?
C1 N1 C6 C7 . . . . 175.6(2) ?
O2 C6 C7 C12 . . . . -70.4(3) ?
N1 C6 C7 C12 . . . . 109.7(2) ?
O2 C6 C7 C8 . . . . 107.0(3) ?
N1 C6 C7 C8 . . . . -72.9(3) ?
C12 C7 C8 C9 . . . . 1.9(3) ?
C6 C7 C8 C9 . . . . -175.5(2) ?
C7 C8 C9 C10 . . . . -2.4(3) ?
C7 C8 C9 C13 . . . . -176.9(2) ?
C8 C9 C10 C11 . . . . 0.7(3) ?
C13 C9 C10 C11 . . . . 175.0(2) ?
C9 C10 C11 C12 . . . . 1.5(4) ?
C10 C11 C12 C7 . . . . -1.9(4) ?
C8 C7 C12 C11 . . . . 0.3(3) ?
C6 C7 C12 C11 . . . . 177.7(2) ?
C14 N2 C13 O3 . . . . -175.3(3) ?
C18 N2 C13 O3 . . . . 4.9(4) ?
C14 N2 C13 C9 . . . . 3.8(4) ?
C18 N2 C13 C9 . . . . -176.1(2) ?
C8 C9 C13 O3 . . . . 60.7(3) ?
C10 C9 C13 O3 . . . . -113.7(3) ?
C8 C9 C13 N2 . . . . -118.4(3) ?
C10 C9 C13 N2 . . . . 67.2(3) ?
C13 N2 C14 C15 . . . . 123.8(3) ?
C18 N2 C14 C15 . . . . -56.4(3) ?
N2 C14 C15 C16 . . . . 50.7(3) ?
C14 C15 C16 O4 . . . . 129.6(3) ?
C14 C15 C16 C17 . . . . -49.9(3) ?
O4 C16 C17 C18 . . . . -128.2(3) ?
C15 C16 C17 C18 . . . . 51.3(3) ?
C13 N2 C18 C17 . . . . -122.2(3) ?
C14 N2 C18 C17 . . . . 58.0(3) ?
C16 C17 C18 N2 . . . . -53.9(3) ?
C24 N3 C19 C20 . . . . 113.6(2) ?
C23 N3 C19 C20 . . . . -60.3(3) ?
N3 C19 C20 C21 . . . . 45.5(3) ?
C19 C20 C21 O5 . . . . 148.6(3) ?
C19 C20 C21 C22 . . . . -35.2(3) ?
O5 C21 C22 C23 . . . . -147.1(3) ?
C20 C21 C22 C23 . . . . 36.7(3) ?
C24 N3 C23 C22 . . . . -111.1(3) ?
C19 N3 C23 C22 . . . . 62.4(3) ?
C21 C22 C23 N3 . . . . -48.9(3) ?
C23 N3 C24 O6 . . . . 178.1(2) ?
C19 N3 C24 O6 . . . . 5.1(4) ?
C23 N3 C24 C25 . . . . -2.1(3) ?
C19 N3 C24 C25 . . . . -175.1(2) ?
O6 C24 C25 C30 . . . . 71.4(3) ?
N3 C24 C25 C30 . . . . -108.4(3) ?
O6 C24 C25 C26 . . . . -105.7(3) ?
N3 C24 C25 C26 . . . . 74.5(3) ?
C30 C25 C26 C27 . . . . -0.2(3) ?
C24 C25 C26 C27 . . . . 176.9(2) ?
C25 C26 C27 C28 . . . . 0.8(3) ?
C25 C26 C27 C31 . . . . 176.0(2) ?
C26 C27 C28 C29 . . . . -0.6(4) ?
C31 C27 C28 C29 . . . . -175.6(2) ?
C27 C28 C29 C30 . . . . -0.3(4) ?
C26 C25 C30 C29 . . . . -0.7(4) ?
C24 C25 C30 C29 . . . . -177.9(2) ?
C28 C29 C30 C25 . . . . 1.0(4) ?
C28 C27 C31 O7 . . . . 94.2(3) ?
C26 C27 C31 O7 . . . . -80.7(3) ?
C28 C27 C31 N4' . . . . -86.9(3) ?
C26 C27 C31 N4' . . . . 98.2(3) ?
C28 C27 C31 N4 . . . . -86.9(3) ?
C26 C27 C31 N4 . . . . 98.2(3) ?
O7 C31 N4 C32 . . . . 162.4(3) ?
C27 C31 N4 C32 . . . . -16.6(5) ?
O7 C31 N4 C36 . . . . 13.3(5) ?
C27 C31 N4 C36 . . . . -165.6(3) ?
C31 N4 C32 C33 . . . . 138.5(4) ?
C36 N4 C32 C33 . . . . -69.7(4) ?
N4 C32 C33 C34 . . . . 62.4(5) ?
C32 C33 C34 O8 . . . . 142.8(4) ?
C32 C33 C34 C35 . . . . -57.2(5) ?
O8 C34 C35 C36 . . . . -145.0(4) ?
C33 C34 C35 C36 . . . . 54.7(5) ?
C31 N4 C36 C35 . . . . -139.9(3) ?
C32 N4 C36 C35 . . . . 67.1(4) ?
C34 C35 C36 N4 . . . . -56.5(4) ?
O7 C31 N4' C36' . . . . -24.0(6) ?
C27 C31 N4' C36' . . . . 157.1(5) ?
O7 C31 N4' C32' . . . . -148.4(4) ?
C27 C31 N4' C32' . . . . 32.7(5) ?
C31 N4' C32' C33' . . . . -155.4(4) ?
C36' N4' C32' C33' . . . . 73.5(6) ?
N4' C32' C33' C34' . . . . -68.4(8) ?
C32' C33' C34' O8 . . . . -149.6(5) ?
C32' C33' C34' C35' . . . . 68.6(8) ?
O8 C34' C35' C36' . . . . 148.0(5) ?
C33' C34' C35' C36' . . . . -71.1(7) ?
C31 N4' C36' C35' . . . . 152.4(5) ?
C32' N4' C36' C35' . . . . -77.4(7) ?
C34' C35' C36' N4' . . . . 75.8(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079314
