#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223374.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_2223374
loop_
_publ_author_name
'Su, Qing'
'Wu, Qiao-Lin'
'Ye, Ling'
'Mu, Ying'
_publ_section_title
;
 2-[(2,6-Diethylphenyl)iminomethyl]-<i>N</i>-(2-methoxyphenyl)aniline
;
_journal_coeditor_code           FL2258
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2537
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C24 H26 N2 O'
_chemical_formula_moiety         'C24 H26 N2 O'
_chemical_formula_sum            'C24 H26 N2 O'
_chemical_formula_weight         358.47
_chemical_melting_point          ?
_chemical_name_systematic
;
2-[(2,6-Diethylphenyl)iminomethyl]-<i>N</i>-(2-methoxyphenyl)aniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.88(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.930(3)
_cell_length_b                   7.4757(15)
_cell_length_c                   21.303(4)
_cell_measurement_reflns_used    14731
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.16
_cell_volume                     2039.7(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'XP in SHELXTL Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19406
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.170
_refine_ls_extinction_coef       0.0251(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0403
_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/[\s^2^(Fo^2^)+(0.0487P)^2^+0.2475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                3515
_reflns_number_total             4670
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fl2258.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223374
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O1 0.52847(8) 1.56960(13) 0.17089(5) 0.0608(3) Uani d . 1
N N1 0.28321(8) 0.98441(15) 0.08469(5) 0.0460(3) Uani d . 1
N N2 0.12969(8) 0.75355(13) 0.10555(5) 0.0405(2) Uani d . 1
C C1 0.28918(8) 0.88995(15) 0.03007(5) 0.0363(3) Uani d . 1
C C2 0.22193(8) 0.74272(15) 0.01420(5) 0.0367(3) Uani d . 1
C C3 0.22900(9) 0.64858(17) -0.04164(6) 0.0436(3) Uani d . 1
H H3 0.1840 0.5530 -0.0523 0.052 Uiso calc R 1
C C4 0.30038(10) 0.69250(19) -0.08147(6) 0.0507(3) Uani d . 1
H H4 0.3037 0.6282 -0.1185 0.061 Uiso calc R 1
C C5 0.36708(10) 0.83456(19) -0.06505(6) 0.0500(3) Uani d . 1
H H5 0.4164 0.8647 -0.0912 0.060 Uiso calc R 1
C C6 0.36198(9) 0.93198(17) -0.01092(6) 0.0443(3) Uani d . 1
H H6 0.4075 1.0274 -0.0012 0.053 Uiso calc R 1
C C7 0.14318(9) 0.68530(16) 0.05253(5) 0.0390(3) Uani d . 1
H H7 0.0994 0.5918 0.0372 0.047 Uiso calc R 1
C C8 0.04576(9) 0.68824(16) 0.13614(5) 0.0392(3) Uani d . 1
C C9 0.06378(10) 0.54991(16) 0.18027(6) 0.0455(3) Uani d . 1
C C10 -0.01957(12) 0.49231(18) 0.21017(7) 0.0554(4) Uani d . 1
H H10 -0.0096 0.3997 0.2395 0.067 Uiso calc R 1
C C11 -0.11638(12) 0.5703(2) 0.19697(7) 0.0582(4) Uani d . 1
H H11 -0.1714 0.5293 0.2170 0.070 Uiso calc R 1
C C12 -0.13204(10) 0.7088(2) 0.15432(7) 0.0535(4) Uani d . 1
H H12 -0.1978 0.7610 0.1461 0.064 Uiso calc R 1
C C13 -0.05162(9) 0.77272(17) 0.12316(6) 0.0439(3) Uani d . 1
C C14 0.17116(13) 0.4706(2) 0.19727(7) 0.0612(4) Uani d . 1
H H14A 0.2026 0.4539 0.1589 0.073 Uiso calc R 1
H H14B 0.1649 0.3540 0.2164 0.073 Uiso calc R 1
C C15 0.24158(13) 0.5868(3) 0.24255(9) 0.0841(5) Uani d . 1
H H15A 0.2506 0.7006 0.2231 0.126 Uiso calc R 1
H H15B 0.3082 0.5296 0.2528 0.126 Uiso calc R 1
H H15C 0.2107 0.6041 0.2806 0.126 Uiso calc R 1
C C16 -0.06704(11) 0.9317(2) 0.07983(7) 0.0566(4) Uani d . 1
H H16A -0.1412 0.9560 0.0700 0.068 Uiso calc R 1
H H16B -0.0408 0.9033 0.0405 0.068 Uiso calc R 1
C C17 -0.01226(13) 1.0986(2) 0.10827(9) 0.0700(4) Uani d . 1
H H17A -0.0415 1.1328 0.1455 0.105 Uiso calc R 1
H H17B -0.0215 1.1940 0.0779 0.105 Uiso calc R 1
H H17C 0.0609 1.0744 0.1194 0.105 Uiso calc R 1
C C18 0.34258(9) 1.13770(16) 0.10489(6) 0.0398(3) Uani d . 1
C C19 0.39696(10) 1.14282(17) 0.16584(6) 0.0452(3) Uani d . 1
H H19 0.3931 1.0463 0.1929 0.054 Uiso calc R 1
C C20 0.45650(10) 1.28936(18) 0.18645(6) 0.0487(3) Uani d . 1
H H20 0.4920 1.2915 0.2275 0.058 Uiso calc R 1
C C21 0.46397(9) 1.43359(17) 0.14663(6) 0.0434(3) Uani d . 1
C C22 0.40796(10) 1.43273(17) 0.08638(6) 0.0455(3) Uani d . 1
H H22 0.4112 1.5299 0.0595 0.055 Uiso calc R 1
C C23 0.34714(9) 1.28581(17) 0.06663(6) 0.0445(3) Uani d . 1
H H23 0.3083 1.2867 0.0265 0.053 Uiso calc R 1
C C24 0.54257(13) 1.7158(2) 0.13088(9) 0.0701(5) Uani d . 1
H H24A 0.5698 1.6736 0.0938 0.105 Uiso calc R 1
H H24B 0.5908 1.7992 0.1531 0.105 Uiso calc R 1
H H24C 0.4767 1.7739 0.1185 0.105 Uiso calc R 1
H H1 0.2406(11) 0.937(2) 0.1104(7) 0.056(4) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0714(6) 0.0509(6) 0.0578(6) -0.0154(5) 0.0004(5) -0.0115(5)
N1 0.0485(6) 0.0493(6) 0.0423(6) -0.0118(5) 0.0134(5) -0.0073(5)
N2 0.0442(5) 0.0395(5) 0.0387(5) -0.0029(4) 0.0090(4) 0.0020(4)
C1 0.0339(5) 0.0391(6) 0.0354(6) 0.0038(4) 0.0026(4) 0.0005(5)
C2 0.0359(5) 0.0382(6) 0.0355(6) 0.0032(5) 0.0035(5) 0.0024(5)
C3 0.0442(6) 0.0432(7) 0.0432(6) 0.0000(5) 0.0051(5) -0.0054(5)
C4 0.0533(7) 0.0565(8) 0.0442(7) 0.0027(6) 0.0135(6) -0.0108(6)
C5 0.0448(7) 0.0593(8) 0.0491(7) 0.0014(6) 0.0179(6) -0.0019(6)
C6 0.0372(6) 0.0471(7) 0.0498(7) -0.0025(5) 0.0100(5) -0.0018(6)
C7 0.0407(6) 0.0356(6) 0.0403(6) -0.0022(5) 0.0040(5) 0.0010(5)
C8 0.0452(6) 0.0371(6) 0.0364(6) -0.0069(5) 0.0096(5) -0.0048(5)
C9 0.0601(7) 0.0365(6) 0.0422(7) -0.0020(5) 0.0155(6) -0.0023(5)
C10 0.0805(10) 0.0415(7) 0.0488(7) -0.0124(7) 0.0252(7) -0.0025(6)
C11 0.0649(9) 0.0601(9) 0.0549(8) -0.0248(7) 0.0274(7) -0.0164(7)
C12 0.0436(7) 0.0638(9) 0.0543(8) -0.0100(6) 0.0105(6) -0.0166(7)
C13 0.0430(6) 0.0475(7) 0.0403(6) -0.0063(5) 0.0027(5) -0.0077(5)
C14 0.0806(10) 0.0491(8) 0.0576(9) 0.0180(7) 0.0223(8) 0.0147(7)
C15 0.0681(10) 0.0977(14) 0.0828(12) 0.0204(10) -0.0036(9) 0.0036(11)
C16 0.0490(7) 0.0647(9) 0.0534(8) 0.0063(6) -0.0028(6) 0.0061(7)
C17 0.0731(10) 0.0509(9) 0.0823(11) 0.0074(7) -0.0021(8) 0.0104(8)
C18 0.0384(6) 0.0414(6) 0.0404(6) -0.0009(5) 0.0078(5) -0.0056(5)
C19 0.0549(7) 0.0443(7) 0.0369(6) -0.0011(6) 0.0081(5) 0.0005(5)
C20 0.0579(8) 0.0530(8) 0.0338(6) -0.0018(6) 0.0009(5) -0.0055(5)
C21 0.0444(6) 0.0408(7) 0.0447(7) -0.0008(5) 0.0057(5) -0.0096(5)
C22 0.0494(7) 0.0398(7) 0.0467(7) 0.0027(5) 0.0043(5) 0.0024(5)
C23 0.0440(6) 0.0467(7) 0.0404(6) 0.0017(5) -0.0026(5) 0.0000(5)
C24 0.0739(10) 0.0446(8) 0.0899(12) -0.0133(7) 0.0053(9) -0.0044(8)
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
C21 O1 C24 117.94(11)
C1 N1 C18 125.73(10)
C1 N1 H1 115.0(9)
C18 N1 H1 119.1(9)
C7 N2 C8 118.26(10)
N1 C1 C6 122.17(11)
N1 C1 C2 119.91(10)
C6 C1 C2 117.90(10)
C3 C2 C1 119.07(10)
C3 C2 C7 117.53(11)
C1 C2 C7 123.38(10)
C4 C3 C2 122.20(12)
C4 C3 H3 118.9
C2 C3 H3 118.9
C3 C4 C5 118.36(12)
C3 C4 H4 120.8
C5 C4 H4 120.8
C6 C5 C4 121.32(11)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 121.12(12)
C5 C6 H6 119.4
C1 C6 H6 119.4
N2 C7 C2 124.84(11)
N2 C7 H7 117.6
C2 C7 H7 117.6
C9 C8 C13 121.95(11)
C9 C8 N2 119.61(11)
C13 C8 N2 118.34(11)
C10 C9 C8 117.96(12)
C10 C9 C14 120.89(12)
C8 C9 C14 121.10(11)
C11 C10 C9 121.01(13)
C11 C10 H10 119.5
C9 C10 H10 119.5
C12 C11 C10 120.16(12)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 121.45(13)
C11 C12 H12 119.3
C13 C12 H12 119.3
C12 C13 C8 117.43(13)
C12 C13 C16 121.32(12)
C8 C13 C16 121.18(11)
C9 C14 C15 112.50(13)
C9 C14 H14A 109.1
C15 C14 H14A 109.1
C9 C14 H14B 109.1
C15 C14 H14B 109.1
H14A C14 H14B 107.8
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C13 C16 C17 112.94(12)
C13 C16 H16A 109.0
C17 C16 H16A 109.0
C13 C16 H16B 109.0
C17 C16 H16B 109.0
H16A C16 H16B 107.8
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C23 C18 C19 118.18(11)
C23 C18 N1 122.41(11)
C19 C18 N1 119.40(11)
C20 C19 C18 120.62(12)
C20 C19 H19 119.7
C18 C19 H19 119.7
C19 C20 C21 120.54(12)
C19 C20 H20 119.7
C21 C20 H20 119.7
O1 C21 C20 115.93(11)
O1 C21 C22 124.53(12)
C20 C21 C22 119.54(12)
C23 C22 C21 119.29(12)
C23 C22 H22 120.4
C21 C22 H22 120.4
C18 C23 C22 121.73(12)
C18 C23 H23 119.1
C22 C23 H23 119.1
O1 C24 H24A 109.5
O1 C24 H24B 109.5
H24A C24 H24B 109.5
O1 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C21 1.3704(15)
O1 C24 1.4130(18)
N1 C1 1.3723(15)
N1 C18 1.4131(16)
N1 H1 0.902(14)
N2 C7 1.2730(15)
N2 C8 1.4265(15)
C1 C6 1.4045(16)
C1 C2 1.4147(16)
C2 C3 1.3959(16)
C2 C7 1.4545(16)
C3 C4 1.3765(17)
C3 H3 0.9300
C4 C5 1.3824(19)
C4 H4 0.9300
C5 C6 1.3731(18)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.3955(17)
C8 C13 1.4019(17)
C9 C10 1.3932(18)
C9 C14 1.507(2)
C10 C11 1.375(2)
C10 H10 0.9300
C11 C12 1.374(2)
C11 H11 0.9300
C12 C13 1.3925(18)
C12 H12 0.9300
C13 C16 1.5011(19)
C14 C15 1.508(2)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C17 1.519(2)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C23 1.3809(18)
C18 C19 1.3898(18)
C19 C20 1.3758(18)
C19 H19 0.9300
C20 C21 1.3833(19)
C20 H20 0.9300
C21 C22 1.3846(19)
C22 C23 1.3824(18)
C22 H22 0.9300
C23 H23 0.9300
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
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
N1 H1 N2 1_555 0.902(14) 1.976(15) 2.7126(15) 137.8(12) y
C5 H5 Cg2 2_665 0.93 2.793 3.5296(8) 136.856 y
C10 H10 Cg1 3_545 0.93 2.837 3.7651(6) 175.652 y
C16 H16A Cg3 2_575 0.97 2.816 3.6614(7) 146.117 y