#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:26:45 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179246 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/66/4316689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4316689
loop_
_publ_author_name
'Octavia A. Blackburn'
'Benjamin J. Coe'
'John Fielden'
'Madeleine Helliwell'
'Joseph J. W. McDouall'
'Michael G. Hutchings'
_publ_section_title
;
 Nickel(II) and Palladium(II) Complexes of Azobenzene-Containing Ligands
 as Dichroic Dyes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9136
_journal_page_last               9150
_journal_paper_doi               10.1021/ic1000842
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C24 H31 N3 O3'
_chemical_formula_weight         409.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.544(5)
_cell_angle_beta                 90.773(5)
_cell_angle_gamma                105.117(5)
_cell_formula_units_Z            2
_cell_length_a                   5.6096(17)
_cell_length_b                   8.297(3)
_cell_length_c                   24.364(7)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.17
_cell_measurement_theta_min      2.51
_cell_volume                     1094.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7832
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0477
_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/[σ²(Fo²)+(0.0395P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2621
_reflns_number_total             3827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1000842_si_002_1.cif
_cod_data_source_block           2e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4316689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1889(2) 0.99038(14) 0.68765(4) 0.0236(3) Uani 1 1 d . . .
O2 O 0.2046(2) 1.12697(15) 0.67175(5) 0.0298(3) Uani 1 1 d . . .
O3 O 0.0108(2) 0.28495(15) 0.23868(5) 0.0328(3) Uani 1 1 d . . .
H3 H 0.1368 0.3190 0.2195 0.049 Uiso 1 1 calc R . .
N1 N -0.0835(3) 0.64226(17) 0.45980(6) 0.0236(4) Uani 1 1 d . . .
N2 N 0.0984(2) 0.67369(17) 0.42824(6) 0.0234(4) Uani 1 1 d . . .
N3 N 0.4459(3) 0.46351(18) 0.21310(6) 0.0291(4) Uani 1 1 d . . .
C1 C -0.4036(3) 1.0144(2) 0.76996(7) 0.0312(5) Uani 1 1 d . . .
H1A H -0.5343 1.0413 0.7476 0.047 Uiso 1 1 calc R . .
H1B H -0.3926 1.0708 0.8058 0.047 Uiso 1 1 calc R . .
H1C H -0.4420 0.8934 0.7752 0.047 Uiso 1 1 calc R . .
C2 C -0.1612(3) 1.0720(2) 0.74133(7) 0.0247(4) Uani 1 1 d . . .
H2A H -0.1170 1.1948 0.7372 0.030 Uiso 1 1 calc R . .
H2B H -0.0287 1.0418 0.7629 0.030 Uiso 1 1 calc R . .
C3 C 0.0141(3) 1.0279(2) 0.65677(7) 0.0222(4) Uani 1 1 d . . .
C4 C -0.0155(3) 0.9329(2) 0.60437(7) 0.0211(4) Uani 1 1 d . . .
C5 C 0.1885(3) 0.9524(2) 0.57053(7) 0.0224(4) Uani 1 1 d . . .
H5 H 0.3395 1.0306 0.5805 0.027 Uiso 1 1 calc R . .
C6 C 0.1738(3) 0.8595(2) 0.52271(7) 0.0228(4) Uani 1 1 d . . .
H6 H 0.3139 0.8733 0.5000 0.027 Uiso 1 1 calc R . .
C7 C -0.0482(3) 0.7455(2) 0.50801(7) 0.0210(4) Uani 1 1 d . . .
C8 C -0.2536(3) 0.7264(2) 0.54112(7) 0.0237(4) Uani 1 1 d . . .
H8 H -0.4050 0.6491 0.5309 0.028 Uiso 1 1 calc R . .
C9 C -0.2375(3) 0.8201(2) 0.58894(7) 0.0243(4) Uani 1 1 d . . .
H9 H -0.3783 0.8075 0.6113 0.029 Uiso 1 1 calc R . .
C10 C 0.0649(3) 0.5708(2) 0.38054(7) 0.0219(4) Uani 1 1 d . . .
C11 C 0.2618(3) 0.5992(2) 0.34503(7) 0.0229(4) Uani 1 1 d . A .
H11 H 0.4081 0.6837 0.3538 0.028 Uiso 1 1 calc R . .
C12 C 0.2494(3) 0.5062(2) 0.29650(7) 0.0232(4) Uani 1 1 d . . .
C13 C 0.0325(3) 0.3801(2) 0.28459(7) 0.0246(4) Uani 1 1 d . A .
C14 C -0.1657(3) 0.3523(2) 0.32039(7) 0.0275(4) Uani 1 1 d . . .
H14 H -0.3118 0.2670 0.3121 0.033 Uiso 1 1 calc R A .
C15 C -0.1515(3) 0.4466(2) 0.36727(7) 0.0257(4) Uani 1 1 d . A .
H15 H -0.2889 0.4280 0.3910 0.031 Uiso 1 1 calc R . .
C16 C 0.4548(3) 0.5424(2) 0.25878(7) 0.0268(4) Uani 1 1 d . A .
H16 H 0.5998 0.6270 0.2683 0.032 Uiso 1 1 calc R . .
C17 C 0.647(3) 0.4967(18) 0.1808(5) 0.026(3) Uani 0.501(4) 1 d PD A 1
H17A H 0.6579 0.3933 0.1615 0.031 Uiso 0.501(4) 1 calc PR A 1
H17B H 0.7985 0.5374 0.2037 0.031 Uiso 0.501(4) 1 calc PR A 1
C18 C 0.6292(6) 0.6278(6) 0.13920(16) 0.0272(11) Uani 0.501(4) 1 d PD A 1
H18A H 0.6313 0.7322 0.1594 0.033 Uiso 0.501(4) 1 calc PR A 1
H18B H 0.7791 0.6506 0.1165 0.033 Uiso 0.501(4) 1 calc PR A 1
C19 C 0.4075(15) 0.5874(9) 0.1012(4) 0.0276(18) Uani 0.501(4) 1 d PD A 1
H19A H 0.2564 0.5721 0.1232 0.033 Uiso 0.501(4) 1 calc PR A 1
H19B H 0.3990 0.4806 0.0818 0.033 Uiso 0.501(4) 1 calc PR A 1
C20 C 0.4121(8) 0.7216(6) 0.05902(19) 0.0273(11) Uani 0.501(4) 1 d PD A 1
H20A H 0.4166 0.8271 0.0788 0.033 Uiso 0.501(4) 1 calc PR A 1
H20B H 0.5673 0.7394 0.0383 0.033 Uiso 0.501(4) 1 calc PR A 1
C21 C 0.2001(10) 0.6868(7) 0.0185(2) 0.0296(13) Uani 0.501(4) 1 d PD A 1
H21A H 0.0453 0.6735 0.0391 0.036 Uiso 0.501(4) 1 calc PR A 1
H21B H 0.1914 0.5791 -0.0002 0.036 Uiso 0.501(4) 1 calc PR A 1
C22 C 0.2109(13) 0.8183(8) -0.0248(2) 0.0273(15) Uani 0.501(4) 1 d PD A 1
H22A H 0.2229 0.9265 -0.0060 0.033 Uiso 0.501(4) 1 calc PR A 1
H22B H 0.3643 0.8300 -0.0457 0.033 Uiso 0.501(4) 1 calc PR A 1
C23 C -0.0025(8) 0.7859(7) -0.06474(16) 0.0332(12) Uani 0.501(4) 1 d PD A 1
H23A H -0.1556 0.7761 -0.0438 0.040 Uiso 0.501(4) 1 calc PR A 1
H23B H -0.0163 0.6769 -0.0831 0.040 Uiso 0.501(4) 1 calc PR A 1
C24 C 0.011(4) 0.9160(18) -0.1085(4) 0.037(3) Uani 0.501(4) 1 d PD A 1
H24A H 0.0190 1.0243 -0.0911 0.055 Uiso 0.501(4) 1 calc PR A 1
H24B H -0.1367 0.8833 -0.1323 0.055 Uiso 0.501(4) 1 calc PR A 1
H24C H 0.1584 0.9246 -0.1305 0.055 Uiso 0.501(4) 1 calc PR A 1
C17A C 0.677(3) 0.5230(19) 0.1749(5) 0.031(3) Uani 0.499(4) 1 d PD A 2
H17C H 0.7697 0.6369 0.1866 0.037 Uiso 0.499(4) 1 calc PR A 2
H17D H 0.7865 0.4483 0.1802 0.037 Uiso 0.499(4) 1 calc PR A 2
C18A C 0.6115(6) 0.5248(5) 0.11470(15) 0.0241(11) Uani 0.499(4) 1 d PD A 2
H18C H 0.5154 0.4113 0.1033 0.029 Uiso 0.499(4) 1 calc PR A 2
H18D H 0.7662 0.5517 0.0936 0.029 Uiso 0.499(4) 1 calc PR A 2
C19A C 0.4627(16) 0.6490(8) 0.0993(3) 0.0271(18) Uani 0.499(4) 1 d PD A 2
H19C H 0.5512 0.7618 0.1130 0.033 Uiso 0.499(4) 1 calc PR A 2
H19D H 0.3003 0.6167 0.1174 0.033 Uiso 0.499(4) 1 calc PR A 2
C20A C 0.4230(8) 0.6541(6) 0.03704(18) 0.0265(11) Uani 0.499(4) 1 d PD A 2
H20C H 0.5859 0.6905 0.0194 0.032 Uiso 0.499(4) 1 calc PR A 2
H20D H 0.3421 0.5399 0.0234 0.032 Uiso 0.499(4) 1 calc PR A 2
C21A C 0.2655(10) 0.7711(7) 0.0198(2) 0.0290(13) Uani 0.499(4) 1 d PD A 2
H21C H 0.1011 0.7334 0.0366 0.035 Uiso 0.499(4) 1 calc PR A 2
H21D H 0.3444 0.8850 0.0339 0.035 Uiso 0.499(4) 1 calc PR A 2
C22A C 0.2325(13) 0.7773(8) -0.0425(2) 0.0246(14) Uani 0.499(4) 1 d PD A 2
H22C H 0.3969 0.8161 -0.0594 0.029 Uiso 0.499(4) 1 calc PR A 2
H22D H 0.1550 0.6632 -0.0567 0.029 Uiso 0.499(4) 1 calc PR A 2
C23A C 0.0738(8) 0.8926(7) -0.05968(17) 0.0308(11) Uani 0.499(4) 1 d PD A 2
H23C H 0.1569 1.0079 -0.0475 0.037 Uiso 0.499(4) 1 calc PR A 2
H23D H -0.0865 0.8582 -0.0409 0.037 Uiso 0.499(4) 1 calc PR A 2
C24A C 0.026(4) 0.891(2) -0.1216(4) 0.041(3) Uani 0.499(4) 1 d PD A 2
H24D H 0.1837 0.9279 -0.1405 0.061 Uiso 0.499(4) 1 calc PR A 2
H24E H -0.0766 0.9673 -0.1301 0.061 Uiso 0.499(4) 1 calc PR A 2
H24F H -0.0597 0.7780 -0.1339 0.061 Uiso 0.499(4) 1 calc PR A 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 115.07(13) . . ?
C13 O3 H3 109.5 . . ?
N2 N1 C7 113.94(14) . . ?
N1 N2 C10 114.16(14) . . ?
C16 N3 C17 119.4(6) . . ?
C16 N3 C17A 116.2(5) . . ?
C17 N3 C17A 6.5(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 107.59(14) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 122.53(16) . . ?
O2 C3 C4 123.97(16) . . ?
O1 C3 C4 113.47(15) . . ?
C9 C4 C5 119.25(16) . . ?
C9 C4 C3 121.98(16) . . ?
C5 C4 C3 118.72(15) . . ?
C6 C5 C4 120.86(16) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.45(16) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.17(16) . . ?
C8 C7 N1 115.68(15) . . ?
C6 C7 N1 124.15(16) . . ?
C9 C8 C7 120.04(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 120.23(16) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C11 C10 C15 119.28(16) . . ?
C11 C10 N2 116.15(15) . . ?
C15 C10 N2 124.57(16) . . ?
C10 C11 C12 121.24(16) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 118.50(16) . . ?
C11 C12 C16 120.33(16) . . ?
C13 C12 C16 121.15(16) . . ?
O3 C13 C14 118.76(16) . . ?
O3 C13 C12 121.19(16) . . ?
C14 C13 C12 120.05(16) . . ?
C15 C14 C13 120.56(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.35(17) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N3 C16 C12 121.90(17) . . ?
N3 C16 H16 119.1 . . ?
C12 C16 H16 119.1 . . ?
N3 C17 C18 109.8(10) . . ?
N3 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
N3 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C17 116.9(7) . . ?
C19 C18 H18A 108.1 . . ?
C17 C18 H18A 108.1 . . ?
C19 C18 H18B 108.1 . . ?
C17 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C18 C19 C20 113.2(5) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 116.0(5) . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C19 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C20 C21 C22 115.8(5) . . ?
C20 C21 H21A 108.3 . . ?
C22 C21 H21A 108.3 . . ?
C20 C21 H21B 108.3 . . ?
C22 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C23 C22 C21 116.1(6) . . ?
C23 C22 H22A 108.3 . . ?
C21 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
C21 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 C24 116.0(8) . . ?
C22 C23 H23A 108.3 . . ?
C24 C23 H23A 108.3 . . ?
C22 C23 H23B 108.3 . . ?
C24 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
C18A C17A N3 114.0(10) . . ?
C18A C17A H17C 108.7 . . ?
N3 C17A H17C 108.7 . . ?
C18A C17A H17D 108.7 . . ?
N3 C17A H17D 108.7 . . ?
H17C C17A H17D 107.6 . . ?
C17A C18A C19A 114.7(8) . . ?
C17A C18A H18C 108.6 . . ?
C19A C18A H18C 108.6 . . ?
C17A C18A H18D 108.6 . . ?
C19A C18A H18D 108.6 . . ?
H18C C18A H18D 107.6 . . ?
C18A C19A C20A 111.6(6) . . ?
C18A C19A H19C 109.3 . . ?
C20A C19A H19C 109.3 . . ?
C18A C19A H19D 109.3 . . ?
C20A C19A H19D 109.3 . . ?
H19C C19A H19D 108.0 . . ?
C21A C20A C19A 113.5(5) . . ?
C21A C20A H20C 108.9 . . ?
C19A C20A H20C 108.9 . . ?
C21A C20A H20D 108.9 . . ?
C19A C20A H20D 108.9 . . ?
H20C C20A H20D 107.7 . . ?
C22A C21A C20A 112.8(5) . . ?
C22A C21A H21C 109.0 . . ?
C20A C21A H21C 109.0 . . ?
C22A C21A H21D 109.0 . . ?
C20A C21A H21D 109.0 . . ?
H21C C21A H21D 107.8 . . ?
C23A C22A C21A 112.8(5) . . ?
C23A C22A H22C 109.0 . . ?
C21A C22A H22C 109.0 . . ?
C23A C22A H22D 109.0 . . ?
C21A C22A H22D 109.0 . . ?
H22C C22A H22D 107.8 . . ?
C22A C23A C24A 113.2(8) . . ?
C22A C23A H23C 108.9 . . ?
C24A C23A H23C 108.9 . . ?
C22A C23A H23D 108.9 . . ?
C24A C23A H23D 108.9 . . ?
H23C C23A H23D 107.7 . . ?
C23A C24A H24D 109.5 . . ?
C23A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
C23A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3423(19) . ?
O1 C2 1.4547(19) . ?
O2 C3 1.2154(19) . ?
O3 C13 1.3485(19) . ?
O3 H3 0.8400 . ?
N1 N2 1.2594(19) . ?
N1 C7 1.428(2) . ?
N2 C10 1.417(2) . ?
N3 C16 1.279(2) . ?
N3 C17 1.356(17) . ?
N3 C17A 1.578(18) . ?
C1 C2 1.502(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.478(2) . ?
C4 C9 1.393(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 C15 1.404(2) . ?
C11 C12 1.397(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.407(2) . ?
C12 C16 1.454(2) . ?
C13 C14 1.395(2) . ?
C14 C15 1.368(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.514(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.504(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.502(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.515(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.500(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.513(11) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C17A C18A 1.509(10) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.532(8) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A C20A 1.534(9) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A C21A 1.531(7) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A C22A 1.529(7) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C22A C23A 1.524(7) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C23A C24A 1.528(11) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 N3 0.84 1.84 2.591(2) 147.6 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C10 179.56(13) . . . . ?
C3 O1 C2 C1 -179.41(13) . . . . ?
C2 O1 C3 O2 -2.4(2) . . . . ?
C2 O1 C3 C4 175.60(13) . . . . ?
O2 C3 C4 C9 179.83(16) . . . . ?
O1 C3 C4 C9 1.9(2) . . . . ?
O2 C3 C4 C5 2.4(2) . . . . ?
O1 C3 C4 C5 -175.54(14) . . . . ?
C9 C4 C5 C6 -1.1(2) . . . . ?
C3 C4 C5 C6 176.36(14) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C5 C6 C7 N1 -179.49(14) . . . . ?
N2 N1 C7 C8 173.68(14) . . . . ?
N2 N1 C7 C6 -6.4(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
N1 C7 C8 C9 179.57(14) . . . . ?
C7 C8 C9 C4 -0.5(2) . . . . ?
C5 C4 C9 C8 1.2(2) . . . . ?
C3 C4 C9 C8 -176.21(15) . . . . ?
N1 N2 C10 C11 -179.06(14) . . . . ?
N1 N2 C10 C15 1.8(2) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
N2 C10 C11 C12 -179.56(14) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C10 C11 C12 C16 177.67(15) . . . . ?
C11 C12 C13 O3 -179.24(14) . . . . ?
C16 C12 C13 O3 2.2(2) . . . . ?
C11 C12 C13 C14 1.1(2) . . . . ?
C16 C12 C13 C14 -177.45(15) . . . . ?
O3 C13 C14 C15 -179.70(15) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C10 -1.3(2) . . . . ?
C11 C10 C15 C14 1.5(2) . . . . ?
N2 C10 C15 C14 -179.42(15) . . . . ?
C17 N3 C16 C12 -176.8(6) . . . . ?
C17A N3 C16 C12 176.7(5) . . . . ?
C11 C12 C16 N3 -177.46(15) . . . . ?
C13 C12 C16 N3 1.1(3) . . . . ?
C16 N3 C17 C18 -93.6(7) . . . . ?
C17A N3 C17 C18 -31(7) . . . . ?
N3 C17 C18 C19 -58.6(12) . . . . ?
C17 C18 C19 C20 -176.8(8) . . . . ?
C18 C19 C20 C21 178.1(5) . . . . ?
C19 C20 C21 C22 -177.8(6) . . . . ?
C20 C21 C22 C23 -179.0(4) . . . . ?
C21 C22 C23 C24 -179.0(8) . . . . ?
C16 N3 C17A C18A -140.3(7) . . . . ?
C17 N3 C17A C18A 99(8) . . . . ?
N3 C17A C18A C19A 64.3(11) . . . . ?
C17A C18A C19A C20A 175.2(8) . . . . ?
C18A C19A C20A C21A 177.5(4) . . . . ?
C19A C20A C21A C22A 178.8(5) . . . . ?
C20A C21A C22A C23A 179.5(4) . . . . ?
C21A C22A C23A C24A -176.4(9) . . . . ?
