#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/46/2234684.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_2234684
loop_
_publ_author_name
'Li, Dong-Jiao'
_publ_section_title
;
 Tris(nitrato-κ²O,O')bis[4,4,5,5-tetramethyl-2-(pyridin-2-yl-κN)imidazoline-1-oxyl
 3-oxide-κO]holmium(III)
;
_journal_coeditor_code           IS5078
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m550
_journal_paper_doi               10.1107/S1600536812012445
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ho (N O3)3 (C12 H16 N3 O2)2]'
_chemical_formula_moiety         'C24 H32 Ho N9 O13'
_chemical_formula_sum            'C24 H32 Ho N9 O13'
_chemical_formula_weight         819.52
_chemical_name_systematic
;
Tris(nitrato-κ²O,O')bis[4,4,5,5-tetramethyl-2-(pyridin-
2-yl-κN)imidazoline-1-oxyl 3-oxide-κO]holmium(III)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 98.391(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2627(10)
_cell_length_b                   11.1044(8)
_cell_length_c                   23.2861(17)
_cell_measurement_reflns_used    2811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7933
_cell_measurement_theta_min      2.5105
_cell_volume                     3136.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17689
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.19
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.866
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         5530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0167P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                4895
_reflns_number_total             5530
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5078.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234684
_cod_database_fobs_code          2234684
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Ho Ho1 0.179214(16) 0.661468(16) 0.104145(7) 0.02420(7) Uani d . 1 1
O O1 0.3290(2) 0.5763(2) 0.16176(10) 0.0300(7) Uani d . 1 1
O O2 0.4048(3) 0.1762(3) 0.12909(15) 0.0620(10) Uani d . 1 1
O O3 -0.0085(2) 0.6824(2) 0.06574(10) 0.0292(7) Uani d . 1 1
O O4 -0.2481(3) 0.7880(3) 0.19251(11) 0.0419(8) Uani d . 1 1
O O5 0.2368(3) 0.7701(3) 0.19958(12) 0.0409(8) Uani d . 1 1
O O6 0.1138(3) 0.8544(2) 0.13632(12) 0.0399(8) Uani d . 1 1
O O7 0.1635(3) 0.9416(3) 0.21931(13) 0.0589(10) Uani d . 1 1
O O8 0.1982(3) 0.8043(3) 0.02635(12) 0.0448(9) Uani d . 1 1
O O9 0.3316(3) 0.7986(3) 0.09759(13) 0.0473(9) Uani d . 1 1
O O10 0.3446(4) 0.9135(4) 0.02325(19) 0.1036(16) Uani d . 1 1
O O11 0.1190(2) 0.5707(3) 0.00788(11) 0.0368(8) Uani d . 1 1
O O12 0.2943(2) 0.5667(3) 0.03594(11) 0.0367(8) Uani d . 1 1
O O13 0.2278(3) 0.5218(3) -0.05394(11) 0.0496(9) Uani d . 1 1
N N1 0.3807(3) 0.4780(3) 0.15077(12) 0.0260(8) Uani d . 1 1
N N2 0.4172(3) 0.2890(3) 0.13669(14) 0.0356(9) Uani d . 1 1
N N3 0.1487(3) 0.4267(3) 0.11502(12) 0.0260(8) Uani d . 1 1
N N4 -0.0860(3) 0.7361(3) 0.08828(12) 0.0222(8) Uani d . 1 1
N N5 -0.2006(3) 0.7847(3) 0.14709(13) 0.0297(9) Uani d . 1 1
N N6 0.0492(3) 0.6136(3) 0.18514(12) 0.0274(8) Uani d . 1 1
N N7 0.1718(3) 0.8572(3) 0.18637(15) 0.0381(10) Uani d . 1 1
N N8 0.2937(4) 0.8419(4) 0.04853(19) 0.0535(11) Uani d . 1 1
N N9 0.2134(3) 0.5520(3) -0.00485(14) 0.0309(9) Uani d . 1 1
C C1 0.5041(4) 0.4773(4) 0.15474(16) 0.0336(11) Uani d . 1 1
C C2 0.5205(4) 0.3531(4) 0.12639(18) 0.0392(12) Uani d . 1 1
C C3 0.3361(4) 0.3693(4) 0.14364(16) 0.0272(10) Uani d . 1 1
C C4 0.2199(4) 0.3408(4) 0.13886(15) 0.0269(10) Uani d . 1 1
C C5 0.1855(4) 0.2282(4) 0.15475(17) 0.0375(12) Uani d . 1 1
H H5 0.2361 0.1725 0.1726 0.045 Uiso calc R 1 1
C C6 0.0752(5) 0.2005(4) 0.1436(2) 0.0530(14) Uani d . 1 1
H H6 0.0501 0.1258 0.1542 0.064 Uiso calc R 1 1
C C7 0.0022(4) 0.2843(4) 0.11667(19) 0.0470(13) Uani d . 1 1
H H7 -0.0724 0.2665 0.1075 0.056 Uiso calc R 1 1
C C8 0.0427(4) 0.3952(4) 0.10373(17) 0.0349(11) Uani d . 1 1
H H8 -0.0071 0.4518 0.0860 0.042 Uiso calc R 1 1
C C9 0.5416(4) 0.5855(4) 0.12275(19) 0.0467(13) Uani d . 1 1
H H9A 0.5027 0.5872 0.0839 0.070 Uiso calc R 1 1
H H9B 0.6193 0.5798 0.1216 0.070 Uiso calc R 1 1
H H9C 0.5263 0.6580 0.1426 0.070 Uiso calc R 1 1
C C10 0.5497(4) 0.4825(4) 0.21934(17) 0.0529(14) Uani d . 1 1
H H10A 0.5257 0.5556 0.2357 0.079 Uiso calc R 1 1
H H10B 0.6288 0.4807 0.2242 0.079 Uiso calc R 1 1
H H10C 0.5232 0.4146 0.2387 0.079 Uiso calc R 1 1
C C11 0.5140(4) 0.3573(4) 0.05990(18) 0.0517(14) Uani d . 1 1
H H11A 0.5135 0.2767 0.0449 0.077 Uiso calc R 1 1
H H11B 0.5768 0.3998 0.0499 0.077 Uiso calc R 1 1
H H11C 0.4477 0.3980 0.0434 0.077 Uiso calc R 1 1
C C12 0.6227(4) 0.2824(5) 0.1523(2) 0.0628(16) Uani d . 1 1
H H12A 0.6217 0.2704 0.1930 0.094 Uiso calc R 1 1
H H12B 0.6877 0.3266 0.1468 0.094 Uiso calc R 1 1
H H12C 0.6231 0.2056 0.1333 0.094 Uiso calc R 1 1
C C13 -0.1611(3) 0.8248(4) 0.05230(15) 0.0266(10) Uani d . 1 1
C C14 -0.2272(4) 0.8757(3) 0.09915(16) 0.0279(10) Uani d . 1 1
C C15 -0.1146(3) 0.7139(3) 0.13957(15) 0.0239(10) Uani d . 1 1
C C16 -0.0604(4) 0.6276(3) 0.18221(16) 0.0256(10) Uani d . 1 1
C C17 -0.1219(4) 0.5649(4) 0.21723(17) 0.0391(12) Uani d . 1 1
H H17 -0.1977 0.5764 0.2139 0.047 Uiso calc R 1 1
C C18 -0.0689(4) 0.4842(4) 0.25749(18) 0.0503(14) Uani d . 1 1
H H18 -0.1091 0.4376 0.2801 0.060 Uiso calc R 1 1
C C19 0.0436(4) 0.4743(4) 0.26343(17) 0.0444(13) Uani d . 1 1
H H19 0.0815 0.4243 0.2915 0.053 Uiso calc R 1 1
C C20 0.0991(4) 0.5405(4) 0.22672(16) 0.0337(11) Uani d . 1 1
H H20 0.1755 0.5341 0.2311 0.040 Uiso calc R 1 1
C C21 -0.0891(4) 0.9138(4) 0.02590(19) 0.0496(14) Uani d . 1 1
H H21A -0.0373 0.9493 0.0561 0.074 Uiso calc R 1 1
H H21B -0.1343 0.9758 0.0060 0.074 Uiso calc R 1 1
H H21C -0.0499 0.8728 -0.0011 0.074 Uiso calc R 1 1
C C22 -0.2297(4) 0.7515(4) 0.00520(17) 0.0478(14) Uani d . 1 1
H H22A -0.1819 0.7113 -0.0178 0.072 Uiso calc R 1 1
H H22B -0.2787 0.8040 -0.0191 0.072 Uiso calc R 1 1
H H22C -0.2720 0.6928 0.0227 0.072 Uiso calc R 1 1
C C23 -0.1829(4) 0.9964(4) 0.12467(19) 0.0556(15) Uani d . 1 1
H H23A -0.2192 1.0168 0.1572 0.083 Uiso calc R 1 1
H H23B -0.1967 1.0580 0.0956 0.083 Uiso calc R 1 1
H H23C -0.1050 0.9899 0.1372 0.083 Uiso calc R 1 1
C C24 -0.3505(4) 0.8831(4) 0.08100(19) 0.0468(13) Uani d . 1 1
H H24A -0.3787 0.8048 0.0693 0.070 Uiso calc R 1 1
H H24B -0.3665 0.9382 0.0491 0.070 Uiso calc R 1 1
H H24C -0.3848 0.9112 0.1131 0.070 Uiso calc R 1 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'
Ho Ho -0.2175 4.6783 '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
O1 Ho1 O3 . 155.46(9)
O1 Ho1 O9 . 74.95(10)
O3 Ho1 O9 . 129.14(10)
O1 Ho1 O6 . 116.69(9)
O3 Ho1 O6 . 71.56(9)
O9 Ho1 O6 . 76.09(10)
O1 Ho1 O8 . 122.81(11)
O3 Ho1 O8 . 81.26(10)
O9 Ho1 O8 . 52.42(10)
O6 Ho1 O8 . 74.28(10)
O1 Ho1 O11 . 117.79(9)
O3 Ho1 O11 . 63.23(9)
O9 Ho1 O11 . 109.23(10)
O6 Ho1 O11 . 124.62(9)
O8 Ho1 O11 . 68.94(10)
O1 Ho1 O12 . 73.90(9)
O3 Ho1 O12 . 114.22(9)
O9 Ho1 O12 . 73.41(10)
O6 Ho1 O12 . 143.44(10)
O8 Ho1 O12 . 71.31(10)
O11 Ho1 O12 . 51.30(9)
O1 Ho1 O5 . 65.83(10)
O3 Ho1 O5 . 114.66(10)
O9 Ho1 O5 . 68.85(10)
O6 Ho1 O5 . 51.40(9)
O8 Ho1 O5 . 107.23(10)
O12 Ho1 O5 . 130.15(10)
O1 Ho1 N3 . 69.74(10)
O3 Ho1 N3 . 89.40(10)
O9 Ho1 N3 . 137.92(11)
O6 Ho1 N3 . 140.87(10)
O8 Ho1 N3 . 137.65(10)
O11 Ho1 N3 . 69.98(9)
O12 Ho1 N3 . 75.40(10)
O5 Ho1 N3 . 114.15(9)
O1 Ho1 N6 . 90.83(10)
O3 Ho1 N6 . 68.89(9)
O9 Ho1 N6 . 134.89(10)
O6 Ho1 N6 . 72.78(10)
O8 Ho1 N6 . 140.96(11)
O11 Ho1 N6 . 115.18(10)
O12 Ho1 N6 . 143.77(10)
O5 Ho1 N6 . 66.29(10)
N3 Ho1 N6 . 68.47(10)
N1 O1 Ho1 . 126.5(2)
N4 O3 Ho1 . 128.7(2)
N7 O5 Ho1 . 93.8(2)
N7 O6 Ho1 . 97.9(2)
N8 O8 Ho1 . 95.3(2)
N8 O9 Ho1 . 96.4(3)
N9 O11 Ho1 . 96.8(2)
N9 O12 Ho1 . 94.4(2)
O1 N1 C3 . 125.7(4)
O1 N1 C1 . 120.3(3)
C3 N1 C1 . 113.3(4)
O2 N2 C3 1 125.9(4)
O2 N2 C3 . 125.9(4)
O2 N2 C2 1 122.1(4)
O2 N2 C2 . 122.1(4)
C3 N2 C2 . 110.9(3)
C8 N3 C4 . 116.6(4)
C8 N3 Ho1 . 112.7(3)
C4 N3 Ho1 . 129.7(3)
O3 N4 C15 . 126.1(3)
O3 N4 C13 . 119.8(3)
C15 N4 C13 . 113.8(3)
O4 N5 C15 1 125.7(3)
O4 N5 C15 . 125.7(3)
O4 N5 C14 1 121.2(3)
O4 N5 C14 . 121.2(3)
C15 N5 C14 . 112.6(3)
C20 N6 C16 . 117.0(3)
C20 N6 Ho1 . 111.7(3)
C16 N6 Ho1 . 129.1(2)
O7 N7 O5 . 122.8(4)
O7 N7 O6 . 120.3(4)
O5 N7 O6 . 116.9(3)
O10 N8 O9 . 122.7(5)
O10 N8 O8 . 121.5(5)
O9 N8 O8 . 115.8(4)
O13 N9 O11 . 121.9(3)
O13 N9 O12 . 121.6(4)
O11 N9 O12 . 116.5(3)
N1 C1 C9 . 109.8(3)
N1 C1 C10 . 106.3(3)
C9 C1 C10 . 111.0(4)
N1 C1 C2 . 99.8(3)
C9 C1 C2 . 115.2(4)
C10 C1 C2 . 113.6(4)
N2 C2 C12 . 110.9(4)
N2 C2 C11 . 104.7(3)
C12 C2 C11 . 109.4(4)
N2 C2 C1 . 100.8(3)
C12 C2 C1 . 116.0(4)
C11 C2 C1 . 114.2(3)
N1 C3 N2 . 108.4(4)
N1 C3 C4 . 126.3(4)
N2 C3 C4 . 125.1(4)
N3 C4 C5 . 122.7(4)
N3 C4 C3 . 116.5(4)
C5 C4 C3 . 120.7(4)
C6 C5 C4 . 118.7(4)
C6 C5 H5 . 120.6
C4 C5 H5 . 120.6
C5 C6 C7 . 119.4(5)
C5 C6 H6 . 120.3
C7 C6 H6 . 120.3
C8 C7 C6 . 118.2(5)
C8 C7 H7 . 120.9
C6 C7 H7 . 120.9
N3 C8 C7 . 124.3(4)
N3 C8 H8 . 117.9
C7 C8 H8 . 117.9
C1 C9 H9A . 109.5
C1 C9 H9B . 109.5
H9A C9 H9B . 109.5
C1 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C1 C10 H10A . 109.5
C1 C10 H10B . 109.5
H10A C10 H10B . 109.5
C1 C10 H10C . 109.5
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
C2 C11 H11A . 109.5
C2 C11 H11B . 109.5
H11A C11 H11B . 109.5
C2 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
C2 C12 H12A . 109.5
C2 C12 H12B . 109.5
H12A C12 H12B . 109.5
C2 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
N4 C13 C21 . 107.8(3)
N4 C13 C22 . 106.2(3)
C21 C13 C22 . 110.6(3)
N4 C13 C14 . 100.7(3)
C21 C13 C14 . 116.2(3)
C22 C13 C14 . 114.3(4)
N5 C14 C24 . 110.1(3)
N5 C14 C23 . 105.9(3)
C24 C14 C23 . 110.2(4)
N5 C14 C13 . 101.3(3)
C24 C14 C13 . 115.2(3)
C23 C14 C13 . 113.4(4)
N4 C15 N5 . 109.0(3)
N4 C15 C16 . 125.6(4)
N5 C15 C16 . 125.4(3)
N6 C16 C17 . 122.8(4)
N6 C16 C15 . 117.4(3)
C17 C16 C15 . 119.8(4)
C16 C17 C18 . 118.9(4)
C16 C17 H17 . 120.6
C18 C17 H17 . 120.6
C19 C18 C17 . 119.0(4)
C19 C18 H18 . 120.5
C17 C18 H18 . 120.5
C18 C19 C20 . 118.4(4)
C18 C19 H19 . 120.8
C20 C19 H19 . 120.8
N6 C20 C19 . 123.7(4)
N6 C20 H20 . 118.2
C19 C20 H20 . 118.2
C13 C21 H21A . 109.5
C13 C21 H21B . 109.5
H21A C21 H21B . 109.5
C13 C21 H21C . 109.5
H21A C21 H21C . 109.5
H21B C21 H21C . 109.5
C13 C22 H22A . 109.5
C13 C22 H22B . 109.5
H22A C22 H22B . 109.5
C13 C22 H22C . 109.5
H22A C22 H22C . 109.5
H22B C22 H22C . 109.5
C14 C23 H23A . 109.5
C14 C23 H23B . 109.5
H23A C23 H23B . 109.5
C14 C23 H23C . 109.5
H23A C23 H23C . 109.5
H23B C23 H23C . 109.5
C14 C24 H24A . 109.5
C14 C24 H24B . 109.5
H24A C24 H24B . 109.5
C14 C24 H24C . 109.5
H24A C24 H24C . 109.5
H24B C24 H24C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ho1 O1 . 2.313(3)
Ho1 O3 . 2.356(3)
Ho1 O9 . 2.432(3)
Ho1 O6 . 2.443(3)
Ho1 O8 . 2.445(3)
Ho1 O11 . 2.471(3)
Ho1 O12 . 2.505(3)
Ho1 O5 . 2.537(3)
Ho1 N3 . 2.651(3)
Ho1 N6 . 2.694(3)
O1 N1 . 1.305(4)
O2 N2 . 1.271(4)
O3 N4 . 1.296(4)
O4 N5 . 1.280(4)
O5 N7 . 1.262(4)
O6 N7 . 1.274(4)
O7 N7 . 1.225(4)
O8 N8 . 1.280(5)
O9 N8 . 1.264(5)
O10 N8 . 1.214(5)
O11 N9 . 1.253(4)
O12 N9 . 1.280(4)
O13 N9 . 1.228(4)
N1 C3 . 1.325(5)
N1 C1 . 1.503(5)
N2 O2 1 1.271(4)
N2 C3 . 1.363(5)
N2 C2 . 1.502(6)
N3 C8 . 1.335(5)
N3 C4 . 1.356(5)
N4 C15 . 1.316(4)
N4 C13 . 1.515(5)
N5 O4 1 1.280(4)
N5 C15 . 1.347(5)
N5 C14 . 1.506(5)
N6 C20 . 1.341(5)
N6 C16 . 1.344(5)
C1 C9 . 1.520(6)
C1 C10 . 1.527(5)
C1 C2 . 1.555(6)
C2 C12 . 1.527(6)
C2 C11 . 1.539(6)
C3 C4 . 1.448(6)
C4 C5 . 1.388(5)
C5 C6 . 1.374(6)
C5 H5 . 0.9300
C6 C7 . 1.378(6)
C6 H6 . 0.9300
C7 C8 . 1.377(6)
C7 H7 . 0.9300
C8 H8 . 0.9300
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 C21 . 1.515(6)
C13 C22 . 1.518(5)
C13 C14 . 1.557(5)
C14 C24 . 1.512(6)
C14 C23 . 1.533(5)
C15 C16 . 1.467(5)
C16 C17 . 1.378(5)
C17 C18 . 1.388(6)
C17 H17 . 0.9300
C18 C19 . 1.370(6)
C18 H18 . 0.9300
C19 C20 . 1.380(5)
C19 H19 . 0.9300
C20 H20 . 0.9300
C21 H21A . 0.9600
C21 H21B . 0.9600
C21 H21C . 0.9600
C22 H22A . 0.9600
C22 H22B . 0.9600
C22 H22C . 0.9600
C23 H23A . 0.9600
C23 H23B . 0.9600
C23 H23C . 0.9600
C24 H24A . 0.9600
C24 H24B . 0.9600
C24 H24C . 0.9600
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
C8 H8 O11 3_565 0.93 2.42 3.053(5) 126
C11 H11B O13 3_665 0.96 2.54 3.460(6) 161
C18 H18 O4 2_445 0.93 2.56 3.450(6) 160
C20 H20 O7 2_545 0.93 2.37 3.193(5) 147
C22 H22C O13 3_565 0.96 2.53 3.239(6) 131
C24 H24B O10 3_575 0.96 2.40 3.324(6) 162
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
O3 Ho1 O1 N1 . 79.9(4)
O9 Ho1 O1 N1 . -110.1(3)
O6 Ho1 O1 N1 . -175.7(3)
O8 Ho1 O1 N1 . -87.8(3)
O11 Ho1 O1 N1 . -6.0(3)
O12 Ho1 O1 N1 . -33.4(3)
O5 Ho1 O1 N1 . 176.7(3)
N3 Ho1 O1 N1 . 46.6(3)
N6 Ho1 O1 N1 . 113.3(3)
O1 Ho1 O3 N4 . 81.5(3)
O9 Ho1 O3 N4 . -86.0(3)
O6 Ho1 O3 N4 . -32.7(3)
O8 Ho1 O3 N4 . -109.0(3)
O11 Ho1 O3 N4 . -179.7(3)
O12 Ho1 O3 N4 . -173.9(2)
O5 Ho1 O3 N4 . -4.0(3)
N3 Ho1 O3 N4 . 112.5(3)
N6 Ho1 O3 N4 . 45.4(3)
O1 Ho1 O5 N7 . 171.9(3)
O3 Ho1 O5 N7 . -35.1(3)
O9 Ho1 O5 N7 . 89.5(2)
O6 Ho1 O5 N7 . 0.7(2)
O8 Ho1 O5 N7 . 53.1(3)
O12 Ho1 O5 N7 . 132.9(2)
N3 Ho1 O5 N7 . -136.2(2)
N6 Ho1 O5 N7 . -85.7(3)
O1 Ho1 O6 N7 . -9.6(3)
O3 Ho1 O6 N7 . 145.3(3)
O9 Ho1 O6 N7 . -74.6(2)
O8 Ho1 O6 N7 . -128.9(3)
O11 Ho1 O6 N7 . -178.5(2)
O12 Ho1 O6 N7 . -108.7(2)
O5 Ho1 O6 N7 . -0.7(2)
N3 Ho1 O6 N7 . 80.6(3)
N6 Ho1 O6 N7 . 72.4(2)
O1 Ho1 O8 N8 . -25.7(3)
O3 Ho1 O8 N8 . 159.5(3)
O9 Ho1 O8 N8 . 1.9(2)
O6 Ho1 O8 N8 . 86.3(3)
O11 Ho1 O8 N8 . -135.9(3)
O12 Ho1 O8 N8 . -81.2(3)
O5 Ho1 O8 N8 . 46.3(3)
N3 Ho1 O8 N8 . -121.2(3)
N6 Ho1 O8 N8 . 119.6(3)
O1 Ho1 O9 N8 . 154.3(3)
O3 Ho1 O9 N8 . -31.1(3)
O6 Ho1 O9 N8 . -82.7(3)
O8 Ho1 O9 N8 . -2.0(2)
O11 Ho1 O9 N8 . 39.6(3)
O12 Ho1 O9 N8 . 76.9(3)
O5 Ho1 O9 N8 . -136.3(3)
N3 Ho1 O9 N8 . 120.7(3)
N6 Ho1 O9 N8 . -130.0(3)
O1 Ho1 O11 N9 . -40.5(2)
O3 Ho1 O11 N9 . 167.2(2)
O9 Ho1 O11 N9 . 42.2(2)
O6 Ho1 O11 N9 . 128.3(2)
O8 Ho1 O11 N9 . 76.5(2)
O12 Ho1 O11 N9 . -5.9(2)
N3 Ho1 O11 N9 . -93.0(2)
N6 Ho1 O11 N9 . -145.9(2)
O1 Ho1 O12 N9 . 154.3(2)
O3 Ho1 O12 N9 . -1.0(2)
O9 Ho1 O12 N9 . -127.0(2)
O6 Ho1 O12 N9 . -92.4(3)
O8 Ho1 O12 N9 . -71.8(2)
O11 Ho1 O12 N9 . 5.8(2)
O5 Ho1 O12 N9 . -168.90(19)
N3 Ho1 O12 N9 . 81.6(2)
N6 Ho1 O12 N9 . 85.9(3)
Ho1 O1 N1 C3 . -60.2(4)
Ho1 O1 N1 C1 . 129.9(3)
O2 O2 N2 C3 1 0.0(5)
O2 O2 N2 C2 1 0.0(5)
O1 Ho1 N3 C8 . 159.2(3)
O3 Ho1 N3 C8 . -7.6(3)
O9 Ho1 N3 C8 . -166.1(2)
O6 Ho1 N3 C8 . 51.4(3)
O8 Ho1 N3 C8 . -83.9(3)
O11 Ho1 N3 C8 . -69.2(3)
O12 Ho1 N3 C8 . -122.9(3)
O5 Ho1 N3 C8 . 109.3(3)
N6 Ho1 N3 C8 . 59.8(3)
O1 Ho1 N3 C4 . -8.7(3)
O3 Ho1 N3 C4 . -175.5(3)
O9 Ho1 N3 C4 . 26.1(4)
O6 Ho1 N3 C4 . -116.4(3)
O8 Ho1 N3 C4 . 108.2(3)
O11 Ho1 N3 C4 . 122.9(3)
O12 Ho1 N3 C4 . 69.3(3)
O5 Ho1 N3 C4 . -58.6(3)
N6 Ho1 N3 C4 . -108.0(3)
Ho1 O3 N4 C15 . -55.6(5)
Ho1 O3 N4 C13 . 131.0(3)
O4 O4 N5 C15 1 0.0(3)
O4 O4 N5 C14 1 0.0(2)
O1 Ho1 N6 C20 . -10.9(3)
O3 Ho1 N6 C20 . 154.9(3)
O9 Ho1 N6 C20 . -80.3(3)
O6 Ho1 N6 C20 . -128.7(3)
O8 Ho1 N6 C20 . -162.3(2)
O11 Ho1 N6 C20 . 110.6(3)
O12 Ho1 N6 C20 . 52.4(3)
O5 Ho1 N6 C20 . -73.9(3)
N3 Ho1 N6 C20 . 56.9(3)
O1 Ho1 N6 C16 . -173.5(3)
O3 Ho1 N6 C16 . -7.7(3)
O9 Ho1 N6 C16 . 117.1(3)
O6 Ho1 N6 C16 . 68.7(3)
O8 Ho1 N6 C16 . 35.0(4)
O11 Ho1 N6 C16 . -52.1(3)
O12 Ho1 N6 C16 . -110.2(3)
O5 Ho1 N6 C16 . 123.4(3)
N3 Ho1 N6 C16 . -105.7(3)
Ho1 O5 N7 O7 . 178.9(4)
Ho1 O5 N7 O6 . -1.2(4)
Ho1 O6 N7 O7 . -178.9(3)
Ho1 O6 N7 O5 . 1.2(4)
Ho1 O9 N8 O10 . -175.8(5)
Ho1 O9 N8 O8 . 3.3(4)
Ho1 O8 N8 O10 . 175.8(5)
Ho1 O8 N8 O9 . -3.3(4)
Ho1 O11 N9 O13 . -169.4(3)
Ho1 O11 N9 O12 . 10.2(3)
Ho1 O12 N9 O13 . 169.6(3)
Ho1 O12 N9 O11 . -10.0(3)
O1 N1 C1 C9 . -47.7(4)
C3 N1 C1 C9 . 141.2(4)
O1 N1 C1 C10 . 72.5(4)
C3 N1 C1 C10 . -98.6(4)
O1 N1 C1 C2 . -169.2(3)
C3 N1 C1 C2 . 19.7(4)
O2 N2 C2 C12 1 -44.4(5)
O2 N2 C2 C12 . -44.4(5)
C3 N2 C2 C12 . 147.2(4)
O2 N2 C2 C11 1 73.5(5)
O2 N2 C2 C11 . 73.5(5)
C3 N2 C2 C11 . -94.9(4)
O2 N2 C2 C1 1 -167.7(4)
O2 N2 C2 C1 . -167.7(4)
C3 N2 C2 C1 . 23.8(4)
N1 C1 C2 N2 . -23.9(3)
C9 C1 C2 N2 . -141.5(4)
C10 C1 C2 N2 . 88.8(4)
N1 C1 C2 C12 . -143.7(4)
C9 C1 C2 C12 . 98.8(5)
C10 C1 C2 C12 . -30.9(6)
N1 C1 C2 C11 . 87.7(4)
C9 C1 C2 C11 . -29.8(5)
C10 C1 C2 C11 . -159.5(4)
O1 N1 C3 N2 . -176.1(3)
C1 N1 C3 N2 . -5.5(4)
O1 N1 C3 C4 . 8.9(6)
C1 N1 C3 C4 . 179.5(3)
O2 N2 C3 N1 1 179.6(4)
O2 N2 C3 N1 . 179.6(4)
C2 N2 C3 N1 . -12.5(4)
O2 N2 C3 C4 1 -5.3(6)
O2 N2 C3 C4 . -5.3(6)
C2 N2 C3 C4 . 162.6(4)
C8 N3 C4 C5 . -4.3(5)
Ho1 N3 C4 C5 . 163.1(3)
C8 N3 C4 C3 . 171.7(3)
Ho1 N3 C4 C3 . -20.8(5)
N1 C3 C4 N3 . 30.2(6)
N2 C3 C4 N3 . -144.0(4)
N1 C3 C4 C5 . -153.7(4)
N2 C3 C4 C5 . 32.1(6)
N3 C4 C5 C6 . 2.9(6)
C3 C4 C5 C6 . -173.0(4)
C4 C5 C6 C7 . 0.6(7)
C5 C6 C7 C8 . -2.3(7)
C4 N3 C8 C7 . 2.5(6)
Ho1 N3 C8 C7 . -167.1(3)
C6 C7 C8 N3 . 0.8(7)
O3 N4 C13 C21 . -50.9(4)
C15 N4 C13 C21 . 135.0(4)
O3 N4 C13 C22 . 67.7(4)
C15 N4 C13 C22 . -106.5(4)
O3 N4 C13 C14 . -173.0(3)
C15 N4 C13 C14 . 12.9(4)
O4 N5 C14 C24 1 -51.0(5)
O4 N5 C14 C24 . -51.0(5)
C15 N5 C14 C24 . 136.9(4)
O4 N5 C14 C23 1 68.0(5)
O4 N5 C14 C23 . 68.0(5)
C15 N5 C14 C23 . -104.0(4)
O4 N5 C14 C13 1 -173.4(4)
O4 N5 C14 C13 . -173.4(4)
C15 N5 C14 C13 . 14.6(4)
N4 C13 C14 N5 . -14.9(4)
C21 C13 C14 N5 . -130.9(4)
C22 C13 C14 N5 . 98.5(4)
N4 C13 C14 C24 . -133.6(3)
C21 C13 C14 C24 . 110.3(4)
C22 C13 C14 C24 . -20.3(5)
N4 C13 C14 C23 . 98.1(4)
C21 C13 C14 C23 . -17.9(5)
C22 C13 C14 C23 . -148.5(4)
O3 N4 C15 N5 . -178.0(3)
C13 N4 C15 N5 . -4.3(5)
O3 N4 C15 C16 . 3.1(6)
C13 N4 C15 C16 . 176.8(4)
O4 N5 C15 N4 1 -178.7(4)
O4 N5 C15 N4 . -178.7(4)
C14 N5 C15 N4 . -7.1(5)
O4 N5 C15 C16 1 0.2(7)
O4 N5 C15 C16 . 0.2(7)
C14 N5 C15 C16 . 171.8(4)
C20 N6 C16 C17 . -4.2(6)
Ho1 N6 C16 C17 . 157.7(3)
C20 N6 C16 C15 . 175.8(3)
Ho1 N6 C16 C15 . -22.3(5)
N4 C15 C16 N6 . 34.2(6)
N5 C15 C16 N6 . -144.6(4)
N4 C15 C16 C17 . -145.8(4)
N5 C15 C16 C17 . 35.4(6)
N6 C16 C17 C18 . 0.3(6)
C15 C16 C17 C18 . -179.6(4)
C16 C17 C18 C19 . 3.6(7)
C17 C18 C19 C20 . -3.5(7)
C16 N6 C20 C19 . 4.3(6)
Ho1 N6 C20 C19 . -160.6(3)
C18 C19 C20 N6 . -0.5(7)
