#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/86/2238688.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_2238688
loop_
_publ_author_name
'Mili, Assia'
'Benosmane, Ali'
'Benaouida, Mohamed Amine'
'Bouchoul, Abdelkader'
'Bouaoud, Salah Eddine'
_publ_section_title
;
 (E)-1-(3-Formylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium
;
_journal_coeditor_code           XU5735
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1498
_journal_paper_doi               10.1107/S1600536813024112
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C17 H12 N2 O2'
_chemical_formula_moiety         'C17 H12 N2 O2'
_chemical_formula_sum            'C17 H12 N2 O2'
_chemical_formula_weight         276.29
_chemical_name_systematic
;
(E)-1-(3-Formylphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.624(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.601(4)
_cell_length_b                   7.780(5)
_cell_length_c                   29.70(2)
_cell_measurement_reflns_used    3964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7
_cell_measurement_theta_min      1.3
_cell_volume                     1290.0(15)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1999)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16470
_diffrn_reflns_theta_full        30.71
_diffrn_reflns_theta_max         30.71
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0680P)²+0.0107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                2155
_reflns_number_total             3964
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5735.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238688
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'
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
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
