##############################################################################
# #
# 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 Acta Crystallographica 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. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
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##############################################################################
data_global
_audit_creation_method 'form.cif (version 2.0)'
_journal_data_validation_number ?
_journal_date_recd_electronic 2012-06-09
_journal_date_accepted 2012-06-20
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2012
_journal_volume 68
_journal_issue 7
_journal_page_first o2185
_journal_page_last o2186
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536812027948
_journal_coeditor_code SU2458
_publ_contact_author_name 'Prof. Tahir, Muhammad Nawaz '
_publ_contact_author_address
;
Department of Physics
University of Sargodha
Punjab, Pakistan
;
_publ_contact_author_email 'dmntahir_uos@yahoo.com, zsrkk@yahoo.com'
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_section_title
;
(E)-4-Amino-N'-(2-hydroxy-5-methylbenzylidene)benzohydrazide
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Kargar, Hadi' .
;
Department of Chemistry,
Payame Noor University,
PO Box 19395-3697 Tehran,
Iran
;
'Kia, Reza'
;
Present address: Structural Dynamics of (Bio)Chemical Systems,
Max Planck Institute for Biophysical Chemistry,
Am Fassberg 11,
37077 G\"ottingen,
Germany
;
;
Department of Chemistry,
Science and Research Branch,
Islamic Azad University,
Tehran,
Iran
;
'Tahir, Muhammad Nawaz' .
;
Department of Physics
University of Sargodha
Punjab, Pakistan
;
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(E)-4-Amino-N'-(2-hydroxy-5-methylbenzylidene)benzohydrazide
;
_chemical_name_common
;
;
_chemical_formula_moiety 'C15 H15 N3 O2'
_chemical_formula_sum 'C15 H15 N3 O2'
_chemical_formula_iupac 'C15 H15 N3 O2'
_chemical_formula_weight 269.30
_chemical_melting_point ?
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.2717(8)
_cell_length_b 11.5668(10)
_cell_length_c 11.9152(9)
_cell_angle_alpha 94.544(3)
_cell_angle_beta 100.583(3)
_cell_angle_gamma 95.880(3)
_cell_volume 1377.28(19)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 1125
_cell_measurement_theta_min 2.45
_cell_measurement_theta_max 27.40
_cell_measurement_temperature 291(2)
_exptl_crystal_description prism
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.24
_exptl_crystal_density_diffrn 1.299
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 568
_exptl_absorpt_coefficient_mu 0.089
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min 0.9739
_exptl_absorpt_correction_T_max 0.9790
_exptl_special_details ?
_diffrn_ambient_temperature 291(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 CCD area-detector
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 21355
_diffrn_reflns_av_R_equivalents 0.0280
_diffrn_reflns_av_sigmaI/netI 0.0313
_diffrn_reflns_theta_min 1.75
_diffrn_reflns_theta_max 27.16
_diffrn_reflns_theta_full 27.16
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 13
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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 6081
_reflns_number_gt 3917
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0788
_refine_ls_R_factor_gt 0.0471
_refine_ls_wR_factor_gt 0.1197
_refine_ls_wR_factor_ref 0.1371
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_refine_ls_number_reflns 6081
_refine_ls_number_parameters 365
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.2031P] 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 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.187
_refine_diff_density_min -0.173
_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'
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement 'SAINT (Bruker, 2005)'
_computing_data_reduction 'SAINT (Bruker, 2005)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.41397(14) 0.93883(14) 0.73216(13) 0.0416(4) Uani d . 1 1 . .
C C2 0.34820(17) 0.95319(16) 0.62200(14) 0.0525(4) Uani d . 1 1 . .
H H2A 0.2819 0.8953 0.5835 0.063 Uiso calc R 1 1 . .
C C3 0.37828(18) 1.04928(17) 0.56949(15) 0.0580(5) Uani d . 1 1 . .
H H3A 0.3332 1.0558 0.4955 0.070 Uiso calc R 1 1 . .
C C4 0.47549(17) 1.13830(16) 0.62444(14) 0.0505(4) Uani d . 1 1 . .
C C5 0.54375(16) 1.12428(15) 0.73354(14) 0.0507(4) Uani d . 1 1 . .
H H5A 0.6107 1.1819 0.7714 0.061 Uiso calc R 1 1 . .
C C6 0.51343(15) 1.02622(15) 0.78609(14) 0.0467(4) Uani d . 1 1 . .
H H6A 0.5604 1.0183 0.8591 0.056 Uiso calc R 1 1 . .
C C7 0.36676(14) 0.83795(14) 0.78761(13) 0.0426(4) Uani d . 1 1 . .
C C8 0.48321(16) 0.68945(14) 1.02368(14) 0.0456(4) Uani d . 1 1 . .
H H8A 0.5691 0.7281 1.0467 0.055 Uiso calc R 1 1 . .
C C9 0.43816(16) 0.59517(14) 1.08529(14) 0.0446(4) Uani d . 1 1 . .
C C10 0.31463(17) 0.52710(15) 1.04709(15) 0.0515(4) Uani d . 1 1 . .
C C11 0.2798(2) 0.43601(16) 1.10815(19) 0.0650(5) Uani d . 1 1 . .
H H11A 0.1992 0.3889 1.0822 0.078 Uiso calc R 1 1 . .
C C12 0.3624(2) 0.41382(16) 1.20672(18) 0.0648(5) Uani d . 1 1 . .
H H12A 0.3353 0.3532 1.2473 0.078 Uiso calc R 1 1 . .
C C13 0.4847(2) 0.47943(16) 1.24696(15) 0.0584(5) Uani d . 1 1 . .
C C14 0.51992(18) 0.56874(15) 1.18424(15) 0.0525(4) Uani d . 1 1 . .
H H14A 0.6023 0.6134 1.2093 0.063 Uiso calc R 1 1 . .
C C15 0.5763(3) 0.4523(2) 1.35265(18) 0.0848(7) Uani d . 1 1 . .
H H15A 0.6484 0.4149 1.3308 0.127 Uiso calc R 1 1 . .
H H15B 0.5276 0.4011 1.3942 0.127 Uiso calc R 1 1 . .
H H15C 0.6115 0.5234 1.4005 0.127 Uiso calc R 1 1 . .
C C16 0.06408(16) 0.30308(14) 0.48957(14) 0.0469(4) Uani d . 1 1 . .
C C17 -0.05809(17) 0.34582(17) 0.48283(16) 0.0572(5) Uani d . 1 1 . .
H H17A -0.1126 0.3465 0.4114 0.069 Uiso calc R 1 1 . .
C C18 -0.1001(2) 0.38722(18) 0.57992(17) 0.0681(5) Uani d . 1 1 . .
H H18A -0.1829 0.4145 0.5733 0.082 Uiso calc R 1 1 . .
C C19 -0.0209(2) 0.38872(19) 0.68691(17) 0.0691(5) Uani d . 1 1 . .
C C20 0.1007(2) 0.3453(2) 0.69390(17) 0.0709(6) Uani d . 1 1 . .
H H20A 0.1551 0.3446 0.7654 0.085 Uiso calc R 1 1 . .
C C21 0.14190(18) 0.30375(17) 0.59809(15) 0.0590(5) Uani d . 1 1 . .
H H21A 0.2241 0.2751 0.6053 0.071 Uiso calc R 1 1 . .
C C22 0.11833(16) 0.26239(15) 0.38986(14) 0.0466(4) Uani d . 1 1 . .
C C23 -0.00670(15) 0.18859(14) 0.09605(14) 0.0458(4) Uani d . 1 1 . .
H H23A -0.0949 0.2024 0.0929 0.055 Uiso calc R 1 1 . .
C C24 0.03676(15) 0.14797(14) -0.00741(13) 0.0433(4) Uani d . 1 1 . .
C C25 0.16631(15) 0.12065(14) -0.00588(14) 0.0454(4) Uani d . 1 1 . .
C C26 0.20213(17) 0.07912(16) -0.10588(16) 0.0576(5) Uani d . 1 1 . .
H H26A 0.2885 0.0610 -0.1046 0.069 Uiso calc R 1 1 . .
C C27 0.11136(18) 0.06414(16) -0.20780(16) 0.0597(5) Uani d . 1 1 . .
H H27A 0.1376 0.0364 -0.2746 0.072 Uiso calc R 1 1 . .
C C28 -0.01883(18) 0.08963(16) -0.21308(15) 0.0557(5) Uani d . 1 1 . .
C C29 -0.05284(16) 0.13124(15) -0.11215(14) 0.0495(4) Uani d . 1 1 . .
H H29A -0.1394 0.1490 -0.1139 0.059 Uiso calc R 1 1 . .
C C30 -0.1168(2) 0.0702(2) -0.32422(16) 0.0785(6) Uani d . 1 1 . .
H H30A -0.1578 0.1401 -0.3377 0.118 Uiso calc R 1 1 . .
H H30B -0.1841 0.0073 -0.3208 0.118 Uiso calc R 1 1 . .
H H30C -0.0715 0.0509 -0.3856 0.118 Uiso calc R 1 1 . .
N N1 0.50273(18) 1.23589(15) 0.57157(14) 0.0716(5) Uani d . 1 1 . .
H H1A 0.4596 1.2425 0.5038 0.086 Uiso calc R 1 1 . .
H H1B 0.5630 1.2907 0.6060 0.086 Uiso calc R 1 1 . .
N N2 0.45092(13) 0.80883(12) 0.88017(11) 0.0473(3) Uani d . 1 1 . .
H H1N2 0.5423 0.8349 0.8962 0.057 Uiso d R 1 1 . .
N N3 0.40512(13) 0.71958(12) 0.93778(12) 0.0474(3) Uani d . 1 1 . .
N N4 -0.0612(2) 0.4296(2) 0.78470(17) 0.1166(8) Uani d . 1 1 . .
H H4A -0.1376 0.4551 0.7801 0.140 Uiso calc R 1 1 . .
H H4B -0.0101 0.4297 0.8506 0.140 Uiso calc R 1 1 . .
N N5 0.03008(13) 0.24063(13) 0.28828(11) 0.0509(4) Uani d . 1 1 . .
H H1N5 -0.0634 0.2399 0.2848 0.061 Uiso d R 1 1 . .
N N6 0.07587(12) 0.20552(12) 0.19168(11) 0.0464(3) Uani d . 1 1 . .
O O1 0.25527(10) 0.78344(11) 0.75600(10) 0.0585(3) Uani d . 1 1 . .
O O2 0.22764(12) 0.54605(12) 0.95216(12) 0.0704(4) Uani d . 1 1 . .
H H2 0.2591 0.6017 0.9231 0.106 Uiso calc R 1 1 . .
O O3 0.23698(11) 0.24990(12) 0.39557(10) 0.0596(3) Uani d . 1 1 . .
O O4 0.25969(10) 0.13154(11) 0.09292(10) 0.0552(3) Uani d . 1 1 . .
H H4 0.2266 0.1546 0.1469 0.083 Uiso calc R 1 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
C1 0.0320(8) 0.0510(10) 0.0423(9) 0.0098(7) 0.0070(7) 0.0025(7)
C2 0.0493(10) 0.0606(11) 0.0427(10) 0.0039(8) -0.0005(8) 0.0006(8)
C3 0.0627(11) 0.0695(13) 0.0394(10) 0.0108(9) 0.0012(8) 0.0074(9)
C4 0.0528(10) 0.0540(11) 0.0490(10) 0.0141(8) 0.0146(8) 0.0099(8)
C5 0.0425(9) 0.0509(10) 0.0554(11) 0.0041(7) 0.0035(8) 0.0024(8)
C6 0.0385(8) 0.0546(10) 0.0448(9) 0.0091(7) 0.0001(7) 0.0065(8)
C7 0.0316(8) 0.0521(10) 0.0436(9) 0.0071(7) 0.0065(7) -0.0001(7)
C8 0.0412(9) 0.0468(9) 0.0474(9) -0.0015(7) 0.0095(7) 0.0034(7)
C9 0.0476(9) 0.0415(9) 0.0466(9) 0.0020(7) 0.0176(8) 0.0011(7)
C10 0.0489(10) 0.0495(10) 0.0574(11) 0.0009(8) 0.0183(9) 0.0002(8)
C11 0.0615(12) 0.0503(11) 0.0861(15) -0.0065(9) 0.0314(11) 0.0020(10)
C12 0.0815(14) 0.0470(11) 0.0766(14) 0.0047(10) 0.0428(12) 0.0118(10)
C13 0.0804(13) 0.0466(10) 0.0548(11) 0.0138(9) 0.0259(10) 0.0076(8)
C14 0.0581(10) 0.0463(10) 0.0529(10) 0.0014(8) 0.0132(8) 0.0041(8)
C15 0.122(2) 0.0713(14) 0.0660(14) 0.0185(13) 0.0191(13) 0.0254(11)
C16 0.0413(9) 0.0496(10) 0.0476(10) -0.0005(7) 0.0056(7) 0.0073(8)
C17 0.0481(10) 0.0683(12) 0.0524(11) 0.0077(9) 0.0026(8) 0.0037(9)
C18 0.0568(11) 0.0783(14) 0.0694(13) 0.0172(10) 0.0118(10) -0.0016(11)
C19 0.0748(14) 0.0764(14) 0.0577(12) 0.0163(11) 0.0172(11) -0.0033(10)
C20 0.0685(13) 0.0935(16) 0.0475(11) 0.0181(11) 0.0021(10) -0.0009(10)
C21 0.0513(10) 0.0749(13) 0.0485(11) 0.0110(9) 0.0023(8) 0.0044(9)
C22 0.0393(9) 0.0522(10) 0.0464(10) -0.0011(7) 0.0042(7) 0.0109(8)
C23 0.0337(8) 0.0553(10) 0.0484(10) 0.0044(7) 0.0071(7) 0.0073(8)
C24 0.0355(8) 0.0450(9) 0.0474(9) -0.0010(7) 0.0053(7) 0.0064(7)
C25 0.0357(8) 0.0454(9) 0.0523(10) -0.0022(7) 0.0055(7) 0.0050(7)
C26 0.0436(9) 0.0596(11) 0.0700(12) 0.0034(8) 0.0177(9) -0.0029(9)
C27 0.0588(11) 0.0628(12) 0.0567(11) -0.0015(9) 0.0187(9) -0.0044(9)
C28 0.0565(11) 0.0569(11) 0.0494(10) -0.0032(8) 0.0057(8) 0.0024(8)
C29 0.0377(8) 0.0581(11) 0.0504(10) 0.0030(7) 0.0037(7) 0.0061(8)
C30 0.0803(14) 0.0929(17) 0.0531(12) -0.0014(12) 0.0007(11) -0.0035(11)
N1 0.0848(12) 0.0661(11) 0.0637(10) 0.0052(9) 0.0104(9) 0.0193(8)
N2 0.0338(7) 0.0550(9) 0.0521(8) -0.0008(6) 0.0053(6) 0.0145(7)
N3 0.0425(7) 0.0497(8) 0.0504(8) -0.0001(6) 0.0121(7) 0.0066(7)
N4 0.1149(17) 0.170(2) 0.0722(13) 0.0597(17) 0.0252(12) -0.0143(14)
N5 0.0348(7) 0.0746(10) 0.0412(8) 0.0023(6) 0.0060(6) 0.0026(7)
N6 0.0358(7) 0.0556(9) 0.0475(8) 0.0006(6) 0.0083(6) 0.0077(6)
O1 0.0343(6) 0.0699(8) 0.0650(8) -0.0040(5) -0.0003(5) 0.0048(6)
O2 0.0516(7) 0.0749(10) 0.0781(9) -0.0115(6) 0.0052(7) 0.0092(7)
O3 0.0382(7) 0.0875(9) 0.0533(7) 0.0084(6) 0.0064(5) 0.0136(6)
O4 0.0332(6) 0.0699(8) 0.0591(8) 0.0054(5) 0.0015(5) 0.0041(6)
_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 C6 . 1.387(2) ?
C1 C2 . 1.392(2) ?
C1 C7 . 1.469(2) ?
C2 C3 . 1.354(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.389(2) ?
C3 H3A . 0.9300 ?
C4 N1 . 1.365(2) ?
C4 C5 . 1.389(2) ?
C5 C6 . 1.374(2) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 O1 . 1.2274(18) ?
C7 N2 . 1.3585(19) ?
C8 N3 . 1.2745(19) ?
C8 C9 . 1.446(2) ?
C8 H8A . 0.9300 ?
C9 C14 . 1.391(2) ?
C9 C10 . 1.401(2) ?
C10 O2 . 1.354(2) ?
C10 C11 . 1.381(3) ?
C11 C12 . 1.375(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.382(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.379(2) ?
C13 C15 . 1.503(3) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C17 . 1.386(2) ?
C16 C21 . 1.389(2) ?
C16 C22 . 1.467(2) ?
C17 C18 . 1.375(3) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.378(3) ?
C18 H18A . 0.9300 ?
C19 N4 . 1.372(3) ?
C19 C20 . 1.384(3) ?
C20 C21 . 1.359(3) ?
C20 H20A . 0.9300 ?
C21 H21A . 0.9300 ?
C22 O3 . 1.2320(19) ?
C22 N5 . 1.361(2) ?
C23 N6 . 1.2773(19) ?
C23 C24 . 1.447(2) ?
C23 H23A . 0.9300 ?
C24 C29 . 1.395(2) ?
C24 C25 . 1.396(2) ?
C25 O4 . 1.3633(18) ?
C25 C26 . 1.376(2) ?
C26 C27 . 1.375(2) ?
C26 H26A . 0.9300 ?
C27 C28 . 1.390(3) ?
C27 H27A . 0.9300 ?
C28 C29 . 1.377(2) ?
C28 C30 . 1.495(2) ?
C29 H29A . 0.9300 ?
C30 H30A . 0.9600 ?
C30 H30B . 0.9600 ?
C30 H30C . 0.9600 ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
N2 N3 . 1.3746(18) ?
N2 H1N2 . 0.9357 ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
N5 N6 . 1.3693(18) ?
N5 H1N5 . 0.9526 ?
O2 H2 . 0.8200 ?
O4 H4 . 0.8200 ?
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 C1 C2 . . 117.47(15) ?
C6 C1 C7 . . 123.98(14) ?
C2 C1 C7 . . 118.34(14) ?
C3 C2 C1 . . 121.66(16) ?
C3 C2 H2A . . 119.2 ?
C1 C2 H2A . . 119.2 ?
C2 C3 C4 . . 120.99(16) ?
C2 C3 H3A . . 119.5 ?
C4 C3 H3A . . 119.5 ?
N1 C4 C3 . . 120.40(16) ?
N1 C4 C5 . . 121.57(17) ?
C3 C4 C5 . . 118.03(16) ?
C6 C5 C4 . . 120.71(16) ?
C6 C5 H5A . . 119.6 ?
C4 C5 H5A . . 119.6 ?
C5 C6 C1 . . 121.12(15) ?
C5 C6 H6A . . 119.4 ?
C1 C6 H6A . . 119.4 ?
O1 C7 N2 . . 120.24(15) ?
O1 C7 C1 . . 122.84(14) ?
N2 C7 C1 . . 116.88(13) ?
N3 C8 C9 . . 119.98(15) ?
N3 C8 H8A . . 120.0 ?
C9 C8 H8A . . 120.0 ?
C14 C9 C10 . . 118.37(15) ?
C14 C9 C8 . . 119.70(15) ?
C10 C9 C8 . . 121.92(15) ?
O2 C10 C11 . . 118.23(16) ?
O2 C10 C9 . . 122.92(16) ?
C11 C10 C9 . . 118.84(17) ?
C12 C11 C10 . . 121.07(18) ?
C12 C11 H11A . . 119.5 ?
C10 C11 H11A . . 119.5 ?
C11 C12 C13 . . 121.56(18) ?
C11 C12 H12A . . 119.2 ?
C13 C12 H12A . . 119.2 ?
C14 C13 C12 . . 116.99(18) ?
C14 C13 C15 . . 121.74(19) ?
C12 C13 C15 . . 121.25(18) ?
C13 C14 C9 . . 123.14(17) ?
C13 C14 H14A . . 118.4 ?
C9 C14 H14A . . 118.4 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C21 . . 117.31(16) ?
C17 C16 C22 . . 124.35(15) ?
C21 C16 C22 . . 118.28(15) ?
C18 C17 C16 . . 121.16(17) ?
C18 C17 H17A . . 119.4 ?
C16 C17 H17A . . 119.4 ?
C17 C18 C19 . . 120.81(18) ?
C17 C18 H18A . . 119.6 ?
C19 C18 H18A . . 119.6 ?
N4 C19 C18 . . 121.6(2) ?
N4 C19 C20 . . 120.3(2) ?
C18 C19 C20 . . 118.12(18) ?
C21 C20 C19 . . 121.11(18) ?
C21 C20 H20A . . 119.4 ?
C19 C20 H20A . . 119.4 ?
C20 C21 C16 . . 121.48(18) ?
C20 C21 H21A . . 119.3 ?
C16 C21 H21A . . 119.3 ?
O3 C22 N5 . . 120.98(16) ?
O3 C22 C16 . . 122.88(15) ?
N5 C22 C16 . . 116.13(14) ?
N6 C23 C24 . . 120.07(14) ?
N6 C23 H23A . . 120.0 ?
C24 C23 H23A . . 120.0 ?
C29 C24 C25 . . 117.95(15) ?
C29 C24 C23 . . 120.09(14) ?
C25 C24 C23 . . 121.93(14) ?
O4 C25 C26 . . 118.01(14) ?
O4 C25 C24 . . 122.05(15) ?
C26 C25 C24 . . 119.92(15) ?
C27 C26 C25 . . 120.60(16) ?
C27 C26 H26A . . 119.7 ?
C25 C26 H26A . . 119.7 ?
C26 C27 C28 . . 121.37(17) ?
C26 C27 H27A . . 119.3 ?
C28 C27 H27A . . 119.3 ?
C29 C28 C27 . . 117.21(16) ?
C29 C28 C30 . . 122.23(18) ?
C27 C28 C30 . . 120.55(18) ?
C28 C29 C24 . . 122.95(16) ?
C28 C29 H29A . . 118.5 ?
C24 C29 H29A . . 118.5 ?
C28 C30 H30A . . 109.5 ?
C28 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C28 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C4 N1 H1A . . 120.0 ?
C4 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C7 N2 N3 . . 117.71(13) ?
C7 N2 H1N2 . . 122.5 ?
N3 N2 H1N2 . . 118.4 ?
C8 N3 N2 . . 118.76(13) ?
C19 N4 H4A . . 120.0 ?
C19 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
C22 N5 N6 . . 118.69(13) ?
C22 N5 H1N5 . . 121.4 ?
N6 N5 H1N5 . . 119.5 ?
C23 N6 N5 . . 118.36(13) ?
C10 O2 H2 . . 109.5 ?
C25 O4 H4 . . 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
C6 C1 C2 C3 . . . . -0.9(2) ?
C7 C1 C2 C3 . . . . 174.06(16) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
C2 C3 C4 N1 . . . . -178.50(17) ?
C2 C3 C4 C5 . . . . 1.9(3) ?
N1 C4 C5 C6 . . . . 178.96(16) ?
C3 C4 C5 C6 . . . . -1.4(3) ?
C4 C5 C6 C1 . . . . -0.2(3) ?
C2 C1 C6 C5 . . . . 1.3(2) ?
C7 C1 C6 C5 . . . . -173.31(15) ?
C6 C1 C7 O1 . . . . 155.69(16) ?
C2 C1 C7 O1 . . . . -18.9(2) ?
C6 C1 C7 N2 . . . . -21.9(2) ?
C2 C1 C7 N2 . . . . 163.53(14) ?
N3 C8 C9 C14 . . . . -174.96(15) ?
N3 C8 C9 C10 . . . . 6.4(2) ?
C14 C9 C10 O2 . . . . 179.69(16) ?
C8 C9 C10 O2 . . . . -1.6(3) ?
C14 C9 C10 C11 . . . . -0.8(2) ?
C8 C9 C10 C11 . . . . 177.92(16) ?
O2 C10 C11 C12 . . . . -178.53(17) ?
C9 C10 C11 C12 . . . . 1.9(3) ?
C10 C11 C12 C13 . . . . -1.8(3) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C11 C12 C13 C15 . . . . -178.03(18) ?
C12 C13 C14 C9 . . . . 0.7(3) ?
C15 C13 C14 C9 . . . . 179.17(17) ?
C10 C9 C14 C13 . . . . -0.5(3) ?
C8 C9 C14 C13 . . . . -179.26(16) ?
C21 C16 C17 C18 . . . . 0.0(3) ?
C22 C16 C17 C18 . . . . -177.14(17) ?
C16 C17 C18 C19 . . . . 0.8(3) ?
C17 C18 C19 N4 . . . . -179.9(2) ?
C17 C18 C19 C20 . . . . -1.3(3) ?
N4 C19 C20 C21 . . . . 179.6(2) ?
C18 C19 C20 C21 . . . . 0.9(3) ?
C19 C20 C21 C16 . . . . 0.0(3) ?
C17 C16 C21 C20 . . . . -0.4(3) ?
C22 C16 C21 C20 . . . . 176.92(18) ?
C17 C16 C22 O3 . . . . 163.12(17) ?
C21 C16 C22 O3 . . . . -14.1(3) ?
C17 C16 C22 N5 . . . . -15.7(2) ?
C21 C16 C22 N5 . . . . 167.10(15) ?
N6 C23 C24 C29 . . . . -178.99(15) ?
N6 C23 C24 C25 . . . . 3.2(2) ?
C29 C24 C25 O4 . . . . -178.41(14) ?
C23 C24 C25 O4 . . . . -0.5(2) ?
C29 C24 C25 C26 . . . . 0.3(2) ?
C23 C24 C25 C26 . . . . 178.13(16) ?
O4 C25 C26 C27 . . . . 178.73(15) ?
C24 C25 C26 C27 . . . . 0.0(3) ?
C25 C26 C27 C28 . . . . -0.4(3) ?
C26 C27 C28 C29 . . . . 0.4(3) ?
C26 C27 C28 C30 . . . . -178.63(17) ?
C27 C28 C29 C24 . . . . -0.1(3) ?
C30 C28 C29 C24 . . . . 178.90(17) ?
C25 C24 C29 C28 . . . . -0.2(2) ?
C23 C24 C29 C28 . . . . -178.10(16) ?
O1 C7 N2 N3 . . . . -1.8(2) ?
C1 C7 N2 N3 . . . . 175.79(13) ?
C9 C8 N3 N2 . . . . -179.45(14) ?
C7 N2 N3 C8 . . . . 178.80(14) ?
O3 C22 N5 N6 . . . . -0.6(2) ?
C16 C22 N5 N6 . . . . 178.23(14) ?
C24 C23 N6 N5 . . . . -178.08(14) ?
C22 N5 N6 C23 . . . . -177.96(14) ?
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
O2 H2 N3 . 0.82 1.89 2.6079(19) 145 y
O4 H4 N6 . 0.82 1.86 2.5826(17) 146 y
N2 H1N2 O4 2_666 0.94 2.01 2.9342(18) 169 y
N5 H1N5 O1 2_566 0.95 1.93 2.8615(17) 167 y
N1 H1A O3 1_565 0.86 2.42 3.149(2) 142 y
C12 H12A O3 1_556 0.93 2.51 3.400(2) 160 y
C17 H17A O1 2_566 0.93 2.53 3.320(2) 143 y