#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2214492.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_2214492
_space_group_IT_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
loop_
_publ_author_name
'T. Liu'
'Z.-W. Wang'
'Y.-X. Wang'
'Z.-P. Xie'
_publ_section_title
;\
(Dihydroxyglyoxime-\k^2^N,N')bis(1,10-phenanthroline-\
\k^2^N,N')manganese(II) dinitrate dihydrate
;
_journal_coeditor_code AT2344
_journal_issue 8
_journal_name_full 'Acta Crystallographica, Section E'
_journal_page_first m2198
_journal_page_last m2199
_journal_volume 63
_journal_year 2007
_chemical_formula_iupac
'[Mn (C12 H8 N2)2 (C2 H4 N2 O4)] (N O3)2, 2H2 O'
_chemical_formula_moiety 'C26 H20 Mn N6 O4 2+, 2(N O3 -), 2(H2 O)'
_chemical_formula_sum 'C26 H24 Mn N8 O12'
_chemical_formula_weight 695.47
_chemical_name_systematic
;
(Dihydroxyglyoxime-\k^2^N,N')bis(1,10-phenanthroline-\
\k^2^N,N')manganese(II) dinitrate dihydrate
;
_symmetry_cell_setting monoclinic
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 96.228(4)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 13.913(2)
_cell_length_b 11.998(5)
_cell_length_c 18.131(3)
_cell_measurement_reflns_used 5592
_cell_measurement_temperature 273(2)
_cell_measurement_theta_max 25.027
_cell_measurement_theta_min 2.118
_cell_volume 3008.6(14)
_computing_cell_refinement 'SAINT (Siemens, 1996)'
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_data_reduction SAINT
_computing_molecular_graphics 'SHELXTL (Siemens, 1996)'
_computing_publication_material SHELXTL
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 273(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type 'Bruker APEX II area-detector'
_diffrn_measurement_method '\f and \w'
_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 0.0411
_diffrn_reflns_av_sigmaI/netI 0.0889
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 20095
_diffrn_reflns_theta_full 26.70
_diffrn_reflns_theta_max 26.70
_diffrn_reflns_theta_min 2.04
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.516
_exptl_absorpt_correction_T_max 0.9124
_exptl_absorpt_correction_T_min 0.8614
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.535
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 1428
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.18
_refine_diff_density_max 0.645
_refine_diff_density_min -0.490
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.988
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 444
_refine_ls_number_reflns 6179
_refine_ls_number_restraints 12
_refine_ls_restrained_S_all 0.996
_refine_ls_R_factor_all 0.0996
_refine_ls_R_factor_gt 0.0512
_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/[\s^2^(Fo^2^)+(0.0806P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1584
_refine_ls_wR_factor_ref 0.1660
_reflns_number_gt 3132
_reflns_number_total 6179
_reflns_threshold_expression I>2sigma(I)
_[local]_cod_data_source_file at2344.cif
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
Mn Mn1 0.77582(4) 0.75577(4) 0.03825(3) 0.03420(19) Uani d . 1
O O1 0.7959(2) 0.9968(2) 0.04742(16) 0.0605(8) Uani d . 1
H H1A 0.8019 0.9977 0.0029 0.091 Uiso calc R 1
O O2 0.8357(2) 0.6023(3) 0.14815(18) 0.0683(9) Uani d . 1
H H2A 0.8150 0.5969 0.1887 0.102 Uiso calc R 1
O O3 0.9306(4) 0.7550(5) 0.2469(3) 0.1472(19) Uani d . 1
H H3A 0.9890 0.7641 0.2467 0.221 Uiso calc R 1
O O4 0.9029(4) 0.9960(4) 0.1826(4) 0.155(2) Uani d . 1
H H4A 0.9502 0.9809 0.2120 0.233 Uiso calc R 1
O O5 0.7738(3) 0.1306(3) 0.9096(2) 0.0962(13) Uani d . 1
O O6 0.8934(2) 0.0146(3) 0.9287(2) 0.0783(10) Uani d . 1
O O7 0.8897(4) 0.1357(4) 0.8427(3) 0.1356(19) Uani d . 1
O O8 0.7404(6) 0.8835(8) 0.2850(4) 0.219(4) Uani d D 1
O O9 0.6159(6) 0.8842(6) 0.3345(4) 0.209(3) Uani d D 1
O O10 0.6416(8) 1.0073(6) 0.2609(6) 0.388(11) Uani d D 1
O O11 0.5552(13) 0.4230(13) 0.1434(9) 0.574(14) Uani d D 1
O O12 0.695(2) 0.3357(18) 0.2000(11) 0.64(2) Uani d D 1
N N1 0.6533(2) 0.7803(3) 0.0767(2) 0.0492(9) Uani d . 1
N N2 0.7067(2) 0.8181(3) -0.05277(19) 0.0453(9) Uani d . 1
N N3 0.7384(2) 0.6057(3) 0.00436(19) 0.0495(9) Uani d . 1
N N4 0.8938(2) 0.7246(3) -0.00697(18) 0.0459(9) Uani d . 1
N N5 0.8376(2) 0.7049(3) 0.1295(2) 0.0490(9) Uani d . 1
N N6 0.8222(2) 0.8935(3) 0.0762(2) 0.0473(9) Uani d . 1
N N7 0.8510(3) 0.0927(4) 0.8919(3) 0.0713(12) Uani d . 1
N N8 0.6670(6) 0.9299(9) 0.2896(5) 0.155(4) Uani d D 1
C C1 0.6298(3) 0.7618(4) 0.1438(3) 0.0601(12) Uani d . 1
H H1 0.6769 0.7353 0.1798 0.072 Uiso calc R 1
C C2 0.5368(4) 0.7804(4) 0.1633(3) 0.0707(14) Uani d . 1
H H2 0.5236 0.7678 0.2118 0.085 Uiso calc R 1
C C3 0.4665(3) 0.8164(4) 0.1125(3) 0.0666(14) Uani d . 1
H H3 0.4042 0.8270 0.1253 0.080 Uiso calc R 1
C C4 0.4872(3) 0.8374(3) 0.0413(3) 0.0570(12) Uani d . 1
C C5 0.4199(3) 0.8792(4) -0.0160(3) 0.0690(14) Uani d . 1
H H5 0.3561 0.8914 -0.0074 0.083 Uiso calc R 1
C C6 0.4483(4) 0.9013(4) -0.0837(3) 0.0729(15) Uani d . 1
H H6 0.4035 0.9295 -0.1208 0.088 Uiso calc R 1
C C7 0.5460(3) 0.8824(4) -0.0996(3) 0.0575(12) Uani d . 1
C C8 0.5799(4) 0.9054(4) -0.1654(3) 0.0720(15) Uani d . 1
H H8 0.5382 0.9344 -0.2043 0.086 Uiso calc R 1
C C9 0.6765(4) 0.8862(4) -0.1753(3) 0.0742(15) Uani d . 1
H H9 0.6999 0.9041 -0.2200 0.089 Uiso calc R 1
C C10 0.7378(3) 0.8397(3) -0.1172(3) 0.0562(12) Uani d . 1
H H10 0.8016 0.8238 -0.1242 0.067 Uiso calc R 1
C C11 0.6126(3) 0.8395(3) -0.0444(2) 0.0468(10) Uani d . 1
C C12 0.5836(3) 0.8180(3) 0.0252(2) 0.0459(10) Uani d . 1
C C13 0.6605(3) 0.5457(4) 0.0147(3) 0.0667(13) Uani d . 1
H H13 0.6140 0.5755 0.0422 0.080 Uiso calc R 1
C C14 0.6478(4) 0.4399(4) -0.0147(3) 0.0818(17) Uani d . 1
H H14 0.5931 0.3993 -0.0065 0.098 Uiso calc R 1
C C15 0.7135(4) 0.3950(4) -0.0549(3) 0.0762(15) Uani d . 1
H H15 0.7036 0.3244 -0.0755 0.091 Uiso calc R 1
C C16 0.7964(3) 0.4549(3) -0.0657(2) 0.0542(12) Uani d . 1
C C17 0.8730(4) 0.4158(4) -0.1057(3) 0.0659(14) Uani d . 1
H H17 0.8670 0.3463 -0.1285 0.079 Uiso calc R 1
C C18 0.9528(4) 0.4755(4) -0.1116(2) 0.0607(13) Uani d . 1
H H18 1.0010 0.4465 -0.1377 0.073 Uiso calc R 1
C C19 0.9653(3) 0.5827(4) -0.0786(2) 0.0488(10) Uani d . 1
C C20 1.0468(3) 0.6503(4) -0.0802(2) 0.0591(12) Uani d . 1
H H20 1.0987 0.6262 -0.1043 0.071 Uiso calc R 1
C C21 1.0498(3) 0.7506(4) -0.0466(2) 0.0591(12) Uani d . 1
H H21 1.1040 0.7957 -0.0478 0.071 Uiso calc R 1
C C22 0.9729(3) 0.7873(3) -0.0101(2) 0.0516(11) Uani d . 1
H H22 0.9765 0.8569 0.0127 0.062 Uiso calc R 1
C C23 0.8909(3) 0.6235(3) -0.0409(2) 0.0461(10) Uani d . 1
C C24 0.8064(3) 0.5585(3) -0.0346(2) 0.0463(10) Uani d . 1
C C25 0.8807(3) 0.7818(4) 0.1722(2) 0.0509(11) Uani d . 1
C C26 0.8680(3) 0.8923(4) 0.1413(3) 0.0533(11) Uani d . 1
H H11A 0.511(3) 0.401(3) 0.111(3) 0.570(13) Uiso d D 1
H H12A 0.674(8) 0.286(4) 0.228(5) 0.64(3) Uiso d D 1
H H11B 0.5599(19) 0.4908(14) 0.1538(16) 0.573(7) Uiso d D 1
H H12B 0.731(2) 0.307(3) 0.1701(18) 0.642(10) Uiso d D 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
Mn1 0.0323(3) 0.0334(3) 0.0362(3) 0.0025(3) 0.0005(2) -0.0023(3)
O1 0.075(2) 0.0436(17) 0.061(2) 0.0081(14) -0.0009(18) 0.0001(15)
O2 0.075(2) 0.063(2) 0.066(2) 0.0010(16) 0.0004(18) 0.0183(17)
O3 0.143(4) 0.182(5) 0.106(4) 0.004(4) -0.031(3) 0.020(3)
O4 0.175(6) 0.125(4) 0.155(5) -0.013(3) -0.026(4) -0.042(4)
O5 0.067(2) 0.104(3) 0.120(3) 0.020(2) 0.021(2) 0.006(2)
O6 0.078(2) 0.059(2) 0.096(3) 0.0090(18) 0.003(2) 0.018(2)
O7 0.134(4) 0.147(4) 0.136(4) 0.028(3) 0.058(3) 0.064(3)
O8 0.168(6) 0.293(10) 0.204(8) -0.064(7) 0.058(6) -0.083(6)
O9 0.229(9) 0.218(8) 0.175(7) 0.002(6) 0.000(6) -0.022(6)
O10 0.55(2) 0.142(6) 0.380(14) -0.070(8) -0.355(14) 0.128(7)
O11 0.55(3) 0.76(3) 0.48(3) 0.09(3) 0.39(2) 0.16(2)
O12 0.56(3) 0.94(5) 0.40(3) 0.04(3) -0.09(2) -0.40(3)
N1 0.048(2) 0.044(2) 0.055(2) 0.0009(15) 0.0006(18) -0.0012(17)
N2 0.052(2) 0.039(2) 0.044(2) 0.0024(15) 0.0001(17) -0.0074(16)
N3 0.046(2) 0.048(2) 0.054(2) -0.0017(17) 0.0016(17) -0.0013(18)
N4 0.046(2) 0.040(2) 0.050(2) 0.0034(15) -0.0021(16) -0.0018(16)
N5 0.046(2) 0.047(2) 0.054(2) 0.0020(16) 0.0027(17) 0.0055(19)
N6 0.045(2) 0.046(2) 0.050(2) 0.0041(16) 0.0028(17) 0.0006(17)
N7 0.063(3) 0.069(3) 0.082(4) -0.006(2) 0.010(2) 0.010(3)
N8 0.108(6) 0.245(12) 0.116(7) -0.070(7) 0.031(5) -0.083(7)
C1 0.055(3) 0.074(3) 0.052(3) 0.007(2) 0.007(2) 0.009(3)
C2 0.061(3) 0.082(4) 0.070(4) 0.006(3) 0.013(3) -0.003(3)
C3 0.049(3) 0.068(3) 0.086(4) -0.004(2) 0.022(3) -0.012(3)
C4 0.044(3) 0.046(3) 0.079(4) 0.002(2) -0.002(2) -0.010(2)
C5 0.048(3) 0.067(3) 0.090(4) 0.007(2) -0.003(3) -0.006(3)
C6 0.061(3) 0.061(3) 0.090(4) 0.012(2) -0.022(3) -0.004(3)
C7 0.061(3) 0.052(3) 0.057(3) 0.005(2) -0.009(2) -0.003(2)
C8 0.077(4) 0.064(3) 0.069(4) 0.012(3) -0.019(3) -0.002(3)
C9 0.108(5) 0.058(3) 0.053(3) 0.002(3) -0.005(3) -0.006(3)
C10 0.070(3) 0.053(3) 0.045(3) 0.002(2) 0.002(2) -0.003(2)
C11 0.047(3) 0.038(2) 0.052(3) 0.0021(19) -0.005(2) -0.001(2)
C12 0.042(2) 0.038(2) 0.056(3) 0.0024(18) 0.000(2) -0.003(2)
C13 0.055(3) 0.052(3) 0.094(4) -0.009(2) 0.010(3) -0.004(3)
C14 0.066(3) 0.054(3) 0.125(5) -0.015(3) 0.012(3) -0.009(3)
C15 0.078(4) 0.047(3) 0.101(5) -0.006(3) -0.002(3) -0.015(3)
C16 0.064(3) 0.039(2) 0.057(3) 0.005(2) -0.005(2) -0.003(2)
C17 0.093(4) 0.053(3) 0.049(3) 0.018(3) -0.005(3) -0.007(2)
C18 0.077(3) 0.058(3) 0.046(3) 0.021(3) 0.002(2) -0.006(2)
C19 0.050(3) 0.054(3) 0.041(3) 0.013(2) 0.000(2) 0.004(2)
C20 0.054(3) 0.073(3) 0.052(3) 0.015(2) 0.012(2) 0.003(3)
C21 0.048(3) 0.068(3) 0.062(3) -0.001(2) 0.006(2) 0.003(3)
C22 0.044(3) 0.051(2) 0.059(3) 0.000(2) 0.002(2) -0.003(2)
C23 0.047(2) 0.046(2) 0.043(3) 0.007(2) -0.0049(19) 0.003(2)
C24 0.053(3) 0.042(2) 0.042(3) 0.009(2) -0.002(2) 0.000(2)
C25 0.045(2) 0.060(3) 0.046(3) 0.004(2) -0.001(2) 0.002(2)
C26 0.052(3) 0.057(3) 0.051(3) -0.002(2) 0.001(2) -0.011(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 N1 1.933(3) yes
Mn1 N2 1.966(3) yes
Mn1 N3 1.955(3) yes
Mn1 N4 1.949(3) yes
Mn1 N5 1.881(4) yes
Mn1 N6 1.877(3) yes
O1 N6 1.378(4) ?
O1 H1A 0.8200 ?
O2 N5 1.278(4) ?
O2 H2A 0.8200 ?
O3 C25 1.488(6) ?
O3 H3A 0.8200 ?
O4 C26 1.505(6) ?
O4 H4A 0.8200 ?
O5 N7 1.240(5) ?
O6 N7 1.259(5) ?
O7 N7 1.207(5) ?
O8 N8 1.174(9) ?
O9 N8 1.262(8) ?
O10 N8 1.104(11) ?
O11 H11A 0.85(5) ?
O11 H11B 0.836(10) ?
O12 H12A 0.86(8) ?
O12 H12B 0.85(4) ?
N1 C1 1.313(5) ?
N1 C12 1.349(5) ?
N2 C10 1.315(5) ?
N2 C11 1.358(5) ?
N3 C13 1.331(5) ?
N3 C24 1.363(5) ?
N4 C22 1.340(5) ?
N4 C23 1.358(5) ?
N5 C25 1.308(5) ?
N6 C26 1.280(5) ?
C1 C2 1.395(6) ?
C1 H1 0.9300 ?
C2 C3 1.339(7) ?
C2 H2 0.9300 ?
C3 C4 1.376(6) ?
C3 H3 0.9300 ?
C4 C5 1.414(6) ?
C4 C12 1.421(5) ?
C5 C6 1.355(7) ?
C5 H5 0.9300 ?
C6 C7 1.437(7) ?
C6 H6 0.9300 ?
C7 C8 1.359(6) ?
C7 C11 1.387(6) ?
C8 C9 1.395(7) ?
C8 H8 0.9300 ?
C9 C10 1.398(6) ?
C9 H9 0.9300 ?
C10 H10 0.9300 ?
C11 C12 1.390(6) ?
C13 C14 1.380(6) ?
C13 H13 0.9300 ?
C14 C15 1.342(6) ?
C14 H14 0.9300 ?
C15 C16 1.390(6) ?
C15 H15 0.9300 ?
C16 C24 1.366(5) ?
C16 C17 1.432(6) ?
C17 C18 1.335(6) ?
C17 H17 0.9300 ?
C18 C19 1.420(6) ?
C18 H18 0.9300 ?
C19 C23 1.390(5) ?
C19 C20 1.397(6) ?
C20 C21 1.348(6) ?
C20 H20 0.9300 ?
C21 C22 1.389(5) ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
C23 C24 1.427(5) ?
C25 C26 1.443(6) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 Mn1 N2 82.79(15) yes
N1 Mn1 N3 92.23(14) yes
N1 Mn1 N4 175.49(14) yes
N1 Mn1 N5 93.95(15) yes
N1 Mn1 N6 90.86(14) yes
N2 Mn1 N3 89.86(13) yes
N2 Mn1 N4 94.46(14) yes
N2 Mn1 N5 175.53(14) yes
N2 Mn1 N6 95.16(14) yes
N3 Mn1 N4 84.17(14) yes
N3 Mn1 N5 93.32(15) yes
N3 Mn1 N6 174.40(14) yes
N4 Mn1 N5 88.99(14) yes
N4 Mn1 N6 92.95(13) yes
N5 Mn1 N6 81.81(15) yes
N6 O1 H1A 109.5 ?
N5 O2 H2A 109.5 ?
C25 O3 H3A 109.5 ?
C26 O4 H4A 109.5 ?
H11A O11 H11B 120(3) ?
H12A O12 H12B 111(7) ?
C1 N1 C12 117.7(4) ?
C1 N1 Mn1 128.8(3) ?
C12 N1 Mn1 113.4(3) ?
C10 N2 C11 118.5(4) ?
C10 N2 Mn1 130.0(3) ?
C11 N2 Mn1 111.6(3) ?
C13 N3 C24 118.0(4) ?
C13 N3 Mn1 130.3(3) ?
C24 N3 Mn1 111.7(3) ?
C22 N4 C23 117.8(4) ?
C22 N4 Mn1 130.0(3) ?
C23 N4 Mn1 112.1(3) ?
O2 N5 C25 122.9(4) ?
O2 N5 Mn1 121.7(3) ?
C25 N5 Mn1 115.4(3) ?
C26 N6 O1 116.4(3) ?
C26 N6 Mn1 116.5(3) ?
O1 N6 Mn1 125.9(3) ?
O7 N7 O5 120.2(5) ?
O7 N7 O6 119.3(5) ?
O5 N7 O6 120.3(5) ?
O10 N8 O8 127.0(11) ?
O10 N8 O9 119.7(11) ?
O8 N8 O9 113.3(11) ?
N1 C1 C2 122.6(4) ?
N1 C1 H1 118.7 ?
C2 C1 H1 118.7 ?
C3 C2 C1 120.4(5) ?
C3 C2 H2 119.8 ?
C1 C2 H2 119.8 ?
C2 C3 C4 119.5(5) ?
C2 C3 H3 120.3 ?
C4 C3 H3 120.3 ?
C3 C4 C5 124.4(5) ?
C3 C4 C12 117.4(4) ?
C5 C4 C12 118.2(5) ?
C6 C5 C4 120.0(5) ?
C6 C5 H5 120.0 ?
C4 C5 H5 120.0 ?
C5 C6 C7 121.7(5) ?
C5 C6 H6 119.2 ?
C7 C6 H6 119.2 ?
C8 C7 C11 116.2(5) ?
C8 C7 C6 124.7(5) ?
C11 C7 C6 119.1(5) ?
C7 C8 C9 120.7(5) ?
C7 C8 H8 119.6 ?
C9 C8 H8 119.6 ?
C8 C9 C10 119.1(5) ?
C8 C9 H9 120.4 ?
C10 C9 H9 120.4 ?
N2 C10 C9 121.0(5) ?
N2 C10 H10 119.5 ?
C9 C10 H10 119.5 ?
N2 C11 C7 124.4(4) ?
N2 C11 C12 116.4(4) ?
C7 C11 C12 119.1(4) ?
N1 C12 C11 115.6(4) ?
N1 C12 C4 122.5(4) ?
C11 C12 C4 121.9(4) ?
N3 C13 C14 121.0(5) ?
N3 C13 H13 119.5 ?
C14 C13 H13 119.5 ?
C15 C14 C13 120.9(5) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 119.5(5) ?
C14 C15 H15 120.2 ?
C16 C15 H15 120.2 ?
C24 C16 C15 117.5(4) ?
C24 C16 C17 117.3(4) ?
C15 C16 C17 125.2(4) ?
C18 C17 C16 122.3(4) ?
C18 C17 H17 118.8 ?
C16 C17 H17 118.8 ?
C17 C18 C19 121.2(4) ?
C17 C18 H18 119.4 ?
C19 C18 H18 119.4 ?
C23 C19 C20 117.0(4) ?
C23 C19 C18 117.5(4) ?
C20 C19 C18 125.5(4) ?
C21 C20 C19 119.7(4) ?
C21 C20 H20 120.1 ?
C19 C20 H20 120.1 ?
C20 C21 C22 120.7(4) ?
C20 C21 H21 119.7 ?
C22 C21 H21 119.7 ?
N4 C22 C21 121.4(4) ?
N4 C22 H22 119.3 ?
C21 C22 H22 119.3 ?
N4 C23 C19 123.4(4) ?
N4 C23 C24 115.9(4) ?
C19 C23 C24 120.7(4) ?
N3 C24 C16 123.1(4) ?
N3 C24 C23 116.0(4) ?
C16 C24 C23 120.9(4) ?
N5 C25 C26 112.9(4) ?
N5 C25 O3 121.7(4) ?
C26 C25 O3 125.2(4) ?
N6 C26 C25 113.3(4) ?
N6 C26 O4 123.5(4) ?
C25 C26 O4 123.2(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
_geom_hbond_publ_flag
O1 H1A N2 . 0.82 2.67 2.991(4) 105 yes
O2 H2A O3 . 0.82 2.63 2.791(7) 93 yes
C1 H1 N5 . 0.93 2.53 3.009(5) 112 yes
C13 H13 N1 . 0.93 2.58 3.037(6) 111 yes
C22 H22 N6 . 0.93 2.58 3.030(5) 110 yes
O1 H1A O5 1_564 0.82 2.33 2.958(5) 134 yes
O1 H1A O6 1_564 0.82 1.96 2.674(5) 145 yes
C3 H3 O5 3_666 0.93 2.54 3.385(6) 151 yes
C5 H5 O1 3_675 0.93 2.54 3.344(6) 145 yes
C18 H18 O2 3_765 0.93 2.37 3.225(6) 152 yes
C22 H22 O6 3_766 0.93 2.52 3.269(6) 137 yes
C15 H15 O5 1_554 0.93 2.55 3.361(6) 146 yes