#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/15/2221567.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_2221567
loop_
_publ_author_name
'Rofouei, Mohammad Kazem'
'Melardi, Mohammad Reza'
'Salemi, Yasaman'
'Kazemi, Saba Razi'
_publ_section_title
;
 1,3-Bis(2-ethoxyphenyl)triazene
;
_journal_coeditor_code           ZL2178
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o719
_journal_paper_doi               10.1107/S1600536809008034
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H19 N3 O2'
_chemical_formula_moiety         'C16 H19 N3 O2'
_chemical_formula_sum            'C16 H19 N3 O2'
_chemical_formula_weight         285.34
_chemical_name_systematic
;
1,3-Bis(2-ethoxyphenyl)triazene
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.467(5)
_cell_angle_beta                 98.598(5)
_cell_angle_gamma                116.512(5)
_cell_formula_units_Z            4
_cell_length_a                   11.3971(7)
_cell_length_b                   11.8696(7)
_cell_length_c                   14.0627(9)
_cell_measurement_reflns_used    887
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1545.7(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17109
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         8181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0576
_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)+(0.0517P)²+0.497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                4988
_reflns_number_total             8181
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2178.cif
_cod_data_source_block           I
_cod_database_code               2221567
_cod_database_fobs_code          2221567
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
N N1 0.65754(14) 0.89887(15) 0.26280(11) 0.0273(3) Uani d . 1 . .
H H1N 0.6187 0.8521 0.3017 0.033 Uiso d R 1 . .
N N2 0.57346(14) 0.91539(14) 0.20038(10) 0.0247(3) Uani d . 1 . .
N N3 0.44508(14) 0.83193(14) 0.18591(11) 0.0253(3) Uani d . 1 . .
O O1 0.81959(12) 0.82358(12) 0.34265(9) 0.0309(3) Uani d . 1 . .
O O2 0.17841(12) 0.66700(12) 0.14955(9) 0.0308(3) Uani d . 1 . .
C C1 0.80038(16) 0.98331(17) 0.28546(12) 0.0244(4) Uani d . 1 . .
C C2 0.88658(17) 0.94198(17) 0.32698(13) 0.0256(4) Uani d . 1 . .
C C3 1.02882(17) 1.01982(18) 0.34861(14) 0.0304(4) Uani d . 1 . .
H H3A 1.0873 0.9918 0.3765 0.036 Uiso calc R 1 . .
C C4 1.08542(18) 1.13829(18) 0.32955(14) 0.0323(4) Uani d . 1 . .
H H4A 1.1827 1.1913 0.3445 0.039 Uiso calc R 1 . .
C C5 1.00087(18) 1.17975(18) 0.28886(14) 0.0317(4) Uani d . 1 . .
H H5A 1.0401 1.2610 0.2758 0.038 Uiso calc R 1 . .
C C6 0.85879(17) 1.10262(17) 0.26714(13) 0.0277(4) Uani d . 1 . .
H H6A 0.8010 1.1315 0.2396 0.033 Uiso calc R 1 . .
C C7 0.90069(18) 0.77429(18) 0.38370(14) 0.0314(4) Uani d . 1 . .
H H7A 0.9703 0.8444 0.4523 0.038 Uiso calc R 1 . .
H H7B 0.9498 0.7535 0.3353 0.038 Uiso calc R 1 . .
C C8 0.8034(2) 0.6466(2) 0.39582(15) 0.0386(5) Uani d . 1 . .
H H8A 0.8561 0.6107 0.4247 0.058 Uiso calc R 1 . .
H H8B 0.7358 0.5775 0.3273 0.058 Uiso calc R 1 . .
H H8C 0.7548 0.6682 0.4434 0.058 Uiso calc R 1 . .
C C9 0.35033(16) 0.84446(16) 0.11871(12) 0.0217(3) Uani d . 1 . .
C C10 0.20907(17) 0.75634(16) 0.10018(13) 0.0244(3) Uani d . 1 . .
C C11 0.10996(17) 0.76308(17) 0.03477(13) 0.0278(4) Uani d . 1 . .
H H11A 0.0143 0.7043 0.0226 0.033 Uiso calc R 1 . .
C C12 0.15150(18) 0.85612(18) -0.01262(14) 0.0294(4) Uani d . 1 . .
H H12A 0.0837 0.8594 -0.0582 0.035 Uiso calc R 1 . .
C C13 0.29049(18) 0.94394(17) 0.00583(13) 0.0279(4) Uani d . 1 . .
H H13A 0.3180 1.0074 -0.0268 0.034 Uiso calc R 1 . .
C C14 0.38903(17) 0.93889(17) 0.07190(12) 0.0245(3) Uani d . 1 . .
H H14A 0.4845 1.0006 0.0857 0.029 Uiso calc R 1 . .
C C15 0.03901(18) 0.59545(18) 0.14986(14) 0.0310(4) Uani d . 1 . .
H H15A -0.0245 0.5332 0.0776 0.037 Uiso calc R 1 . .
H H15B 0.0101 0.6613 0.1796 0.037 Uiso calc R 1 . .
C C16 0.0351(2) 0.5146(2) 0.21591(15) 0.0396(5) Uani d . 1 . .
H H16A -0.0596 0.4627 0.2168 0.059 Uiso calc R 1 . .
H H16B 0.0970 0.5775 0.2876 0.059 Uiso calc R 1 . .
H H16C 0.0656 0.4511 0.1864 0.059 Uiso calc R 1 . .
N N4 0.50110(14) 0.71697(14) 0.36671(10) 0.0249(3) Uani d . 1 . .
N N5 0.42582(13) 0.58882(14) 0.30543(10) 0.0230(3) Uani d . 1 . .
N N6 0.39770(14) 0.57030(13) 0.20569(10) 0.0246(3) Uani d . 1 . .
H H6N 0.4166 0.6468 0.1933 0.030 Uiso d R 1 . .
O O3 0.65249(12) 0.97589(11) 0.49894(9) 0.0283(3) Uani d . 1 . .
O O4 0.36188(12) 0.53622(11) 0.00756(8) 0.0262(3) Uani d . 1 . .
C C17 0.52863(16) 0.74425(16) 0.47504(12) 0.0220(3) Uani d . 1 . .
C C18 0.60555(16) 0.88364(17) 0.54400(13) 0.0238(3) Uani d . 1 . .
C C19 0.62867(17) 0.91875(18) 0.65110(13) 0.0277(4) Uani d . 1 . .
H H19A 0.6786 1.0125 0.6978 0.033 Uiso calc R 1 . .
C C20 0.57898(18) 0.81711(19) 0.68985(13) 0.0305(4) Uani d . 1 . .
H H20A 0.5950 0.8417 0.7630 0.037 Uiso calc R 1 . .
C C21 0.50605(18) 0.67988(19) 0.62246(13) 0.0303(4) Uani d . 1 . .
H H21A 0.4743 0.6106 0.6494 0.036 Uiso calc R 1 . .
C C22 0.47978(17) 0.64436(17) 0.51545(13) 0.0261(4) Uani d . 1 . .
H H22A 0.4276 0.5503 0.4692 0.031 Uiso calc R 1 . .
C C23 0.70481(18) 1.11735(17) 0.56228(13) 0.0290(4) Uani d . 1 . .
H H23A 0.7870 1.1528 0.6224 0.035 Uiso calc R 1 . .
H H23B 0.6332 1.1272 0.5895 0.035 Uiso calc R 1 . .
C C24 0.74328(19) 1.19540(18) 0.49298(14) 0.0328(4) Uani d . 1 . .
H H24A 0.7725 1.2913 0.5318 0.049 Uiso calc R 1 . .
H H24B 0.6629 1.1546 0.4309 0.049 Uiso calc R 1 . .
H H24C 0.8194 1.1910 0.4713 0.049 Uiso calc R 1 . .
C C25 0.31797(16) 0.43556(16) 0.12976(12) 0.0217(3) Uani d . 1 . .
C C26 0.30226(16) 0.41821(16) 0.02469(12) 0.0222(3) Uani d . 1 . .
C C27 0.22978(17) 0.28660(17) -0.05366(13) 0.0251(4) Uani d . 1 . .
H H27A 0.2193 0.2742 -0.1248 0.030 Uiso calc R 1 . .
C C28 0.17266(17) 0.17315(17) -0.02762(13) 0.0274(4) Uani d . 1 . .
H H28A 0.1229 0.0834 -0.0813 0.033 Uiso calc R 1 . .
C C29 0.18774(17) 0.19007(17) 0.07571(13) 0.0269(4) Uani d . 1 . .
H H29A 0.1484 0.1122 0.0929 0.032 Uiso calc R 1 . .
C C30 0.26063(16) 0.32121(17) 0.15456(13) 0.0243(3) Uani d . 1 . .
H H30A 0.2713 0.3328 0.2256 0.029 Uiso calc R 1 . .
C C31 0.35336(17) 0.52266(17) -0.09816(12) 0.0250(4) Uani d . 1 . .
H H31A 0.2552 0.4705 -0.1429 0.030 Uiso calc R 1 . .
H H31B 0.3990 0.4729 -0.1264 0.030 Uiso calc R 1 . .
C C32 0.42454(19) 0.66412(18) -0.09738(14) 0.0319(4) Uani d . 1 . .
H H32A 0.4228 0.6579 -0.1686 0.048 Uiso calc R 1 . .
H H32B 0.5208 0.7156 -0.0514 0.048 Uiso calc R 1 . .
H H32C 0.3765 0.7112 -0.0716 0.048 Uiso calc R 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'
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
N2 N1 C1 . . 117.93(14) ?
N2 N1 H1N . . 115.2 ?
C1 N1 H1N . . 124.3 ?
N3 N2 N1 . . 111.87(13) ?
N2 N3 C9 . . 114.20(13) ?
C2 O1 C7 . . 118.23(13) ?
C10 O2 C15 . . 117.52(13) ?
C6 C1 N1 . . 123.34(15) ?
C6 C1 C2 . . 119.40(15) ?
N1 C1 C2 . . 117.25(15) ?
O1 C2 C3 . . 125.06(15) ?
O1 C2 C1 . . 115.10(14) ?
C3 C2 C1 . . 119.84(15) ?
C4 C3 C2 . . 120.06(16) ?
C4 C3 H3A . . 120.0 ?
C2 C3 H3A . . 120.0 ?
C5 C4 C3 . . 120.33(16) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C4 C5 C6 . . 119.94(16) ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C5 C6 C1 . . 120.43(16) ?
C5 C6 H6A . . 119.8 ?
C1 C6 H6A . . 119.8 ?
O1 C7 C8 . . 107.45(15) ?
O1 C7 H7A . . 110.2 ?
C8 C7 H7A . . 110.2 ?
O1 C7 H7B . . 110.2 ?
C8 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C14 C9 C10 . . 119.11(14) ?
C14 C9 N3 . . 124.14(14) ?
C10 C9 N3 . . 116.74(14) ?
O2 C10 C11 . . 124.14(15) ?
O2 C10 C9 . . 116.04(14) ?
C11 C10 C9 . . 119.82(15) ?
C12 C11 C10 . . 119.79(15) ?
C12 C11 H11A . . 120.1 ?
C10 C11 H11A . . 120.1 ?
C13 C12 C11 . . 120.73(16) ?
C13 C12 H12A . . 119.6 ?
C11 C12 H12A . . 119.6 ?
C14 C13 C12 . . 119.60(16) ?
C14 C13 H13A . . 120.2 ?
C12 C13 H13A . . 120.2 ?
C13 C14 C9 . . 120.92(15) ?
C13 C14 H14A . . 119.5 ?
C9 C14 H14A . . 119.5 ?
O2 C15 C16 . . 107.22(15) ?
O2 C15 H15A . . 110.3 ?
C16 C15 H15A . . 110.3 ?
O2 C15 H15B . . 110.3 ?
C16 C15 H15B . . 110.3 ?
H15A C15 H15B . . 108.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N5 N4 C17 . . 114.76(13) ?
N4 N5 N6 . . 111.94(13) ?
N5 N6 C25 . . 118.29(13) ?
N5 N6 H6N . . 115.3 ?
C25 N6 H6N . . 125.1 ?
C18 O3 C23 . . 117.69(13) ?
C26 O4 C31 . . 117.43(12) ?
C22 C17 C18 . . 119.30(15) ?
C22 C17 N4 . . 124.46(15) ?
C18 C17 N4 . . 116.16(14) ?
O3 C18 C19 . . 124.44(15) ?
O3 C18 C17 . . 116.05(14) ?
C19 C18 C17 . . 119.51(15) ?
C20 C19 C18 . . 120.20(16) ?
C20 C19 H19A . . 119.9 ?
C18 C19 H19A . . 119.9 ?
C21 C20 C19 . . 120.42(16) ?
C21 C20 H20A . . 119.8 ?
C19 C20 H20A . . 119.8 ?
C20 C21 C22 . . 119.60(16) ?
C20 C21 H21A . . 120.2 ?
C22 C21 H21A . . 120.2 ?
C21 C22 C17 . . 120.93(16) ?
C21 C22 H22A . . 119.5 ?
C17 C22 H22A . . 119.5 ?
O3 C23 C24 . . 106.93(14) ?
O3 C23 H23A . . 110.3 ?
C24 C23 H23A . . 110.3 ?
O3 C23 H23B . . 110.3 ?
C24 C23 H23B . . 110.3 ?
H23A C23 H23B . . 108.6 ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C30 C25 N6 . . 123.08(14) ?
C30 C25 C26 . . 119.77(14) ?
N6 C25 C26 . . 117.08(14) ?
O4 C26 C27 . . 124.58(14) ?
O4 C26 C25 . . 115.80(14) ?
C27 C26 C25 . . 119.62(14) ?
C26 C27 C28 . . 119.93(15) ?
C26 C27 H27A . . 120.0 ?
C28 C27 H27A . . 120.0 ?
C29 C28 C27 . . 120.51(15) ?
C29 C28 H28A . . 119.7 ?
C27 C28 H28A . . 119.7 ?
C28 C29 C30 . . 119.94(15) ?
C28 C29 H29A . . 120.0 ?
C30 C29 H29A . . 120.0 ?
C29 C30 C25 . . 120.22(15) ?
C29 C30 H30A . . 119.9 ?
C25 C30 H30A . . 119.9 ?
O4 C31 C32 . . 107.73(13) ?
O4 C31 H31A . . 110.2 ?
C32 C31 H31A . . 110.2 ?
O4 C31 H31B . . 110.2 ?
C32 C31 H31B . . 110.2 ?
H31A C31 H31B . . 108.5 ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
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
N1 N2 . 1.3196(18) ?
N1 C1 . 1.401(2) ?
N1 H1N . 0.9100 ?
N2 N3 . 1.2909(18) ?
N3 C9 . 1.414(2) ?
O1 C2 . 1.369(2) ?
O1 C7 . 1.430(2) ?
O2 C10 . 1.3739(19) ?
O2 C15 . 1.430(2) ?
C1 C6 . 1.390(2) ?
C1 C2 . 1.403(2) ?
C2 C3 . 1.389(2) ?
C3 C4 . 1.386(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.384(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.387(2) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C8 . 1.503(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C14 . 1.396(2) ?
C9 C10 . 1.404(2) ?
C10 C11 . 1.393(2) ?
C11 C12 . 1.390(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.383(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.381(2) ?
C13 H13A . 0.9500 ?
C14 H14A . 0.9500 ?
C15 C16 . 1.505(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
N4 N5 . 1.2896(18) ?
N4 C17 . 1.418(2) ?
N5 N6 . 1.3214(18) ?
N6 C25 . 1.403(2) ?
N6 H6N . 0.9100 ?
O3 C18 . 1.3634(19) ?
O3 C23 . 1.4380(19) ?
O4 C26 . 1.3684(19) ?
O4 C31 . 1.4327(18) ?
C17 C22 . 1.388(2) ?
C17 C18 . 1.410(2) ?
C18 C19 . 1.392(2) ?
C19 C20 . 1.389(2) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.387(2) ?
C20 H20A . 0.9500 ?
C21 C22 . 1.387(2) ?
C21 H21A . 0.9500 ?
C22 H22A . 0.9500 ?
C23 C24 . 1.509(2) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
C25 C30 . 1.391(2) ?
C25 C26 . 1.405(2) ?
C26 C27 . 1.392(2) ?
C27 C28 . 1.393(2) ?
C27 H27A . 0.9500 ?
C28 C29 . 1.382(2) ?
C28 H28A . 0.9500 ?
C29 C30 . 1.391(2) ?
C29 H29A . 0.9500 ?
C30 H30A . 0.9500 ?
C31 C32 . 1.499(2) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
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
N1 H1N N4 1_555 0.91 2.12 3.018(2) 170 yes
N6 H6N N3 1_555 0.91 2.11 3.008(2) 170 yes
C4 H4A Cg1 2_776 0.95 2.85 3.686(2) 147 yes
C32 H32B Cg2 2_665 0.98 2.78 3.549(3) 136 yes
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
C1 N1 N2 N3 . . . . -179.87(14) ?
N1 N2 N3 C9 . . . . -179.45(13) ?
N2 N1 C1 C6 . . . . 15.8(2) ?
N2 N1 C1 C2 . . . . -163.08(14) ?
C7 O1 C2 C3 . . . . -0.5(2) ?
C7 O1 C2 C1 . . . . 179.30(14) ?
C6 C1 C2 O1 . . . . 179.75(14) ?
N1 C1 C2 O1 . . . . -1.4(2) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
N1 C1 C2 C3 . . . . 178.44(15) ?
O1 C2 C3 C4 . . . . 180.00(15) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C4 C5 C6 C1 . . . . -0.3(3) ?
N1 C1 C6 C5 . . . . -178.32(16) ?
C2 C1 C6 C5 . . . . 0.5(2) ?
C2 O1 C7 C8 . . . . 178.55(14) ?
N2 N3 C9 C14 . . . . -0.7(2) ?
N2 N3 C9 C10 . . . . -179.91(14) ?
C15 O2 C10 C11 . . . . -12.3(2) ?
C15 O2 C10 C9 . . . . 167.79(14) ?
C14 C9 C10 O2 . . . . -179.35(14) ?
N3 C9 C10 O2 . . . . -0.1(2) ?
C14 C9 C10 C11 . . . . 0.8(2) ?
N3 C9 C10 C11 . . . . 179.99(15) ?
O2 C10 C11 C12 . . . . -179.23(16) ?
C9 C10 C11 C12 . . . . 0.6(2) ?
C10 C11 C12 C13 . . . . -1.1(3) ?
C11 C12 C13 C14 . . . . 0.1(3) ?
C12 C13 C14 C9 . . . . 1.3(3) ?
C10 C9 C14 C13 . . . . -1.8(2) ?
N3 C9 C14 C13 . . . . 179.08(15) ?
C10 O2 C15 C16 . . . . -175.19(14) ?
C17 N4 N5 N6 . . . . 176.67(13) ?
N4 N5 N6 C25 . . . . 179.15(13) ?
N5 N4 C17 C22 . . . . -0.5(2) ?
N5 N4 C17 C18 . . . . -177.30(14) ?
C23 O3 C18 C19 . . . . -13.0(2) ?
C23 O3 C18 C17 . . . . 166.92(14) ?
C22 C17 C18 O3 . . . . 178.74(14) ?
N4 C17 C18 O3 . . . . -4.3(2) ?
C22 C17 C18 C19 . . . . -1.3(2) ?
N4 C17 C18 C19 . . . . 175.66(14) ?
O3 C18 C19 C20 . . . . -178.65(15) ?
C17 C18 C19 C20 . . . . 1.4(2) ?
C18 C19 C20 C21 . . . . 0.0(3) ?
C19 C20 C21 C22 . . . . -1.6(3) ?
C20 C21 C22 C17 . . . . 1.7(3) ?
C18 C17 C22 C21 . . . . -0.2(2) ?
N4 C17 C22 C21 . . . . -176.97(16) ?
C18 O3 C23 C24 . . . . -177.46(14) ?
N5 N6 C25 C30 . . . . 3.8(2) ?
N5 N6 C25 C26 . . . . -173.27(14) ?
C31 O4 C26 C27 . . . . -2.5(2) ?
C31 O4 C26 C25 . . . . 177.30(13) ?
C30 C25 C26 O4 . . . . 179.94(14) ?
N6 C25 C26 O4 . . . . -2.9(2) ?
C30 C25 C26 C27 . . . . -0.2(2) ?
N6 C25 C26 C27 . . . . 176.98(14) ?
O4 C26 C27 C28 . . . . -179.79(15) ?
C25 C26 C27 C28 . . . . 0.4(2) ?
C26 C27 C28 C29 . . . . -0.2(2) ?
C27 C28 C29 C30 . . . . -0.1(2) ?
C28 C29 C30 C25 . . . . 0.3(2) ?
N6 C25 C30 C29 . . . . -177.13(15) ?
C26 C25 C30 C29 . . . . -0.1(2) ?
C26 O4 C31 C32 . . . . 179.72(13) ?
