#------------------------------------------------------------------------------
#$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $
#$Revision: 326 $
#$URL: svn://www.crystallography.net/cod/cif/2/2214262.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_2214262
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')copper(II) dinitrate dihydrate
;
_journal_coeditor_code HK2273
_journal_issue 7
_journal_name_full 'Acta Crystallographica, Section E'
_journal_page_first m1887
_journal_page_last m1888
_journal_volume 63
_journal_year 2007
_chemical_formula_iupac
'[Cu (C12 H8 N2)2 (C2 H4 N2 O4)] (N O3)2, 2H2 O'
_chemical_formula_moiety 'C26 H20 Cu N6 O4 2+, 2(N O3 -), 2(H2 O)'
_chemical_formula_sum 'C26 H24 Cu N8 O12'
_chemical_formula_weight 704.07
_chemical_name_systematic
;
(Dihydroxyglyoxime-\k^2^N,N')bis(1,10-phenanthroline-\k^2^N,N')copper(II)
dinitrate dihydrate
;
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90
_cell_angle_beta 95.897(5)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 13.9108(7)
_cell_length_b 12.011(3)
_cell_length_c 18.338(4)
_cell_measurement_reflns_used 5663
_cell_measurement_temperature 273(2)
_cell_measurement_theta_max 24.867
_cell_measurement_theta_min 2.218
_cell_volume 3047.8(10)
_computing_cell_refinement APEX2
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_data_reduction APEX2
_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 APEXII 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 0.0407
_diffrn_reflns_av_sigmaI/netI 0.0861
_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 19706
_diffrn_reflns_theta_full 26.35
_diffrn_reflns_theta_max 26.35
_diffrn_reflns_theta_min 2.03
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.793
_exptl_absorpt_correction_T_max 0.8711
_exptl_absorpt_correction_T_min 0.7980
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour blue
_exptl_crystal_density_diffrn 1.534
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 1444
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.18
_refine_diff_density_max 0.785
_refine_diff_density_min -0.606
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.998
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 444
_refine_ls_number_reflns 6028
_refine_ls_number_restraints 12
_refine_ls_restrained_S_all 1.004
_refine_ls_R_factor_all 0.0808
_refine_ls_R_factor_gt 0.0450
_refine_ls_shift/su_max 0.005
_refine_ls_shift/su_mean 0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0966P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1590
_refine_ls_wR_factor_ref 0.1670
_reflns_number_gt 3118
_reflns_number_total 6028
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file hk2273.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'
Cu Cu 0.3201 1.2651 '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
Cu Cu1 0.77579(4) 0.75553(5) 0.03828(3) 0.0432(2) Uani d . 1
O O1 0.7961(3) 0.9961(3) 0.04774(18) 0.0483(9) Uani d . 1
H H1A 0.8000 0.9954 0.0034 0.072 Uiso calc R 1
O O2 0.8338(3) 0.6031(3) 0.1481(2) 0.0563(10) Uani d . 1
H H2A 0.8712 0.5921 0.1850 0.085 Uiso calc R 1
O O3 0.9324(4) 0.7551(5) 0.2458(3) 0.1201(19) Uani d . 1
H H3A 0.9908 0.7545 0.2431 0.180 Uiso calc R 1
O O4 0.9039(5) 0.9954(5) 0.1835(4) 0.133(2) Uani d . 1
H H4A 0.9520 0.9796 0.2111 0.199 Uiso calc R 1
O O5 0.7739(3) 0.1302(3) 0.9096(3) 0.0814(13) Uani d . 1
O O6 0.8930(3) 0.0159(3) 0.9283(2) 0.0641(11) Uani d . 1
O O7 0.8887(4) 0.1343(4) 0.8437(3) 0.116(2) Uani d . 1
O O8 0.7394(6) 0.8785(7) 0.2880(4) 0.166(3) Uani d D 1
O O9 0.6158(7) 0.8835(7) 0.3358(5) 0.184(3) Uani d D 1
O O10 0.6387(9) 1.0077(7) 0.2627(6) 0.345(11) Uani d D 1
O O11 0.5584(13) 0.4277(14) 0.1452(12) 0.497(14) Uani d D 1
O O12 0.701(2) 0.340(2) 0.2000(12) 0.59(2) Uani d D 1
N N1 0.6533(3) 0.7801(3) 0.0767(2) 0.0376(9) Uani d . 1
N N2 0.7067(3) 0.8187(3) -0.0534(2) 0.0355(9) Uani d . 1
N N3 0.7384(3) 0.6056(3) 0.0042(2) 0.0396(9) Uani d . 1
N N4 0.8936(2) 0.7245(3) -0.0073(2) 0.0343(9) Uani d . 1
N N5 0.8376(3) 0.7047(3) 0.1298(2) 0.0391(9) Uani d . 1
N N6 0.8219(2) 0.8937(3) 0.0767(2) 0.0350(9) Uani d . 1
N N7 0.8515(3) 0.0921(4) 0.8922(3) 0.0569(12) Uani d . 1
N N8 0.6658(6) 0.9287(9) 0.2899(5) 0.130(4) Uani d D 1
C C1 0.6305(4) 0.7620(4) 0.1432(3) 0.0491(13) Uani d . 1
H H1 0.6778 0.7368 0.1789 0.059 Uiso calc R 1
C C2 0.5357(4) 0.7800(5) 0.1620(3) 0.0604(15) Uani d . 1
H H2 0.5213 0.7658 0.2095 0.072 Uiso calc R 1
C C3 0.4666(4) 0.8173(4) 0.1120(3) 0.0557(15) Uani d . 1
H H3 0.4044 0.8291 0.1248 0.067 Uiso calc R 1
C C4 0.4874(3) 0.8387(4) 0.0409(3) 0.0461(13) Uani d . 1
C C5 0.4204(4) 0.8802(4) -0.0169(4) 0.0583(15) Uani d . 1
H H5 0.3566 0.8924 -0.0081 0.070 Uiso calc R 1
C C6 0.4477(4) 0.9023(4) -0.0846(4) 0.0615(16) Uani d . 1
H H6 0.4025 0.9298 -0.1211 0.074 Uiso calc R 1
C C7 0.5462(4) 0.8834(4) -0.1004(3) 0.0497(13) Uani d . 1
C C8 0.5808(4) 0.9063(4) -0.1659(3) 0.0594(15) Uani d . 1
H H8 0.5398 0.9356 -0.2044 0.071 Uiso calc R 1
C C9 0.6761(5) 0.8862(4) -0.1748(3) 0.0598(15) Uani d . 1
H H9 0.7001 0.9030 -0.2190 0.072 Uiso calc R 1
C C10 0.7367(4) 0.8403(4) -0.1171(3) 0.0464(13) Uani d . 1
H H10 0.8006 0.8247 -0.1242 0.056 Uiso calc R 1
C C11 0.6124(3) 0.8403(3) -0.0443(3) 0.0398(12) Uani d . 1
C C12 0.5832(3) 0.8180(3) 0.0253(3) 0.0371(11) Uani d . 1
C C13 0.6609(4) 0.5462(4) 0.0146(3) 0.0554(14) Uani d . 1
H H13 0.6147 0.5761 0.0422 0.066 Uiso calc R 1
C C14 0.6468(4) 0.4405(5) -0.0147(4) 0.0681(18) Uani d . 1
H H14 0.5913 0.4008 -0.0069 0.082 Uiso calc R 1
C C15 0.7131(4) 0.3945(4) -0.0545(3) 0.0674(17) Uani d . 1
H H15 0.7034 0.3235 -0.0741 0.081 Uiso calc R 1
C C16 0.7968(4) 0.4544(4) -0.0662(3) 0.0447(12) Uani d . 1
C C17 0.8721(4) 0.4155(4) -0.1062(3) 0.0511(14) Uani d . 1
H H17 0.8655 0.3468 -0.1296 0.061 Uiso calc R 1
C C18 0.9512(4) 0.4742(4) -0.1111(3) 0.0533(14) Uani d . 1
H H18 0.9997 0.4447 -0.1366 0.064 Uiso calc R 1
C C19 0.9650(3) 0.5830(4) -0.0780(3) 0.0415(12) Uani d . 1
C C20 1.0481(4) 0.6512(4) -0.0796(3) 0.0487(13) Uani d . 1
H H20 1.1003 0.6273 -0.1034 0.058 Uiso calc R 1
C C21 1.0500(3) 0.7503(4) -0.0464(3) 0.0479(12) Uani d . 1
H H21 1.1040 0.7957 -0.0474 0.057 Uiso calc R 1
C C22 0.9725(3) 0.7865(4) -0.0103(3) 0.0429(12) Uani d . 1
H H22 0.9758 0.8560 0.0122 0.051 Uiso calc R 1
C C23 0.8906(3) 0.6243(4) -0.0405(2) 0.0367(11) Uani d . 1
C C24 0.8064(3) 0.5595(4) -0.0348(2) 0.0367(11) Uani d . 1
C C25 0.8804(3) 0.7815(4) 0.1715(3) 0.0401(11) Uani d . 1
C C26 0.8672(3) 0.8918(4) 0.1413(3) 0.0430(12) Uani d . 1
H H11A 0.514(4) 0.400(3) 0.116(3) 0.500(16) Uiso d D 1
H H12A 0.673(10) 0.286(4) 0.220(6) 0.59(5) Uiso d D 1
H H11B 0.557(2) 0.4964(15) 0.1531(19) 0.450(8) Uiso d D 1
H H12B 0.729(3) 0.317(3) 0.1644(18) 0.587(12) 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
Cu1 0.0397(4) 0.0421(4) 0.0469(4) 0.0020(3) 0.0012(3) -0.0024(3)
O1 0.060(2) 0.0367(18) 0.047(2) 0.0085(15) 0.0012(18) -0.0016(16)
O2 0.059(2) 0.050(2) 0.057(3) 0.0037(17) -0.0072(18) 0.0168(18)
O3 0.106(4) 0.149(5) 0.097(4) 0.000(4) -0.027(3) 0.018(3)
O4 0.148(6) 0.112(4) 0.133(6) -0.017(4) -0.010(4) -0.042(4)
O5 0.059(3) 0.079(3) 0.107(4) 0.012(2) 0.016(3) 0.008(3)
O6 0.064(2) 0.051(2) 0.076(3) 0.0083(19) 0.004(2) 0.014(2)
O7 0.117(4) 0.116(4) 0.124(5) 0.031(3) 0.054(4) 0.053(4)
O8 0.149(6) 0.189(8) 0.158(7) -0.025(6) 0.007(6) -0.034(5)
O9 0.222(10) 0.186(8) 0.142(7) 0.006(7) 0.009(6) -0.017(6)
O10 0.49(2) 0.122(7) 0.349(15) -0.081(8) -0.327(14) 0.109(8)
O11 0.46(3) 0.62(3) 0.47(3) 0.05(3) 0.35(3) 0.10(3)
O12 0.48(3) 0.94(6) 0.34(3) -0.12(3) 0.01(2) -0.40(3)
N1 0.037(2) 0.034(2) 0.042(3) 0.0023(16) 0.0026(18) -0.0003(18)
N2 0.040(2) 0.030(2) 0.035(3) 0.0036(16) -0.0011(18) -0.0033(18)
N3 0.035(2) 0.034(2) 0.049(3) -0.0009(17) 0.0014(19) -0.0016(19)
N4 0.031(2) 0.031(2) 0.040(2) 0.0034(15) -0.0023(16) -0.0020(17)
N5 0.035(2) 0.040(2) 0.042(3) 0.0049(18) 0.0047(18) 0.006(2)
N6 0.034(2) 0.031(2) 0.040(3) 0.0020(16) 0.0013(18) -0.0020(18)
N7 0.051(3) 0.054(3) 0.067(4) -0.007(2) 0.011(3) 0.009(3)
N8 0.084(6) 0.195(11) 0.108(7) -0.026(6) 0.003(5) -0.081(8)
C1 0.043(3) 0.058(3) 0.046(3) 0.008(2) 0.005(2) 0.006(3)
C2 0.053(3) 0.070(4) 0.060(4) 0.001(3) 0.016(3) -0.002(3)
C3 0.037(3) 0.056(3) 0.077(5) -0.002(2) 0.016(3) -0.016(3)
C4 0.037(3) 0.032(3) 0.068(4) -0.002(2) -0.002(3) -0.009(3)
C5 0.036(3) 0.050(3) 0.087(5) 0.004(2) -0.003(3) -0.006(3)
C6 0.051(3) 0.045(3) 0.084(5) 0.010(3) -0.020(3) -0.007(3)
C7 0.053(3) 0.038(3) 0.054(4) 0.001(2) -0.014(3) -0.006(3)
C8 0.075(4) 0.048(3) 0.050(4) 0.011(3) -0.016(3) -0.001(3)
C9 0.092(5) 0.045(3) 0.040(4) -0.003(3) -0.004(3) -0.001(3)
C10 0.060(3) 0.041(3) 0.038(3) 0.004(2) 0.003(3) -0.005(2)
C11 0.043(3) 0.027(2) 0.047(3) 0.002(2) -0.009(2) -0.001(2)
C12 0.034(3) 0.030(2) 0.047(3) 0.0008(19) 0.000(2) -0.005(2)
C13 0.043(3) 0.045(3) 0.079(4) -0.004(2) 0.008(3) -0.005(3)
C14 0.053(4) 0.045(3) 0.107(5) -0.013(3) 0.007(3) -0.011(3)
C15 0.070(4) 0.035(3) 0.093(5) -0.009(3) -0.008(4) -0.012(3)
C16 0.052(3) 0.033(3) 0.046(3) 0.006(2) -0.010(2) -0.001(2)
C17 0.072(4) 0.037(3) 0.042(3) 0.009(3) -0.003(3) -0.007(2)
C18 0.075(4) 0.051(3) 0.033(3) 0.031(3) 0.001(3) -0.006(3)
C19 0.046(3) 0.047(3) 0.031(3) 0.013(2) -0.002(2) 0.004(2)
C20 0.043(3) 0.063(4) 0.041(3) 0.013(3) 0.008(2) 0.005(3)
C21 0.037(3) 0.060(3) 0.047(3) -0.003(3) 0.004(2) 0.003(3)
C22 0.042(3) 0.039(3) 0.047(3) 0.003(2) 0.000(2) -0.003(2)
C23 0.038(3) 0.038(3) 0.033(3) 0.007(2) -0.005(2) 0.002(2)
C24 0.042(3) 0.032(2) 0.034(3) 0.005(2) -0.004(2) 0.000(2)
C25 0.039(3) 0.049(3) 0.032(3) 0.002(2) 0.001(2) 0.002(2)
C26 0.042(3) 0.043(3) 0.043(3) -0.002(2) 0.005(2) -0.013(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 1.933(4) yes
Cu1 N2 1.999(4) yes
Cu1 N3 1.959(4) yes
Cu1 N4 1.950(3) yes
Cu1 N5 1.906(4) yes
Cu1 N6 1.889(4) yes
O1 N6 1.372(4) ?
O1 H1A 0.8200 ?
O2 N5 1.269(5) ?
O2 H2A 0.8200 ?
O3 C25 1.509(6) ?
O3 H3A 0.8200 ?
O4 C26 1.525(6) ?
O4 H4A 0.8200 ?
O5 N7 1.244(5) ?
O6 N7 1.237(5) ?
O7 N7 1.188(6) ?
O8 N8 1.192(9) ?
O9 N8 1.268(9) ?
O10 N8 1.119(10) ?
O11 H11A 0.84(5) ?
O11 H11B 0.84(3) ?
O12 H12A 0.86(9) ?
O12 H12B 0.84(4) ?
N1 C1 1.309(6) ?
N1 C12 1.363(6) ?
N2 C10 1.305(6) ?
N2 C11 1.365(5) ?
N3 C13 1.323(6) ?
N3 C24 1.360(5) ?
N4 C22 1.332(6) ?
N4 C23 1.348(5) ?
N5 C25 1.302(6) ?
N6 C26 1.284(6) ?
C1 C2 1.414(7) ?
C1 H1 0.9300 ?
C2 C3 1.336(8) ?
C2 H2 0.9300 ?
C3 C4 1.388(7) ?
C3 H3 0.9300 ?
C4 C12 1.414(6) ?
C4 C5 1.428(7) ?
C5 C6 1.361(8) ?
C5 H5 0.9300 ?
C6 C7 1.448(7) ?
C6 H6 0.9300 ?
C7 C8 1.365(7) ?
C7 C11 1.408(7) ?
C8 C9 1.374(7) ?
C8 H8 0.9300 ?
C9 C10 1.397(7) ?
C9 H9 0.9300 ?
C10 H10 0.9300 ?
C11 C12 1.403(6) ?
C13 C14 1.384(7) ?
C13 H13 0.9300 ?
C14 C15 1.353(7) ?
C14 H14 0.9300 ?
C15 C16 1.403(7) ?
C15 H15 0.9300 ?
C16 C24 1.389(6) ?
C16 C17 1.419(7) ?
C17 C18 1.317(7) ?
C17 H17 0.9300 ?
C18 C19 1.445(7) ?
C18 H18 0.9300 ?
C19 C23 1.391(6) ?
C19 C20 1.419(7) ?
C20 C21 1.336(6) ?
C20 H20 0.9300 ?
C21 C22 1.392(6) ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
C23 C24 1.419(6) ?
C25 C26 1.440(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 Cu1 N2 83.30(16) yes
N1 Cu1 N3 92.39(15) yes
N1 Cu1 N4 175.33(15) yes
N1 Cu1 N5 93.57(16) yes
N1 Cu1 N6 90.45(15) yes
N2 Cu1 N3 89.54(15) yes
N2 Cu1 N4 93.71(15) yes
N2 Cu1 N5 175.49(15) yes
N2 Cu1 N6 95.51(15) yes
N3 Cu1 N4 83.97(15) yes
N3 Cu1 N5 93.86(17) yes
N3 Cu1 N6 174.47(16) yes
N4 Cu1 N5 89.60(15) yes
N4 Cu1 N6 93.42(15) yes
N5 Cu1 N6 81.23(17) yes
N6 O1 H1A 109.5 ?
N5 O2 H2A 109.5 ?
C25 O3 H3A 109.5 ?
C26 O4 H4A 109.5 ?
H11A O11 H11B 118(3) ?
H12A O12 H12B 111(7) ?
C1 N1 C12 118.4(4) ?
C1 N1 Cu1 128.4(3) ?
C12 N1 Cu1 113.1(3) ?
C10 N2 C11 118.2(4) ?
C10 N2 Cu1 131.1(3) ?
C11 N2 Cu1 110.7(3) ?
C13 N3 C24 118.5(4) ?
C13 N3 Cu1 130.1(3) ?
C24 N3 Cu1 111.4(3) ?
C22 N4 C23 117.9(4) ?
C22 N4 Cu1 130.0(3) ?
C23 N4 Cu1 112.1(3) ?
O2 N5 C25 123.7(4) ?
O2 N5 Cu1 120.9(3) ?
C25 N5 Cu1 115.3(3) ?
C26 N6 O1 117.2(4) ?
C26 N6 Cu1 116.4(3) ?
O1 N6 Cu1 125.3(3) ?
O7 N7 O6 120.1(5) ?
O7 N7 O5 119.4(5) ?
O6 N7 O5 120.3(5) ?
O10 N8 O8 131.8(13) ?
O10 N8 O9 118.5(11) ?
O8 N8 O9 109.5(11) ?
N1 C1 C2 121.5(5) ?
N1 C1 H1 119.2 ?
C2 C1 H1 119.2 ?
C3 C2 C1 120.4(5) ?
C3 C2 H2 119.8 ?
C1 C2 H2 119.8 ?
C2 C3 C4 120.2(5) ?
C2 C3 H3 119.9 ?
C4 C3 H3 119.9 ?
C3 C4 C12 116.7(5) ?
C3 C4 C5 125.3(5) ?
C12 C4 C5 117.9(5) ?
C6 C5 C4 121.5(5) ?
C6 C5 H5 119.2 ?
C4 C5 H5 119.2 ?
C5 C6 C7 120.7(5) ?
C5 C6 H6 119.6 ?
C7 C6 H6 119.6 ?
C8 C7 C11 117.0(5) ?
C8 C7 C6 124.8(5) ?
C11 C7 C6 118.2(5) ?
C7 C8 C9 120.0(5) ?
C7 C8 H8 120.0 ?
C9 C8 H8 120.0 ?
C8 C9 C10 119.6(5) ?
C8 C9 H9 120.2 ?
C10 C9 H9 120.2 ?
N2 C10 C9 122.1(5) ?
N2 C10 H10 118.9 ?
C9 C10 H10 118.9 ?
N2 C11 C12 116.5(4) ?
N2 C11 C7 123.0(5) ?
C12 C11 C7 120.5(5) ?
N1 C12 C11 116.1(4) ?
N1 C12 C4 122.7(5) ?
C11 C12 C4 121.1(4) ?
N3 C13 C14 121.6(5) ?
N3 C13 H13 119.2 ?
C14 C13 H13 119.2 ?
C15 C14 C13 120.4(5) ?
C15 C14 H14 119.8 ?
C13 C14 H14 119.8 ?
C14 C15 C16 119.7(5) ?
C14 C15 H15 120.1 ?
C16 C15 H15 120.1 ?
C24 C16 C15 116.7(5) ?
C24 C16 C17 118.0(5) ?
C15 C16 C17 125.3(5) ?
C18 C17 C16 121.6(5) ?
C18 C17 H17 119.2 ?
C16 C17 H17 119.2 ?
C17 C18 C19 122.2(5) ?
C17 C18 H18 118.9 ?
C19 C18 H18 118.9 ?
C23 C19 C20 117.0(5) ?
C23 C19 C18 117.1(5) ?
C20 C19 C18 125.9(5) ?
C21 C20 C19 118.9(5) ?
C21 C20 H20 120.6 ?
C19 C20 H20 120.6 ?
C20 C21 C22 121.0(5) ?
C20 C21 H21 119.5 ?
C22 C21 H21 119.5 ?
N4 C22 C21 121.8(4) ?
N4 C22 H22 119.1 ?
C21 C22 H22 119.1 ?
N4 C23 C19 123.5(4) ?
N4 C23 C24 116.3(4) ?
C19 C23 C24 120.2(4) ?
N3 C24 C16 123.1(4) ?
N3 C24 C23 116.1(4) ?
C16 C24 C23 120.8(4) ?
N5 C25 C26 113.1(4) ?
N5 C25 O3 121.9(5) ?
C26 C25 O3 124.8(5) ?
N6 C26 C25 113.8(4) ?
N6 C26 O4 124.0(5) ?
C25 C26 O4 122.2(5) ?
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
C22 H22 O6 3_766 0.93 2.55 3.289(6) 137 yes
C18 H18 O2 3_765 0.93 2.42 3.269(7) 152 yes
C5 H5 O1 3_675 0.93 2.55 3.354(6) 145 yes
C3 H3 O5 3_666 0.93 2.54 3.387(7) 151 yes
O1 H1A O6 1_564 0.82 2.00 2.697(5) 143 yes
O1 H1A O5 1_564 0.82 2.36 2.991(5) 134 yes