#------------------------------------------------------------------------------
#$Date: 2023-07-29 04:54:37 +0300 (Sat, 29 Jul 2023) $
#$Revision: 285383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/21/2312157.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_2312157
loop_
_publ_author_name
'Yahiaoui, Ahmed Abderrahim'
'Ghichi, Nadir'
'Hannachi, Douniazed'
'Mezhoud, Bilel'
'Djedouani, Amel'
'Kraim, Khairedine'
'Crochet, Aurélien'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 The synthesis and crystal structure of
 (E)-2-{[(4-methoxynaphthalen-1-yl)methylidene]amino}-4-methylphenol:
 Hirshfeld surface analysis, DFT calculations and anticorrosion studies.
;
_journal_coeditor_code           ZO3036
_journal_issue                   8
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229623005867
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C19 H17 N O2'
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33
_chemical_name_systematic
;
(E)-2-{[(4-Methoxynaphthalen-1-yl)methylidene]amino}-4-methylphenol
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                106.383(4)
_cell_angle_beta                 98.191(4)
_cell_angle_gamma                93.279(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7740(4)
_cell_length_b                   7.9955(4)
_cell_length_c                   12.4836(6)
_cell_measurement_reflns_used    11095
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      1.72
_cell_volume                     732.96(7)
_computing_cell_refinement
;
Recipe in X-AREA (Stoe & Cie, 2022)
;
_computing_data_collection
;
WinXpose in X-AREA (Stoe & Cie, 2022)
;
_computing_data_reduction
;
Integrate and LANA in X-AREA (Stoe & Cie, 2022)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015), PLATON (Spek, 2020) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      250
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11018
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.782
_diffrn_reflns_theta_min         1.724
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS; Spek, 2020)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.393
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0629P)²+0.1103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2742
_reflns_number_total             3090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zo3036sup1.cif
_cod_data_source_block           I
_cod_database_code               2312157
_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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.37640(11) 0.70357(10) 0.74315(6) 0.0478(2) Uani d 1 . .
O O2 0.00186(12) 0.95474(11) 0.15984(8) 0.0533(2) Uani d 1 . .
H H2O 0.031(2) 0.935(2) 0.2219(16) 0.084(6) Uiso d 1 . .
N N1 -0.00350(12) 0.69499(12) 0.25196(8) 0.0417(2) Uani d 1 . .
C C1 0.13306(13) 0.60555(14) 0.40839(9) 0.0361(2) Uani d 1 . .
C C2 0.13789(14) 0.76848(14) 0.48464(9) 0.0402(2) Uani d 1 . .
H H2 0.085081 0.856781 0.459797 0.048 Uiso calc 1 . .
C C3 0.21806(15) 0.80813(14) 0.59750(9) 0.0415(2) Uani d 1 . .
H H3 0.219226 0.921233 0.647190 0.050 Uiso calc 1 . .
C C4 0.29521(13) 0.68039(14) 0.63528(9) 0.0379(2) Uani d 1 . .
C C5 0.37175(15) 0.37629(15) 0.59984(10) 0.0431(3) Uani d 1 . .
H H5 0.423752 0.401751 0.676141 0.052 Uiso calc 1 . .
C C6 0.37224(16) 0.21274(15) 0.52838(11) 0.0478(3) Uani d 1 . .
H H6 0.423091 0.125544 0.555505 0.057 Uiso calc 1 . .
C C7 0.29682(16) 0.17444(14) 0.41423(10) 0.0465(3) Uani d 1 . .
H H7 0.299056 0.061774 0.364824 0.056 Uiso calc 1 . .
C C8 0.22010(14) 0.29895(14) 0.37397(9) 0.0413(2) Uani d 1 . .
H H8 0.170368 0.270557 0.297080 0.050 Uiso calc 1 . .
C C9 0.21401(12) 0.47005(13) 0.44580(8) 0.0349(2) Uani d 1 . .
C C10 0.29405(13) 0.50852(13) 0.56089(9) 0.0360(2) Uani d 1 . .
C C11 0.3970(2) 0.87468(17) 0.81915(11) 0.0625(4) Uani d 1 . .
H H11C 0.463971 0.874752 0.890943 0.094 Uiso calc 1 . .
H H11B 0.283063 0.912636 0.830827 0.094 Uiso calc 1 . .
H H11A 0.458215 0.954118 0.787835 0.094 Uiso calc 1 . .
C C12 0.04229(13) 0.57172(14) 0.29245(9) 0.0387(2) Uani d 1 . .
H H12 0.016817 0.455204 0.246166 0.046 Uiso calc 1 . .
C C13 -0.09569(13) 0.65748(14) 0.14067(9) 0.0383(2) Uani d 1 . .
C C14 -0.18898(14) 0.49935(14) 0.07476(9) 0.0414(3) Uani d 1 . .
H H14 -0.194706 0.404229 0.104854 0.050 Uiso calc 1 . .
C C15 -0.27369(14) 0.47931(15) -0.03449(9) 0.0414(3) Uani d 1 . .
C C16 -0.26515(15) 0.62281(16) -0.07652(9) 0.0447(3) Uani d 1 . .
H H16 -0.322371 0.611432 -0.150197 0.054 Uiso calc 1 . .
C C17 -0.17448(16) 0.78190(15) -0.01252(10) 0.0459(3) Uani d 1 . .
H H17 -0.170458 0.877361 -0.042377 0.055 Uiso calc 1 . .
C C18 -0.09002(14) 0.79882(14) 0.09561(9) 0.0407(2) Uani d 1 . .
C C19 -0.37175(17) 0.30697(16) -0.10504(10) 0.0523(3) Uani d 1 . .
H H19A -0.495364 0.310829 -0.101543 0.078 Uiso calc 1 . .
H H19B -0.329154 0.213780 -0.076131 0.078 Uiso calc 1 . .
H H19C -0.354011 0.285087 -0.182962 0.078 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'
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_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C11 . . 117.78(9) ?
C18 O2 H2O . . 102.0(12) ?
C12 N1 C13 . . 120.69(9) ?
C2 C1 C9 . . 118.94(9) ?
C2 C1 C12 . . 119.73(9) ?
C9 C1 C12 . . 121.31(9) ?
C1 C2 C3 . . 122.66(10) ?
C1 C2 H2 . . 118.7 ?
C3 C2 H2 . . 118.7 ?
C4 C3 C2 . . 119.40(10) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
O1 C4 C3 . . 124.60(10) ?
O1 C4 C10 . . 114.58(9) ?
C3 C4 C10 . . 120.82(9) ?
C6 C5 C10 . . 120.86(10) ?
C6 C5 H5 . . 119.6 ?
C10 C5 H5 . . 119.6 ?
C5 C6 C7 . . 119.88(10) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C8 C7 C6 . . 120.73(10) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C9 . . 121.27(10) ?
C7 C8 H8 . . 119.4 ?
C9 C8 H8 . . 119.4 ?
C8 C9 C10 . . 117.52(9) ?
C8 C9 C1 . . 123.66(9) ?
C10 C9 C1 . . 118.82(9) ?
C5 C10 C9 . . 119.71(10) ?
C5 C10 C4 . . 120.94(10) ?
C9 C10 C4 . . 119.35(9) ?
O1 C11 H11C . . 109.5 ?
O1 C11 H11B . . 109.5 ?
H11C C11 H11B . . 109.5 ?
O1 C11 H11A . . 109.5 ?
H11C C11 H11A . . 109.5 ?
H11B C11 H11A . . 109.5 ?
N1 C12 C1 . . 122.15(10) ?
N1 C12 H12 . . 118.9 ?
C1 C12 H12 . . 118.9 ?
C14 C13 C18 . . 118.84(10) ?
C14 C13 N1 . . 127.09(9) ?
C18 C13 N1 . . 114.07(9) ?
C15 C14 C13 . . 121.35(10) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C16 . . 118.20(10) ?
C14 C15 C19 . . 120.66(10) ?
C16 C15 C19 . . 121.14(10) ?
C17 C16 C15 . . 121.64(10) ?
C17 C16 H16 . . 119.2 ?
C15 C16 H16 . . 119.2 ?
C18 C17 C16 . . 119.29(10) ?
C18 C17 H17 . . 120.4 ?
C16 C17 H17 . . 120.4 ?
O2 C18 C17 . . 120.14(10) ?
O2 C18 C13 . . 119.18(10) ?
C17 C18 C13 . . 120.67(10) ?
C15 C19 H19A . . 109.5 ?
C15 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C15 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.3601(12) ?
O1 C11 . 1.4131(14) ?
O2 C18 . 1.3705(14) ?
O2 H2O . 0.835(18) ?
N1 C12 . 1.2741(14) ?
N1 C13 . 1.4109(13) ?
C1 C2 . 1.3745(15) ?
C1 C9 . 1.4379(14) ?
C1 C12 . 1.4603(14) ?
C2 C3 . 1.3961(15) ?
C2 H2 . 0.9400 ?
C3 C4 . 1.3735(15) ?
C3 H3 . 0.9400 ?
C4 C10 . 1.4238(15) ?
C5 C6 . 1.3599(17) ?
C5 C10 . 1.4137(15) ?
C5 H5 . 0.9400 ?
C6 C7 . 1.4012(16) ?
C6 H6 . 0.9400 ?
C7 C8 . 1.3653(16) ?
C7 H7 . 0.9400 ?
C8 C9 . 1.4161(15) ?
C8 H8 . 0.9400 ?
C9 C10 . 1.4212(14) ?
C11 H11C . 0.9700 ?
C11 H11B . 0.9700 ?
C11 H11A . 0.9700 ?
C12 H12 . 0.9400 ?
C13 C14 . 1.3927(15) ?
C13 C18 . 1.3983(15) ?
C14 C15 . 1.3886(15) ?
C14 H14 . 0.9400 ?
C15 C16 . 1.3917(16) ?
C15 C19 . 1.5031(16) ?
C16 C17 . 1.3845(16) ?
C16 H16 . 0.9400 ?
C17 C18 . 1.3805(15) ?
C17 H17 . 0.9400 ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 H19C . 0.9700 ?
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
O2 H2O N1 . 0.84(2) 2.069(18) 2.6436(13) 126(2) yes
C11 H11B O2 2_576 0.97 2.51 3.4725(19) 170 yes
C19 H19A Cg1 2_465 0.97 2.79 3.7362(14) 165 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 C3 . . . . -0.17(16) ?
C12 C1 C2 C3 . . . . 178.14(9) ?
C1 C2 C3 C4 . . . . -0.26(17) ?
C11 O1 C4 C3 . . . . -6.08(17) ?
C11 O1 C4 C10 . . . . 174.26(11) ?
C2 C3 C4 O1 . . . . -179.75(10) ?
C2 C3 C4 C10 . . . . -0.11(17) ?
C10 C5 C6 C7 . . . . 0.76(18) ?
C5 C6 C7 C8 . . . . -1.01(18) ?
C6 C7 C8 C9 . . . . -0.06(18) ?
C7 C8 C9 C10 . . . . 1.32(16) ?
C7 C8 C9 C1 . . . . -179.17(10) ?
C2 C1 C9 C8 . . . . -178.57(10) ?
C12 C1 C9 C8 . . . . 3.15(16) ?
C2 C1 C9 C10 . . . . 0.94(15) ?
C12 C1 C9 C10 . . . . -177.34(9) ?
C6 C5 C10 C9 . . . . 0.53(17) ?
C6 C5 C10 C4 . . . . -179.26(10) ?
C8 C9 C10 C5 . . . . -1.54(15) ?
C1 C9 C10 C5 . . . . 178.92(9) ?
C8 C9 C10 C4 . . . . 178.25(9) ?
C1 C9 C10 C4 . . . . -1.29(14) ?
O1 C4 C10 C5 . . . . 0.35(15) ?
C3 C4 C10 C5 . . . . -179.33(10) ?
O1 C4 C10 C9 . . . . -179.44(8) ?
C3 C4 C10 C9 . . . . 0.89(16) ?
C13 N1 C12 C1 . . . . -178.08(9) ?
C2 C1 C12 N1 . . . . 14.20(16) ?
C9 C1 C12 N1 . . . . -167.54(10) ?
C12 N1 C13 C14 . . . . 19.32(17) ?
C12 N1 C13 C18 . . . . -161.18(10) ?
C18 C13 C14 C15 . . . . 0.86(16) ?
N1 C13 C14 C15 . . . . -179.66(10) ?
C13 C14 C15 C16 . . . . -0.84(16) ?
C13 C14 C15 C19 . . . . 179.16(10) ?
C14 C15 C16 C17 . . . . 0.33(17) ?
C19 C15 C16 C17 . . . . -179.66(11) ?
C15 C16 C17 C18 . . . . 0.14(18) ?
C16 C17 C18 O2 . . . . 179.35(10) ?
C16 C17 C18 C13 . . . . -0.12(17) ?
C14 C13 C18 O2 . . . . -179.84(10) ?
N1 C13 C18 O2 . . . . 0.61(15) ?
C14 C13 C18 C17 . . . . -0.37(17) ?
N1 C13 C18 C17 . . . . -179.92(10) ?

_cod_database_fobs_code 2312157
