##############################################################################
#                                                                            #
# 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_global
_journal_date_recd_electronic     2013-06-13
_journal_date_accepted     2013-06-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      7
_journal_page_first     m405
_journal_page_last     m405
_journal_paper_category     QM
_journal_paper_doi     10.1107/S1600536813016681
_journal_coeditor_code     SU2613
_publ_contact_author_name     'Benaouida, Mohamed Amine'
_publ_contact_author_address
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale
(CHEMS), Faculté des Sciences Exactes, Département de Chimie,
Université Constantine 1, Algeria
;
_publ_contact_author_email     mbenaouida@yahoo.fr
_publ_contact_author_fax     '00 (213) 31 57 42 52'
_publ_contact_author_phone     '00 (213) 550 80 40 92'
_publ_section_title
;
Bis{1-[(E)-(2-chlorophenyl)diazenyl]naphthalen-2-olato}copper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Benaouida, Mohamed Amine'
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale
(CHEMS), Faculté des Sciences Exactes, Département de Chimie,
Université Constantine 1, Algeria
;
    'Benosmane, Ali'
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale
(CHEMS), Faculté des Sciences Exactes, Département de Chimie,
Université Constantine 1, Algeria
;
    'Bouguerria, Hassiba'
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale
(CHEMS), Faculté des Sciences Exactes, Département de Chimie,
Université Constantine 1, Algeria
;
    'Bouaoud, Salah Eddine'
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale
(CHEMS), Faculté des Sciences Exactes, Département de Chimie,
Université Constantine 1, Algeria
;
    'Merazig, Hocine'
;
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale
(CHEMS), Faculté des Sciences Exactes, Département de Chimie,
Université Constantine 1, Algeria
;
data_I
_chemical_name_systematic
;
Bis{1-[(E)-(2-chlorophenyl)diazenyl]naphthalen-2-olato}copper(II)
;
_chemical_formula_moiety     'C32 H20 Cl2 Cu N4 O2'
_chemical_formula_sum     'C32 H20 Cl2 Cu N4 O2'
_chemical_formula_structural     'C32 H20 Cl2 Cu N4 O2'
_chemical_formula_iupac     '[Cu (C16 H10 Cl N2 O)2]'
_chemical_formula_weight     626.99
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,1/2+y,1/2-z
    3 -x,-y,-z
    4 x,1/2-y,1/2+z
_cell_length_a     10.2218(4)
_cell_length_b     7.8348(3)
_cell_length_c     17.5678(6)
_cell_angle_alpha     90
_cell_angle_beta     111.941(2)
_cell_angle_gamma     90
_cell_volume     1305.03(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     273
_cell_special_details
;
Least Squares Treatment of 25 SET4 setting angles.
;
_exptl_crystal_description     block
_exptl_crystal_colour     black
_exptl_crystal_size_max     0.01
_exptl_crystal_size_mid     0.01
_exptl_crystal_size_min     0.01
_exptl_crystal_density_diffrn     1.595
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     638
_exptl_absorpt_coefficient_mu     1.082
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     273
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7327
_diffrn_reflns_av_R_equivalents     0.0301
_diffrn_reflns_av_sigmaI/netI     0.0306
_diffrn_reflns_theta_min     2.62
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs 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     2299
_reflns_number_gt     1979
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0421
_refine_ls_R_factor_gt     0.0336
_refine_ls_wR_factor_gt     0.0788
_refine_ls_wR_factor_ref     0.0822
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     2299
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0406P)²+0.9147P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.476
_refine_diff_density_min     -0.275
_refine_ls_extinction_method     'none'
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'
    Cu Cu 0.3201 1.2651 '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'
    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     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'SAINT (Bruker, 2006)'
_computing_data_reduction     'SAINT (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
 'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    Cu Cu1 1.00000 0.00000 0.50000 0.02010(10)
                                             Uani . . 1.000
    Cl Cl1 0.86221(8) 0.03646(8) 0.30754(4) 0.0321(2) Uani . . 1.000
    O O1 0.87383(17) -0.1495(2) 0.52340(10) 0.0247(6) Uani . . 1.000
    N N1 0.7529(2) 0.1928(3) 0.49516(12) 0.0215(6) Uani . . 1.000
    N N2 0.8458(2) 0.1667(3) 0.46293(12) 0.0211(6) Uani . . 1.000
    C C1 0.8501(2) 0.2972(3) 0.40751(15) 0.0214(7) Uani . . 1.000
    C C2 0.8675(3) 0.2510(3) 0.33477(15) 0.0232(8) Uani . . 1.000
    C C3 0.8873(3) 0.3725(4) 0.28366(16) 0.0282(8) Uani . . 1.000
    C C4 0.8913(3) 0.5422(4) 0.30481(17) 0.0310(9) Uani . . 1.000
    C C5 0.8705(3) 0.5902(3) 0.37502(16) 0.0291(8) Uani . . 1.000
    C C6 0.8498(3) 0.4678(3) 0.42576(16) 0.0263(8) Uani . . 1.000
    C C7 0.7306(2) 0.0731(3) 0.54482(15) 0.0207(7) Uani . . 1.000
    C C8 0.7818(3) -0.0968(3) 0.55231(15) 0.0219(7) Uani . . 1.000
    C C9 0.7262(3) -0.2196(3) 0.59274(16) 0.0274(8) Uani . . 1.000
    C C10 0.6318(3) -0.1733(4) 0.62659(16) 0.0304(9) Uani . . 1.000
    C C11 0.5848(3) -0.0025(4) 0.62456(16) 0.0267(8) Uani . . 1.000
    C C12 0.4917(3) 0.0451(4) 0.66382(16) 0.0317(9) Uani . . 1.000
    C C13 0.4493(3) 0.2096(4) 0.66213(17) 0.0360(10) Uani . . 1.000
    C C14 0.4949(3) 0.3334(4) 0.62085(17) 0.0345(9) Uani . . 1.000
    C C15 0.5854(3) 0.2909(4) 0.58222(16) 0.0286(8) Uani . . 1.000
    C C16 0.6323(2) 0.1228(3) 0.58341(15) 0.0227(8) Uani . . 1.000
    H H3 0.89790 0.34050 0.23530 0.0340 Uiso calc R 1.000
    H H4 0.90820 0.62490 0.27160 0.0370 Uiso calc R 1.000
    H H5 0.87050 0.70520 0.38810 0.0350 Uiso calc R 1.000
    H H6 0.83550 0.50100 0.47290 0.0310 Uiso calc R 1.000
    H H9 0.75520 -0.33280 0.59580 0.0330 Uiso calc R 1.000
    H H10 0.59690 -0.25620 0.65190 0.0360 Uiso calc R 1.000
    H H12 0.45960 -0.03700 0.69090 0.0380 Uiso calc R 1.000
    H H13 0.38930 0.23990 0.68870 0.0430 Uiso calc R 1.000
    H H14 0.46410 0.44550 0.61940 0.0410 Uiso calc R 1.000
    H H15 0.61560 0.37480 0.55510 0.0340 Uiso calc R 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cu1 Cl1 . . 3.1525(7) no
    Cu1 O1 . . 1.8975(17) no
    Cu1 N2 . . 1.961(2) no
    Cu1 Cl1 . 3_756 3.1525(7) no
    Cu1 O1 . 3_756 1.8975(17) no
    Cu1 N2 . 3_756 1.961(2) no
    Cl1 C2 . . 1.743(2) no
    O1 C8 . . 1.292(4) no
    N1 N2 . . 1.291(3) no
    N1 C7 . . 1.357(3) no
    N2 C1 . . 1.424(3) no
    C1 C2 . . 1.402(4) no
    C1 C6 . . 1.375(3) no
    C2 C3 . . 1.375(4) no
    C3 C4 . . 1.377(4) no
    C4 C5 . . 1.380(4) no
    C5 C6 . . 1.378(4) no
    C7 C8 . . 1.418(3) no
    C7 C16 . . 1.459(3) no
    C8 C9 . . 1.434(4) no
    C9 C10 . . 1.358(4) no
    C10 C11 . . 1.418(4) no
    C11 C12 . . 1.418(4) no
    C11 C16 . . 1.409(4) no
    C12 C13 . . 1.357(4) no
    C13 C14 . . 1.392(4) no
    C14 C15 . . 1.377(4) no
    C15 C16 . . 1.399(4) no
    C3 H3 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C9 H9 . . 0.9300 no
    C10 H10 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C13 H13 . . 0.9300 no
    C14 H14 . . 0.9300 no
    C15 H15 . . 0.9300 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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    Cl1 Cu1 O1 . . . 102.76(5) no
    Cl1 Cu1 N2 . . . 66.55(6) no
    Cl1 Cu1 Cl1 . . 3_756 180.00 no
    Cl1 Cu1 O1 . . 3_756 77.24(5) no
    Cl1 Cu1 N2 . . 3_756 113.45(6) no
    O1 Cu1 N2 . . . 87.48(8) no
    Cl1 Cu1 O1 3_756 . . 77.24(5) no
    O1 Cu1 O1 . . 3_756 180.00 no
    O1 Cu1 N2 . . 3_756 92.52(8) no
    Cl1 Cu1 N2 3_756 . . 113.45(6) no
    O1 Cu1 N2 3_756 . . 92.52(8) no
    N2 Cu1 N2 . . 3_756 180.00 no
    Cl1 Cu1 O1 3_756 . 3_756 102.76(5) no
    Cl1 Cu1 N2 3_756 . 3_756 66.55(6) no
    O1 Cu1 N2 3_756 . 3_756 87.48(8) no
    Cu1 Cl1 C2 . . . 80.64(8) no
    Cu1 O1 C8 . . . 122.78(15) no
    N2 N1 C7 . . . 120.0(2) no
    Cu1 N2 N1 . . . 126.26(17) no
    Cu1 N2 C1 . . . 118.61(16) no
    N1 N2 C1 . . . 113.7(2) no
    N2 C1 C2 . . . 119.0(2) no
    N2 C1 C6 . . . 122.4(2) no
    C2 C1 C6 . . . 118.4(2) no
    Cl1 C2 C1 . . . 119.85(19) no
    Cl1 C2 C3 . . . 119.1(2) no
    C1 C2 C3 . . . 121.1(2) no
    C2 C3 C4 . . . 119.3(3) no
    C3 C4 C5 . . . 120.4(3) no
    C4 C5 C6 . . . 120.0(2) no
    C1 C6 C5 . . . 120.8(2) no
    N1 C7 C8 . . . 124.3(2) no
    N1 C7 C16 . . . 115.1(2) no
    C8 C7 C16 . . . 120.1(2) no
    O1 C8 C7 . . . 124.1(2) no
    O1 C8 C9 . . . 117.5(2) no
    C7 C8 C9 . . . 118.4(3) no
    C8 C9 C10 . . . 121.0(2) no
    C9 C10 C11 . . . 122.0(3) no
    C10 C11 C12 . . . 121.2(3) no
    C10 C11 C16 . . . 119.5(3) no
    C12 C11 C16 . . . 119.3(3) no
    C11 C12 C13 . . . 120.4(3) no
    C12 C13 C14 . . . 120.5(3) no
    C13 C14 C15 . . . 120.4(3) no
    C14 C15 C16 . . . 120.7(3) no
    C7 C16 C11 . . . 118.8(2) no
    C7 C16 C15 . . . 122.4(2) no
    C11 C16 C15 . . . 118.8(2) no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 120.00 no
    C3 C4 H4 . . . 120.00 no
    C5 C4 H4 . . . 120.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C1 C6 H6 . . . 120.00 no
    C5 C6 H6 . . . 120.00 no
    C8 C9 H9 . . . 119.00 no
    C10 C9 H9 . . . 120.00 no
    C9 C10 H10 . . . 119.00 no
    C11 C10 H10 . . . 119.00 no
    C11 C12 H12 . . . 120.00 no
    C13 C12 H12 . . . 120.00 no
    C12 C13 H13 . . . 120.00 no
    C14 C13 H13 . . . 120.00 no
    C13 C14 H14 . . . 120.00 no
    C15 C14 H14 . . . 120.00 no
    C14 C15 H15 . . . 120.00 no
    C16 C15 H15 . . . 120.00 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 Cu1 Cl1 C2 . . . . 123.11(12) no
    N2 Cu1 Cl1 C2 . . . . 41.58(13) no
    O1 Cu1 Cl1 C2 3_756 . . . -56.89(12) no
    N2 Cu1 Cl1 C2 3_756 . . . -138.42(13) no
    Cl1 Cu1 O1 C8 . . . . -102.24(18) no
    N2 Cu1 O1 C8 . . . . -36.98(19) no
    Cl1 Cu1 O1 C8 3_756 . . . 77.76(18) no
    N2 Cu1 O1 C8 3_756 . . . 143.03(19) no
    Cl1 Cu1 N2 N1 . . . . 142.2(2) no
    Cl1 Cu1 N2 C1 . . . . -52.32(16) no
    O1 Cu1 N2 N1 . . . . 37.1(2) no
    O1 Cu1 N2 C1 . . . . -157.39(18) no
    Cl1 Cu1 N2 N1 3_756 . . . -37.8(2) no
    Cl1 Cu1 N2 C1 3_756 . . . 127.68(16) no
    O1 Cu1 N2 N1 3_756 . . . -142.9(2) no
    O1 Cu1 N2 C1 3_756 . . . 22.61(18) no
    Cu1 Cl1 C2 C1 . . . . -33.3(2) no
    Cu1 Cl1 C2 C3 . . . . 147.4(3) no
    Cu1 O1 C8 C7 . . . . 21.9(3) no
    Cu1 O1 C8 C9 . . . . -159.62(18) no
    C7 N1 N2 Cu1 . . . . -18.4(3) no
    C7 N1 N2 C1 . . . . 175.5(2) no
    N2 N1 C7 C8 . . . . -13.2(4) no
    N2 N1 C7 C16 . . . . 174.8(2) no
    Cu1 N2 C1 C2 . . . . 53.1(3) no
    Cu1 N2 C1 C6 . . . . -121.3(2) no
    N1 N2 C1 C2 . . . . -139.7(2) no
    N1 N2 C1 C6 . . . . 46.0(3) no
    N2 C1 C2 Cl1 . . . . 7.7(3) no
    N2 C1 C2 C3 . . . . -173.0(3) no
    C6 C1 C2 Cl1 . . . . -177.7(2) no
    C6 C1 C2 C3 . . . . 1.6(4) no
    N2 C1 C6 C5 . . . . 172.4(3) no
    C2 C1 C6 C5 . . . . -2.0(4) no
    Cl1 C2 C3 C4 . . . . 179.9(2) no
    C1 C2 C3 C4 . . . . 0.6(5) no
    C2 C3 C4 C5 . . . . -2.4(5) no
    C3 C4 C5 C6 . . . . 2.0(5) no
    C4 C5 C6 C1 . . . . 0.3(5) no
    N1 C7 C8 O1 . . . . 11.7(4) no
    N1 C7 C8 C9 . . . . -166.8(2) no
    C16 C7 C8 O1 . . . . -176.7(2) no
    C16 C7 C8 C9 . . . . 4.8(4) no
    N1 C7 C16 C11 . . . . 169.5(2) no
    N1 C7 C16 C15 . . . . -11.7(3) no
    C8 C7 C16 C11 . . . . -2.9(4) no
    C8 C7 C16 C15 . . . . 176.0(2) no
    O1 C8 C9 C10 . . . . 178.3(2) no
    C7 C8 C9 C10 . . . . -3.1(4) no
    C8 C9 C10 C11 . . . . -0.7(4) no
    C9 C10 C11 C12 . . . . -176.8(3) no
    C9 C10 C11 C16 . . . . 2.7(4) no
    C10 C11 C12 C13 . . . . 179.1(3) no
    C16 C11 C12 C13 . . . . -0.3(4) no
    C10 C11 C16 C7 . . . . -0.8(4) no
    C10 C11 C16 C15 . . . . -179.8(3) no
    C12 C11 C16 C7 . . . . 178.6(2) no
    C12 C11 C16 C15 . . . . -0.3(4) no
    C11 C12 C13 C14 . . . . 1.0(4) no
    C12 C13 C14 C15 . . . . -1.0(4) no
    C13 C14 C15 C16 . . . . 0.4(4) no
    C14 C15 C16 C7 . . . . -178.6(3) no
    C14 C15 C16 C11 . . . . 0.3(4) no
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
    C5 H5 O1 1_565 0.93 2.62 3.300(3) 130 yes
    C5 H5 Cl1 1_565 0.93 2.94 3.682(3) 138 yes
