#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/99/2239942.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_2239942
loop_
_publ_author_name
'Wu, Liang-Tao'
'Kong, Ming'
'Wu, Jie-Ying'
_publ_section_title
;
 Crystal structure of
 4-ethoxy-N-(4-ethoxyphenyl)-N-phenylaniline
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1077
_journal_paper_doi               10.1107/S160053681401900X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C22 H23 N O2'
_chemical_formula_moiety         'C22 H23 N O2'
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.41
_chemical_name_systematic
;
4-Ethoxy-N-(4-ethoxyphenyl)-N-phenylaniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3634(7)
_cell_length_b                   31.908(3)
_cell_length_c                   8.1372(8)
_cell_measurement_reflns_used    2593
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      2.5
_cell_volume                     1822.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega'
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13155
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.077
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.0295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2288
_reflns_number_total             3274
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5812sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2239942
_cod_database_fobs_code          2239942
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.56747(19) 0.12535(4) 0.45337(16) 0.0565(4) Uani d . 1 1
O O1 0.53889(15) 0.25318(3) -0.02262(14) 0.0552(3) Uani d . 1 1
O O2 -0.07739(15) 0.02297(3) 0.28521(16) 0.0634(3) Uani d . 1 1
C C1 0.5355(2) 0.28483(5) -0.2863(2) 0.0621(5) Uani d . 1 1
H H1A 0.4353 0.3026 -0.2738 0.093 Uiso calc R 1 1
H H1B 0.5177 0.2798 -0.4064 0.093 Uiso calc R 1 1
H H1C 0.6563 0.2982 -0.2358 0.093 Uiso calc R 1 1
C C2 0.5312(2) 0.24385(5) -0.1966(2) 0.0543(4) Uani d . 1 1
H H2A 0.4153 0.2287 -0.2540 0.065 Uiso calc R 1 1
H H2B 0.6393 0.2267 -0.1985 0.065 Uiso calc R 1 1
C C3 0.5385(2) 0.22017(5) 0.08506(19) 0.0441(4) Uani d . 1 1
C C4 0.5504(2) 0.23063(5) 0.2528(2) 0.0510(4) Uani d . 1 1
H H4 0.5517 0.2587 0.2843 0.061 Uiso calc R 1 1
C C5 0.5603(2) 0.19973(5) 0.3734(2) 0.0530(4) Uani d . 1 1
H H5 0.5684 0.2072 0.4859 0.064 Uiso calc R 1 1
C C6 0.5319(2) 0.17841(5) 0.0390(2) 0.0513(4) Uani d . 1 1
H H6 0.5204 0.1709 -0.0741 0.062 Uiso calc R 1 1
C C7 0.5424(2) 0.14783(5) 0.1615(2) 0.0522(4) Uani d . 1 1
H H7 0.5385 0.1198 0.1295 0.063 Uiso calc R 1 1
C C8 0.5585(2) 0.15785(5) 0.33024(19) 0.0458(4) Uani d . 1 1
C C9 -0.2755(3) -0.03507(6) 0.1792(3) 0.0809(6) Uani d . 1 1
H H9A -0.3214 -0.0332 0.2775 0.121 Uiso calc R 1 1
H H9B -0.2783 -0.0638 0.1429 0.121 Uiso calc R 1 1
H H9C -0.3551 -0.0185 0.0869 0.121 Uiso calc R 1 1
C C10 -0.0747(2) -0.01898(5) 0.2265(2) 0.0628(5) Uani d . 1 1
H H10A 0.0083 -0.0362 0.3167 0.075 Uiso calc R 1 1
H H10B -0.0282 -0.0197 0.1270 0.075 Uiso calc R 1 1
C C11 0.0897(2) 0.04537(5) 0.32911(19) 0.0494(4) Uani d . 1 1
C C12 0.2629(2) 0.03055(5) 0.3206(2) 0.0575(4) Uani d . 1 1
H H12 0.2738 0.0031 0.2863 0.069 Uiso calc R 1 1
C C13 0.4208(2) 0.05683(5) 0.3634(2) 0.0591(5) Uani d . 1 1
H H13 0.5368 0.0470 0.3559 0.071 Uiso calc R 1 1
C C14 0.0770(2) 0.08574(5) 0.3849(2) 0.0542(4) Uani d . 1 1
H H14 -0.0388 0.0957 0.3926 0.065 Uiso calc R 1 1
C C15 0.2339(2) 0.11136(5) 0.4291(2) 0.0541(4) Uani d . 1 1
H H15 0.2238 0.1384 0.4678 0.065 Uiso calc R 1 1
C C16 0.4072(2) 0.09730(5) 0.41669(19) 0.0494(4) Uani d . 1 1
C C17 0.7052(2) 0.12510(5) 0.61526(19) 0.0462(4) Uani d . 1 1
C C18 0.8721(2) 0.14857(5) 0.6470(2) 0.0536(4) Uani d . 1 1
H H18 0.8907 0.1656 0.5608 0.064 Uiso calc R 1 1
C C19 1.0098(2) 0.14661(5) 0.8058(2) 0.0628(5) Uani d . 1 1
H H19 1.1204 0.1624 0.8248 0.075 Uiso calc R 1 1
C C20 0.6829(2) 0.10018(5) 0.7488(2) 0.0549(4) Uani d . 1 1
H H20 0.5727 0.0843 0.7314 0.066 Uiso calc R 1 1
C C21 0.8226(3) 0.09876(6) 0.9064(2) 0.0637(5) Uani d . 1 1
H H21 0.8052 0.0819 0.9937 0.076 Uiso calc R 1 1
C C22 0.9866(3) 0.12182(6) 0.9362(2) 0.0674(5) Uani d . 1 1
H H22 1.0802 0.1207 1.0426 0.081 Uiso calc R 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'
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
C17 N1 C8 122.07(12)
C17 N1 C16 120.50(12)
C8 N1 C16 116.40(12)
C3 O1 C2 117.76(12)
C11 O2 C10 118.31(12)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C1 107.40(13)
O1 C2 H2A 110.2
C1 C2 H2A 110.2
O1 C2 H2B 110.2
C1 C2 H2B 110.2
H2A C2 H2B 108.5
O1 C3 C6 125.08(13)
O1 C3 C4 115.74(13)
C6 C3 C4 119.16(14)
C5 C4 C3 120.33(15)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C8 121.12(14)
C4 C5 H5 119.4
C8 C5 H5 119.4
C7 C6 C3 119.78(14)
C7 C6 H6 120.1
C3 C6 H6 120.1
C8 C7 C6 121.61(14)
C8 C7 H7 119.2
C6 C7 H7 119.2
C7 C8 C5 117.96(14)
C7 C8 N1 120.09(14)
C5 C8 N1 121.92(14)
C10 C9 H9A 109.5
C10 C9 H9B 109.5
H9A C9 H9B 109.5
C10 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O2 C10 C9 107.15(14)
O2 C10 H10A 110.3
C9 C10 H10A 110.3
O2 C10 H10B 110.3
C9 C10 H10B 110.3
H10A C10 H10B 108.5
O2 C11 C14 115.30(14)
O2 C11 C12 125.23(14)
C14 C11 C12 119.48(14)
C11 C12 C13 119.72(15)
C11 C12 H12 120.1
C13 C12 H12 120.1
C16 C13 C12 120.71(15)
C16 C13 H13 119.6
C12 C13 H13 119.6
C15 C14 C11 120.51(15)
C15 C14 H14 119.7
C11 C14 H14 119.7
C14 C15 C16 120.63(15)
C14 C15 H15 119.7
C16 C15 H15 119.7
C13 C16 C15 118.91(14)
C13 C16 N1 121.09(15)
C15 C16 N1 119.96(14)
C18 C17 C20 117.78(14)
C18 C17 N1 121.23(14)
C20 C17 N1 120.95(14)
C19 C18 C17 120.33(16)
C19 C18 H18 119.8
C17 C18 H18 119.8
C22 C19 C18 121.37(17)
C22 C19 H19 119.3
C18 C19 H19 119.3
C21 C20 C17 120.81(16)
C21 C20 H20 119.6
C17 C20 H20 119.6
C22 C21 C20 121.00(17)
C22 C21 H21 119.5
C20 C21 H21 119.5
C21 C22 C19 118.70(16)
C21 C22 H22 120.6
C19 C22 H22 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C17 1.3985(19)
N1 C8 1.4296(18)
N1 C16 1.4384(18)
O1 C3 1.3705(17)
O1 C2 1.4312(18)
O2 C11 1.3736(17)
O2 C10 1.4237(19)
C1 C2 1.502(2)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 H2A 0.9700
C2 H2B 0.9700
C3 C6 1.381(2)
C3 C4 1.382(2)
C4 C5 1.378(2)
C4 H4 0.9300
C5 C8 1.381(2)
C5 H5 0.9300
C6 C7 1.380(2)
C6 H6 0.9300
C7 C8 1.379(2)
C7 H7 0.9300
C9 C10 1.501(2)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9700
C10 H10B 0.9700
C11 C14 1.378(2)
C11 C12 1.382(2)
C12 C13 1.389(2)
C12 H12 0.9300
C13 C16 1.376(2)
C13 H13 0.9300
C14 C15 1.372(2)
C14 H14 0.9300
C15 C16 1.385(2)
C15 H15 0.9300
C17 C18 1.395(2)
C17 C20 1.395(2)
C18 C19 1.382(2)
C18 H18 0.9300
C19 C22 1.375(2)
C19 H19 0.9300
C20 C21 1.381(2)
C20 H20 0.9300
C21 C22 1.372(2)
C21 H21 0.9300
C22 H22 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
C1 H1A Cg1 4_565 0.96 2.83 3.6763(17) 148
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 18996804
