#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2007439.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_2007439
loop_
_publ_author_name
'Elmali, A.'
'Elerman, Y.'
'Svoboda, I.'
'Fuess, H.'
_publ_section_title
;
 <i>N</i>-(3,5-Dichlorophenyl)naphthaldimine
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              974
_journal_page_last               976
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C17 H11 Cl2 N O'
_chemical_formula_sum            'C17 H11 Cl2 N O'
_chemical_formula_weight         316.19
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7410(9)
_cell_length_b                   15.293(5)
_cell_length_c                   19.610(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.00
_cell_measurement_theta_min      2.47
_cell_volume                     1421.8(6)
_computing_cell_refinement
;
Nonius diffractometer control software (Nonius, 1993)
;
_computing_data_collection
;
Nonius diffractometer control software (Nonius, 1993)
;
_computing_data_reduction        'REDU4 (Stoe & Cie, 1991)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71093
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2326
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        3.7
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   ' (North, Phillips & Mathews, 1968) '
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.275
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.077
_refine_ls_goodness_of_fit_obs   1.084
_refine_ls_hydrogen_treatment    H_atoms:_see_text_below
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_restrained_S_obs      1.084
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_obs          0.0358
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.2183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1034
_refine_ls_wR_factor_obs         0.0954
_reflns_number_observed          1912
_reflns_number_total             2240
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ha1210.cif
_[local]_cod_data_source_block   ha1210
_cod_database_code               2007439
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
C1 0.0469(15) 0.0529(13) 0.0393(11) 0.0070(12) -0.0017(11) 0.0033(9)
C2 0.061(2) 0.0543(14) 0.0432(12) 0.0060(13) -0.0001(12) -0.0026(11)
C3 0.060(2) 0.0557(14) 0.0470(12) -0.0027(13) -0.0058(14) 0.0062(11)
C4 0.061(2) 0.067(2) 0.0426(11) 0.001(2) 0.0001(13) 0.0073(11)
C5 0.060(2) 0.063(2) 0.0431(12) 0.0102(15) 0.0039(13) -0.0019(12)
C6 0.057(2) 0.0521(14) 0.0513(14) 0.0024(13) 0.0027(13) -0.0025(11)
C7 0.050(2) 0.0553(14) 0.0403(11) 0.0084(13) -0.0036(11) -0.0034(10)
C8 0.045(2) 0.0509(13) 0.0416(11) 0.0050(11) -0.0056(11) 0.0021(10)
C9 0.055(2) 0.0545(15) 0.0431(12) 0.0035(13) -0.0021(12) 0.0010(10)
C10 0.064(2) 0.059(2) 0.0457(13) 0.0083(14) 0.0055(14) -0.0011(11)
C11 0.059(2) 0.072(2) 0.0438(12) 0.006(2) 0.0032(13) 0.0108(12)
C12 0.048(2) 0.058(2) 0.0491(13) 0.0019(13) -0.0072(12) 0.0109(12)
C13 0.042(2) 0.0545(13) 0.0464(11) 0.0072(12) -0.0099(12) 0.0021(10)
C14 0.056(2) 0.067(2) 0.067(2) -0.001(2) -0.004(2) -0.0141(14)
C15 0.063(2) 0.071(2) 0.096(2) -0.001(2) -0.010(2) -0.025(2)
C16 0.062(2) 0.061(2) 0.102(2) -0.008(2) -0.018(2) 0.001(2)
C17 0.054(2) 0.068(2) 0.078(2) -0.004(2) -0.009(2) 0.016(2)
N1 0.0518(15) 0.0554(12) 0.0437(10) 0.0031(11) 0.0034(10) -0.0004(9)
O1 0.072(2) 0.0554(11) 0.0639(12) -0.0034(11) 0.0151(12) -0.0103(9)
Cl1 0.1136(8) 0.0681(4) 0.0637(4) -0.0262(5) 0.0019(5) 0.0031(4)
Cl2 0.1143(9) 0.0839(6) 0.0733(5) 0.0039(6) 0.0361(6) -0.0225(4)
loop_
_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_occupancy
_atom_site_type_symbol
C1 -0.3818(6) 0.3395(2) 0.16654(11) 0.0464(6) Uani d 1 C
C2 -0.5050(6) 0.2577(2) 0.16305(12) 0.0527(7) Uani d 1 C
H2 -0.4577 0.2198 0.1278 0.055 Uiso calc 1 H
C3 -0.6964(7) 0.2325(2) 0.21142(13) 0.0544(7) Uani d 1 C
C4 -0.7789(7) 0.2867(2) 0.26323(12) 0.0568(7) Uani d 1 C
H4 -0.9120 0.2692 0.2953 0.069 Uiso calc 1 H
C5 -0.6563(6) 0.3685(2) 0.26595(12) 0.0554(7) Uani d 1 C
C6 -0.4602(7) 0.3960(2) 0.21931(13) 0.0535(7) Uani d 1 C
H6 -0.3804 0.4514 0.2227 0.085 Uiso calc 1 H
C7 -0.0423(6) 0.4320(2) 0.11527(12) 0.0486(6) Uani d 1 C
H7 -0.0804 0.4734 0.1488 0.061 Uiso calc 1 H
C8 0.1662(6) 0.4514(2) 0.06557(12) 0.0458(6) Uani d 1 C
C9 0.2318(7) 0.3897(2) 0.01483(12) 0.0510(6) Uani d 1 C
C10 0.4432(7) 0.4063(2) -0.03311(13) 0.0561(7) Uani d 1 C
H10 0.4886 0.3638 -0.0653 0.066 Uiso calc 1 H
C11 0.5829(7) 0.4837(2) -0.03320(13) 0.0581(7) Uani d 1 C
H11 0.7214 0.4938 -0.0658 0.055 Uiso calc 1 H
C12 0.5216(6) 0.5494(2) 0.01548(13) 0.0516(7) Uani d 1 C
C13 0.3164(6) 0.5333(2) 0.06605(12) 0.0478(6) Uani d 1 C
C14 0.2687(7) 0.6001(2) 0.11445(15) 0.0635(7) Uani d 1 C
H14 0.1377 0.5912 0.1491 0.062 Uiso calc 1 H
C15 0.4110(8) 0.6771(2) 0.1113(2) 0.0764(10) Uani d 1 C
H15 0.3737 0.7203 0.1434 0.105 Uiso calc 1 H
C16 0.6098(8) 0.6925(2) 0.0614(2) 0.0751(9) Uani d 1 C
H16 0.7054 0.7455 0.0600 0.089 Uiso calc 1 H
C17 0.6651(7) 0.6299(2) 0.0144(2) 0.0668(8) Uani d 1 C
H17 0.7999 0.6403 -0.0191 0.067 Uiso calc 1 H
N1 -0.1813(5) 0.35947(14) 0.11597(10) 0.0503(5) Uani d 1 N
O1 0.0996(5) 0.31375(13) 0.00970(11) 0.0637(6) Uani d 1 O
H1O -0.017(11) 0.313(3) 0.041(2) 0.115(17) Uiso d 1 H
Cl1 -0.8446(2) 0.12860(6) 0.20800(4) 0.0818(3) Uani d 1 Cl
Cl2 -0.7513(2) 0.43790(6) 0.33210(4) 0.0905(4) Uani d 1 Cl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0020 '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'
N N 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1320 0.1590 '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
_geom_angle_publ_flag
C2 C1 C6 118.9(3) ?
C2 C1 N1 116.6(2) y
C6 C1 N1 124.5(2) y
C3 C2 C1 120.1(2) ?
C3 C2 H2 120.0(3) ?
C1 C2 H2 120.0(3) ?
C2 C3 C4 122.2(3) ?
C2 C3 Cl1 119.9(2) y
C4 C3 Cl1 117.9(2) y
C3 C4 C5 117.2(3) ?
C3 C4 H4 121.4(3) ?
C5 C4 H4 121.4(3) ?
C6 C5 C4 122.5(2) ?
C6 C5 Cl2 119.2(2) y
C4 C5 Cl2 118.3(2) y
C5 C6 C1 119.0(3) ?
C5 C6 H6 120.5(3) ?
C1 C6 H6 120.5(3) ?
N1 C7 C8 122.8(2) y
N1 C7 H7 118.6(3) ?
C8 C7 H7 118.6(3) ?
C9 C8 C7 120.0(2) ?
C9 C8 C13 118.6(2) ?
C7 C8 C13 121.4(2) ?
O1 C9 C10 116.6(2) y
O1 C9 C8 122.5(3) y
C10 C9 C8 120.8(3) ?
C11 C10 C9 120.6(2) ?
C11 C10 H10 119.7(3) ?
C9 C10 H10 119.7(3) ?
C10 C11 C12 121.2(3) ?
C10 C11 H11 119.4(3) ?
C12 C11 H11 119.4(3) ?
C17 C12 C13 119.8(3) ?
C17 C12 C11 120.8(3) ?
C13 C12 C11 119.4(3) ?
C12 C13 C14 117.2(3) ?
C12 C13 C8 119.2(2) ?
C14 C13 C8 123.6(2) ?
C15 C14 C13 121.1(3) ?
C15 C14 H14 119.5(3) ?
C13 C14 H14 119.5(3) ?
C14 C15 C16 121.3(3) ?
C14 C15 H15 119.4(4) ?
C16 C15 H15 119.4(4) ?
C17 C16 C15 119.7(3) ?
C17 C16 H16 120.2(4) ?
C15 C16 H16 120.2(4) ?
C16 C17 C12 121.0(3) ?
C16 C17 H17 119.5(3) ?
C12 C17 H17 119.5(3) ?
C7 N1 C1 122.6(2) y
C9 O1 H1O 106.(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.382(4) ?
C1 C6 1.398(3) ?
C1 N1 1.407(3) y
C2 C3 1.368(4) ?
C2 H2 0.930(3) ?
C3 C4 1.369(4) ?
C3 Cl1 1.738(3) y
C4 C5 1.380(4) ?
C4 H4 0.930(3) ?
C5 C6 1.370(4) ?
C5 Cl2 1.735(3) y
C6 H6 0.930(3) ?
C7 N1 1.290(3) y
C7 C8 1.420(4) ?
C7 H7 0.930(2) ?
C8 C9 1.406(3) ?
C8 C13 1.442(4) ?
C9 O1 1.323(3) y
C9 C10 1.397(4) ?
C10 C11 1.357(4) ?
C10 H10 0.930(3) ?
C11 C12 1.416(4) ?
C11 H11 0.930(3) ?
C12 C17 1.406(4) ?
C12 C13 1.411(4) ?
C13 C14 1.412(4) ?
C14 C15 1.359(4) ?
C14 H14 0.930(3) ?
C15 C16 1.379(5) ?
C15 H15 0.930(3) ?
C16 C17 1.353(5) ?
C16 H16 0.930(3) ?
C17 H17 0.930(3) ?
O1 H1O 0.83(5) ?
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
C6 C1 C2 C3 -1.2(4)
N1 C1 C2 C3 178.3(2)
C1 C2 C3 C4 1.8(4)
C1 C2 C3 Cl1 -178.5(2)
C2 C3 C4 C5 -1.3(4)
Cl1 C3 C4 C5 179.0(2)
C3 C4 C5 C6 0.1(4)
C3 C4 C5 Cl2 -178.7(2)
C4 C5 C6 C1 0.5(4)
Cl2 C5 C6 C1 179.3(2)
C2 C1 C6 C5 0.1(4)
N1 C1 C6 C5 -179.3(3)
N1 C7 C8 C9 -1.0(4)
N1 C7 C8 C13 179.6(2)
C7 C8 C9 O1 2.2(4)
C13 C8 C9 O1 -178.3(2)
C7 C8 C9 C10 -177.8(3)
C13 C8 C9 C10 1.6(4)
O1 C9 C10 C11 177.6(3)
C8 C9 C10 C11 -2.4(4)
C9 C10 C11 C12 0.7(4)
C10 C11 C12 C17 -179.2(3)
C10 C11 C12 C13 1.6(4)
C17 C12 C13 C14 -0.9(4)
C11 C12 C13 C14 178.3(3)
C17 C12 C13 C8 178.5(2)
C11 C12 C13 C8 -2.2(4)
C9 C8 C13 C12 0.6(3)
C7 C8 C13 C12 -180.0(2)
C9 C8 C13 C14 -180.0(3)
C7 C8 C13 C14 -0.6(4)
C12 C13 C14 C15 1.3(4)
C8 C13 C14 C15 -178.1(3)
C13 C14 C15 C16 -0.9(5)
C14 C15 C16 C17 0.1(6)
C15 C16 C17 C12 0.3(5)
C13 C12 C17 C16 0.1(4)
C11 C12 C17 C16 -179.1(3)
C8 C7 N1 C1 178.1(2)
C2 C1 N1 C7 -176.9(2)
C6 C1 N1 C7 2.5(4)