#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/57/2235767.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_2235767
loop_
_publ_author_name
'Vesek, Hilal'
'Kazak, Canan'
'Alaman Ağar, Ayşen'
'Macit, Mustafa'
'Soylu, Mustafa Serkan'
_publ_section_title
;
 (E)-3-Chloro-N-[(2-ethoxynaphthalen-1-yl)methylidene]aniline
;
_journal_coeditor_code           BX2419
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2518
_journal_paper_doi               10.1107/S1600536812032114
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C19 H16 Cl N O'
_chemical_formula_moiety         'C19 H16 Cl N O'
_chemical_formula_sum            'C19 H16 Cl N O'
_chemical_formula_weight         309.78
_chemical_name_systematic
;
(E)-3-Chloro-N-[(2-ethoxynaphthalen-1-yl)methylidene]aniline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.253(13)
_cell_angle_beta                 79.794(10)
_cell_angle_gamma                84.337(17)
_cell_formula_units_Z            2
_cell_length_a                   8.0084(14)
_cell_length_b                   8.7315(19)
_cell_length_c                   11.7043(8)
_cell_measurement_reflns_used    1666
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.6871
_cell_measurement_theta_min      3.3171
_cell_volume                     781.0(2)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2001)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.0454
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Stoe IPDS II two-circle
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5144
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA and X-RED32; Stoe & Cie, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0836P)²+0.0386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1801
_reflns_number_gt                2098
_reflns_number_total             3057
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2419.cif
_cod_data_source_block           I
_cod_database_code               2235767
_cod_database_fobs_code          2235767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.1125(3) -0.4097(4) 0.1075(3) 0.0711(9) Uani d . 1 1
C C2 0.1030(4) -0.4953(4) 0.2214(3) 0.0742(9) Uani d . 1 1
C C3 0.1347(4) -0.4241(4) 0.3093(3) 0.0672(8) Uani d . 1 1
C C4 0.1766(3) -0.2695(3) 0.2822(2) 0.0556(6) Uani d . 1 1
C C5 0.1905(3) -0.1770(3) 0.1640(2) 0.0479(6) Uani d . 1 1
C C6 0.1568(3) -0.2514(3) 0.0751(2) 0.0568(7) Uani d . 1 1
C C7 0.1717(3) -0.1636(4) -0.0440(2) 0.0647(8) Uani d . 1 1
C C8 0.2206(3) -0.0141(4) -0.0766(2) 0.0622(7) Uani d . 1 1
C C9 0.2572(3) 0.0618(3) 0.01000(19) 0.0516(6) Uani d . 1 1
C C10 0.2407(3) -0.0173(3) 0.12978(18) 0.0463(6) Uani d . 1 1
C C11 0.2871(3) 0.0684(3) 0.21183(19) 0.0463(5) Uani d . 1 1
C C12 0.3167(3) 0.1180(3) 0.39163(17) 0.0443(5) Uani d . 1 1
C C13 0.2129(3) 0.1546(3) 0.49135(19) 0.0519(6) Uani d . 1 1
H H13 0.1021 0.1226 0.5121 0.062 Uiso calc R 1 1
C C14 0.2746(3) 0.2383(3) 0.5593(2) 0.0587(7) Uani d . 1 1
H H14 0.2037 0.2650 0.6246 0.070 Uiso calc R 1 1
C C15 0.4401(3) 0.2833(3) 0.5319(2) 0.0570(6) Uani d . 1 1
H H15 0.4814 0.3395 0.5781 0.068 Uiso calc R 1 1
C C16 0.5424(3) 0.2431(3) 0.43502(19) 0.0514(6) Uani d . 1 1
C C17 0.4833(3) 0.1615(3) 0.36474(18) 0.0478(6) Uani d . 1 1
H H17 0.5549 0.1355 0.2995 0.057 Uiso calc R 1 1
C C18 0.3509(3) 0.2904(3) -0.13867(19) 0.0616(7) Uani d . 1 1
H H18A 0.2530 0.3109 -0.1796 0.074 Uiso calc R 1 1
H H18B 0.4349 0.2246 -0.1785 0.074 Uiso calc R 1 1
C C19 0.4234(4) 0.4418(4) -0.1407(2) 0.0731(8) Uani d . 1 1
H H19A 0.4575 0.4964 -0.2218 0.110 Uiso calc R 1 1
H H19B 0.5203 0.4202 -0.1002 0.110 Uiso calc R 1 1
H H19C 0.3391 0.5062 -0.1015 0.110 Uiso calc R 1 1
Cl Cl1 0.75193(9) 0.29581(10) 0.40024(6) 0.0792(3) Uani d . 1 1
O O1 0.3019(2) 0.2125(2) -0.01705(13) 0.0651(5) Uani d . 1 1
N N1 0.2496(3) 0.0308(2) 0.32487(15) 0.0513(5) Uani d . 1 1
H H1 0.100(4) -0.449(4) 0.045(3) 0.100(11) Uiso d . 1 1
H H2 0.076(4) -0.609(5) 0.246(3) 0.106(11) Uiso d . 1 1
H H3 0.125(5) -0.485(5) 0.387(3) 0.128(14) Uiso d . 1 1
H H4 0.197(3) -0.222(3) 0.344(2) 0.072(8) Uiso d . 1 1
H H7 0.154(4) -0.209(4) -0.107(2) 0.085(9) Uiso d . 1 1
H H8 0.232(3) 0.048(3) -0.159(2) 0.054(6) Uiso d . 1 1
H H11 0.352(3) 0.164(3) 0.1718(19) 0.048(6) 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
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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
C2 C1 C6 121.8(3)
C2 C1 H1 124(2)
C6 C1 H1 114(2)
C1 C2 C3 119.3(3)
C1 C2 H2 123.2(19)
C3 C2 H2 117.6(19)
C4 C3 C2 121.0(3)
C4 C3 H3 122(2)
C2 C3 H3 118(2)
C3 C4 C5 121.4(3)
C3 C4 H4 120.0(16)
C5 C4 H4 118.6(16)
C4 C5 C6 116.9(2)
C4 C5 C10 123.8(2)
C6 C5 C10 119.2(2)
C1 C6 C7 121.9(2)
C1 C6 C5 119.5(3)
C7 C6 C5 118.5(3)
C8 C7 C6 122.3(2)
C8 C7 H7 116.0(18)
C6 C7 H7 121.6(18)
C7 C8 C9 120.2(3)
C7 C8 H8 123.2(14)
C9 C8 H8 116.6(14)
O1 C9 C10 117.03(19)
O1 C9 C8 122.7(2)
C10 C9 C8 120.2(3)
C9 C10 C5 119.4(2)
C9 C10 C11 116.3(2)
C5 C10 C11 124.1(2)
N1 C11 C10 125.3(2)
N1 C11 H11 120.4(12)
C10 C11 H11 114.3(12)
C17 C12 C13 119.2(2)
C17 C12 N1 122.46(19)
C13 C12 N1 118.3(2)
C14 C13 C12 119.9(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 120.9(2)
C13 C14 H14 119.5
C15 C14 H14 119.5
C16 C15 C14 118.6(2)
C16 C15 H15 120.7
C14 C15 H15 120.7
C15 C16 C17 121.7(2)
C15 C16 Cl1 119.33(18)
C17 C16 Cl1 119.01(18)
C16 C17 C12 119.7(2)
C16 C17 H17 120.2
C12 C17 H17 120.2
O1 C18 C19 107.9(2)
O1 C18 H18A 110.1
C19 C18 H18A 110.1
O1 C18 H18B 110.1
C19 C18 H18B 110.1
H18A C18 H18B 108.4
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C9 O1 C18 119.71(19)
C11 N1 C12 118.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.358(5)
C1 C6 1.407(4)
C1 H1 0.90(3)
C2 C3 1.392(4)
C2 H2 1.00(4)
C3 C4 1.372(4)
C3 H3 0.93(4)
C4 C5 1.418(3)
C4 H4 0.96(3)
C5 C6 1.425(3)
C5 C10 1.434(3)
C6 C7 1.413(4)
C7 C8 1.347(4)
C7 H7 0.95(3)
C8 C9 1.420(3)
C8 H8 0.98(2)
C9 O1 1.347(3)
C9 C10 1.397(3)
C10 C11 1.464(3)
C11 N1 1.273(3)
C11 H11 1.00(2)
C12 C17 1.385(3)
C12 C13 1.391(3)
C12 N1 1.411(3)
C13 C14 1.377(3)
C13 H13 0.9300
C14 C15 1.381(4)
C14 H14 0.9300
C15 C16 1.372(3)
C15 H15 0.9300
C16 C17 1.375(3)
C16 Cl1 1.737(2)
C17 H17 0.9300
C18 O1 1.427(3)
C18 C19 1.488(4)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4 N1 0.96(3) 2.24(3) 2.915(3) 127(2)
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)
C1 C2 C3 C4 -0.5(4)
C2 C3 C4 C5 -0.6(4)
C3 C4 C5 C6 0.8(3)
C3 C4 C5 C10 -177.3(2)
C2 C1 C6 C7 178.1(2)
C2 C1 C6 C5 -0.9(4)
C4 C5 C6 C1 -0.1(3)
C10 C5 C6 C1 178.1(2)
C4 C5 C6 C7 -179.1(2)
C10 C5 C6 C7 -0.9(3)
C1 C6 C7 C8 -177.3(2)
C5 C6 C7 C8 1.7(4)
C6 C7 C8 C9 -0.9(4)
C7 C8 C9 O1 -178.1(2)
C7 C8 C9 C10 -0.8(4)
O1 C9 C10 C5 178.94(19)
C8 C9 C10 C5 1.5(3)
O1 C9 C10 C11 -4.7(3)
C8 C9 C10 C11 177.9(2)
C4 C5 C10 C9 177.4(2)
C6 C5 C10 C9 -0.6(3)
C4 C5 C10 C11 1.4(3)
C6 C5 C10 C11 -176.68(19)
C9 C10 C11 N1 165.2(2)
C5 C10 C11 N1 -18.7(4)
C17 C12 C13 C14 2.4(3)
N1 C12 C13 C14 179.4(2)
C12 C13 C14 C15 -1.8(4)
C13 C14 C15 C16 0.2(4)
C14 C15 C16 C17 0.7(4)
C14 C15 C16 Cl1 -179.04(19)
C15 C16 C17 C12 0.0(4)
Cl1 C16 C17 C12 179.73(17)
C13 C12 C17 C16 -1.5(3)
N1 C12 C17 C16 -178.4(2)
C10 C9 O1 C18 168.6(2)
C8 C9 O1 C18 -14.0(3)
C19 C18 O1 C9 -169.7(2)
C10 C11 N1 C12 174.6(2)
C17 C12 N1 C11 -42.5(3)
C13 C12 N1 C11 140.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 632789
