##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-1-(3-Formylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H12 N2 O2'
_chemical_formula_sum     'C17 H12 N2 O2'
_chemical_formula_iupac     'C17 H12 N2 O2'
_chemical_formula_weight     276.29
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     5.601(4)
_cell_length_b     7.780(5)
_cell_length_c     29.70(2)
_cell_angle_alpha     90.00
_cell_angle_beta     94.624(16)
_cell_angle_gamma     90.00
_cell_volume     1290.0(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3964
_cell_measurement_theta_min     1.3
_cell_measurement_theta_max     30.7
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.09
_exptl_crystal_size_mid     0.04
_exptl_crystal_size_min     0.01
_exptl_crystal_density_diffrn     1.423
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_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     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_device     '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16470
_diffrn_reflns_av_R_equivalents     0.0776
_diffrn_reflns_av_sigmaI/netI     0.0751
_diffrn_reflns_theta_min     1.38
_diffrn_reflns_theta_max     30.71
_diffrn_reflns_theta_full     30.71
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -42
_diffrn_reflns_limit_l_max     42
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3964
_reflns_number_gt     2155
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1272
_refine_ls_R_factor_gt     0.0573
_refine_ls_wR_factor_gt     0.1249
_refine_ls_wR_factor_ref     0.1543
_refine_ls_goodness_of_fit_ref     1.007
_refine_ls_restrained_S_all     1.007
_refine_ls_number_reflns     3963
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0680P)²+0.0107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.242
_refine_diff_density_min     -0.229
_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' 0.0106 0.0060
                         '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'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KappaCCD Server Software (Nonius, 1999)'
_computing_cell_refinement     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.1128(2) 0.36260(19) 0.05566(4) 0.0354(4) Uani d . 1 1 . .
    O O2 -0.0805(2) 0.98626(19) 0.12237(5) 0.0382(4) Uani d . 1 1 . .
    N N1 0.7771(3) 0.5614(2) 0.07936(5) 0.0262(4) Uani d . 1 1 . .
    N N2 0.8540(3) 0.53524(19) 0.12186(5) 0.0244(3) Uani d . 1 1 . .
    C C1 0.5770(3) 0.6695(2) 0.06949(6) 0.0236(4) Uani d . 1 1 . .
    C C2 0.4368(3) 0.7287(2) 0.10308(6) 0.0233(4) Uani d . 1 1 . .
    H H2 0.4746 0.6980 0.1331 0.028 Uiso calc R 1 1 . .
    C C3 0.2409(3) 0.8333(2) 0.09152(6) 0.0252(4) Uani d . 1 1 . .
    C C4 0.1826(4) 0.8796(3) 0.04653(6) 0.0311(5) Uani d . 1 1 . .
    H H4 0.0514 0.9500 0.0388 0.037 Uiso calc R 1 1 . .
    C C5 0.3226(4) 0.8194(3) 0.01347(7) 0.0339(5) Uani d . 1 1 . .
    H H5 0.2836 0.8488 -0.0166 0.041 Uiso calc R 1 1 . .
    C C6 0.5206(4) 0.7156(3) 0.02464(6) 0.0307(5) Uani d . 1 1 . .
    H H6 0.6147 0.6772 0.0023 0.037 Uiso calc R 1 1 . .
    C C7 1.0448(3) 0.4360(2) 0.13145(6) 0.0244(4) Uani d . 1 1 . .
    C C8 1.1796(3) 0.3516(2) 0.09708(6) 0.0275(4) Uani d . 1 1 . .
    C C9 1.3961(3) 0.2599(2) 0.11294(7) 0.0299(4) Uani d . 1 1 . .
    H H9 1.4850 0.2050 0.0921 0.036 Uiso calc R 1 1 . .
    C C10 1.4711(3) 0.2523(2) 0.15691(7) 0.0289(4) Uani d . 1 1 . .
    H H10 1.6132 0.1947 0.1654 0.035 Uiso calc R 1 1 . .
    C C11 1.3401(3) 0.3301(2) 0.19198(6) 0.0260(4) Uani d . 1 1 . .
    C C12 1.1257(3) 0.4201(2) 0.17941(6) 0.0231(4) Uani d . 1 1 . .
    C C13 0.9988(3) 0.4950(2) 0.21333(6) 0.0262(4) Uani d . 1 1 . .
    H H13 0.8574 0.5543 0.2054 0.031 Uiso calc R 1 1 . .
    C C14 1.0815(3) 0.4817(2) 0.25807(6) 0.0291(4) Uani d . 1 1 . .
    H H14 0.9957 0.5322 0.2801 0.035 Uiso calc R 1 1 . .
    C C15 1.2930(4) 0.3929(2) 0.27070(7) 0.0306(5) Uani d . 1 1 . .
    H H15 1.3478 0.3842 0.3010 0.037 Uiso calc R 1 1 . .
    C C16 1.4203(3) 0.3179(2) 0.23791(6) 0.0289(4) Uani d . 1 1 . .
    H H16 1.5610 0.2586 0.2464 0.035 Uiso calc R 1 1 . .
    C C17 0.0939(4) 0.8931(2) 0.12780(7) 0.0299(4) Uani d . 1 1 . .
    H H17 0.1386 0.8564 0.1571 0.036 Uiso calc R 1 1 . .
    H H1 0.862(5) 0.511(4) 0.0554(10) 0.079(9) Uiso d . 1 1 . .
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
    O1 0.0355(8) 0.0430(8) 0.0283(8) 0.0046(7) 0.0063(6) -0.0055(6)
    O2 0.0316(8) 0.0381(8) 0.0459(9) 0.0057(7) 0.0096(7) -0.0013(7)
    N1 0.0251(8) 0.0315(9) 0.0222(8) 0.0016(7) 0.0040(7) 0.0001(7)
    N2 0.0250(8) 0.0244(8) 0.0240(8) -0.0036(6) 0.0036(6) 0.0014(6)
    C1 0.0221(9) 0.0239(9) 0.0250(9) -0.0017(7) 0.0026(7) 0.0012(7)
    C2 0.0228(9) 0.0274(9) 0.0197(9) -0.0023(7) 0.0005(7) 0.0001(7)
    C3 0.0236(9) 0.0261(9) 0.0261(10) -0.0037(8) 0.0020(7) -0.0011(8)
    C4 0.0278(10) 0.0339(11) 0.0312(11) 0.0044(8) -0.0003(8) 0.0035(8)
    C5 0.0372(12) 0.0425(12) 0.0217(9) 0.0040(9) 0.0002(8) 0.0050(9)
    C6 0.0325(11) 0.0360(11) 0.0246(10) 0.0001(9) 0.0079(8) 0.0002(8)
    C7 0.0225(9) 0.0224(9) 0.0289(10) -0.0012(7) 0.0048(8) 0.0007(7)
    C8 0.0281(10) 0.0258(10) 0.0295(10) -0.0039(8) 0.0081(8) -0.0015(8)
    C9 0.0253(10) 0.0283(10) 0.0374(12) 0.0005(8) 0.0104(8) -0.0037(8)
    C10 0.0210(10) 0.0240(9) 0.0422(12) 0.0018(8) 0.0055(8) 0.0026(8)
    C11 0.0223(9) 0.0221(9) 0.0339(10) -0.0032(7) 0.0037(8) 0.0015(8)
    C12 0.0203(9) 0.0223(9) 0.0270(10) -0.0033(7) 0.0029(7) 0.0018(7)
    C13 0.0254(9) 0.0252(9) 0.0284(10) 0.0016(8) 0.0056(8) 0.0014(8)
    C14 0.0327(11) 0.0278(10) 0.0272(10) 0.0004(8) 0.0049(8) 0.0004(8)
    C15 0.0368(11) 0.0270(10) 0.0271(10) -0.0039(8) -0.0035(9) 0.0036(8)
    C16 0.0248(10) 0.0250(10) 0.0362(11) -0.0001(8) -0.0021(8) 0.0044(8)
    C17 0.0293(10) 0.0297(10) 0.0310(11) 0.0003(8) 0.0040(8) -0.0023(8)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 . 1.260(2) ?
    O2 C17 . 1.217(2) ?
    N1 N2 . 1.316(2) ?
    N1 C1 . 1.413(2) ?
    N1 H1 . 0.97(3) ?
    N2 C7 . 1.331(2) ?
    C1 C6 . 1.391(3) ?
    C1 C2 . 1.397(3) ?
    C2 C3 . 1.387(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.397(3) ?
    C3 C17 . 1.483(3) ?
    C4 C5 . 1.387(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.390(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C12 . 1.465(3) ?
    C7 C8 . 1.472(3) ?
    C8 C9 . 1.453(3) ?
    C9 C10 . 1.340(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.454(3) ?
    C10 H10 . 0.9300 ?
    C11 C16 . 1.405(3) ?
    C11 C12 . 1.414(3) ?
    C12 C13 . 1.405(3) ?
    C13 C14 . 1.375(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.396(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.382(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
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
    N2 N1 C1 . . 118.93(16) ?
    N2 N1 H1 . . 119.8(17) ?
    C1 N1 H1 . . 121.2(17) ?
    N1 N2 C7 . . 119.34(16) ?
    C6 C1 C2 . . 120.10(17) ?
    C6 C1 N1 . . 117.88(17) ?
    C2 C1 N1 . . 122.02(17) ?
    C3 C2 C1 . . 119.72(17) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 120.49(17) ?
    C2 C3 C17 . . 118.60(17) ?
    C4 C3 C17 . . 120.91(18) ?
    C5 C4 C3 . . 119.22(19) ?
    C5 C4 H4 . . 120.4 ?
    C3 C4 H4 . . 120.4 ?
    C4 C5 C6 . . 120.87(18) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C5 C6 C1 . . 119.59(18) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 H6 . . 120.2 ?
    N2 C7 C12 . . 115.93(16) ?
    N2 C7 C8 . . 123.94(17) ?
    C12 C7 C8 . . 120.07(17) ?
    O1 C8 C9 . . 121.63(17) ?
    O1 C8 C7 . . 121.23(18) ?
    C9 C8 C7 . . 117.11(17) ?
    C10 C9 C8 . . 121.69(18) ?
    C10 C9 H9 . . 119.2 ?
    C8 C9 H9 . . 119.2 ?
    C9 C10 C11 . . 122.90(18) ?
    C9 C10 H10 . . 118.6 ?
    C11 C10 H10 . . 118.6 ?
    C16 C11 C12 . . 119.23(17) ?
    C16 C11 C10 . . 121.81(18) ?
    C12 C11 C10 . . 118.96(18) ?
    C13 C12 C11 . . 118.94(17) ?
    C13 C12 C7 . . 121.84(17) ?
    C11 C12 C7 . . 119.20(17) ?
    C14 C13 C12 . . 120.71(18) ?
    C14 C13 H13 . . 119.6 ?
    C12 C13 H13 . . 119.6 ?
    C13 C14 C15 . . 120.62(18) ?
    C13 C14 H14 . . 119.7 ?
    C15 C14 H14 . . 119.7 ?
    C16 C15 C14 . . 119.64(18) ?
    C16 C15 H15 . . 120.2 ?
    C14 C15 H15 . . 120.2 ?
    C15 C16 C11 . . 120.86(18) ?
    C15 C16 H16 . . 119.6 ?
    C11 C16 H16 . . 119.6 ?
    O2 C17 C3 . . 125.28(19) ?
    O2 C17 H17 . . 117.4 ?
    C3 C17 H17 . . 117.4 ?
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
    N1 H1 O1 . 0.97(3) 1.83(3) 2.577(3) 133(3)
    C6 H6 O1 3_765 0.93 2.41 3.327(4) 168
data_global
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2013-08-22
_journal_date_accepted     2013-08-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue     10
_journal_page_first     o1498
_journal_page_last     o1498
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813024112
_journal_coeditor_code     XU5735
_publ_contact_author_name     'Ali Benosmane*'
_publ_contact_author_address
;
Unité de recherche de Chimie de l'Environnement
et Moléculaire Structurale
Faculté du sciences exactes,
Université de Constantine 1,
25000 Constantine,
Algeria
;
_publ_contact_author_email     'king.ali@hotmail.fr'
_publ_contact_author_fax     '00 (213) 31 81 84 97'
_publ_contact_author_phone     '00 (213) 772 00 00 60'
_publ_section_title
;
(E)-1-(3-Formylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium
;
loop_
    _publ_author_name
    _publ_author_address
    'Mili, Assia'
;
Unité de recherche de Chimie de l'Environnement
et Moléculaire Structurale
Faculté du sciences exactes,
Université de Constantine 1,
25000 Constantine,
Algeria
;
    'Benosmane, Ali'
;
Unité de recherche de Chimie de l'Environnement
et Moléculaire Structurale
Faculté du sciences exactes,
Université de Constantine 1,
25000 Constantine,
Algeria
;
    'Benaouida, Mohamed Amine'
;
Unité de recherche de Chimie de l'Environnement
et Moléculaire Structurale
Faculté du sciences exactes,
Université de Constantine 1,
25000 Constantine,
Algeria
;
    'Bouchoul, Abdelkader'
;
Unité de recherche de Chimie de l'Environnement
et Moléculaire Structurale
Faculté du sciences exactes,
Université de Constantine 1,
25000 Constantine,
Algeria
;
    'Bouaoud, Salah Eddine'
;
Unité de recherche de Chimie de l'Environnement
et Moléculaire Structurale
Faculté du sciences exactes,
Université de Constantine 1,
25000 Constantine,
Algeria
;
_publ_section_synopsis     .
_chemical_melting_point     ?
