#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/42/2224286.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_2224286
loop_
_publ_author_name
'Arman, Hadi D.'
'Miller, Tyler'
'Poplaukhin, Pavel'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-[(4-Hydroxyphenyl)diazenyl]benzoic
 acid--N,N'-bis(4-pyridylmethyl)oxamide (2/1)
;
_journal_coeditor_code           HG2597
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3178
_journal_page_last               o3179
_journal_paper_doi               10.1107/S1600536809049228
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C13 H10 N2 O3, C14 H14 N4 O2'
_chemical_formula_moiety         '2(C13 H10 N2 O3), C14 H14 N4 O2'
_chemical_formula_sum            'C40 H34 N8 O8'
_chemical_formula_weight         754.75
_chemical_name_systematic
;
2-[(4-Hydroxyphenyl)diazenyl]benzoic
acid--N,N'-bis(4-pyridylmethyl)oxamide (2/1)
;
_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
_cell_angle_alpha                72.748(16)
_cell_angle_beta                 88.92(2)
_cell_angle_gamma                79.43(2)
_cell_formula_units_Z            1
_cell_length_a                   5.523(3)
_cell_length_b                   11.132(4)
_cell_length_c                   15.066(7)
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.6
_cell_measurement_theta_min      2.0
_cell_volume                     869.0(7)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.049
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6882
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.054
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0675P)²+0.3418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.136
_refine_ls_wR_factor_ref         0.143
_reflns_number_gt                3477
_reflns_number_total             3945
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2597.cif
_cod_data_source_block           I
_cod_database_code               2224286
_cod_database_fobs_code          2224286
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
O O1 1.0476(2) -0.00128(11) 0.38418(8) 0.0287(3) Uani d . 1 . .
O O2 0.7677(2) 0.68650(12) 0.51985(8) 0.0293(3) Uani d . 1 . .
O O3 0.5687(2) 0.83724(11) 0.40195(8) 0.0264(3) Uani d D 1 . .
H H1O 0.5873 0.8673 0.3446 0.040 Uiso d D 1 . .
O O4 0.0094(2) 1.33786(11) -0.01572(8) 0.0298(3) Uani d D 1 . .
H H2O 0.0524 1.3892 -0.0638 0.045 Uiso d D 1 . .
N N1 0.8421(3) 0.48340(13) 0.16157(9) 0.0268(3) Uani d . 1 . .
N N2 0.7290(2) 0.10782(13) 0.44396(9) 0.0238(3) Uani d D 1 . .
H H1N 0.6700 0.1179 0.4965 0.029 Uiso d D 1 . .
N N3 0.7538(2) 0.87835(12) 0.24039(9) 0.0222(3) Uani d . 1 . .
N N4 0.7707(2) 0.94258(12) 0.15667(9) 0.0230(3) Uani d . 1 . .
C C1 0.6793(3) 0.27688(14) 0.28993(10) 0.0216(3) Uani d . 1 . .
C C2 0.5771(3) 0.32819(15) 0.19998(11) 0.0267(3) Uani d . 1 . .
H H2 0.4492 0.2940 0.1805 0.032 Uiso calc R 1 . .
C C3 0.6641(3) 0.42965(16) 0.13916(11) 0.0299(4) Uani d . 1 . .
H H3 0.5930 0.4631 0.0778 0.036 Uiso calc R 1 . .
C C4 0.9377(3) 0.43484(15) 0.24874(11) 0.0264(3) Uani d . 1 . .
H H4 1.0628 0.4723 0.2666 0.032 Uiso calc R 1 . .
C C5 0.8634(3) 0.33260(15) 0.31435(11) 0.0252(3) Uani d . 1 . .
H H5 0.9376 0.3011 0.3752 0.030 Uiso calc R 1 . .
C C6 0.5892(3) 0.16366(15) 0.35621(11) 0.0244(3) Uani d . 1 . .
H H6A 0.4150 0.1914 0.3693 0.029 Uiso calc R 1 . .
H H6B 0.5944 0.0966 0.3250 0.029 Uiso calc R 1 . .
C C7 0.9439(3) 0.02757(14) 0.44999(10) 0.0221(3) Uani d . 1 . .
C C8 0.9611(3) 0.71595(14) 0.37441(10) 0.0208(3) Uani d . 1 . .
C C9 0.9623(3) 0.78081(14) 0.27915(10) 0.0212(3) Uani d . 1 . .
C C10 1.1625(3) 0.74920(15) 0.22689(11) 0.0258(3) Uani d . 1 . .
H H10 1.1636 0.7929 0.1624 0.031 Uiso calc R 1 . .
C C11 1.3589(3) 0.65398(16) 0.26952(12) 0.0279(4) Uani d . 1 . .
H H11 1.4954 0.6330 0.2341 0.034 Uiso calc R 1 . .
C C12 1.3583(3) 0.58874(15) 0.36356(12) 0.0265(3) Uani d . 1 . .
H H12 1.4932 0.5229 0.3922 0.032 Uiso calc R 1 . .
C C13 1.1604(3) 0.61987(15) 0.41561(11) 0.0237(3) Uani d . 1 . .
H H13 1.1606 0.5753 0.4800 0.028 Uiso calc R 1 . .
C C14 0.7599(3) 0.74462(14) 0.43795(10) 0.0222(3) Uani d . 1 . .
C C15 0.5672(3) 1.03918(14) 0.11805(10) 0.0224(3) Uani d . 1 . .
C C16 0.3394(3) 1.05976(15) 0.15929(11) 0.0233(3) Uani d . 1 . .
H H16 0.3115 1.0047 0.2186 0.028 Uiso calc R 1 . .
C C17 0.1561(3) 1.16005(15) 0.11346(11) 0.0251(3) Uani d . 1 . .
H H17 0.0018 1.1737 0.1414 0.030 Uiso calc R 1 . .
C C18 0.1956(3) 1.24225(15) 0.02580(11) 0.0238(3) Uani d . 1 . .
C C19 0.4230(3) 1.22184(16) -0.01495(11) 0.0263(3) Uani d . 1 . .
H H19 0.4520 1.2777 -0.0738 0.032 Uiso calc R 1 . .
C C20 0.6053(3) 1.12046(15) 0.03040(11) 0.0252(3) Uani d . 1 . .
H H20 0.7582 1.1057 0.0018 0.030 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
C14 O3 H1O . . 108.7 ?
C18 O4 H2O . . 112.5 ?
C3 N1 C4 . . 116.75(14) ?
C7 N2 C6 . . 120.86(13) ?
C7 N2 H1N . . 116.6 ?
C6 N2 H1N . . 122.1 ?
N4 N3 C9 . . 115.26(13) ?
N3 N4 C15 . . 115.72(13) ?
C2 C1 C5 . . 117.49(14) ?
C2 C1 C6 . . 119.45(14) ?
C5 C1 C6 . . 123.05(14) ?
C3 C2 C1 . . 119.17(16) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
N1 C3 C2 . . 123.90(15) ?
N1 C3 H3 . . 118.0 ?
C2 C3 H3 . . 118.0 ?
N1 C4 C5 . . 123.41(16) ?
N1 C4 H4 . . 118.3 ?
C5 C4 H4 . . 118.3 ?
C4 C5 C1 . . 119.28(15) ?
C4 C5 H5 . . 120.4 ?
C1 C5 H5 . . 120.4 ?
N2 C6 C1 . . 114.78(14) ?
N2 C6 H6A . . 108.6 ?
C1 C6 H6A . . 108.6 ?
N2 C6 H6B . . 108.6 ?
C1 C6 H6B . . 108.6 ?
H6A C6 H6B . . 107.5 ?
O1 C7 N2 . . 125.14(15) ?
O1 C7 C7 . 2_756 121.86(17) ?
N2 C7 C7 . 2_756 112.99(16) ?
C13 C8 C9 . . 119.19(14) ?
C13 C8 C14 . . 116.22(14) ?
C9 C8 C14 . . 124.57(14) ?
C10 C9 C8 . . 119.98(14) ?
C10 C9 N3 . . 123.07(14) ?
C8 C9 N3 . . 116.96(13) ?
C11 C10 C9 . . 119.74(15) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C12 . . 120.63(15) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.81(15) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C8 . . 120.65(15) ?
C12 C13 H13 . . 119.7 ?
C8 C13 H13 . . 119.7 ?
O2 C14 O3 . . 119.58(14) ?
O2 C14 C8 . . 122.19(14) ?
O3 C14 C8 . . 118.23(13) ?
C20 C15 N4 . . 114.33(14) ?
C20 C15 C16 . . 119.49(14) ?
N4 C15 C16 . . 126.18(14) ?
C17 C16 C15 . . 119.85(15) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.54(15) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
O4 C18 C19 . . 122.69(14) ?
O4 C18 C17 . . 117.82(14) ?
C19 C18 C17 . . 119.49(14) ?
C20 C19 C18 . . 119.95(15) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 120.66(15) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
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
O1 C7 . 1.2304(19) ?
O2 C14 . 1.2088(19) ?
O3 C14 . 1.3276(19) ?
O3 H1O . 0.8402 ?
O4 C18 . 1.3450(19) ?
O4 H2O . 0.8401 ?
N1 C3 . 1.337(2) ?
N1 C4 . 1.340(2) ?
N2 C7 . 1.335(2) ?
N2 C6 . 1.451(2) ?
N2 H1N . 0.8801 ?
N3 N4 . 1.2632(19) ?
N3 C9 . 1.427(2) ?
N4 C15 . 1.403(2) ?
C1 C2 . 1.390(2) ?
C1 C5 . 1.391(2) ?
C1 C6 . 1.516(2) ?
C2 C3 . 1.384(2) ?
C2 H2 . 0.9500 ?
C3 H3 . 0.9500 ?
C4 C5 . 1.389(2) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C7 2_756 1.542(3) ?
C8 C13 . 1.393(2) ?
C8 C9 . 1.403(2) ?
C8 C14 . 1.505(2) ?
C9 C10 . 1.398(2) ?
C10 C11 . 1.383(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.387(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.386(2) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C15 C20 . 1.399(2) ?
C15 C16 . 1.404(2) ?
C16 C17 . 1.379(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.405(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.398(2) ?
C19 C20 . 1.381(2) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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
O3 H1o N3 1_555 0.84 1.79 2.568(2) 154
N2 H1n O3 2_666 0.88 2.11 2.966(2) 163
O4 H2o N1 2_675 0.84 1.88 2.720(2) 173
C5 H5 O2 2_766 0.95 2.34 3.187(3) 148
C6 H6a O2 2_666 0.99 2.54 3.265(3) 130
C2 H2 Cg(3) 1_545 0.95 2.76 3.542(3) 140
C4 H4 Cg(2) 1_555 0.95 2.87 3.684(3) 145
C11 H11 Cg(1) 1_655 0.95 2.96 3.642(3) 130
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
C9 N3 N4 C15 . . . . -179.67(12) ?
C5 C1 C2 C3 . . . . 0.9(2) ?
C6 C1 C2 C3 . . . . -178.53(14) ?
C4 N1 C3 C2 . . . . -0.5(2) ?
C1 C2 C3 N1 . . . . -0.5(3) ?
C3 N1 C4 C5 . . . . 0.9(2) ?
N1 C4 C5 C1 . . . . -0.5(2) ?
C2 C1 C5 C4 . . . . -0.5(2) ?
C6 C1 C5 C4 . . . . 178.93(14) ?
C7 N2 C6 C1 . . . . -79.82(19) ?
C2 C1 C6 N2 . . . . 172.60(14) ?
C5 C1 C6 N2 . . . . -6.8(2) ?
C6 N2 C7 O1 . . . . 3.7(2) ?
C6 N2 C7 C7 . . . 2_756 -176.57(15) ?
C13 C8 C9 C10 . . . . -0.4(2) ?
C14 C8 C9 C10 . . . . 178.01(14) ?
C13 C8 C9 N3 . . . . 180.00(13) ?
C14 C8 C9 N3 . . . . -1.6(2) ?
N4 N3 C9 C10 . . . . -5.8(2) ?
N4 N3 C9 C8 . . . . 173.84(13) ?
C8 C9 C10 C11 . . . . 0.0(2) ?
N3 C9 C10 C11 . . . . 179.58(15) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C10 C11 C12 C13 . . . . -0.6(3) ?
C11 C12 C13 C8 . . . . 0.2(2) ?
C9 C8 C13 C12 . . . . 0.3(2) ?
C14 C8 C13 C12 . . . . -178.21(14) ?
C13 C8 C14 O2 . . . . -1.2(2) ?
C9 C8 C14 O2 . . . . -179.56(15) ?
C13 C8 C14 O3 . . . . 178.70(14) ?
C9 C8 C14 O3 . . . . 0.3(2) ?
N3 N4 C15 C20 . . . . 171.10(13) ?
N3 N4 C15 C16 . . . . -8.5(2) ?
C20 C15 C16 C17 . . . . -0.4(2) ?
N4 C15 C16 C17 . . . . 179.19(15) ?
C15 C16 C17 C18 . . . . -0.2(2) ?
C16 C17 C18 O4 . . . . 179.60(14) ?
C16 C17 C18 C19 . . . . 0.0(2) ?
O4 C18 C19 C20 . . . . -178.74(15) ?
C17 C18 C19 C20 . . . . 0.9(2) ?
C18 C19 C20 C15 . . . . -1.5(2) ?
N4 C15 C20 C19 . . . . -178.39(14) ?
C16 C15 C20 C19 . . . . 1.2(2) ?
