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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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_journal_date_recd_electronic     2000-10-11
_journal_date_accepted     2001-01-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue      4
_journal_page_first     397
_journal_page_last     399
_journal_paper_category     FM
_publ_contact_author_name     'Dr. Alexandr V. Yatsenko'
_publ_contact_author_address
;
      Chemistry Department,
      Moscow State University,
      119899 Moscow,
      Russia
;
_publ_contact_author_email     'yatsenko@biocryst.phys.msu.su'
_publ_contact_author_fax     '+ 7-095-9390898'
_publ_contact_author_phone     '+ 7-095-9393654'
_publ_section_title
;
Sodium 4-(2-pyridinylazo)resorcinolate monohydrate and ammonium
2,4-dinitro-1-naphthalenolate from powder diffraction data
;
loop_
    _publ_author_name
    _publ_author_address
    'Yatsenko, A. V.'
;     Chemistry Department,
      Moscow State University,
      119899 Moscow,
      Russia
;
    'Paseshnichenko, K. A.'
;     Chemistry Department,
      Moscow State University,
      119899 Moscow,
      Russia
;
    'Chernyshev, V. V.'
;     Chemistry Department,
      Moscow State University,
      119899 Moscow,
      Russia
;
    'Schenk, H.'
;     Laboratory for Crystallography,
      University of Amsterdam,
      Nieuwe Achtergracht 166,
      Amsterdam, 1018 WV,
      The Netherlands
;
_publ_section_synopsis
; ?
;
data_I
_chemical_name_systematic
;
sodium 4-(2-pyridinylazo)-1,3-benzenediolate monohydrate
;
_chemical_name_common     '4-(2-pyridylazo)-resorcinol'
_chemical_formula_moiety     'C11 H8 N3 O2 1-, Na 1+, O H2'
_chemical_formula_sum     'C11 H10 N3 Na O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'Na(C11 H8 N3 O2 ) , H2 O '
_chemical_formula_weight     255.21
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, 1/2+y, 1/2-z'
    '-x, -y, -z'
    'x, 1/2-y, 1/2+z'
_cell_length_a     16.703(3)
_cell_length_b     3.6340(10)
_cell_length_c     20.248(3)
_cell_angle_alpha     90.0
_cell_angle_beta     117.380(10)
_cell_angle_gamma     90.0
_cell_volume     1091.4(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     56
_cell_measurement_theta_min     3.0
_cell_measurement_theta_max     32.1
_cell_measurement_temperature     295(2)
_exptl_crystal_density_diffrn     1.553
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     1.31
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 specimen was rotated in its plane
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator     'Ni filtered'
_diffrn_measurement_device_type
; DRON-3M diffractometer (Burevestnik, Russia)
;
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     2
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
; hydrogen atoms were constrained at calculated positions, and planarity
of pyridine and resorcinol rings was restrained.
;
_refine_ls_structure_factor_coef     Inet
_refine_ls_matrix_type     fullcycle
_refine_ls_goodness_of_fit_all     2.14
_refine_ls_restrained_S_all     ?
_refine_ls_restrained_S_obs     ?
_refine_ls_number_parameters     104
_refine_ls_number_restraints     10
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     sigma
_refine_ls_shift/su_max     .045
_refine_ls_shift/su_mean     .007
_refine_diff_density_max      .6
_refine_diff_density_min      -.8
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'Na' 'Na'  .129  .124
                      'International Tables for X-Ray Crystallography (Vol. IV)'
    'O' 'O'  .047  .032
                      'International Tables for X-Ray Crystallography (Vol. IV)'
    'N' 'N'  .029  .018
                      'International Tables for X-Ray Crystallography (Vol. IV)'
    'C' 'C'  .017  .009
                      'International Tables for X-Ray Crystallography (Vol. IV)'
    'H' 'H'  .000  .000
                      'International Tables for X-Ray Crystallography (Vol. IV)'
_computing_data_collection     'home-written program'
_computing_cell_refinement     'LSPAID (Visser, 1986)'
_computing_data_reduction     ?
_computing_structure_solution     'MRIA (Zlokazov & Chernyshev, 1992)'
_computing_structure_refinement     'MRIA'
_computing_molecular_graphics     'PLUTON (Spek, 1992)'
_computing_publication_material     'PARST (Nardelli, 1983)'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_occupancy
    _atom_site_type_symbol
    Na .5465(3) .4571(16) .4216(3)  .030(2) Uiso 1 Na
    O1 .5688(4) .491(2) .1151(3)  .037(2) Uiso 1 O
    O2 .6156(5) -.086(2) .5105(4)  .049(3) Uiso 1 O
    O3 .6297(4) .293(2) .3663(4)  .037(2) Uiso 1 O
    N1 .8041(6) -.026(3) .3980(4)  .037(2) Uiso 1 N
    N2 .7808(5) .015(2) .4499(4)  .037(2) Uiso 1 N
    N8 .8107(5) -.1700(10)
                         .5631(5)  .041(2) Uiso 1 N
    C1 .6184(5) .372(3) .1784(4)  .024(2) Uiso 1 C
    C2 .5986(5) .392(2) .2400(4)  .024(2) Uiso 1 C
    C3 .6565(5) .256(3) .3101(4)  .024(2) Uiso 1 C
    C4 .7464(5) .106(2) .3293(4)  .024(2) Uiso 1 C
    C5 .7669(5) .105(3) .2684(4)  .024(2) Uiso 1 C
    C6 .7068(5) .221(2) .1967(4)  .024(2) Uiso 1 C
    C7 .8398(6) -.149(2) .5127(4)  .041(2) Uiso 1 C
    C9 .8672(6) -.287(2) .6336(5)  .041(2) Uiso 1 C
    C10 .9575(6) -.400(2) .6573(4)  .041(2) Uiso 1 C
    C11 .9839(6) -.360(3) .6047(5)  .041(2) Uiso 1 C
    C12 .9302(5) -.220(2) .5343(4)  .041(2) Uiso 1 C
    H3 .6862 .1840 .4123  .051 Uiso 1 H
    H17 .5349 .5146 .2316  .051 Uiso 1 H
    H18 .7260 .2099 .1525  .051 Uiso 1 H
    H19 .8321 -.0187 .2766  .051 Uiso 1 H
    H20 .8350 -.3304 .6687  .051 Uiso 1 H
    H21 .9948 -.5114 .7136  .051 Uiso 1 H
    H22 1.0558 -.4295 .6181  .051 Uiso 1 H
    H23 .9574 -.1865 .4954  .051 Uiso 1 H
_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
    Na O2 1_555 2.561(13) yes
    Na O3 1_555 2.231(11) yes
    Na O2 1_565 2.328(13) yes
    Na O1 2_645 2.411(11) yes
    Na O1 2_655 2.590(12) yes
    O2 N8 1_555 2.942(15) yes
    O2 O1 4_555 2.596(14) yes
    O1 C1 . 1.240(9) no
    O3 C3 . 1.407(13) no
    O3 H3 . 1.053 no
    N1 N2 . 1.287(14) no
    N1 C4 . 1.365(10) no
    N2 C7 . 1.338(9) no
    N8 C7 . 1.317(16) no
    N8 C9 . 1.368(11) no
    C1 C2 . 1.432(14) no
    C1 C6 . 1.454(12) no
    C2 C3 . 1.390(9) no
    C2 H17 . 1.094 no
    C3 C4 . 1.471(12) no
    C4 C5 . 1.423(14) no
    C5 C6 . 1.397(9) no
    C5 H19 . 1.117 no
    C6 H18 . 1.081 no
    C7 C12 . 1.391(13) no
    C9 C10 . 1.417(13) no
    C9 H20 . 1.081 no
    C10 C11 . 1.336(16) no
    C10 H21 . 1.095 no
    C11 C12 . 1.384(11) no
    C11 H22 . 1.131 no
    C12 H23 . 1.083 no
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
    Na O2 N8 1_555 1_555 114.0(10)
                                yes
    Na O2 Na 1_555 1_545 96.0(8) yes
    Na O2 O1 1_555 4_555 105.0(10)
                                yes
    N8 O2 Na 1_555 1_545 106.0(10)
                                yes
    N8 O2 O1 1_555 4_555 115.0(10)
                                yes
    Na O2 O1 1_545 4_555 120.0(10)
                                yes
    C3 O3 H3 . . 101 no
    N2 N1 C4 . . 117.0(7) no
    N1 N2 H3 . . 106 no
    N1 N2 C7 . . 111.0(7) no
    C7 N8 C9 . . 120.3(8) no
    O1 C1 C6 . . 120.8(8) no
    O1 C1 C2 . . 124.8(7) no
    C2 C1 C6 . . 114.2(8) no
    C1 C2 H17 . . 119 no
    C1 C2 C3 . . 122.8(7) no
    C3 C2 H17 . . 118 no
    O3 C3 C2 . . 117.5(7) no
    C2 C3 C4 . . 123.1(7) no
    O3 C3 C4 . . 119.2(8) no
    N1 C4 C3 . . 123.8(8) no
    C3 C4 C5 . . 113.3(8) no
    N1 C4 C5 . . 122.9(7) no
    C4 C5 H19 . . 119 no
    C4 C5 C6 . . 123.7(7) no
    C6 C5 H19 . . 117 no
    C1 C6 C5 . . 122.6(7) no
    C5 C6 H18 . . 120 no
    C1 C6 H18 . . 117 no
    N2 C7 N8 . . 112.9(7) no
    N8 C7 C12 . . 118.6(9) no
    N2 C7 C12 . . 126.9(8) no
    N8 C9 H20 . . 115 no
    N8 C9 C10 . . 124.0(8) no
    C10 C9 H20 . . 121 no
    C9 C10 H21 . . 118 no
    C9 C10 C11 . . 112.9(10) no
    C11 C10 H21 . . 129 no
    C10 C11 H22 . . 119 no
    C10 C11 C12 . . 124.5(8) no
    C12 C11 H22 . . 116 no
    C7 C12 C11 . . 119.2(8) no
    C11 C12 H23 . . 120 no
    C7 C12 H23 . . 120 no
data_II
_chemical_name_systematic
;
ammonium 2,4-dinitro-1-naphthalenolate
;
_chemical_name_common     'Acid Yellow 24'
_chemical_formula_moiety     'N H4 + , C10 H5 N2 O5 - '
_chemical_formula_sum     'C10 H9 N3 O5'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'N H4 + , C10 H5 N2 O5 - '
_chemical_formula_weight     251.20
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, 1/2+y, 1/2-z'
    '-x, -y, -z'
    'x, 1/2-y, 1/2+z'
_cell_length_a     3.9240(10)
_cell_length_b     20.314(4)
_cell_length_c     13.336(3)
_cell_angle_alpha     90.0
_cell_angle_beta     94.310(10)
_cell_angle_gamma     90.0
_cell_volume     1060.0(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     48
_cell_measurement_theta_min     3.9
_cell_measurement_theta_max     22.6
_cell_measurement_temperature     295(2)
_exptl_crystal_density_diffrn     1.574
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     1.11
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 specimen was rotated in its plane
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator     'Ni filtered'
_diffrn_measurement_device_type
; DRON-3M diffractometer (Burevestnik, Russia)
;
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     2
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_refine_special_details
; hydrogen atoms were constrained at calculated positions, and planarity
of phenyl ring and naphthalene residue was restrained.
;
_refine_ls_structure_factor_coef     Inet
_refine_ls_matrix_type     fullcycle
_refine_ls_goodness_of_fit_all     2.01
_refine_ls_restrained_S_all     ?
_refine_ls_restrained_S_obs     ?
_refine_ls_number_parameters     106
_refine_ls_number_restraints     12
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     sigma
_refine_ls_shift/su_max     .04
_refine_ls_shift/su_mean     .007
_refine_diff_density_max      .8
_refine_diff_density_min      -.7
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'O' 'O'  .047  .032
                      'International Tables for X-Ray Crystallography (Vol. IV)'
    'N' 'N'  .029  .018
                      'International Tables for X-Ray Crystallography (Vol. IV)'
    'C' 'C'  .017  .009
                      'International Tables for X-Ray Crystallography (Vol. IV)'
    'H' 'H'  .000  .000
                      'International Tables for X-Ray Crystallography (Vol. IV)'
_computing_data_collection     'home-written program'
_computing_cell_refinement     'LSPAID (Visser, 1986)'
_computing_data_reduction     ?
_computing_structure_solution     'MRIA (Zlokazov & Chernyshev, 1992)'
_computing_structure_refinement     'MRIA'
_computing_molecular_graphics     'PLUTON (Spek, 1992)'
_computing_publication_material     'PARST (Nardelli, 1983)'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_occupancy
    _atom_site_type_symbol
    O1 .049(4) .0265(3) .2437(5)  .064(3) Uiso 1 O
    O21 .420(3) .1504(3) .0309(5)  .092(2) Uiso 1 O
    O22 .179(3) .0589(3) .0503(6)  .092(2) Uiso 1 O
    O41 -.129(4) .3244(3) .3512(5)  .092(2) Uiso 1 O
    O42 .195(3) .3263(4) .2255(5)  .092(2) Uiso 1 O
    N1 .466(4) .4475(4) .3438(7)  .087(5) Uiso 1 N
    N2 .269(2) .1127(4) .0847(5)  .064(3) Uiso 1 N
    N4 .032(3) .2985(4) .2905(6)  .064(3) Uiso 1 N
    C1 .046(2) .0875(4) .2534(6)  .046(2) Uiso 1 C
    C2 .156(3) .1321(4) .1790(5)  .046(2) Uiso 1 C
    C3 .133(3) .1991(4) .1964(6)  .046(2) Uiso 1 C
    C4 .029(3) .2250(3) .2861(6)  .046(2) Uiso 1 C
    C5 -.208(2) .2048(3) .4530(6)  .046(2) Uiso 1 C
    C6 -.308(3) .1611(4) .5264(6)  .046(2) Uiso 1 C
    C7 -.301(3) .0953(4) .5029(6)  .046(2) Uiso 1 C
    C8 -.181(2) .0687(3) .4189(6)  .046(2) Uiso 1 C
    C9 -.067(3) .1149(4) .3463(5)  .046(2) Uiso 1 C
    C10 -.086(4) .1817(4) .3635(6)  .046(2) Uiso 1 C
    H3 .2168 .2328 .1375  .076 Uiso 1 H
    H5 -.2154 .2587 .4669  .076 Uiso 1 H
    H6 -.4052 .1806 .5938  .076 Uiso 1 H
    H7 -.3798 .0586 .5624  .076 Uiso 1 H
    H8 -.1628 .0170 .4031  .076 Uiso 1 H
    H11 .6091 .4445 .2879  .095 Uiso 1 H
    H12 .2522 .4234 .3352  .095 Uiso 1 H
    H13 .4004 .4978 .3502  .095 Uiso 1 H
    H14 .5937 .4358 .4099  .095 Uiso 1 H
_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
    N1 O41 1_555 3.430(10)
                         yes
    N1 O42 1_555 3.070(10)
                         yes
    N1 O1 2_555 2.770(10)
                        yes
    N1 O1 2_655 2.810(10)
                        yes
    N1 O22 2_655 2.960(10)
                         yes
    N1 O41 1_655 2.960(10)
                         yes
    N1 O22 4_555 3.060(10)
                         yes
    N1 O21 4_555 3.210(10)
                         yes
    C1 C2 . 1.434(12) no
    C1 C9 . 1.457(11) no
    C1 O1 . 1.246(10) no
    C2 C3 . 1.385(12) no
    C2 N2 . 1.420(11) no
    C3 C4 . 1.396(12) no
    C3 H3 . 1.109 no
    C4 C10 . 1.454(13) no
    C4 N4 . 1.494(10) no
    C5 C6 . 1.401(12) no
    C5 C10 . 1.400(13) no
    C5 H5 . 1.111 no
    C6 C7 . 1.372(12) no
    C6 H6 . 1.078 no
    C7 C8 . 1.361(12) no
    C7 H7 . 1.149 no
    C8 C9 . 1.444(11) no
    C8 H8 . 1.073 no
    C9 C10 . 1.378(12) no
    N1 H11 . .970 no
    N1 H12 . .971 no
    N1 H13 . 1.058 no
    N1 H14 . 1.009 no
    N2 O21 . 1.230(11) no
    N2 O22 . 1.228(10) no
    N4 O41 . 1.188(14) no
    N4 O42 . 1.250(13) no
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
    C9 C1 O1 . . 118.3(7) no
    C2 C1 O1 . . 123.4(8) no
    C2 C1 C9 . . 118.2(7) no
    C1 C2 N2 . . 124.6(7) no
    C1 C2 C3 . . 118.6(7) no
    C3 C2 N2 . . 116.7(7) no
    C2 C3 H3 . . 117 no
    C2 C3 C4 . . 122.8(7) no
    C4 C3 H3 . . 120 no
    C3 C4 N4 . . 114.1(6) no
    C3 C4 C10 . . 120.4(8) no
    C10 C4 N4 . . 125.4(6) no
    C10 C5 H5 . . 119 no
    C6 C5 H5 . . 120 no
    C6 C5 C10 . . 121.0(8) no
    C5 C6 H6 . . 119 no
    C5 C6 C7 . . 116.5(7) no
    C7 C6 H6 . . 124 no
    C6 C7 H7 . . 118 no
    C6 C7 C8 . . 126.2(8) no
    C8 C7 H7 . . 116 no
    C7 C8 H8 . . 126 no
    C7 C8 C9 . . 115.9(7) no
    C9 C8 H8 . . 118 no
    C1 C9 C8 . . 116.7(7) no
    C8 C9 C10 . . 120.3(7) no
    C1 C9 C10 . . 122.8(7) no
    C5 C10 C9 . . 119.9(7) no
    C4 C10 C9 . . 116.9(7) no
    C4 C10 C5 . . 123.1(8) no
    H13 N1 H14 . . 106 no
    H12 N1 H14 . . 110 no
    H12 N1 H13 . . 107 no
    H11 N1 H14 . . 112 no
    H11 N1 H13 . . 106 no
    H11 N1 H12 . . 114 no
    C2 N2 O22 . . 118.5(7) no
    C2 N2 O21 . . 122.7(7) no
    O21 N2 O22 . . 118.3(8) no
    C4 N4 O42 . . 115.3(8) no
    C4 N4 O41 . . 117.8(7) no
    O41 N4 O42 . . 126.7(9) no
