#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220928.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_2220928
loop_
_publ_author_name
'Chen, Min-E'
'Li, Jia-Ming'
_publ_section_title
;
 (E)-N'-(4-Pyridylmethylene)-4-(8-quinolyloxy)butanohydrazide
 0.25-hydrate
;
_journal_coeditor_code           TK2355
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o295
_journal_paper_doi               10.1107/S160053680900110X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H18 N4 O2, 0.25H2 O'
_chemical_formula_moiety         'C19 H18 N4 O2, 0.25(H2 O)'
_chemical_formula_sum            'C19 H18.5 N4 O2.25'
_chemical_formula_weight         338.88
_chemical_melting_point          438
_chemical_name_systematic
;
(E)-N'-(4-Pyridylmethylene)-4-(8-quinolyloxy)butanohydrazide
0.25-hydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.765(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8816(13)
_cell_length_b                   17.420(2)
_cell_length_c                   11.3624(17)
_cell_measurement_reflns_used    1165
_cell_measurement_temperature    295
_cell_measurement_theta_max      20.03
_cell_measurement_theta_min      2.17
_cell_volume                     1727.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.050
_diffrn_reflns_av_sigmaI/netI    0.059
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9142
_diffrn_reflns_theta_full        25.1
_diffrn_reflns_theta_max         25.1
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             714
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details nd
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.105
_refine_ls_R_factor_gt           0.058
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0877P)²+0.001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.132
_refine_ls_wR_factor_ref         0.162
_reflns_number_gt                1927
_reflns_number_total             3169
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2355.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2220928
_cod_database_fobs_code          2220928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N N1 1.1571(5) 0.0923(3) 0.6124(4) 0.0478(12) Uani d . 1 . .
N N2 0.7191(6) 0.1522(3) 0.1045(4) 0.0566(14) Uani d . 1 . .
H H2 0.7211 0.1460 0.0297 0.068 Uiso calc R 1 . .
N N3 0.6437(6) 0.1008(3) 0.1636(4) 0.0510(13) Uani d . 1 . .
N N4 0.3307(7) -0.1253(4) 0.2546(6) 0.0817(18) Uani d . 1 . .
N N5 0.6503(5) 0.1139(3) 0.8355(4) 0.0495(12) Uani d . 1 . .
N N6 1.0930(6) 0.0735(3) 1.3512(4) 0.0510(13) Uani d . 1 . .
H H6 1.0909 0.0810 1.4257 0.061 Uiso calc R 1 . .
N N7 1.1691(6) 0.1246(3) 1.2916(4) 0.0474(12) Uani d . 1 . .
N N8 1.4779(7) 0.3522(3) 1.1941(6) 0.0674(15) Uani d . 1 . .
O O1 0.9800(4) 0.2139(2) 0.5363(3) 0.0497(10) Uani d . 1 . .
O O2 0.8522(6) 0.2626(3) 0.1125(4) 0.0769(14) Uani d . 1 . .
O O3 0.8302(5) -0.0034(2) 0.9236(3) 0.0511(10) Uani d . 1 . .
O O4 0.9623(6) -0.0348(2) 1.3516(4) 0.0707(14) Uani d . 1 . .
O O5 0.2645(9) 0.3398(5) 0.6539(8) 0.072(3) Uani d PD 0.50 . .
H H39 0.2124 0.3805 0.6357 0.107 Uiso d PRD 0.50 . .
H H40 0.2794 0.3362 0.7297 0.107 Uiso d PRD 0.50 . .
C C1 1.0067(7) 0.1999(3) 0.6560(5) 0.0430(14) Uani d . 1 . .
C C2 0.9470(7) 0.2422(3) 0.7384(5) 0.0491(15) Uani d . 1 . .
H H1 0.8840 0.2840 0.7134 0.059 Uiso calc R 1 . .
C C3 0.9807(7) 0.2225(4) 0.8599(5) 0.0557(16) Uani d . 1 . .
H H3 0.9389 0.2514 0.9147 0.067 Uiso calc R 1 . .
C C4 1.0719(7) 0.1628(4) 0.8992(5) 0.0569(17) Uani d . 1 . .
H H4 1.0932 0.1515 0.9806 0.068 Uiso calc R 1 . .
C C5 1.1361(7) 0.1168(3) 0.8187(5) 0.0478(15) Uani d . 1 . .
C C6 1.2298(7) 0.0529(4) 0.8537(5) 0.0583(17) Uani d . 1 . .
H H5 1.2534 0.0389 0.9340 0.070 Uiso calc R 1 . .
C C7 1.2853(8) 0.0120(4) 0.7713(6) 0.0662(18) Uani d . 1 . .
H H7 1.3495 -0.0298 0.7938 0.079 Uiso calc R 1 . .
C C8 1.2449(8) 0.0333(4) 0.6505(6) 0.0608(17) Uani d . 1 . .
H H8 1.2824 0.0039 0.5940 0.073 Uiso calc R 1 . .
C C9 1.1020(6) 0.1352(3) 0.6951(4) 0.0391(13) Uani d . 1 . .
C C10 0.8914(7) 0.2810(3) 0.4948(5) 0.0508(15) Uani d . 1 . .
H H10A 0.9416 0.3268 0.5318 0.061 Uiso calc R 1 . .
H H10B 0.7903 0.2776 0.5152 0.061 Uiso calc R 1 . .
C C11 0.8788(7) 0.2845(3) 0.3596(5) 0.0537(16) Uani d . 1 . .
H H11A 0.8270 0.3315 0.3295 0.064 Uiso calc R 1 . .
H H11B 0.9808 0.2854 0.3406 0.064 Uiso calc R 1 . .
C C12 0.7917(7) 0.2168(3) 0.2986(4) 0.0498(15) Uani d . 1 . .
H H12A 0.6867 0.2192 0.3110 0.060 Uiso calc R 1 . .
H H12B 0.8370 0.1699 0.3353 0.060 Uiso calc R 1 . .
C C13 0.7914(7) 0.2139(4) 0.1658(5) 0.0517(15) Uani d . 1 . .
C C14 0.5817(7) 0.0439(4) 0.1021(5) 0.0523(15) Uani d . 1 . .
H H14 0.5915 0.0389 0.0224 0.063 Uiso calc R 1 . .
C C15 0.4960(7) -0.0130(3) 0.1556(5) 0.0491(15) Uani d . 1 . .
C C16 0.4348(7) -0.0766(4) 0.0895(6) 0.0593(16) Uani d . 1 . .
H H16 0.4488 -0.0832 0.0110 0.071 Uiso calc R 1 . .
C C17 0.3533(8) -0.1299(4) 0.1419(7) 0.075(2) Uani d . 1 . .
H H17 0.3116 -0.1715 0.0960 0.090 Uiso calc R 1 . .
C C18 0.3892(9) -0.0646(5) 0.3151(7) 0.076(2) Uani d . 1 . .
H H18 0.3749 -0.0600 0.3938 0.091 Uiso calc R 1 . .
C C19 0.4703(7) -0.0070(4) 0.2711(5) 0.0581(17) Uani d . 1 . .
H H19 0.5068 0.0350 0.3186 0.070 Uiso calc R 1 . .
C C20 0.8106(7) 0.0064(3) 0.8035(5) 0.0442(14) Uani d . 1 . .
C C21 0.8736(7) -0.0391(4) 0.7273(5) 0.0558(16) Uani d . 1 . .
H H21 0.9340 -0.0807 0.7577 0.067 Uiso calc R 1 . .
C C22 0.8485(8) -0.0239(4) 0.6043(6) 0.0649(19) Uani d . 1 . .
H H22 0.8948 -0.0546 0.5543 0.078 Uiso calc R 1 . .
C C23 0.7566(8) 0.0355(4) 0.5573(5) 0.0649(19) Uani d . 1 . .
H H23 0.7396 0.0446 0.4752 0.078 Uiso calc R 1 . .
C C24 0.6872(7) 0.0832(4) 0.6320(5) 0.0512(16) Uani d . 1 . .
C C25 0.5906(8) 0.1436(4) 0.5884(6) 0.070(2) Uani d . 1 . .
H H25 0.5701 0.1542 0.5068 0.084 Uiso calc R 1 . .
C C26 0.5250(8) 0.1879(4) 0.6658(6) 0.070(2) Uani d . 1 . .
H H26 0.4589 0.2280 0.6378 0.083 Uiso calc R 1 . .
C C27 0.5617(8) 0.1702(4) 0.7890(6) 0.0663(18) Uani d . 1 . .
H H27 0.5194 0.2010 0.8412 0.080 Uiso calc R 1 . .
C C28 0.7132(7) 0.0686(3) 0.7572(5) 0.0455(14) Uani d . 1 . .
C C29 0.9213(7) -0.0686(3) 0.9732(5) 0.0523(15) Uani d . 1 . .
H H29A 1.0227 -0.0659 0.9533 0.063 Uiso calc R 1 . .
H H29B 0.8731 -0.1161 0.9414 0.063 Uiso calc R 1 . .
C C30 0.9317(7) -0.0652(3) 1.1079(5) 0.0472(14) Uani d . 1 . .
H H30A 0.8291 -0.0649 1.1259 0.057 Uiso calc R 1 . .
H H30B 0.9839 -0.1107 1.1441 0.057 Uiso calc R 1 . .
C C31 1.0176(7) 0.0060(3) 1.1622(5) 0.0479(14) Uani d . 1 . .
H H31A 1.1217 0.0044 1.1477 0.057 Uiso calc R 1 . .
H H31B 0.9684 0.0514 1.1232 0.057 Uiso calc R 1 . .
C C32 1.0214(7) 0.0116(3) 1.2951(5) 0.0492(14) Uani d . 1 . .
C C33 1.2327(7) 0.1813(4) 1.3530(5) 0.0517(15) Uani d . 1 . .
H H33 1.2256 0.1860 1.4333 0.062 Uiso calc R 1 . .
C C34 1.3162(6) 0.2387(3) 1.2971(5) 0.0448(14) Uani d . 1 . .
C C35 1.3416(7) 0.2328(4) 1.1804(5) 0.0580(17) Uani d . 1 . .
H H35 1.3053 0.1904 1.1339 0.070 Uiso calc R 1 . .
C C36 1.4204(8) 0.2895(4) 1.1339(6) 0.071(2) Uani d . 1 . .
H H36 1.4347 0.2840 1.0553 0.085 Uiso calc R 1 . .
C C37 1.4515(8) 0.3568(4) 1.3043(6) 0.0665(19) Uani d . 1 . .
H H37 1.4879 0.4002 1.3482 0.080 Uiso calc R 1 . .
C C38 1.3756(7) 0.3035(4) 1.3600(6) 0.0603(17) Uani d . 1 . .
H H38 1.3640 0.3107 1.4389 0.072 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C8 N1 C9 . . 118.0(5) ?
C13 N2 N3 . . 119.3(5) ?
C13 N2 H2 . . 120.4 ?
N3 N2 H2 . . 120.4 ?
C14 N3 N2 . . 116.1(5) ?
C18 N4 C17 . . 115.7(6) ?
C27 N5 C28 . . 117.0(5) ?
C32 N6 N7 . . 121.2(4) ?
C32 N6 H6 . . 119.4 ?
N7 N6 H6 . . 119.4 ?
C33 N7 N6 . . 116.2(5) ?
C37 N8 C36 . . 114.6(6) ?
C1 O1 C10 . . 117.2(4) ?
C20 O3 C29 . . 116.7(4) ?
H39 O5 H40 . . 106.4 ?
O1 C1 C2 . . 124.6(5) ?
O1 C1 C9 . . 115.8(4) ?
C2 C1 C9 . . 119.5(5) ?
C1 C2 C3 . . 120.2(6) ?
C1 C2 H1 . . 119.9 ?
C3 C2 H1 . . 119.9 ?
C4 C3 C2 . . 121.4(5) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 121.1(6) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C9 . . 117.8(5) ?
C6 C5 C4 . . 123.8(6) ?
C9 C5 C4 . . 118.4(5) ?
C7 C6 C5 . . 120.0(6) ?
C7 C6 H5 . . 120.0 ?
C5 C6 H5 . . 120.0 ?
C6 C7 C8 . . 118.8(6) ?
C6 C7 H7 . . 120.6 ?
C8 C7 H7 . . 120.6 ?
N1 C8 C7 . . 123.9(6) ?
N1 C8 H8 . . 118.1 ?
C7 C8 H8 . . 118.1 ?
N1 C9 C5 . . 121.5(5) ?
N1 C9 C1 . . 119.2(5) ?
C5 C9 C1 . . 119.4(5) ?
O1 C10 C11 . . 107.2(4) ?
O1 C10 H10A . . 110.3 ?
C11 C10 H10A . . 110.3 ?
O1 C10 H10B . . 110.3 ?
C11 C10 H10B . . 110.3 ?
H10A C10 H10B . . 108.5 ?
C12 C11 C10 . . 111.7(5) ?
C12 C11 H11A . . 109.3 ?
C10 C11 H11A . . 109.3 ?
C12 C11 H11B . . 109.3 ?
C10 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C11 C12 C13 . . 113.1(5) ?
C11 C12 H12A . . 109.0 ?
C13 C12 H12A . . 109.0 ?
C11 C12 H12B . . 109.0 ?
C13 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
O2 C13 N2 . . 120.0(5) ?
O2 C13 C12 . . 123.5(6) ?
N2 C13 C12 . . 116.5(5) ?
N3 C14 C15 . . 120.5(5) ?
N3 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C19 C15 C16 . . 117.3(6) ?
C19 C15 C14 . . 122.7(5) ?
C16 C15 C14 . . 120.0(5) ?
C17 C16 C15 . . 119.1(6) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
N4 C17 C16 . . 124.0(7) ?
N4 C17 H17 . . 118.0 ?
C16 C17 H17 . . 118.0 ?
N4 C18 C19 . . 125.2(7) ?
N4 C18 H18 . . 117.4 ?
C19 C18 H18 . . 117.4 ?
C15 C19 C18 . . 118.6(6) ?
C15 C19 H19 . . 120.7 ?
C18 C19 H19 . . 120.7 ?
O3 C20 C21 . . 125.0(5) ?
O3 C20 C28 . . 115.0(5) ?
C21 C20 C28 . . 119.9(5) ?
C20 C21 C22 . . 121.0(6) ?
C20 C21 H21 . . 119.5 ?
C22 C21 H21 . . 119.5 ?
C23 C22 C21 . . 120.5(6) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C22 C23 C24 . . 120.6(6) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C25 C24 C23 . . 122.8(6) ?
C25 C24 C28 . . 117.8(6) ?
C23 C24 C28 . . 119.3(6) ?
C24 C25 C26 . . 120.2(6) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C25 C26 C27 . . 117.7(7) ?
C25 C26 H26 . . 121.2 ?
C27 C26 H26 . . 121.2 ?
N5 C27 C26 . . 125.2(7) ?
N5 C27 H27 . . 117.4 ?
C26 C27 H27 . . 117.4 ?
N5 C28 C24 . . 122.2(6) ?
N5 C28 C20 . . 119.1(5) ?
C24 C28 C20 . . 118.7(5) ?
O3 C29 C30 . . 106.6(4) ?
O3 C29 H29A . . 110.4 ?
C30 C29 H29A . . 110.4 ?
O3 C29 H29B . . 110.4 ?
C30 C29 H29B . . 110.4 ?
H29A C29 H29B . . 108.6 ?
C31 C30 C29 . . 111.8(5) ?
C31 C30 H30A . . 109.2 ?
C29 C30 H30A . . 109.2 ?
C31 C30 H30B . . 109.2 ?
C29 C30 H30B . . 109.2 ?
H30A C30 H30B . . 107.9 ?
C32 C31 C30 . . 112.0(5) ?
C32 C31 H31A . . 109.2 ?
C30 C31 H31A . . 109.2 ?
C32 C31 H31B . . 109.2 ?
C30 C31 H31B . . 109.2 ?
H31A C31 H31B . . 107.9 ?
O4 C32 N6 . . 119.7(5) ?
O4 C32 C31 . . 123.8(6) ?
N6 C32 C31 . . 116.5(5) ?
N7 C33 C34 . . 120.0(5) ?
N7 C33 H33 . . 120.0 ?
C34 C33 H33 . . 120.0 ?
C38 C34 C35 . . 116.0(5) ?
C38 C34 C33 . . 120.6(5) ?
C35 C34 C33 . . 123.4(5) ?
C36 C35 C34 . . 119.9(6) ?
C36 C35 H35 . . 120.0 ?
C34 C35 H35 . . 120.0 ?
N8 C36 C35 . . 124.3(6) ?
N8 C36 H36 . . 117.9 ?
C35 C36 H36 . . 117.9 ?
N8 C37 C38 . . 126.1(6) ?
N8 C37 H37 . . 117.0 ?
C38 C37 H37 . . 117.0 ?
C37 C38 C34 . . 119.0(6) ?
C37 C38 H38 . . 120.5 ?
C34 C38 H38 . . 120.5 ?
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
N1 C8 . 1.314(7) ?
N1 C9 . 1.361(6) ?
N2 C13 . 1.373(8) ?
N2 N3 . 1.368(6) ?
N2 H2 . 0.8600 ?
N3 C14 . 1.277(7) ?
N4 C18 . 1.314(9) ?
N4 C17 . 1.335(9) ?
N5 C27 . 1.306(8) ?
N5 C28 . 1.381(7) ?
N6 C32 . 1.349(7) ?
N6 N7 . 1.371(6) ?
N6 H6 . 0.8600 ?
N7 C33 . 1.278(7) ?
N8 C37 . 1.317(8) ?
N8 C36 . 1.339(9) ?
O1 C1 . 1.359(6) ?
O1 C10 . 1.438(6) ?
O2 C13 . 1.224(7) ?
O3 C20 . 1.354(6) ?
O3 C29 . 1.445(7) ?
O4 C32 . 1.212(7) ?
O5 H39 . 0.8500 ?
O5 H40 . 0.8499 ?
C1 C2 . 1.373(7) ?
C1 C9 . 1.429(7) ?
C2 C3 . 1.400(8) ?
C2 H1 . 0.9300 ?
C3 C4 . 1.342(9) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.414(8) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.402(8) ?
C5 C9 . 1.417(7) ?
C6 C7 . 1.343(9) ?
C6 H5 . 0.9300 ?
C7 C8 . 1.402(9) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C10 C11 . 1.521(7) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.506(8) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.509(7) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C14 C15 . 1.451(8) ?
C14 H14 . 0.9300 ?
C15 C19 . 1.378(8) ?
C15 C16 . 1.391(8) ?
C16 C17 . 1.378(9) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 C19 . 1.382(9) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 C21 . 1.368(7) ?
C20 C28 . 1.425(8) ?
C21 C22 . 1.398(8) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.364(9) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.411(8) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.389(9) ?
C24 C28 . 1.421(7) ?
C25 C26 . 1.377(9) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.410(9) ?
C26 H26 . 0.9300 ?
C27 H27 . 0.9300 ?
C29 C30 . 1.518(7) ?
C29 H29A . 0.9700 ?
C29 H29B . 0.9700 ?
C30 C31 . 1.524(8) ?
C30 H30A . 0.9700 ?
C30 H30B . 0.9700 ?
C31 C32 . 1.507(8) ?
C31 H31A . 0.9700 ?
C31 H31B . 0.9700 ?
C33 C34 . 1.460(8) ?
C33 H33 . 0.9300 ?
C34 C38 . 1.386(8) ?
C34 C35 . 1.389(8) ?
C35 C36 . 1.373(8) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C37 C38 . 1.370(9) ?
C37 H37 . 0.9300 ?
C38 H38 . 0.9300 ?
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
C31 H31B O3 . 0.97 2.55 2.908(7) 102 n
C22 H22 O4 1_554 0.93 2.51 3.224(7) 134 y
C12 H12B O1 . 0.97 2.52 2.900(7) 103 n
C7 H7 N8 2_847 0.93 2.55 3.466(9) 167 y
C3 H3 O2 1_556 0.93 2.52 3.353(7) 150 y
C2 H1 N4 2_656 0.93 2.55 3.390(9) 150 y
O5 H39 O4 2_657 0.85 2.17 2.964(10) 156 y
N6 H6 N1 1_556 0.86 2.10 2.934(6) 163 y
N2 H2 N5 1_554 0.86 2.25 3.077(7) 161 y
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
C13 N2 N3 C14 . . . . -178.6(5) ?
C32 N6 N7 C33 . . . . 179.8(5) ?
C10 O1 C1 C2 . . . . 4.5(8) ?
C10 O1 C1 C9 . . . . -176.7(5) ?
O1 C1 C2 C3 . . . . 179.5(5) ?
C9 C1 C2 C3 . . . . 0.7(8) ?
C1 C2 C3 C4 . . . . 0.4(9) ?
C2 C3 C4 C5 . . . . -0.8(9) ?
C3 C4 C5 C6 . . . . -178.7(6) ?
C3 C4 C5 C9 . . . . 0.1(9) ?
C9 C5 C6 C7 . . . . 0.8(9) ?
C4 C5 C6 C7 . . . . 179.6(6) ?
C5 C6 C7 C8 . . . . -1.5(10) ?
C9 N1 C8 C7 . . . . -0.1(9) ?
C6 C7 C8 N1 . . . . 1.3(11) ?
C8 N1 C9 C5 . . . . -0.7(8) ?
C8 N1 C9 C1 . . . . 179.8(5) ?
C6 C5 C9 N1 . . . . 0.4(8) ?
C4 C5 C9 N1 . . . . -178.5(5) ?
C6 C5 C9 C1 . . . . 179.9(5) ?
C4 C5 C9 C1 . . . . 1.0(8) ?
O1 C1 C9 N1 . . . . -0.8(7) ?
C2 C1 C9 N1 . . . . 178.1(5) ?
O1 C1 C9 C5 . . . . 179.7(5) ?
C2 C1 C9 C5 . . . . -1.4(8) ?
C1 O1 C10 C11 . . . . 179.5(5) ?
O1 C10 C11 C12 . . . . 63.8(6) ?
C10 C11 C12 C13 . . . . -173.9(5) ?
N3 N2 C13 O2 . . . . -176.0(5) ?
N3 N2 C13 C12 . . . . 4.5(8) ?
C11 C12 C13 O2 . . . . -1.8(8) ?
C11 C12 C13 N2 . . . . 177.7(5) ?
N2 N3 C14 C15 . . . . -178.6(5) ?
N3 C14 C15 C19 . . . . 3.4(9) ?
N3 C14 C15 C16 . . . . -177.0(6) ?
C19 C15 C16 C17 . . . . -0.2(9) ?
C14 C15 C16 C17 . . . . -179.8(5) ?
C18 N4 C17 C16 . . . . 1.3(11) ?
C15 C16 C17 N4 . . . . -1.2(10) ?
C17 N4 C18 C19 . . . . 0.0(11) ?
C16 C15 C19 C18 . . . . 1.4(9) ?
C14 C15 C19 C18 . . . . -179.1(6) ?
N4 C18 C19 C15 . . . . -1.3(11) ?
C29 O3 C20 C21 . . . . -1.9(8) ?
C29 O3 C20 C28 . . . . 176.6(5) ?
O3 C20 C21 C22 . . . . -179.2(6) ?
C28 C20 C21 C22 . . . . 2.3(8) ?
C20 C21 C22 C23 . . . . -1.9(9) ?
C21 C22 C23 C24 . . . . 0.9(9) ?
C22 C23 C24 C25 . . . . -178.9(6) ?
C22 C23 C24 C28 . . . . -0.3(9) ?
C23 C24 C25 C26 . . . . 179.4(6) ?
C28 C24 C25 C26 . . . . 0.9(9) ?
C24 C25 C26 C27 . . . . 1.0(10) ?
C28 N5 C27 C26 . . . . 0.3(9) ?
C25 C26 C27 N5 . . . . -1.7(11) ?
C27 N5 C28 C24 . . . . 1.7(8) ?
C27 N5 C28 C20 . . . . -179.9(6) ?
C25 C24 C28 N5 . . . . -2.3(8) ?
C23 C24 C28 N5 . . . . 179.1(5) ?
C25 C24 C28 C20 . . . . 179.3(5) ?
C23 C24 C28 C20 . . . . 0.7(8) ?
O3 C20 C28 N5 . . . . 1.2(7) ?
C21 C20 C28 N5 . . . . 179.9(5) ?
O3 C20 C28 C24 . . . . 179.6(5) ?
C21 C20 C28 C24 . . . . -1.7(8) ?
C20 O3 C29 C30 . . . . 177.7(5) ?
O3 C29 C30 C31 . . . . -64.3(6) ?
C29 C30 C31 C32 . . . . 177.2(5) ?
N7 N6 C32 O4 . . . . 176.0(5) ?
N7 N6 C32 C31 . . . . -5.4(8) ?
C30 C31 C32 O4 . . . . -0.4(8) ?
C30 C31 C32 N6 . . . . -179.0(5) ?
N6 N7 C33 C34 . . . . 180.0(5) ?
N7 C33 C34 C38 . . . . 175.0(6) ?
N7 C33 C34 C35 . . . . -5.0(9) ?
C38 C34 C35 C36 . . . . -0.5(9) ?
C33 C34 C35 C36 . . . . 179.5(6) ?
C37 N8 C36 C35 . . . . -0.9(11) ?
C34 C35 C36 N8 . . . . 0.5(11) ?
C36 N8 C37 C38 . . . . 1.4(10) ?
N8 C37 C38 C34 . . . . -1.5(10) ?
C35 C34 C38 C37 . . . . 0.9(9) ?
C33 C34 C38 C37 . . . . -179.1(5) ?
