#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222438.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_2222438
loop_
_publ_author_name
'Fan, Rui-Qing'
'Ding, Xiao-Dong'
'Zhou, Guang-Peng'
'Yang, Yu-Lin'
_publ_section_title
;
 2,6-Bis[1-(2-methylphenylimino)ethyl]pyridine
;
_journal_coeditor_code           RZ2329
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1480
_journal_paper_doi               10.1107/S1600536809020522
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C23 H23 N3'
_chemical_formula_sum            'C23 H23 N3'
_chemical_formula_weight         341.44
_chemical_name_systematic
;
2,6-bis[1-(2-methylphenylimino)ethyl]pyridine
;
_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                 115.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.966(3)
_cell_length_b                   11.304(2)
_cell_length_c                   14.767(3)
_cell_measurement_reflns_used    18526
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.06
_cell_volume                     1951.6(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18526
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0510
_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)+(0.0848P)²+0.0410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1570
_reflns_number_gt                2804
_reflns_number_total             4435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rz2329.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222438
_cod_database_fobs_code          2222438
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_disorder_assembly
_atom_site_disorder_group
N N2 0.27847(10) 0.74889(10) 0.16139(9) 0.0458(3) Uani d . 1 . .
N N1 -0.01920(11) 0.79913(11) 0.03667(10) 0.0527(3) Uani d . 1 . .
C C6 0.37804(12) 0.80381(12) 0.18433(11) 0.0448(4) Uani d . 1 . .
N N3 0.57761(11) 0.77842(11) 0.25205(11) 0.0565(4) Uani d . 1 . .
C C2 0.18145(13) 0.80916(12) 0.10943(11) 0.0457(4) Uani d . 1 . .
C C1 0.07290(13) 0.74430(12) 0.08606(11) 0.0476(4) Uani d . 1 . .
C C7 0.48407(13) 0.73369(12) 0.24317(11) 0.0466(4) Uani d . 1 . .
C C3 0.18154(13) 0.92576(13) 0.08007(12) 0.0524(4) Uani d . 1 . .
H H3B 0.1130 0.9656 0.0444 0.063 Uiso calc R 1 . .
C C5 0.38449(14) 0.92051(13) 0.15758(13) 0.0543(4) Uani d . 1 . .
H H5A 0.4550 0.9567 0.1751 0.065 Uiso calc R 1 . .
C C10 -0.12858(13) 0.74706(12) 0.00704(12) 0.0489(4) Uani d . 1 . .
C C17 0.68397(13) 0.72253(14) 0.30780(13) 0.0523(4) Uani d . 1 . .
C C15 -0.18677(13) 0.75912(12) 0.06699(12) 0.0522(4) Uani d . 1 . .
C C4 0.28403(14) 0.98142(13) 0.10444(13) 0.0586(4) Uani d . 1 . .
H H4A 0.2858 1.0595 0.0853 0.070 Uiso calc R 1 . .
C C14 -0.29933(15) 0.72146(15) 0.02802(15) 0.0620(5) Uani d . 1 . .
H H14A -0.3395 0.7298 0.0668 0.074 Uiso calc R 1 . .
C C22 0.71360(14) 0.61751(15) 0.27656(14) 0.0633(5) Uani d . 1 . .
H H22A 0.6602 0.5788 0.2202 0.076 Uiso calc R 1 . .
C C9 0.47073(15) 0.62046(14) 0.28932(15) 0.0633(5) Uani d . 1 . .
H H9A 0.5443 0.5840 0.3248 0.095 Uiso calc R 1 . .
H H9B 0.4213 0.5681 0.2375 0.095 Uiso calc R 1 . .
H H9C 0.4381 0.6366 0.3353 0.095 Uiso calc R 1 . .
C C18 0.76376(15) 0.78082(15) 0.39198(13) 0.0579(4) Uani d . 1 . .
C C8 0.08130(16) 0.61968(15) 0.12366(17) 0.0764(6) Uani d . 1 . .
H H8A 0.0058 0.5882 0.1037 0.115 Uiso calc R 1 . .
H H8B 0.1217 0.6191 0.1956 0.115 Uiso calc R 1 . .
H H8C 0.1217 0.5721 0.0958 0.115 Uiso calc R 1 . .
C C13 -0.35352(16) 0.67238(16) -0.06562(16) 0.0697(5) Uani d . 1 . .
H H13A -0.4295 0.6487 -0.0902 0.084 Uiso calc R 1 . .
C C11 -0.18236(16) 0.69527(15) -0.08650(14) 0.0634(5) Uani d . 1 . .
H H11A -0.1426 0.6850 -0.1254 0.076 Uiso calc R 1 . .
C C20 0.90039(16) 0.62620(19) 0.41061(16) 0.0742(6) Uani d . 1 . .
H H20A 0.9733 0.5946 0.4454 0.089 Uiso calc R 1 . .
C C12 -0.29465(17) 0.65852(17) -0.12285(15) 0.0721(5) Uani d . 1 . .
H H12A -0.3304 0.6243 -0.1862 0.087 Uiso calc R 1 . .
C C19 0.87169(16) 0.72988(18) 0.44214(14) 0.0708(5) Uani d . 1 . .
H H19A 0.9259 0.7674 0.4988 0.085 Uiso calc R 1 . .
C C16 -0.12855(18) 0.81252(18) 0.17075(15) 0.0768(6) Uani d . 1 . .
H H16A -0.1809 0.8138 0.2009 0.115 Uiso calc R 1 . .
H H16B -0.1049 0.8918 0.1659 0.115 Uiso calc R 1 . .
H H16C -0.0629 0.7659 0.2114 0.115 Uiso calc R 1 . .
C C21 0.82176(17) 0.56955(18) 0.32815(17) 0.0744(5) Uani d . 1 . .
H H21A 0.8407 0.4990 0.3066 0.089 Uiso calc R 1 . .
C C23 0.7334(2) 0.89394(18) 0.42839(17) 0.0874(6) Uani d . 1 . .
H H23A 0.6561 0.9154 0.3847 0.131 Uiso calc R 1 . .
H H23B 0.7842 0.9558 0.4283 0.131 Uiso calc R 1 . .
H H23C 0.7407 0.8829 0.4953 0.131 Uiso calc R 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'
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
C6 N2 C2 . . 118.22(12) ?
C1 N1 C10 . . 123.03(12) ?
N2 C6 C5 . . 122.59(13) ?
N2 C6 C7 . . 116.43(12) ?
C5 C6 C7 . . 120.96(13) ?
C7 N3 C17 . . 122.08(13) ?
N2 C2 C3 . . 122.25(14) ?
N2 C2 C1 . . 116.17(12) ?
C3 C2 C1 . . 121.58(13) ?
N1 C1 C2 . . 117.13(13) ?
N1 C1 C8 . . 125.07(14) ?
C2 C1 C8 . . 117.79(13) ?
N3 C7 C9 . . 126.06(14) ?
N3 C7 C6 . . 116.53(13) ?
C9 C7 C6 . . 117.37(13) ?
C4 C3 C2 . . 119.07(14) ?
C4 C3 H3B . . 120.5 ?
C2 C3 H3B . . 120.5 ?
C4 C5 C6 . . 118.51(14) ?
C4 C5 H5A . . 120.7 ?
C6 C5 H5A . . 120.7 ?
C11 C10 C15 . . 119.90(15) ?
C11 C10 N1 . . 119.33(16) ?
C15 C10 N1 . . 120.41(15) ?
C22 C17 C18 . . 119.76(15) ?
C22 C17 N3 . . 121.99(15) ?
C18 C17 N3 . . 118.04(15) ?
C14 C15 C10 . . 117.91(16) ?
C14 C15 C16 . . 121.28(17) ?
C10 C15 C16 . . 120.81(15) ?
C3 C4 C5 . . 119.35(14) ?
C3 C4 H4A . . 120.3 ?
C5 C4 H4A . . 120.3 ?
C13 C14 C15 . . 122.21(18) ?
C13 C14 H14A . . 118.9 ?
C15 C14 H14A . . 118.9 ?
C21 C22 C17 . . 120.83(17) ?
C21 C22 H22A . . 119.6 ?
C17 C22 H22A . . 119.6 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C17 C18 C19 . . 117.84(17) ?
C17 C18 C23 . . 120.89(17) ?
C19 C18 C23 . . 121.26(18) ?
C1 C8 H8A . . 109.5 ?
C1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C14 C13 C12 . . 119.32(17) ?
C14 C13 H13A . . 120.3 ?
C12 C13 H13A . . 120.3 ?
C10 C11 C12 . . 120.57(19) ?
C10 C11 H11A . . 119.7 ?
C12 C11 H11A . . 119.7 ?
C21 C20 C19 . . 119.81(17) ?
C21 C20 H20A . . 120.1 ?
C19 C20 H20A . . 120.1 ?
C13 C12 C11 . . 120.05(18) ?
C13 C12 H12A . . 120.0 ?
C11 C12 H12A . . 120.0 ?
C20 C19 C18 . . 122.03(18) ?
C20 C19 H19A . . 119.0 ?
C18 C19 H19A . . 119.0 ?
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 ?
C20 C21 C22 . . 119.73(18) ?
C20 C21 H21A . . 120.1 ?
C22 C21 H21A . . 120.1 ?
C18 C23 H23A . . 109.5 ?
C18 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C18 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 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
N2 C6 . 1.3374(18) ?
N2 C2 . 1.3420(18) ?
N1 C1 . 1.2606(18) ?
N1 C10 . 1.4187(19) ?
C6 C5 . 1.390(2) ?
C6 C7 . 1.497(2) ?
N3 C7 . 1.2674(19) ?
N3 C17 . 1.413(2) ?
C2 C3 . 1.388(2) ?
C2 C1 . 1.489(2) ?
C1 C8 . 1.501(2) ?
C7 C9 . 1.495(2) ?
C3 C4 . 1.370(2) ?
C3 H3B . 0.9300 ?
C5 C4 . 1.379(2) ?
C5 H5A . 0.9300 ?
C10 C11 . 1.380(2) ?
C10 C15 . 1.396(2) ?
C17 C22 . 1.387(2) ?
C17 C18 . 1.392(2) ?
C15 C14 . 1.384(2) ?
C15 C16 . 1.511(3) ?
C4 H4A . 0.9300 ?
C14 C13 . 1.369(3) ?
C14 H14A . 0.9300 ?
C22 C21 . 1.385(2) ?
C22 H22A . 0.9300 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C18 C19 . 1.394(3) ?
C18 C23 . 1.504(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C13 C12 . 1.371(3) ?
C13 H13A . 0.9300 ?
C11 C12 . 1.380(3) ?
C11 H11A . 0.9300 ?
C20 C21 . 1.363(3) ?
C20 C19 . 1.371(3) ?
C20 H20A . 0.9300 ?
C12 H12A . 0.9300 ?
C19 H19A . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C21 H21A . 0.9300 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
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
C2 N2 C6 C5 . . . . 0.8(2) ?
C2 N2 C6 C7 . . . . 179.43(13) ?
C6 N2 C2 C3 . . . . -0.6(2) ?
C6 N2 C2 C1 . . . . -179.79(13) ?
C10 N1 C1 C2 . . . . 178.32(14) ?
C10 N1 C1 C8 . . . . -2.3(3) ?
N2 C2 C1 N1 . . . . -179.50(14) ?
C3 C2 C1 N1 . . . . 1.3(2) ?
N2 C2 C1 C8 . . . . 1.0(2) ?
C3 C2 C1 C8 . . . . -178.12(16) ?
C17 N3 C7 C9 . . . . 1.0(3) ?
C17 N3 C7 C6 . . . . 178.40(14) ?
N2 C6 C7 N3 . . . . 169.72(14) ?
C5 C6 C7 N3 . . . . -11.6(2) ?
N2 C6 C7 C9 . . . . -12.7(2) ?
C5 C6 C7 C9 . . . . 165.96(16) ?
N2 C2 C3 C4 . . . . 0.3(2) ?
C1 C2 C3 C4 . . . . 179.40(15) ?
N2 C6 C5 C4 . . . . -0.6(2) ?
C7 C6 C5 C4 . . . . -179.19(15) ?
C1 N1 C10 C11 . . . . -93.60(19) ?
C1 N1 C10 C15 . . . . 93.31(19) ?
C7 N3 C17 C22 . . . . 68.2(2) ?
C7 N3 C17 C18 . . . . -117.05(18) ?
C11 C10 C15 C14 . . . . -2.1(2) ?
N1 C10 C15 C14 . . . . 170.93(13) ?
C11 C10 C15 C16 . . . . 178.34(15) ?
N1 C10 C15 C16 . . . . -8.6(2) ?
C2 C3 C4 C5 . . . . -0.1(3) ?
C6 C5 C4 C3 . . . . 0.3(3) ?
C10 C15 C14 C13 . . . . 0.8(2) ?
C16 C15 C14 C13 . . . . -179.72(16) ?
C18 C17 C22 C21 . . . . 0.1(3) ?
N3 C17 C22 C21 . . . . 174.74(16) ?
C22 C17 C18 C19 . . . . -0.2(2) ?
N3 C17 C18 C19 . . . . -175.06(15) ?
C22 C17 C18 C23 . . . . -179.14(17) ?
N3 C17 C18 C23 . . . . 6.0(2) ?
C15 C14 C13 C12 . . . . 0.7(3) ?
C15 C10 C11 C12 . . . . 2.1(2) ?
N1 C10 C11 C12 . . . . -171.07(15) ?
C14 C13 C12 C11 . . . . -0.8(3) ?
C10 C11 C12 C13 . . . . -0.5(3) ?
C21 C20 C19 C18 . . . . -0.4(3) ?
C17 C18 C19 C20 . . . . 0.4(3) ?
C23 C18 C19 C20 . . . . 179.31(19) ?
C19 C20 C21 C22 . . . . 0.3(3) ?
C17 C22 C21 C20 . . . . -0.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9446970
