#------------------------------------------------------------------------------
#$Date: 2015-08-30 05:08:24 +0300 (Sun, 30 Aug 2015) $
#$Revision: 153802 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/10/2241065.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_2241065
loop_
_publ_author_name
'Tahir, Muhammad Nawaz'
'Anwar-ul-Haq, Muhammad'
'Shad, Hazoor Ahmad'
_publ_section_title
;
 Crystal structure of
 1-{(E)-[(3,4-dichlorophenyl)imino]methyl}naphthalen-2-ol
;
_journal_coeditor_code           HB7492
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o696
_journal_paper_doi               10.1107/S2056989015015959
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C17 H11 Cl2 N O'
_chemical_formula_moiety         'C17 H11 Cl2 N O'
_chemical_formula_sum            'C17 H11 Cl2 N O'
_chemical_formula_weight         316.17
_chemical_name_systematic
;
1-{(E)-[(3,4-Dichlorophenyl)imino]methyl}naphthalen-2-ol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.287(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.075(4)
_cell_length_b                   3.9284(6)
_cell_length_c                   26.359(4)
_cell_measurement_reflns_used    1624
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.3
_cell_volume                     2791.7(7)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014  (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.70
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0518
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10968
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.263
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2005)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.287
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0410P)²+0.8217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                1624
_reflns_number_total             3006
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7492sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2791.7(8)
_cod_database_code               2241065
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
Cl Cl1 -0.01545(2) 0.1563(2) -0.07226(3) 0.0583(3) Uani d 1
Cl Cl2 0.03878(3) -0.1601(2) -0.16134(3) 0.0657(3) Uani d 1
O O1 0.23523(6) 0.7303(6) 0.05438(8) 0.0661(6) Uani d 1
H H1 0.2167 0.6298 0.0331 0.099 Uiso calc 1
N N1 0.15606(7) 0.4249(6) 0.01785(9) 0.0480(6) Uani d 1
C C1 0.21559(9) 0.7303(7) 0.09872(11) 0.0473(7) Uani d 1
C C2 0.24423(10) 0.8780(8) 0.14042(12) 0.0550(8) Uani d 1
H H2 0.2753 0.9668 0.1359 0.066 Uiso calc 1
C C3 0.22719(10) 0.8919(7) 0.18642(12) 0.0514(8) Uani d 1
H H3 0.2467 0.9929 0.2132 0.062 Uiso calc 1
C C4 0.18026(9) 0.7570(7) 0.19561(10) 0.0434(7) Uani d 1
C C5 0.16273(10) 0.7752(7) 0.24400(11) 0.0510(8) Uani d 1
H H5 0.1823 0.8789 0.2705 0.061 Uiso calc 1
C C6 0.11812(11) 0.6459(8) 0.25307(11) 0.0568(8) Uani d 1
H H6 0.1071 0.6605 0.2854 0.068 Uiso calc 1
C C7 0.08905(10) 0.4908(8) 0.21345(11) 0.0555(8) Uani d 1
H H7 0.0584 0.3998 0.2195 0.067 Uiso calc 1
C C8 0.10470(9) 0.4700(7) 0.16588(11) 0.0465(7) Uani d 1
H H8 0.0844 0.3658 0.1401 0.056 Uiso calc 1
C C9 0.15082(8) 0.6018(6) 0.15477(10) 0.0380(7) Uani d 1
C C10 0.16918(9) 0.5897(7) 0.10521(10) 0.0407(7) Uani d 1
C C11 0.14109(9) 0.4337(7) 0.06279(11) 0.0446(7) Uani d 1
H H11 0.1108 0.3346 0.0679 0.053 Uiso calc 1
C C12 0.12664(9) 0.2802(7) -0.02362(10) 0.0427(7) Uani d 1
C C13 0.07522(9) 0.2847(6) -0.02738(10) 0.0396(6) Uani d 1
H H13 0.0587 0.3810 -0.0015 0.047 Uiso calc 1
C C14 0.04871(9) 0.1476(7) -0.06919(10) 0.0390(6) Uani d 1
C C15 0.07202(10) 0.0081(7) -0.10842(10) 0.0438(7) Uani d 1
C C16 0.12334(10) 0.0042(8) -0.10466(11) 0.0516(8) Uani d 1
H H16 0.1397 -0.0916 -0.1307 0.062 Uiso calc 1
C C17 0.15025(10) 0.1399(8) -0.06306(11) 0.0518(8) Uani d 1
H H17 0.1847 0.1378 -0.0612 0.062 Uiso calc 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 0.0000 0.0000 '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 0.0060 '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
C1 O1 H1 109.5
C11 N1 C12 121.4(2)
O1 C1 C10 123.0(3)
O1 C1 C2 116.7(2)
C10 C1 C2 120.2(3)
C3 C2 C1 120.8(3)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 121.9(3)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C9 119.9(2)
C5 C4 C3 121.3(3)
C9 C4 C3 118.8(3)
C6 C5 C4 121.6(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
C5 C6 C7 119.1(3)
C5 C6 H6 120.5
C7 C6 H6 120.5
C8 C7 C6 121.0(3)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C9 121.8(3)
C7 C8 H8 119.1
C9 C8 H8 119.1
C8 C9 C4 116.6(2)
C8 C9 C10 124.3(2)
C4 C9 C10 119.1(2)
C1 C10 C11 119.5(3)
C1 C10 C9 119.2(2)
C11 C10 C9 121.3(2)
N1 C11 C10 122.7(2)
N1 C11 H11 118.6
C10 C11 H11 118.6
C17 C12 C13 118.8(2)
C17 C12 N1 118.4(2)
C13 C12 N1 122.8(2)
C14 C13 C12 120.1(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 121.3(2)
C13 C14 Cl1 118.6(2)
C15 C14 Cl1 120.1(2)
C14 C15 C16 118.6(2)
C14 C15 Cl2 121.4(2)
C16 C15 Cl2 120.0(2)
C17 C16 C15 120.7(3)
C17 C16 H16 119.7
C15 C16 H16 119.7
C16 C17 C12 120.6(2)
C16 C17 H17 119.7
C12 C17 H17 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.732(2)
Cl2 C15 1.721(3)
O1 C1 1.328(3)
O1 H1 0.8200
N1 C11 1.287(3)
N1 C12 1.411(3)
C1 C10 1.397(3)
C1 C2 1.410(4)
C2 C3 1.338(4)
C2 H2 0.9300
C3 C4 1.418(4)
C3 H3 0.9300
C4 C5 1.403(4)
C4 C9 1.417(3)
C5 C6 1.352(4)
C5 H5 0.9300
C6 C7 1.389(4)
C6 H6 0.9300
C7 C8 1.363(4)
C7 H7 0.9300
C8 C9 1.407(3)
C8 H8 0.9300
C9 C10 1.441(3)
C10 C11 1.431(3)
C11 H11 0.9300
C12 C17 1.384(4)
C12 C13 1.387(3)
C13 C14 1.369(3)
C13 H13 0.9300
C14 C15 1.374(3)
C15 C16 1.384(4)
C16 C17 1.367(4)
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
O1 H1 N1 . 0.82 1.84 2.565(3) 147
C17 H17 O1 7 0.93 2.60 3.413(3) 147
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
O1 C1 C2 C3 179.4(3)
C10 C1 C2 C3 -1.3(4)
C1 C2 C3 C4 0.7(4)
C2 C3 C4 C5 -179.6(3)
C2 C3 C4 C9 0.3(4)
C9 C4 C5 C6 0.4(4)
C3 C4 C5 C6 -179.7(3)
C4 C5 C6 C7 0.1(4)
C5 C6 C7 C8 -0.5(4)
C6 C7 C8 C9 0.3(4)
C7 C8 C9 C4 0.1(4)
C7 C8 C9 C10 -179.5(3)
C5 C4 C9 C8 -0.5(4)
C3 C4 C9 C8 179.6(2)
C5 C4 C9 C10 179.2(2)
C3 C4 C9 C10 -0.7(4)
O1 C1 C10 C11 0.7(4)
C2 C1 C10 C11 -178.5(3)
O1 C1 C10 C9 -179.9(2)
C2 C1 C10 C9 0.8(4)
C8 C9 C10 C1 179.8(2)
C4 C9 C10 C1 0.2(4)
C8 C9 C10 C11 -0.8(4)
C4 C9 C10 C11 179.5(2)
C12 N1 C11 C10 -177.6(2)
C1 C10 C11 N1 -2.1(4)
C9 C10 C11 N1 178.6(2)
C11 N1 C12 C17 -151.6(3)
C11 N1 C12 C13 31.0(4)
C17 C12 C13 C14 0.9(4)
N1 C12 C13 C14 178.4(2)
C12 C13 C14 C15 -1.0(4)
C12 C13 C14 Cl1 179.7(2)
C13 C14 C15 C16 0.9(4)
Cl1 C14 C15 C16 -179.8(2)
C13 C14 C15 Cl2 -179.3(2)
Cl1 C14 C15 Cl2 0.1(3)
C14 C15 C16 C17 -0.7(4)
Cl2 C15 C16 C17 179.4(2)
C15 C16 C17 C12 0.8(5)
C13 C12 C17 C16 -0.8(4)
N1 C12 C17 C16 -178.4(3)

_cod_database_fobs_code 2241065
