#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228713.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_2228713
loop_
_publ_author_name
'Lu, Chunxiong'
'Jiang, Quanfu'
_publ_section_title
;
 2-[4-(2-Methoxyphenyl)piperazin-1-yl]-N-(pyridin-2-yl)acetamide
;
_journal_coeditor_code           FK2033
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o223
_journal_paper_doi               10.1107/S1600536810053067
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H22 N4 O2'
_chemical_formula_moiety         'C18 H22 N4 O2'
_chemical_formula_sum            'C18 H22 N4 O2'
_chemical_formula_weight         326.40
_chemical_name_systematic
;
2-[4-(2-Methoxyphenyl)piperazin-1-yl]-N-(pyridin-2-yl)acetamide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.228(4)
_cell_angle_beta                 91.767(3)
_cell_angle_gamma                114.627(2)
_cell_formula_units_Z            4
_cell_length_a                   11.595(4)
_cell_length_b                   12.382(4)
_cell_length_c                   14.073(4)
_cell_measurement_reflns_used    3991
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.04
_cell_volume                     1738.2(10)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16957
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         7823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0569P)²+0.1680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                4689
_reflns_number_total             7823
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fk2033.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        1738.2(9)
_cod_database_code               2228713
_cod_database_fobs_code          2228713
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 -0.16031(14) 0.19320(13) 0.60110(10) 0.0318(4) Uani d . 1 . .
O O2 0.26509(14) 0.03711(15) 0.17233(10) 0.0389(4) Uani d . 1 . .
N N1 0.04151(16) 0.31688(15) 0.51774(11) 0.0248(4) Uani d . 1 . .
N N2 0.15938(16) 0.22961(16) 0.35729(11) 0.0264(4) Uani d . 1 . .
N N3 0.35747(16) 0.17050(17) 0.33185(12) 0.0260(4) Uani d . 1 . .
N N4 0.54677(16) 0.24391(16) 0.43628(12) 0.0290(4) Uani d . 1 . .
C C1 -0.0797(2) 0.31511(19) 0.65726(14) 0.0263(4) Uani d . 1 . .
C C2 -0.0993(2) 0.3747(2) 0.75015(14) 0.0304(5) Uani d . 1 . .
H H2 -0.1719 0.3312 0.7774 0.037 Uiso calc R 1 . .
C C3 -0.0128(2) 0.4982(2) 0.80355(16) 0.0371(5) Uani d . 1 . .
H H3 -0.0263 0.5386 0.8673 0.044 Uiso calc R 1 . .
C C4 0.0919(2) 0.5616(2) 0.76425(16) 0.0388(6) Uani d . 1 . .
H H4 0.1507 0.6459 0.8005 0.047 Uiso calc R 1 . .
C C5 0.1115(2) 0.5019(2) 0.67106(15) 0.0330(5) Uani d . 1 . .
H H5 0.1846 0.5461 0.6446 0.040 Uiso calc R 1 . .
C C6 0.02656(19) 0.37892(19) 0.61564(13) 0.0254(4) Uani d . 1 . .
C C7 0.0808(2) 0.2177(2) 0.51565(14) 0.0291(5) Uani d . 1 . .
H H7A 0.0225 0.1601 0.5484 0.035 Uiso calc R 1 . .
H H7B 0.1693 0.2557 0.5533 0.035 Uiso calc R 1 . .
C C8 0.0760(2) 0.14470(19) 0.40775(14) 0.0297(5) Uani d . 1 . .
H H8A 0.1047 0.0796 0.4070 0.036 Uiso calc R 1 . .
H H8B -0.0136 0.1023 0.3713 0.036 Uiso calc R 1 . .
C C9 0.1161(2) 0.3261(2) 0.35931(14) 0.0310(5) Uani d . 1 . .
H H9A 0.0260 0.2858 0.3243 0.037 Uiso calc R 1 . .
H H9B 0.1705 0.3827 0.3240 0.037 Uiso calc R 1 . .
C C10 0.1254(2) 0.4008(2) 0.46679(14) 0.0304(5) Uani d . 1 . .
H H10A 0.2155 0.4413 0.5018 0.036 Uiso calc R 1 . .
H H10B 0.0987 0.4675 0.4684 0.036 Uiso calc R 1 . .
C C11 0.1642(2) 0.1621(2) 0.25557(13) 0.0297(5) Uani d . 1 . .
H H11A 0.1808 0.2184 0.2144 0.036 Uiso calc R 1 . .
H H11B 0.0788 0.0898 0.2263 0.036 Uiso calc R 1 . .
C C12 0.26561(19) 0.11417(19) 0.24878(14) 0.0270(5) Uani d . 1 . .
C C13 0.47825(19) 0.17094(19) 0.34499(14) 0.0244(4) Uani d . 1 . .
C C14 0.5227(2) 0.1054(2) 0.27087(15) 0.0326(5) Uani d . 1 . .
H H14 0.4697 0.0520 0.2078 0.039 Uiso calc R 1 . .
C C15 0.6471(2) 0.1202(2) 0.29197(16) 0.0367(5) Uani d . 1 . .
H H15 0.6816 0.0783 0.2425 0.044 Uiso calc R 1 . .
C C16 0.7206(2) 0.1964(2) 0.38561(16) 0.0346(5) Uani d . 1 . .
H H16 0.8062 0.2084 0.4015 0.042 Uiso calc R 1 . .
C C17 0.6659(2) 0.2542(2) 0.45484(16) 0.0336(5) Uani d . 1 . .
H H17 0.7153 0.3045 0.5197 0.040 Uiso calc R 1 . .
C C18 -0.2720(2) 0.1297(2) 0.64012(17) 0.0411(6) Uani d . 1 . .
H H18A -0.2460 0.1235 0.7045 0.062 Uiso calc R 1 . .
H H18B -0.3236 0.0453 0.5926 0.062 Uiso calc R 1 . .
H H18C -0.3234 0.1767 0.6500 0.062 Uiso calc R 1 . .
H H03 0.345(2) 0.224(2) 0.3780(15) 0.036(7) Uiso d . 1 . .
O O3 0.31024(14) 0.19997(13) 0.69524(10) 0.0328(4) Uani d . 1 . .
O O4 -0.20714(14) 0.09195(14) 1.08091(10) 0.0364(4) Uani d . 1 . .
N N5 0.27157(15) 0.34038(15) 0.86559(11) 0.0247(4) Uani d . 1 . .
N N6 0.07490(15) 0.27036(16) 0.98664(11) 0.0258(4) Uani d . 1 . .
N N7 -0.17632(17) 0.22583(16) 0.99004(12) 0.0261(4) Uani d . 1 . .
N N8 -0.31000(17) 0.26615(17) 0.89803(12) 0.0318(4) Uani d . 1 . .
C C19 0.37328(19) 0.3275(2) 0.71544(14) 0.0278(5) Uani d . 1 . .
C C20 0.4550(2) 0.3846(2) 0.65566(15) 0.0341(5) Uani d . 1 . .
H H20 0.4689 0.3348 0.5965 0.041 Uiso calc R 1 . .
C C21 0.5165(2) 0.5145(2) 0.68257(17) 0.0442(6) Uani d . 1 . .
H H21 0.5720 0.5534 0.6414 0.053 Uiso calc R 1 . .
C C22 0.4978(2) 0.5871(2) 0.76827(18) 0.0459(6) Uani d . 1 . .
H H22 0.5411 0.6760 0.7869 0.055 Uiso calc R 1 . .
C C23 0.4155(2) 0.5301(2) 0.82765(16) 0.0362(5) Uani d . 1 . .
H H23 0.4025 0.5812 0.8865 0.043 Uiso calc R 1 . .
C C24 0.35148(19) 0.4006(2) 0.80341(14) 0.0266(5) Uani d . 1 . .
C C25 0.13434(19) 0.26517(19) 0.82010(14) 0.0276(5) Uani d . 1 . .
H H25A 0.1261 0.2088 0.7520 0.033 Uiso calc R 1 . .
H H25B 0.0960 0.3215 0.8139 0.033 Uiso calc R 1 . .
C C26 0.0632(2) 0.1882(2) 0.88466(14) 0.0301(5) Uani d . 1 . .
H H26A -0.0288 0.1382 0.8539 0.036 Uiso calc R 1 . .
H H26B 0.0991 0.1293 0.8883 0.036 Uiso calc R 1 . .
C C27 0.21204(19) 0.3438(2) 1.03070(14) 0.0302(5) Uani d . 1 . .
H H27A 0.2496 0.2865 1.0353 0.036 Uiso calc R 1 . .
H H27B 0.2215 0.3994 1.0994 0.036 Uiso calc R 1 . .
C C28 0.2834(2) 0.4222(2) 0.96688(14) 0.0311(5) Uani d . 1 . .
H H28A 0.2471 0.4808 0.9634 0.037 Uiso calc R 1 . .
H H28B 0.3753 0.4723 0.9977 0.037 Uiso calc R 1 . .
C C29 0.0039(2) 0.1977(2) 1.04953(14) 0.0296(5) Uani d . 1 . .
H H29A 0.0444 0.2460 1.1206 0.036 Uiso calc R 1 . .
H H29B 0.0133 0.1189 1.0326 0.036 Uiso calc R 1 . .
C C30 -0.1381(2) 0.16446(19) 1.04003(14) 0.0264(5) Uani d . 1 . .
C C31 -0.30054(19) 0.21492(19) 0.96784(13) 0.0250(4) Uani d . 1 . .
C C32 -0.4019(2) 0.15893(19) 1.01496(15) 0.0300(5) Uani d . 1 . .
H H32 -0.3907 0.1248 1.0652 0.036 Uiso calc R 1 . .
C C33 -0.5194(2) 0.1543(2) 0.98670(16) 0.0346(5) Uani d . 1 . .
H H33 -0.5907 0.1163 1.0174 0.042 Uiso calc R 1 . .
C C34 -0.5328(2) 0.2049(2) 0.91386(16) 0.0362(5) Uani d . 1 . .
H H34 -0.6130 0.2019 0.8929 0.043 Uiso calc R 1 . .
C C35 -0.4262(2) 0.2599(2) 0.87240(16) 0.0369(5) Uani d . 1 . .
H H35 -0.4350 0.2956 0.8227 0.044 Uiso calc R 1 . .
C C36 0.3320(2) 0.1232(2) 0.60821(16) 0.0408(6) Uani d . 1 . .
H H36A 0.3084 0.1408 0.5487 0.061 Uiso calc R 1 . .
H H36B 0.2793 0.0346 0.6007 0.061 Uiso calc R 1 . .
H H36C 0.4231 0.1414 0.6154 0.061 Uiso calc R 1 . .
H H07 -0.118(2) 0.271(2) 0.9629(15) 0.032(6) Uiso d . 1 . .
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
C1 O1 C18 . . 116.84(15) ?
C6 N1 C10 . . 114.88(16) ?
C6 N1 C7 . . 113.42(15) ?
C10 N1 C7 . . 110.02(15) ?
C11 N2 C8 . . 111.99(16) ?
C11 N2 C9 . . 112.14(16) ?
C8 N2 C9 . . 109.09(15) ?
C12 N3 C13 . . 129.39(18) ?
C12 N3 H03 . . 113.4(15) ?
C13 N3 H03 . . 116.0(15) ?
C13 N4 C17 . . 116.92(17) ?
O1 C1 C2 . . 123.16(18) ?
O1 C1 C6 . . 116.37(16) ?
C2 C1 C6 . . 120.46(19) ?
C1 C2 C3 . . 120.11(19) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 120.17(19) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 119.7(2) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 121.55(19) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C5 C6 C1 . . 118.02(17) ?
C5 C6 N1 . . 122.69(17) ?
C1 C6 N1 . . 119.26(18) ?
N1 C7 C8 . . 110.03(16) ?
N1 C7 H7A . . 109.7 ?
C8 C7 H7A . . 109.7 ?
N1 C7 H7B . . 109.7 ?
C8 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
N2 C8 C7 . . 110.27(16) ?
N2 C8 H8A . . 109.6 ?
C7 C8 H8A . . 109.6 ?
N2 C8 H8B . . 109.6 ?
C7 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
N2 C9 C10 . . 109.63(16) ?
N2 C9 H9A . . 109.7 ?
C10 C9 H9A . . 109.7 ?
N2 C9 H9B . . 109.7 ?
C10 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
N1 C10 C9 . . 109.40(16) ?
N1 C10 H10A . . 109.8 ?
C9 C10 H10A . . 109.8 ?
N1 C10 H10B . . 109.8 ?
C9 C10 H10B . . 109.8 ?
H10A C10 H10B . . 108.2 ?
N2 C11 C12 . . 114.41(16) ?
N2 C11 H11A . . 108.7 ?
C12 C11 H11A . . 108.7 ?
N2 C11 H11B . . 108.7 ?
C12 C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
O2 C12 N3 . . 125.0(2) ?
O2 C12 C11 . . 121.35(18) ?
N3 C12 C11 . . 113.57(17) ?
N4 C13 C14 . . 123.7(2) ?
N4 C13 N3 . . 112.45(17) ?
C14 C13 N3 . . 123.79(18) ?
C13 C14 C15 . . 117.8(2) ?
C13 C14 H14 . . 121.1 ?
C15 C14 H14 . . 121.1 ?
C16 C15 C14 . . 119.6(2) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C17 C16 C15 . . 117.9(2) ?
C17 C16 H16 . . 121.0 ?
C15 C16 H16 . . 121.0 ?
N4 C17 C16 . . 124.0(2) ?
N4 C17 H17 . . 118.0 ?
C16 C17 H17 . . 118.0 ?
O1 C18 H18A . . 109.5 ?
O1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C19 O3 C36 . . 117.38(16) ?
C24 N5 C28 . . 115.19(16) ?
C24 N5 C25 . . 114.62(15) ?
C28 N5 C25 . . 109.58(14) ?
C29 N6 C27 . . 110.89(15) ?
C29 N6 C26 . . 111.33(16) ?
C27 N6 C26 . . 108.63(15) ?
C30 N7 C31 . . 128.76(18) ?
C30 N7 H07 . . 114.5(15) ?
C31 N7 H07 . . 116.3(15) ?
C31 N8 C35 . . 116.63(18) ?
O3 C19 C20 . . 123.64(18) ?
O3 C19 C24 . . 115.77(17) ?
C20 C19 C24 . . 120.6(2) ?
C21 C20 C19 . . 119.8(2) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C22 C21 C20 . . 120.5(2) ?
C22 C21 H21 . . 119.8 ?
C20 C21 H21 . . 119.8 ?
C21 C22 C23 . . 119.7(2) ?
C21 C22 H22 . . 120.1 ?
C23 C22 H22 . . 120.1 ?
C22 C23 C24 . . 121.8(2) ?
C22 C23 H23 . . 119.1 ?
C24 C23 H23 . . 119.1 ?
C23 C24 C19 . . 117.59(18) ?
C23 C24 N5 . . 122.76(18) ?
C19 C24 N5 . . 119.57(19) ?
N5 C25 C26 . . 109.92(16) ?
N5 C25 H25A . . 109.7 ?
C26 C25 H25A . . 109.7 ?
N5 C25 H25B . . 109.7 ?
C26 C25 H25B . . 109.7 ?
H25A C25 H25B . . 108.2 ?
N6 C26 C25 . . 110.55(17) ?
N6 C26 H26A . . 109.5 ?
C25 C26 H26A . . 109.5 ?
N6 C26 H26B . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 108.1 ?
N6 C27 C28 . . 110.30(16) ?
N6 C27 H27A . . 109.6 ?
C28 C27 H27A . . 109.6 ?
N6 C27 H27B . . 109.6 ?
C28 C27 H27B . . 109.6 ?
H27A C27 H27B . . 108.1 ?
N5 C28 C27 . . 109.87(17) ?
N5 C28 H28A . . 109.7 ?
C27 C28 H28A . . 109.7 ?
N5 C28 H28B . . 109.7 ?
C27 C28 H28B . . 109.7 ?
H28A C28 H28B . . 108.2 ?
N6 C29 C30 . . 115.62(17) ?
N6 C29 H29A . . 108.4 ?
C30 C29 H29A . . 108.4 ?
N6 C29 H29B . . 108.4 ?
C30 C29 H29B . . 108.4 ?
H29A C29 H29B . . 107.4 ?
O4 C30 N7 . . 125.2(2) ?
O4 C30 C29 . . 119.63(19) ?
N7 C30 C29 . . 115.06(17) ?
N8 C31 C32 . . 123.6(2) ?
N8 C31 N7 . . 112.81(17) ?
C32 C31 N7 . . 123.57(19) ?
C33 C32 C31 . . 118.1(2) ?
C33 C32 H32 . . 121.0 ?
C31 C32 H32 . . 121.0 ?
C34 C33 C32 . . 119.7(2) ?
C34 C33 H33 . . 120.1 ?
C32 C33 H33 . . 120.1 ?
C35 C34 C33 . . 117.9(2) ?
C35 C34 H34 . . 121.0 ?
C33 C34 H34 . . 121.0 ?
N8 C35 C34 . . 124.0(2) ?
N8 C35 H35 . . 118.0 ?
C34 C35 H35 . . 118.0 ?
O3 C36 H36A . . 109.5 ?
O3 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
O3 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
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 C1 . 1.374(2) ?
O1 C18 . 1.426(2) ?
O2 C12 . 1.220(2) ?
N1 C6 . 1.433(2) ?
N1 C10 . 1.469(2) ?
N1 C7 . 1.470(3) ?
N2 C11 . 1.458(2) ?
N2 C8 . 1.469(2) ?
N2 C9 . 1.470(3) ?
N3 C12 . 1.355(2) ?
N3 C13 . 1.404(3) ?
N3 H03 . 0.85(2) ?
N4 C13 . 1.337(2) ?
N4 C17 . 1.343(3) ?
C1 C2 . 1.387(3) ?
C1 C6 . 1.406(3) ?
C2 C3 . 1.394(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.391(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.521(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.510(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.517(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C13 C14 . 1.386(3) ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.375(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
O3 C19 . 1.372(2) ?
O3 C36 . 1.427(2) ?
O4 C30 . 1.223(2) ?
N5 C24 . 1.421(2) ?
N5 C28 . 1.464(2) ?
N5 C25 . 1.476(2) ?
N6 C29 . 1.464(2) ?
N6 C27 . 1.469(2) ?
N6 C26 . 1.473(2) ?
N7 C30 . 1.352(3) ?
N7 C31 . 1.406(3) ?
N7 H07 . 0.86(2) ?
N8 C31 . 1.334(3) ?
N8 C35 . 1.348(3) ?
C19 C20 . 1.389(3) ?
C19 C24 . 1.414(3) ?
C20 C21 . 1.388(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.372(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.387(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.388(3) ?
C23 H23 . 0.9500 ?
C25 C26 . 1.513(3) ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
C27 C28 . 1.515(3) ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
C28 H28A . 0.9900 ?
C28 H28B . 0.9900 ?
C29 C30 . 1.513(3) ?
C29 H29A . 0.9900 ?
C29 H29B . 0.9900 ?
C31 C32 . 1.388(3) ?
C32 C33 . 1.381(3) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.378(3) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.377(3) ?
C34 H34 . 0.9500 ?
C35 H35 . 0.9500 ?
C36 H36A . 0.9800 ?
C36 H36B . 0.9800 ?
C36 H36C . 0.9800 ?
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
N3 H03 N2 . 0.85(2) 2.20(3) 2.692(3) 117.0(19) yes
N7 H07 N6 . 0.86(2) 2.26(3) 2.734(3) 115.3(19) yes
C2 H2 N8 . 0.95 2.44 3.354(3) 161 yes
C7 H7A O1 . 0.99 2.42 3.010(3) 118 ?
C14 H14 O2 . 0.95 2.33 2.923(3) 120 yes
C20 H20 N4 . 0.95 2.59 3.527(3) 168 yes
C25 H25A O3 . 0.99 2.34 2.950(3) 119 ?
C32 H32 O4 . 0.95 2.34 2.917(3) 118 ?
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
C18 O1 C1 C2 . . . . 3.2(3) ?
C18 O1 C1 C6 . . . . -176.80(19) ?
O1 C1 C2 C3 . . . . 179.3(2) ?
C6 C1 C2 C3 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C4 C5 C6 C1 . . . . -1.0(3) ?
C4 C5 C6 N1 . . . . 177.4(2) ?
O1 C1 C6 C5 . . . . -178.98(18) ?
C2 C1 C6 C5 . . . . 1.0(3) ?
O1 C1 C6 N1 . . . . 2.6(3) ?
C2 C1 C6 N1 . . . . -177.39(18) ?
C10 N1 C6 C5 . . . . -18.5(3) ?
C7 N1 C6 C5 . . . . 109.2(2) ?
C10 N1 C6 C1 . . . . 159.80(18) ?
C7 N1 C6 C1 . . . . -72.5(2) ?
C6 N1 C7 C8 . . . . 171.99(16) ?
C10 N1 C7 C8 . . . . -57.8(2) ?
C11 N2 C8 C7 . . . . 176.23(16) ?
C9 N2 C8 C7 . . . . -59.0(2) ?
N1 C7 C8 N2 . . . . 57.8(2) ?
C11 N2 C9 C10 . . . . -174.60(16) ?
C8 N2 C9 C10 . . . . 60.7(2) ?
C6 N1 C10 C9 . . . . -171.08(16) ?
C7 N1 C10 C9 . . . . 59.5(2) ?
N2 C9 C10 N1 . . . . -61.1(2) ?
C8 N2 C11 C12 . . . . -86.9(2) ?
C9 N2 C11 C12 . . . . 150.02(18) ?
C13 N3 C12 O2 . . . . 11.1(3) ?
C13 N3 C12 C11 . . . . -164.95(19) ?
N2 C11 C12 O2 . . . . 166.17(18) ?
N2 C11 C12 N3 . . . . -17.6(2) ?
C17 N4 C13 C14 . . . . 1.1(3) ?
C17 N4 C13 N3 . . . . -177.56(17) ?
C12 N3 C13 N4 . . . . 175.9(2) ?
C12 N3 C13 C14 . . . . -2.7(3) ?
N4 C13 C14 C15 . . . . -2.3(3) ?
N3 C13 C14 C15 . . . . 176.1(2) ?
C13 C14 C15 C16 . . . . 1.5(3) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C13 N4 C17 C16 . . . . 1.1(3) ?
C15 C16 C17 N4 . . . . -1.9(3) ?
C36 O3 C19 C20 . . . . 0.6(3) ?
C36 O3 C19 C24 . . . . -178.73(19) ?
O3 C19 C20 C21 . . . . -179.0(2) ?
C24 C19 C20 C21 . . . . 0.3(3) ?
C19 C20 C21 C22 . . . . 0.5(4) ?
C20 C21 C22 C23 . . . . -0.9(4) ?
C21 C22 C23 C24 . . . . 0.6(4) ?
C22 C23 C24 C19 . . . . 0.2(3) ?
C22 C23 C24 N5 . . . . 176.9(2) ?
O3 C19 C24 C23 . . . . 178.73(19) ?
C20 C19 C24 C23 . . . . -0.6(3) ?
O3 C19 C24 N5 . . . . 1.9(3) ?
C20 C19 C24 N5 . . . . -177.44(19) ?
C28 N5 C24 C23 . . . . -13.1(3) ?
C25 N5 C24 C23 . . . . 115.4(2) ?
C28 N5 C24 C19 . . . . 163.57(18) ?
C25 N5 C24 C19 . . . . -67.9(2) ?
C24 N5 C25 C26 . . . . 170.29(17) ?
C28 N5 C25 C26 . . . . -58.4(2) ?
C29 N6 C26 C25 . . . . 178.58(17) ?
C27 N6 C26 C25 . . . . -59.0(2) ?
N5 C25 C26 N6 . . . . 59.0(2) ?
C29 N6 C27 C28 . . . . -177.92(16) ?
C26 N6 C27 C28 . . . . 59.4(2) ?
C24 N5 C28 C27 . . . . -170.09(17) ?
C25 N5 C28 C27 . . . . 58.9(2) ?
N6 C27 C28 N5 . . . . -60.2(2) ?
C27 N6 C29 C30 . . . . 154.65(17) ?
C26 N6 C29 C30 . . . . -84.3(2) ?
C31 N7 C30 O4 . . . . -4.8(3) ?
C31 N7 C30 C29 . . . . 179.19(18) ?
N6 C29 C30 O4 . . . . 171.57(17) ?
N6 C29 C30 N7 . . . . -12.2(2) ?
C35 N8 C31 C32 . . . . -1.1(3) ?
C35 N8 C31 N7 . . . . -179.91(18) ?
C30 N7 C31 N8 . . . . -165.16(19) ?
C30 N7 C31 C32 . . . . 16.0(3) ?
N8 C31 C32 C33 . . . . 1.1(3) ?
N7 C31 C32 C33 . . . . 179.82(18) ?
C31 C32 C33 C34 . . . . -0.2(3) ?
C32 C33 C34 C35 . . . . -0.6(3) ?
C31 N8 C35 C34 . . . . 0.2(3) ?
C33 C34 C35 N8 . . . . 0.7(3) ?
