#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200572.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_2200572
loop_
_publ_author_name
'Mahmoudkhani, Amir H.'
'Langer, Vratislav'
_publ_section_title
;
 Two-dimensional hydrogen-bonded arrays in p-phenylazoanilinium
 oxalate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o898
_journal_page_last               o900
_journal_paper_doi               10.1107/S1600536801013885
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '2C12 H12 N3 1+, C2 O4 2-'
_chemical_formula_moiety         '2C12 H12 N3 1+, C2 O4 2-'
_chemical_formula_sum            'C26 H24 N6 O4'
_chemical_formula_weight         484.51
_chemical_name_systematic
;
Bis(p-phenylazoanilinium) oxalate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXTL
_cell_angle_alpha                92.0440(10)
_cell_angle_beta                 100.0450(10)
_cell_angle_gamma                112.9550(10)
_cell_formula_units_Z            1
_cell_length_a                   6.48750(10)
_cell_length_b                   7.01510(10)
_cell_length_c                   14.29910(10)
_cell_measurement_reflns_used    5443
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      1
_cell_volume                     586.169(14)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 1996)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2000)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean no
_diffrn_measured_fraction_theta_full .980
_diffrn_measured_fraction_theta_max .980
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .023
_diffrn_reflns_av_sigmaI/netI    .031
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7891
_diffrn_reflns_theta_full        30.5
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  no
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .096
_exptl_absorpt_correction_T_max  .976
_exptl_absorpt_correction_T_min  .910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             254
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          .50
_exptl_crystal_size_min          .25
_refine_diff_density_max         .32
_refine_diff_density_min         -.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          .052
_refine_ls_R_factor_gt           .041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0677P)²+0.0807P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .129
_reflns_number_gt                2858
_reflns_number_total             3499
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya6039.cif
_cod_data_source_block           I
_cod_original_cell_volume        586.169(13)
_cod_database_code               2200572
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .58318(11) .76598(10) .48700(5) .03369(18) Uani d . 1 . . O
N1 -.14184(16) .74518(16) .04159(7) .0394(2) Uani d . 1 . . N
C1 .08350(15) .79559(15) .33855(7) .0286(2) Uani d . 1 . . C
O2 .79716(11) .58262(12) .52064(6) .0380(2) Uani d . 1 . . O
N2 -.32444(17) .76653(17) .01430(7) .0407(2) Uani d . 1 . . N
C2 -.11676(17) .82239(17) .30468(8) .0344(2) Uani d . 1 . . C
H2 -.199(2) .854(2) .3535(11) .050(4) Uiso d . 1 . . H
N3 .16503(14) .81488(13) .44204(6) .02889(18) Uani d D 1 . . N
H33 .047(2) .746(2) .4699(10) .049(4) Uiso d D 1 . . H
C3 -.19630(18) .80539(18) .20688(8) .0361(2) Uani d . 1 . . C
H3 -.339(2) .822(2) .1802(10) .046(4) Uiso d . 1 . . H
C4 -.07316(17) .76438(16) .14373(7) .0337(2) Uani d . 1 . . C
C5 .12801(19) .73936(19) .17838(8) .0388(2) Uani d . 1 . . C
H5 .214(3) .705(2) .1317(11) .052(4) Uiso d . 1 . . H
C6 .20651(17) .75391(18) .27639(8) .0358(2) Uani d . 1 . . C
H6 .343(3) .734(2) .3013(11) .055(4) Uiso d . 1 . . H
C7 -.39778(18) .74820(17) -.08718(7) .0356(2) Uani d . 1 . . C
C8 -.6040(2) .7661(2) -.11869(8) .0421(3) Uani d . 1 . . C
H8 -.686(3) .793(3) -.0683(12) .058(4) Uiso d . 1 . . H
C9 -.6907(2) .7481(2) -.21620(9) .0444(3) Uani d . 1 . . C
H9 -.837(3) .759(3) -.2406(12) .060(4) Uiso d . 1 . . H
C10 -.5701(2) .7156(2) -.28159(9) .0445(3) Uani d . 1 . . C
H10 -.635(3) .701(3) -.3485(13) .065(5) Uiso d . 1 . . H
C11 -.3627(2) .6996(2) -.24997(9) .0453(3) Uani d . 1 . . C
H11 -.276(3) .677(3) -.2974(13) .063(5) Uiso d . 1 . . H
C12 -.2759(2) .71477(19) -.15315(8) .0411(3) Uani d . 1 . . C
H12 -.132(3) .702(3) -.1313(11) .055(4) Uiso d . 1 . . H
C13 .61097(14) .60138(14) .50227(6) .02527(18) Uani d . 1 . . C
H32 .235(2) .9518(19) .4666(9) .038(3) Uiso d D 1 . . H
H31 .277(2) .763(2) .4568(11) .051(4) Uiso d D 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 .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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C4 . 113.51(9) yes
C6 C1 C2 . 121.26(9) ?
C6 C1 N3 . 120.11(8) ?
C2 C1 N3 . 118.63(9) ?
N1 N2 C7 . 114.92(9) yes
C3 C2 C1 . 119.47(9) ?
C3 C2 H2 . 122.7(8) ?
C1 C2 H2 . 117.9(8) ?
C1 N3 H33 . 109.7(10) ?
C1 N3 H32 . 110.4(8) ?
H33 N3 H32 . 111.0(13) ?
C1 N3 H31 . 111.3(9) ?
H33 N3 H31 . 109.5(13) ?
H32 N3 H31 . 105.0(12) ?
C2 C3 C4 . 119.70(9) ?
C2 C3 H3 . 121.6(8) ?
C4 C3 H3 . 118.7(8) ?
C5 C4 C3 . 120.37(10) ?
C5 C4 N1 . 116.09(9) ?
C3 C4 N1 . 123.54(9) ?
C6 C5 C4 . 119.99(10) ?
C6 C5 H5 . 120.0(8) ?
C4 C5 H5 . 119.9(8) ?
C1 C6 C5 . 119.20(9) ?
C1 C6 H6 . 119.8(10) ?
C5 C6 H6 . 120.9(10) ?
C8 C7 C12 . 120.27(10) ?
C8 C7 N2 . 115.57(10) ?
C12 C7 N2 . 124.16(10) ?
C7 C8 C9 . 119.81(11) ?
C7 C8 H8 . 117.7(9) ?
C9 C8 H8 . 122.5(9) ?
C10 C9 C8 . 120.02(11) ?
C10 C9 H9 . 118.4(10) ?
C8 C9 H9 . 121.6(10) ?
C9 C10 C11 . 120.13(11) ?
C9 C10 H10 . 118.4(10) ?
C11 C10 H10 . 121.5(10) ?
C12 C11 C10 . 120.42(11) ?
C12 C11 H11 . 119.9(10) ?
C10 C11 H11 . 119.7(10) ?
C11 C12 C7 . 119.36(11) ?
C11 C12 H12 . 120.2(9) ?
C7 C12 H12 . 120.5(9) ?
O2 C13 O1 . 126.67(8) yes
O2 C13 C13 2_666 116.66(10) yes
O1 C13 C13 2_666 116.66(9) yes
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 C13 . 1.2571(11) yes
N1 N2 . 1.2487(13) yes
N1 C4 . 1.4359(13) yes
C1 C2 . 1.3911(13) ?
C1 C6 . 1.3868(14) ?
C1 N3 . 1.4645(12) yes
O2 C13 . 1.2494(11) yes
N2 C7 . 1.4306(14) yes
C2 C3 . 1.3873(15) ?
C2 H2 . 1.020(10) ?
N3 H33 . .900(10) ?
N3 H32 . .910(10) ?
N3 H31 . .930(10) ?
C3 C4 . 1.3960(15) ?
C3 H3 . .990(10) ?
C4 C5 . 1.3924(15) ?
C5 C6 . 1.3908(15) ?
C5 H5 . 1.020(10) ?
C6 H6 . .960(10) ?
C7 C8 . 1.3906(16) ?
C7 C12 . 1.3995(16) ?
C8 C9 . 1.3911(17) ?
C8 H8 . 1.020(10) ?
C9 C10 . 1.3848(19) ?
C9 H9 . .98(2) ?
C10 C11 . 1.3915(18) ?
C10 H10 . .96(2) ?
C11 C12 . 1.3843(16) ?
C11 H11 . .99(2) ?
C12 H12 . .97(2) ?
C13 C13 2_666 1.5698(17) yes
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
(a)N3 H31 O1 . .930(10) 1.950(10) 2.8325(15) 158.0(14)
(b)N3 H31 O2 2_666 .930(10) 2.330(10) 2.9520(12) 124.4(12)
(c)N3 H32 O1 2_676 .910(10) 1.890(10) 2.7939(11) 172.0(12)
(d)N3 H33 O2 1_455 .900(10) 1.880(10) 2.7654(11) 175.3(15)
(e)C2 H2 O1 1_455 1.020(10) 2.520(10) 3.4620(13) 153.3(12)
