#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/80/2208066.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_2208066
loop_
_publ_author_name
'Xiu-Li You'
'Yan Zhang'
'De-Chun Zhang'
_publ_section_title
;
 4-(2-Methoxy-4-nitrophenyldiazenyl)phenol monohydrate
;
_journal_coeditor_code           GH6026
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o668
_journal_page_last               o670
_journal_paper_doi               10.1107/S1600536806001553
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H11 N3 O4, H2 O'
_chemical_formula_moiety         'C13 H11 N3 O4, H2 O'
_chemical_formula_sum            'C13 H13 N3 O5'
_chemical_formula_weight         291.26
_chemical_melting_point          499
_chemical_name_systematic
;
4-(2-Methoxy-4-nitrophenyldiazenyl)phenol monohydrate
;
_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                75.286(11)
_cell_angle_beta                 88.505(15)
_cell_angle_gamma                84.737(15)
_cell_formula_units_Z            2
_cell_length_a                   7.2392(18)
_cell_length_b                   8.6741(15)
_cell_length_c                   11.066(3)
_cell_measurement_reflns_used    2640
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_cell_volume                     669.2(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7473
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0552
_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)+(0.0575P)²+0.1914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2568
_reflns_number_total             2996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gh6026.cif
_cod_data_source_block           I
_cod_original_cell_volume        669.3(3)
_cod_database_code               2208066
_cod_database_fobs_code          2208066
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
O1 0.05712(18) -0.62942(13) 0.85645(10) 0.0346(3) Uani d . 1 O
H1 0.0433 -0.6909 0.8103 0.052 Uiso calc R 1 H
O2 0.27545(16) 0.06065(12) 0.22128(10) 0.0299(3) Uani d . 1 O
O3 0.4557(2) 0.70362(14) 0.24945(13) 0.0500(4) Uani d . 1 O
O4 0.4171(2) 0.63411(15) 0.07898(11) 0.0444(3) Uani d . 1 O
O5 0.9941(2) 0.17111(15) 0.71625(12) 0.0381(3) Uani d . 1 O
H5A 1.078(4) 0.122(4) 0.678(3) 0.086(9) Uiso d . 1 H
H5B 0.902(4) 0.121(3) 0.720(2) 0.072(8) Uiso d . 1 H
N1 0.25982(16) -0.00952(14) 0.46748(11) 0.0240(3) Uani d . 1 N
N2 0.23014(17) -0.02976(15) 0.58330(11) 0.0242(3) Uani d . 1 N
N3 0.41916(19) 0.60607(15) 0.19300(13) 0.0299(3) Uani d . 1 N
C1 0.3328(2) 0.26703(18) 0.46383(14) 0.0255(3) Uani d . 1 C
H1A 0.3310 0.2437 0.5525 0.031 Uiso calc R 1 H
C2 0.3694(2) 0.41758(18) 0.39486(14) 0.0259(3) Uani d . 1 C
H2 0.3895 0.4994 0.4349 0.031 Uiso calc R 1 H
C3 0.3761(2) 0.44652(17) 0.26627(14) 0.0235(3) Uani d . 1 C
C4 0.3471(2) 0.33273(17) 0.20297(14) 0.0239(3) Uani d . 1 C
H4A 0.3542 0.3567 0.1144 0.029 Uiso calc R 1 H
C5 0.30725(19) 0.18181(17) 0.27285(14) 0.0225(3) Uani d . 1 C
C6 0.29842(19) 0.14870(17) 0.40423(13) 0.0218(3) Uani d . 1 C
C7 0.1615(2) -0.30650(17) 0.58683(13) 0.0248(3) Uani d . 1 C
H7 0.1713 -0.2853 0.4985 0.030 Uiso calc R 1 H
C8 0.1175(2) -0.45451(17) 0.65558(14) 0.0250(3) Uani d . 1 C
H8 0.0960 -0.5349 0.6145 0.030 Uiso calc R 1 H
C9 0.1046(2) -0.48669(17) 0.78558(13) 0.0235(3) Uani d . 1 C
C10 0.1378(2) -0.36974(19) 0.84615(14) 0.0276(3) Uani d . 1 C
H10 0.1315 -0.3921 0.9347 0.033 Uiso calc R 1 H
C11 0.1801(2) -0.22087(18) 0.77670(14) 0.0264(3) Uani d . 1 C
H11 0.2015 -0.1405 0.8178 0.032 Uiso calc R 1 H
C12 0.19181(19) -0.18742(17) 0.64657(13) 0.0224(3) Uani d . 1 C
C13 0.2944(3) 0.0876(2) 0.08859(15) 0.0427(5) Uani d . 1 C
H13A 0.2027 0.1739 0.0473 0.064 Uiso calc R 1 H
H13B 0.2740 -0.0106 0.0643 0.064 Uiso calc R 1 H
H13C 0.4195 0.1179 0.0634 0.064 Uiso calc R 1 H
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_publ_flag
C9 O1 H1 109.5 ?
C5 O2 C13 117.86(12) y
H5A O5 H5B 105(3) ?
N2 N1 C6 114.24(12) y
N1 N2 C12 114.35(12) y
O3 N3 O4 123.41(14) y
O3 N3 C3 118.18(14) y
O4 N3 C3 118.42(13) y
C2 C1 C6 120.47(14) ?
C2 C1 H1A 119.8 ?
C6 C1 H1A 119.8 ?
C1 C2 C3 118.42(14) ?
C1 C2 H2 120.8 ?
C3 C2 H2 120.8 ?
C4 C3 C2 123.36(13) ?
C4 C3 N3 118.28(13) ?
C2 C3 N3 118.35(13) ?
C3 C4 C5 118.00(14) ?
C3 C4 H4A 121.0 ?
C5 C4 H4A 121.0 ?
O2 C5 C4 123.40(13) ?
O2 C5 C6 116.57(12) ?
C4 C5 C6 120.02(13) ?
C1 C6 C5 119.69(13) ?
C1 C6 N1 124.39(13) ?
C5 C6 N1 115.89(13) ?
C8 C7 C12 120.20(13) ?
C8 C7 H7 119.9 ?
C12 C7 H7 119.9 ?
C7 C8 C9 120.13(14) ?
C7 C8 H8 119.9 ?
C9 C8 H8 119.9 ?
O1 C9 C10 117.90(13) y
O1 C9 C8 122.00(14) y
C10 C9 C8 120.09(13) y
C11 C10 C9 119.56(14) ?
C11 C10 H10 120.2 ?
C9 C10 H10 120.2 ?
C10 C11 C12 120.64(14) ?
C10 C11 H11 119.7 ?
C12 C11 H11 119.7 ?
C7 C12 C11 119.36(13) ?
C7 C12 N2 124.16(13) ?
C11 C12 N2 116.47(13) ?
O2 C13 H13A 109.5 ?
O2 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
O2 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.3551(17) y
O1 H1 0.8400 ?
O2 C5 1.3561(17) y
O2 C13 1.4320(19) y
O3 N3 1.2224(18) y
O4 N3 1.2230(18) y
O5 H5A 0.87(3) ?
O5 H5B 0.83(3) ?
N1 N2 1.2641(17) y
N1 C6 1.4226(18) y
N2 C12 1.4179(18) y
N3 C3 1.4716(19) y
C1 C2 1.380(2) ?
C1 C6 1.396(2) ?
C1 H1A 0.9500 ?
C2 C3 1.381(2) ?
C2 H2 0.9500 ?
C3 C4 1.381(2) ?
C4 C5 1.392(2) ?
C4 H4A 0.9500 ?
C5 C6 1.409(2) ?
C7 C8 1.376(2) ?
C7 C12 1.396(2) ?
C7 H7 0.9500 ?
C8 C9 1.396(2) ?
C8 H8 0.9500 ?
C9 C10 1.391(2) ?
C10 C11 1.381(2) ?
C10 H10 0.9500 ?
C11 C12 1.397(2) ?
C11 H11 0.9500 ?
C13 H13A 0.9800 ?
C13 H13B 0.9800 ?
C13 H13C 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
O5 H5B O2 2_656 0.83(3) 2.09(3) 2.8757(18) 160(3)
O5 H5A N2 1_655 0.87(3) 2.11(3) 2.9572(19) 166(3)
O1 H1 O5 1_445 0.84 1.84 2.6747(18) 175.1
C8 H8 O5 1_445 0.95 2.68 3.346(2) 128
C10 H10 O4 1_546 0.95 2.71 3.323(2) 124
C13 H13A O1 1_564 0.98 2.54 3.439(2) 153
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_publ_flag
C6 N1 N2 C12 -179.94(11) y
C6 C1 C2 C3 -1.8(2) ?
C1 C2 C3 C4 0.3(2) ?
C1 C2 C3 N3 -178.70(13) ?
O3 N3 C3 C4 -175.72(14) ?
O4 N3 C3 C4 4.1(2) ?
O3 N3 C3 C2 3.4(2) ?
O4 N3 C3 C2 -176.82(14) ?
C2 C3 C4 C5 0.7(2) ?
N3 C3 C4 C5 179.74(12) ?
C13 O2 C5 C4 3.6(2) ?
C13 O2 C5 C6 -176.33(14) ?
C3 C4 C5 O2 179.73(13) ?
C3 C4 C5 C6 -0.3(2) ?
C2 C1 C6 C5 2.1(2) ?
C2 C1 C6 N1 179.89(13) ?
O2 C5 C6 C1 178.90(13) ?
C4 C5 C6 C1 -1.0(2) ?
O2 C5 C6 N1 0.94(19) ?
C4 C5 C6 N1 -179.01(12) ?
N2 N1 C6 C1 10.5(2) ?
N2 N1 C6 C5 -171.68(12) ?
C12 C7 C8 C9 -0.6(2) ?
C7 C8 C9 O1 178.33(14) ?
C7 C8 C9 C10 -0.6(2) ?
O1 C9 C10 C11 -177.73(13) ?
C8 C9 C10 C11 1.3(2) ?
C9 C10 C11 C12 -0.7(2) ?
C8 C7 C12 C11 1.1(2) ?
C8 C7 C12 N2 -177.29(13) ?
C10 C11 C12 C7 -0.4(2) ?
C10 C11 C12 N2 178.06(13) ?
N1 N2 C12 C7 -9.0(2) ?
N1 N2 C12 C11 172.55(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179781
