#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/85/2238581.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_2238581
loop_
_publ_author_name
'Damous, Maamar'
'Dénès, George'
'Bouacida, Sofiane'
'Hamlaoui, Meriem'
'Merazig, Hocine'
'Daran, Jean-Claude'
_publ_section_title
;
 3-{[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium
 perchlorate
;
_journal_coeditor_code           XU5730
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1460
_journal_page_last               o1461
_journal_paper_doi               10.1107/S1600536813023015
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H13 N2 O +, Cl O4 -'
_chemical_formula_moiety         'C16 H13 N2 O, Cl O4'
_chemical_formula_sum            'C16 H13 Cl N2 O5'
_chemical_formula_weight         348.73
_chemical_name_systematic
;
3-{[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium
perchlorate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5043(9)
_cell_length_b                   14.6915(19)
_cell_length_c                   15.398(3)
_cell_measurement_reflns_used    1867
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.386
_cell_measurement_theta_min      2.981
_cell_volume                     1471.4(4)
_computing_cell_refinement       'CrysAlis Pro (Agilent, 2011)'
_computing_data_collection       'CrysAlis Pro (Agilent, 2011)'
_computing_data_reduction        'CrysAlis Pro (Agilent, 2011)'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012)
and DIAMOND (Brandenburg & Berndt, 2001)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.2632
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Agilent Xcalibur (Sapphire1)'
_diffrn_measurement_method       'ω scans'
_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  0.0685
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9582
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Agilent, 2011)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.278
_refine_ls_abs_structure_details 'Flack (1983), 1362 Friedel pairs'
_refine_ls_abs_structure_Flack   0.43(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1695
_reflns_number_total             3369
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5730.cif
_cod_data_source_block           I
_cod_database_code               2238581
_cod_database_fobs_code          2238581
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
Cl Cl1 0.26988(16) 0.25979(7) 0.14441(7) 0.0420(3) Uani d . 1 1
O O1 0.3025(4) 0.31465(18) 0.63157(19) 0.0404(7) Uani d . 1 1
H H1 0.3022 0.3556 0.5954 0.061 Uiso calc R 1 1
O O13 0.3797(5) 0.2618(2) 0.0636(2) 0.0567(9) Uani d . 1 1
O O12 0.2121(6) 0.1681(2) 0.1622(2) 0.0702(10) Uani d . 1 1
N N1 0.2985(5) 0.3865(2) 0.4812(2) 0.0283(9) Uani d . 1 1
O O11 0.4044(5) 0.2891(2) 0.2118(2) 0.0647(10) Uani d . 1 1
C C17 0.2947(6) 0.1364(2) 0.4624(3) 0.0271(10) Uani d . 1 1
C C8 0.2991(5) 0.2266(2) 0.5012(2) 0.0267(9) Uani d . 1 1
C C9 0.3004(5) 0.2340(3) 0.5911(3) 0.0297(10) Uani d . 1 1
C C16 0.2929(5) 0.1213(3) 0.3737(3) 0.0357(10) Uani d . 1 1
H H16 0.2964 0.1707 0.3359 0.043 Uiso calc R 1 1
C C10 0.2994(6) 0.1562(3) 0.6438(3) 0.0366(10) Uani d . 1 1
H H10 0.3015 0.1627 0.7039 0.044 Uiso calc R 1 1
C C12 0.2913(6) 0.0598(2) 0.5180(3) 0.0293(9) Uani d . 1 1
N N5 0.2590(6) 0.6228(2) 0.4274(3) 0.0455(10) Uani d . 1 1
H H5 0.2496 0.6728 0.4562 0.055 Uiso calc R 1 1
C C1 0.2895(6) 0.4649(2) 0.4284(3) 0.0302(10) Uani d . 1 1
C C7 0.2958(6) 0.3064(2) 0.4483(3) 0.0284(9) Uani d . 1 1
H H7 0.2915 0.3 0.3882 0.034 Uiso calc R 1 1
C C11 0.2954(6) 0.0720(3) 0.6088(3) 0.0373(11) Uani d . 1 1
H H11 0.2954 0.0214 0.6451 0.045 Uiso calc R 1 1
O O14 0.0992(5) 0.3161(3) 0.1393(3) 0.1075(16) Uani d . 1 1
C C2 0.2884(6) 0.4676(3) 0.3384(3) 0.0360(11) Uani d . 1 1
H H2 0.2999 0.4138 0.307 0.043 Uiso calc R 1 1
C C13 0.2841(7) -0.0278(3) 0.4825(3) 0.0390(11) Uani d . 1 1
H H13 0.2807 -0.0781 0.5192 0.047 Uiso calc R 1 1
C C3 0.2706(7) 0.5487(3) 0.2955(3) 0.0405(11) Uani d . 1 1
H H3 0.2684 0.5499 0.2351 0.049 Uiso calc R 1 1
C C4 0.2562(7) 0.6270(3) 0.3411(3) 0.0443(11) Uani d . 1 1
H H4 0.2445 0.6827 0.3127 0.053 Uiso calc R 1 1
C C15 0.2861(7) 0.0350(3) 0.3406(3) 0.0455(12) Uani d . 1 1
H H15 0.2843 0.0265 0.2807 0.055 Uiso calc R 1 1
C C6 0.2756(7) 0.5459(2) 0.4712(3) 0.0374(11) Uani d . 1 1
H H6 0.2778 0.5469 0.5316 0.045 Uiso calc R 1 1
C C14 0.2819(7) -0.0405(3) 0.3954(3) 0.0471(12) Uani d . 1 1
H H14 0.2777 -0.099 0.3724 0.056 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O14 Cl1 O11 110.6(3)
O14 Cl1 O12 111.3(3)
O11 Cl1 O12 107.9(2)
O14 Cl1 O13 109.7(2)
O11 Cl1 O13 108.6(2)
O12 Cl1 O13 108.5(2)
C9 O1 H1 109.5
C7 N1 C1 121.4(4)
C16 C17 C12 118.0(4)
C16 C17 C8 123.5(4)
C12 C17 C8 118.5(4)
C9 C8 C7 120.3(4)
C9 C8 C17 118.8(3)
C7 C8 C17 120.9(4)
O1 C9 C8 122.2(3)
O1 C9 C10 116.9(4)
C8 C9 C10 120.9(4)
C15 C16 C17 121.1(4)
C15 C16 H16 119.4
C17 C16 H16 119.4
C11 C10 C9 121.1(4)
C11 C10 H10 119.4
C9 C10 H10 119.4
C13 C12 C11 120.4(4)
C13 C12 C17 119.7(4)
C11 C12 C17 119.9(4)
C6 N5 C4 123.4(4)
C6 N5 H5 118.3
C4 N5 H5 118.3
C6 C1 C2 117.3(4)
C6 C1 N1 115.9(4)
C2 C1 N1 126.8(3)
N1 C7 C8 121.9(4)
N1 C7 H7 119.1
C8 C7 H7 119.1
C10 C11 C12 120.9(4)
C10 C11 H11 119.6
C12 C11 H11 119.6
C3 C2 C1 120.6(4)
C3 C2 H2 119.7
C1 C2 H2 119.7
C14 C13 C12 120.9(4)
C14 C13 H13 119.5
C12 C13 H13 119.5
C4 C3 C2 119.8(4)
C4 C3 H3 120.1
C2 C3 H3 120.1
N5 C4 C3 118.6(4)
N5 C4 H4 120.7
C3 C4 H4 120.7
C16 C15 C14 120.8(4)
C16 C15 H15 119.6
C14 C15 H15 119.6
N5 C6 C1 120.4(4)
N5 C6 H6 119.8
C1 C6 H6 119.8
C13 C14 C15 119.3(4)
C13 C14 H14 120.3
C15 C14 H14 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 O14 1.387(3)
Cl1 O11 1.424(3)
Cl1 O12 1.425(3)
Cl1 O13 1.436(3)
O1 C9 1.339(4)
O1 H1 0.82
N1 C7 1.282(4)
N1 C1 1.411(5)
C17 C16 1.384(6)
C17 C12 1.414(5)
C17 C8 1.455(5)
C8 C9 1.388(5)
C8 C7 1.428(5)
C9 C10 1.402(5)
C16 C15 1.367(5)
C16 H16 0.93
C10 C11 1.349(5)
C10 H10 0.93
C12 C13 1.399(5)
C12 C11 1.411(5)
N5 C6 1.321(5)
N5 C4 1.331(5)
N5 H5 0.86
C1 C6 1.363(5)
C1 C2 1.386(5)
C7 H7 0.93
C11 H11 0.93
C2 C3 1.367(5)
C2 H2 0.93
C13 C14 1.353(6)
C13 H13 0.93
C3 C4 1.351(5)
C3 H3 0.93
C4 H4 0.93
C15 C14 1.394(5)
C15 H15 0.93
C6 H6 0.93
C14 H14 0.93
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
_geom_hbond_publ_flag
O1 H1 N1 . 0.82 1.82 2.545(4) 147 yes
N5 H5 O13 2_565 0.86 2.09 2.844(5) 146 yes
C2 H2 O11 . 0.93 2.44 3.354(5) 166 yes
C3 H3 O1 2_564 0.93 2.59 3.260(5) 129 yes
C13 H13 O12 2_555 0.93 2.57 3.451(6) 158 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C16 C17 C8 C9 179.9(4)
C12 C17 C8 C9 0.2(5)
C16 C17 C8 C7 1.8(6)
C12 C17 C8 C7 -177.9(4)
C7 C8 C9 O1 -1.3(5)
C17 C8 C9 O1 -179.4(3)
C7 C8 C9 C10 178.7(4)
C17 C8 C9 C10 0.6(5)
C12 C17 C16 C15 0.6(6)
C8 C17 C16 C15 -179.2(4)
O1 C9 C10 C11 179.4(3)
C8 C9 C10 C11 -0.6(6)
C16 C17 C12 C13 -0.7(6)
C8 C17 C12 C13 179.1(3)
C16 C17 C12 C11 179.3(4)
C8 C17 C12 C11 -1.0(6)
C7 N1 C1 C6 174.5(4)
C7 N1 C1 C2 -3.8(7)
C1 N1 C7 C8 -178.2(4)
C9 C8 C7 N1 1.6(6)
C17 C8 C7 N1 179.7(3)
C9 C10 C11 C12 -0.2(6)
C13 C12 C11 C10 -179.0(4)
C17 C12 C11 C10 1.0(6)
C6 C1 C2 C3 -1.0(7)
N1 C1 C2 C3 177.3(4)
C11 C12 C13 C14 -179.4(4)
C17 C12 C13 C14 0.5(6)
C1 C2 C3 C4 0.7(7)
C6 N5 C4 C3 0.1(8)
C2 C3 C4 N5 -0.2(7)
C17 C16 C15 C14 -0.3(6)
C4 N5 C6 C1 -0.5(7)
C2 C1 C6 N5 0.9(7)
N1 C1 C6 N5 -177.6(4)
C12 C13 C14 C15 -0.3(7)
C16 C15 C14 C13 0.2(7)
