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###           Full Paper (Acta Crystallographica Section C)                ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.0.1.  #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
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#            Copyright International Union of Crystallography                #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2000-01-14
_journal_date_accepted     2000-03-03
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      6
_journal_page_first     697
_journal_page_last     699
_journal_paper_category     FO
_publ_contact_author_name     'Jacek Zaleski'
_publ_contact_author_address
; Institute of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
_publ_contact_author_email     zaleski@uni.opole.pl
_publ_section_title
; 4-Hydroxy-ONN-azoxybenzene, C₁₂H₁₀N₂O₂
;
loop_
    _publ_author_name
    _publ_author_address
    'Ejsmont, Krzysztof'
; Institute of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
    "Domański, Andrzej"
; Institute of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
    'Kyzioł, Janusz'
; Institute of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
    'Zaleski, Jacek'
; Institute of Chemistry
  University of Opole
  Oleska 48
  45-052 Opole
  Poland
;
data_IIa
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H10 N2 O2'
_chemical_formula_sum     'C12 H10 N2 O2'
_chemical_formula_weight     214.22
_symmetry_cell_setting     'orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     7.1870(10)
_cell_length_b     11.261(2)
_cell_length_c     12.812(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1036.9(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     21
_cell_measurement_theta_min     8
_cell_measurement_theta_max     11
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max      .5
_exptl_crystal_size_mid      .4
_exptl_crystal_size_min      .3
_exptl_crystal_density_diffrn     1.372
_exptl_crystal_density_meas     1.370(10)
_exptl_crystal_density_method     'flotation'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu      .096
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'KUMA KM--4'
_diffrn_measurement_method     'ω--θ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2796
_diffrn_reflns_av_R_equivalents      .0291
_diffrn_reflns_av_sigmaI/netI      .0520
_diffrn_reflns_theta_min     2.41
_diffrn_reflns_theta_max     30.13
_diffrn_reflns_theta_full     30.13
_diffrn_measured_fraction_theta_max      .981
_diffrn_measured_fraction_theta_full      .981
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     2
_diffrn_standards_interval_count     50
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%      .52
_refine_special_details
;
 ?
;
_reflns_number_total     1729
_reflns_number_gt     1026
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .1092
_refine_ls_R_factor_gt      .0337
_refine_ls_wR_factor_ref      .0960
_refine_ls_goodness_of_fit_ref      .993
_refine_ls_restrained_S_all      .993
_refine_ls_number_reflns     1729
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'All H atoms refined isotropically'
_refine_ls_weighting_scheme
       'calc w = 1/[\s^2^(Fo^2^)+(0.0252P)^2^+0.1130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_shift/su_max      .000
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .105
_refine_diff_density_min      -.125
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KUMA Diffraction Software (Kuma, 1998)'
_computing_cell_refinement     'KUMA Diffraction Software'
_computing_data_reduction     'KUMA Diffraction Software'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1990)'
_computing_publication_material     'SHELXL97'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    N2  .2024(3)  .24506(17)  .84313(14)  .0548(5) Uani d . 1 . . N
    N1  .1457(3)  .21220(18)  .93209(14)  .0521(5) Uani d . 1 . . N
    O2  .2274(3)  .70176(16)  .68493(14)  .0673(6) Uani d . 1 . . O
    O1  .0781(3)  .27976(13) 1.00334(14)  .0608(5) Uani d . 1 . . O
    C1  .1961(4)  .3645(2)  .81248(16)  .0514(6) Uani d . 1 . . C
    C2  .2936(4)  .3844(2)  .72042(17)  .0634(7) Uani d . 1 . . C
    C3  .3056(4)  .4951(2)  .67680(18)  .0626(7) Uani d . 1 . . C
    C4  .2184(4)  .5901(2)  .72317(16)  .0523(6) Uani d . 1 . . C
    C5  .1148(4)  .5715(2)  .81343(18)  .0569(7) Uani d . 1 . . C
    C6  .1035(4)  .4607(2)  .85810(17)  .0544(6) Uani d . 1 . . C
    C1'  .1562(3)  .0855(2)  .95302(16)  .0491(6) Uani d . 1 . . C
    C6'  .1027(4)  .0457(2) 1.04995(19)  .0619(7) Uani d . 1 . . C
    C5'  .1099(5)  -.0739(3) 1.0707(2)  .0736(9) Uani d . 1 . . C
    C4'  .1677(5)  -.1527(3)  .9970(2)  .0719(8) Uani d . 1 . . C
    C3'  .2199(5)  -.1121(2)  .89940(19)  .0722(8) Uani d . 1 . . C
    C2'  .2135(4)  .0072(3)  .87713(19)  .0625(7) Uani d . 1 . . C
    H22  .298(6)  .703(3)  .632(3)  .108(12) Uiso d . 1 . . H
    H2  .370(5)  .315(3)  .686(3)  .098(10) Uiso d . 1 . . H
    H3  .375(4)  .506(2)  .618(2)  .071(8) Uiso d . 1 . . H
    H5  .045(3)  .639(2)  .8410(18)  .061(7) Uiso d . 1 . . H
    H6  .026(4)  .445(2)  .920(2)  .066(8) Uiso d . 1 . . H
    H6'  .059(4)  .105(2) 1.096(2)  .080(9) Uiso d . 1 . . H
    H5'  .059(5)  -.105(3) 1.135(3)  .123(13) Uiso d . 1 . . H
    H4'  .163(4)  -.236(2) 1.008(2)  .068(7) Uiso d . 1 . . H
    H3'  .254(4)  -.171(2)  .848(2)  .093(10) Uiso d . 1 . . H
    H2'  .246(4)  .038(2)  .808(2)  .074(8) Uiso d . 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N2  .0612(13)  .0648(13)  .0383(9)  -.0017(12)  .0060(10)  -.0019(9)
    N1  .0550(12)  .0659(13)  .0355(8)  -.0005(11)  -.0017(9)  -.0047(9)
    O2  .0893(15)  .0617(11)  .0508(9)  .0053(11)  .0132(10)  .0078(8)
    O1  .0805(12)  .0664(11)  .0353(6)  .0122(10)  .0062(9)  -.0081(9)
    C1  .0620(15)  .0522(13)  .0399(10)  -.0017(13)  -.0015(12)  -.0011(10)
    C2  .0830(19)  .0648(15)  .0423(11)  .0008(16)  .0122(14)  -.0039(11)
    C3  .0787(19)  .0697(17)  .0394(11)  .0032(16)  .0133(14)  .0017(12)
    C4  .0625(15)  .0578(14)  .0367(10)  -.0004(13)  -.0017(11)  .0029(10)
    C5  .0637(16)  .0615(15)  .0454(12)  .0065(14)  .0071(13)  -.0009(11)
    C6  .0569(15)  .0663(16)  .0400(11)  -.0009(13)  .0064(12)  .0009(11)
    C1'  .0537(15)  .0526(14)  .0410(11)  .0003(12)  -.0029(11)  .0019(10)
    C6'  .0772(19)  .0671(17)  .0414(12)  -.0005(15)  .0088(14)  -.0037(12)
    C5'  .106(3)  .0663(17)  .0486(13)  -.0125(18)  .0102(17)  .0082(13)
    C4'  .101(2)  .0572(15)  .0577(14)  -.0097(17)  .0046(18)  .0062(14)
    C3'  .101(2)  .0612(16)  .0546(14)  .0033(17)  .0127(17)  -.0036(13)
    C2'  .0796(19)  .0662(16)  .0417(11)  .0044(16)  .0087(14)  .0024(12)
_geom_special_details
;
 ?
;
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
    N2 N1 . 1.266(3) y
    N2 C1 . 1.402(3) y
    N1 O1 . 1.284(2) y
    N1 C1' . 1.453(3) y
    O2 C4 . 1.351(3) y
    C1 C2 . 1.390(3) ?
    C1 C6 . 1.400(3) ?
    C2 C3 . 1.368(4) ?
    C3 C4 . 1.375(3) ?
    C4 C5 . 1.391(3) ?
    C5 C6 . 1.375(3) ?
    C1' C6' . 1.375(3) ?
    C1' C2' . 1.376(3) ?
    C6' C5' . 1.375(4) ?
    C5' C4' . 1.359(4) ?
    C4' C3' . 1.383(4) ?
    C3' C2' . 1.375(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
    N1 N2 C1 . . 121.5(2) y
    N2 N1 O1 . . 126.1(2) y
    N2 N1 C1' . . 115.9(2) y
    O1 N1 C1' . . 118.0(2) y
    C2 C1 C6 . . 118.0(2) ?
    C2 C1 N2 . . 112.1(2) y
    C6 C1 N2 . . 129.9(2) y
    C3 C2 C1 . . 121.7(3) ?
    C2 C3 C4 . . 120.2(2) ?
    O2 C4 C3 . . 123.1(2) y
    O2 C4 C5 . . 117.8(2) y
    C3 C4 C5 . . 119.1(2) ?
    C6 C5 C4 . . 120.9(2) ?
    C5 C6 C1 . . 120.0(2) ?
    C6' C1' C2' . . 120.9(2) ?
    C6' C1' N1 . . 118.2(2) y
    C2' C1' N1 . . 120.9(2) y
    C1' C6' C5' . . 118.9(2) ?
    C4' C5' C6' . . 121.1(2) ?
    C5' C4' C3' . . 119.7(3) ?
    C2' C3' C4' . . 120.1(3) ?
    C1' C2' C3' . . 119.3(2) ?
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
    O2 H22 O1 2_564  .85(4) 1.88(4) 2.722(3) 170(4)
    C3' H3' O2 1_545  .97(3) 2.54(3) 3.456(3) 158(3)
