##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     'SHELXL-2018/3'
_chemical_name_systematic
;
(E)-N,N-Diethyl-4-{[(4-methoxyphenyl)imino]methyl}aniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H22 N2 O'
_chemical_formula_sum     'C18 H22 N2 O'
_chemical_formula_iupac     'C18 H22 N2 O'
_chemical_formula_weight     282.37
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.3830(7)
_cell_length_b     9.2872(7)
_cell_length_c     11.2981(9)
_cell_angle_alpha     78.991(6)
_cell_angle_beta     71.009(6)
_cell_angle_gamma     74.174(6)
_cell_volume     795.14(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8317
_cell_measurement_theta_min     1.92
_cell_measurement_theta_max     26.62
_cell_measurement_temperature     250(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.680
_exptl_crystal_size_mid     0.470
_exptl_crystal_size_min     0.280
_exptl_crystal_density_diffrn     1.179
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     304
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    13 -15 -13 0.0669
    8 25 30 0.0438
    -9 -6 -10 0.0756
    -30 0 7 0.6901
_exptl_absorpt_coefficient_mu     0.074
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
[X-RED32 (Stoe & Cie, 2018) and
X-AREA LANA (Stoe & Cie, 2018)]
;
_exptl_absorpt_correction_T_min     0.6971
_exptl_absorpt_correction_T_max     0.9894
_diffrn_ambient_temperature     250(2)
_diffrn_source     'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_power     2.000
_diffrn_source_voltage     50
_diffrn_source_current     40
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'STOE IPDS II'
_diffrn_measurement_device     '2-circle diffractometer'
_diffrn_measurement_method     'rotation method, ω scans'
_diffrn_detector     'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     11520
_diffrn_reflns_av_R_equivalents     0.0303
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_theta_min     1.918
_diffrn_reflns_theta_max     26.240
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     3183
_reflns_number_gt     2453
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0496
_refine_ls_R_factor_gt     0.0352
_refine_ls_wR_factor_gt     0.0924
_refine_ls_wR_factor_ref     0.0999
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     3183
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0477P)²+0.0760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.113
_refine_diff_density_min     -0.104
_refine_ls_extinction_method
;
(SHELXL2018; Sheldrick, 2015b)
;
_refine_ls_extinction_coef     0.060(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2018)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2018)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2018) and X-AREA LANA (Stoe & Cie, 2018)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2020) and
publCIF (Westrip, 2010)
;
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 0.90654(10) 0.86089(9) 0.06035(8) 0.0546(2) Uani d 1 . .
    N N1 0.34566(12) 0.58694(11) 0.23619(9) 0.0508(3) Uani d 1 . .
    N N2 -0.20580(13) 0.16536(11) 0.38486(9) 0.0527(3) Uani d 1 . .
    C C1 0.77767(14) 0.78348(12) 0.10357(10) 0.0454(3) Uani d 1 . .
    C C2 0.61011(15) 0.87089(12) 0.12118(11) 0.0502(3) Uani d 1 . .
    H H2 0.591811 0.976243 0.103921 0.060 Uiso calc 1 . .
    C C3 0.47095(15) 0.80443(13) 0.16366(11) 0.0513(3) Uani d 1 . .
    H H3 0.358218 0.865153 0.176449 0.062 Uiso calc 1 . .
    C C4 0.49434(14) 0.64815(12) 0.18812(10) 0.0462(3) Uani d 1 . .
    C C5 0.66201(14) 0.56221(12) 0.17208(11) 0.0490(3) Uani d 1 . .
    H H5 0.680241 0.456927 0.190073 0.059 Uiso calc 1 . .
    C C6 0.80332(14) 0.62806(12) 0.13011(11) 0.0486(3) Uani d 1 . .
    H H6 0.915970 0.567772 0.119672 0.058 Uiso calc 1 . .
    C C7 0.34757(14) 0.46457(13) 0.19969(10) 0.0491(3) Uani d 1 . .
    H H7 0.446601 0.421105 0.138215 0.059 Uiso calc 1 . .
    C C8 0.20522(14) 0.38883(12) 0.24788(10) 0.0459(3) Uani d 1 . .
    C C9 0.05732(14) 0.43984(12) 0.34505(10) 0.0470(3) Uani d 1 . .
    H H9 0.049892 0.525924 0.380601 0.056 Uiso calc 1 . .
    C C10 -0.07673(14) 0.36818(12) 0.38981(11) 0.0474(3) Uani d 1 . .
    H H10 -0.173924 0.406192 0.455066 0.057 Uiso calc 1 . .
    C C11 -0.07201(14) 0.23796(12) 0.33985(10) 0.0445(3) Uani d 1 . .
    C C12 0.07565(15) 0.18844(13) 0.24069(11) 0.0519(3) Uani d 1 . .
    H H12 0.083149 0.103674 0.203407 0.062 Uiso calc 1 . .
    C C13 0.20913(15) 0.26207(13) 0.19749(11) 0.0520(3) Uani d 1 . .
    H H13 0.306292 0.225458 0.131648 0.062 Uiso calc 1 . .
    C C14 1.07994(16) 0.77581(15) 0.04265(14) 0.0675(4) Uani d 1 . .
    H H14A 1.106339 0.705115 -0.017850 0.101 Uiso calc 1 . .
    H H14B 1.093169 0.721030 0.122330 0.101 Uiso calc 1 . .
    H H14C 1.158592 0.843244 0.011381 0.101 Uiso calc 1 . .
    C C15 -0.20452(17) 0.03482(13) 0.33003(12) 0.0570(3) Uani d 1 . .
    H H15A -0.153911 0.050389 0.238532 0.068 Uiso calc 1 . .
    H H15B -0.324234 0.027042 0.346349 0.068 Uiso calc 1 . .
    C C16 -0.1037(2) -0.11202(15) 0.38128(16) 0.0778(4) Uani d 1 . .
    H H16A -0.152434 -0.128065 0.471944 0.117 Uiso calc 1 . .
    H H16B 0.016571 -0.107421 0.361391 0.117 Uiso calc 1 . .
    H H16C -0.110656 -0.194522 0.343312 0.117 Uiso calc 1 . .
    C C17 -0.34025(16) 0.19415(14) 0.50416(11) 0.0563(3) Uani d 1 . .
    H H17A -0.297730 0.241588 0.554642 0.068 Uiso calc 1 . .
    H H17B -0.362182 0.097789 0.551020 0.068 Uiso calc 1 . .
    C C18 -0.50769(18) 0.29363(18) 0.48748(15) 0.0770(4) Uani d 1 . .
    H H18A -0.551352 0.247013 0.438293 0.115 Uiso calc 1 . .
    H H18B -0.488023 0.390729 0.443997 0.115 Uiso calc 1 . .
    H H18C -0.591789 0.307371 0.569374 0.115 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 . 1.3669(13) ?
    O1 C14 . 1.4220(14) ?
    N1 C7 . 1.2754(15) ?
    N1 C4 . 1.4140(14) ?
    N2 C11 . 1.3716(14) ?
    N2 C15 . 1.4592(14) ?
    N2 C17 . 1.4639(15) ?
    C1 C6 . 1.3882(16) ?
    C1 C2 . 1.3891(15) ?
    C2 C3 . 1.3739(16) ?
    C2 H2 . 0.9400 ?
    C3 C4 . 1.3958(16) ?
    C3 H3 . 0.9400 ?
    C4 C5 . 1.3868(15) ?
    C5 C6 . 1.3859(15) ?
    C5 H5 . 0.9400 ?
    C6 H6 . 0.9400 ?
    C7 C8 . 1.4505(16) ?
    C7 H7 . 0.9400 ?
    C8 C13 . 1.3907(15) ?
    C8 C9 . 1.3997(15) ?
    C9 C10 . 1.3678(15) ?
    C9 H9 . 0.9400 ?
    C10 C11 . 1.4153(15) ?
    C10 H10 . 0.9400 ?
    C11 C12 . 1.4081(16) ?
    C12 C13 . 1.3756(16) ?
    C12 H12 . 0.9400 ?
    C13 H13 . 0.9400 ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C14 H14C . 0.9700 ?
    C15 C16 . 1.5158(19) ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C16 H16C . 0.9700 ?
    C17 C18 . 1.5025(19) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C18 H18C . 0.9700 ?
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
    C1 O1 C14 . . 117.48(9) ?
    C7 N1 C4 . . 119.31(10) ?
    C11 N2 C15 . . 121.61(9) ?
    C11 N2 C17 . . 122.15(9) ?
    C15 N2 C17 . . 115.20(9) ?
    O1 C1 C6 . . 124.99(10) ?
    O1 C1 C2 . . 115.67(9) ?
    C6 C1 C2 . . 119.35(10) ?
    C3 C2 C1 . . 120.45(10) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 121.04(10) ?
    C2 C3 H3 . . 119.5 ?
    C4 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 117.97(10) ?
    C5 C4 N1 . . 123.58(10) ?
    C3 C4 N1 . . 118.30(10) ?
    C6 C5 C4 . . 121.49(10) ?
    C6 C5 H5 . . 119.3 ?
    C4 C5 H5 . . 119.3 ?
    C5 C6 C1 . . 119.68(10) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 H6 . . 120.2 ?
    N1 C7 C8 . . 123.56(11) ?
    N1 C7 H7 . . 118.2 ?
    C8 C7 H7 . . 118.2 ?
    C13 C8 C9 . . 116.81(10) ?
    C13 C8 C7 . . 120.93(10) ?
    C9 C8 C7 . . 122.25(10) ?
    C10 C9 C8 . . 121.97(10) ?
    C10 C9 H9 . . 119.0 ?
    C8 C9 H9 . . 119.0 ?
    C9 C10 C11 . . 121.32(10) ?
    C9 C10 H10 . . 119.3 ?
    C11 C10 H10 . . 119.3 ?
    N2 C11 C12 . . 121.94(10) ?
    N2 C11 C10 . . 121.51(10) ?
    C12 C11 C10 . . 116.55(10) ?
    C13 C12 C11 . . 121.08(10) ?
    C13 C12 H12 . . 119.5 ?
    C11 C12 H12 . . 119.5 ?
    C12 C13 C8 . . 122.25(10) ?
    C12 C13 H13 . . 118.9 ?
    C8 C13 H13 . . 118.9 ?
    O1 C14 H14A . . 109.5 ?
    O1 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O1 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    N2 C15 C16 . . 113.41(11) ?
    N2 C15 H15A . . 108.9 ?
    C16 C15 H15A . . 108.9 ?
    N2 C15 H15B . . 108.9 ?
    C16 C15 H15B . . 108.9 ?
    H15A C15 H15B . . 107.7 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    N2 C17 C18 . . 113.31(11) ?
    N2 C17 H17A . . 108.9 ?
    C18 C17 H17A . . 108.9 ?
    N2 C17 H17B . . 108.9 ?
    C18 C17 H17B . . 108.9 ?
    H17A C17 H17B . . 107.7 ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C14 O1 C1 C6 . . . . -0.78(16) ?
    C14 O1 C1 C2 . . . . 179.17(10) ?
    O1 C1 C2 C3 . . . . 179.63(10) ?
    C6 C1 C2 C3 . . . . -0.42(16) ?
    C1 C2 C3 C4 . . . . -1.05(17) ?
    C2 C3 C4 C5 . . . . 2.01(17) ?
    C2 C3 C4 N1 . . . . 177.64(10) ?
    C7 N1 C4 C5 . . . . -41.89(16) ?
    C7 N1 C4 C3 . . . . 142.74(11) ?
    C3 C4 C5 C6 . . . . -1.56(17) ?
    N1 C4 C5 C6 . . . . -176.95(10) ?
    C4 C5 C6 C1 . . . . 0.15(17) ?
    O1 C1 C6 C5 . . . . -179.19(10) ?
    C2 C1 C6 C5 . . . . 0.86(16) ?
    C4 N1 C7 C8 . . . . 176.85(10) ?
    N1 C7 C8 C13 . . . . 174.93(11) ?
    N1 C7 C8 C9 . . . . -4.12(17) ?
    C13 C8 C9 C10 . . . . 0.70(16) ?
    C7 C8 C9 C10 . . . . 179.79(10) ?
    C8 C9 C10 C11 . . . . 0.15(17) ?
    C15 N2 C11 C12 . . . . -1.67(16) ?
    C17 N2 C11 C12 . . . . 166.16(11) ?
    C15 N2 C11 C10 . . . . 177.40(10) ?
    C17 N2 C11 C10 . . . . -14.76(16) ?
    C9 C10 C11 N2 . . . . 179.70(10) ?
    C9 C10 C11 C12 . . . . -1.18(16) ?
    N2 C11 C12 C13 . . . . -179.49(10) ?
    C10 C11 C12 C13 . . . . 1.38(17) ?
    C11 C12 C13 C8 . . . . -0.58(18) ?
    C9 C8 C13 C12 . . . . -0.49(17) ?
    C7 C8 C13 C12 . . . . -179.59(11) ?
    C11 N2 C15 C16 . . . . 83.50(15) ?
    C17 N2 C15 C16 . . . . -85.13(14) ?
    C11 N2 C17 C18 . . . . 102.52(13) ?
    C15 N2 C17 C18 . . . . -88.92(13) ?
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
    C13 H13 Cg1 2_665 0.94 2.98 3.6590(10)
                                         130
_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.
;
_shelx_estimated_absorpt_T_min     0.952
_shelx_estimated_absorpt_T_max     0.980
data_Global
_journal_date_recd_electronic     2024-01-03
_journal_date_accepted     2024-01-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2024
_journal_volume     80
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989024000574
_journal_coeditor_code     HB8091
_publ_contact_author_name     'Helen Stoeckli-Evans'
_publ_contact_author_address
;
Institute of Physics
University of Neuchâtel
Rue Emile-Argand 11
CH-2000 Neuchâtel
Switzerland
;
_publ_contact_author_email     helen.stoeckli-evans@unine.ch
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
(E)-N,N-Diethyl-4-{[(4-methoxyphenyl)imino]methyl}aniline:
crystal structure, Hirshfeld surface analysis and energy framework
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Subashini, A.'
;
PG and Research Department of Physics
Srimad Andavan Arts and Science College (Autonomous)
Affiliated to Bharathidasan University
Tiruchirappalli 620005
Tamilnadu
India
;
    'Kumaravel, R.'
;
Department of Physics
Annapoorana Engineering College (Autonomous)
Salem 636308
Tamilnadu
India
;
    'Tharmalingam, B.'
;
Department of Chemistry
Bharathiyar University
Coimbatore 600 046
Tamilnadu
India
;
    'Ramamurthi, K.'
;
Crystal Growth and Thin Film Laboratory
Department of Physics
Bharathidasan University
Tiruchirappalli 620024, Tamilnadu
India
;
    "Crochet, Aurélien"
;
Chemistry Department
University of Fribourg
Chemin du Musee 9
CH-1700 Fribourg
Switzerland
;
    'Stoeckli-Evans, Helen'
;
Institute of Physics
University of Neuchâtel
Rue Emile-Argand 11
CH-2000 Neuchâtel
Switzerland
;
_publ_section_synopsis
;
In the title compound, a benzylideneaniline Schiff base, the
p-substituted aromatic rings subtend a dihedral angle of 46.01(6)°.
;
