#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230798.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_2230798
loop_
_publ_author_name
'Ranjith, S.'
'SubbiahPandi, A.'
'Suresh, A. D.'
'Pitchumani, K.'
_publ_section_title
;
 3-Ethyl-5-(4-methoxyphenoxy)-2-(pyridin-4-yl)-3H-imidazo[4,5-b]pyridine
;
_journal_coeditor_code           LX2189
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1764
_journal_paper_doi               10.1107/S1600536811023543
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H18 N4 O2'
_chemical_formula_moiety         'C20 H18 N4 O2'
_chemical_formula_sum            'C20 H18 N4 O2'
_chemical_formula_weight         346.38
_chemical_name_systematic
;
3-Ethyl-5-(4-methoxyphenoxy)-2-(pyridin-4-yl)-3H-
imidazo[4,5-b]pyridine
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6591(4)
_cell_length_b                   13.7104(4)
_cell_length_c                   9.3177(2)
_cell_measurement_reflns_used    5887
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      1.5
_cell_volume                     1723.74(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24827
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.05
_diffrn_reflns_theta_min         1.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'white crystalline'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0464
_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)+(0.0680P)²+0.2334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                3938
_reflns_number_total             5887
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2189.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230798
_cod_database_fobs_code          2230798
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.34424(9) 0.10472(9) 0.42615(13) 0.0383(3) Uani d . 1 2 . .
C C2 0.34457(9) 0.18018(9) 0.52777(14) 0.0406(3) Uani d . 1 2 . .
H H2 0.3850 0.2344 0.5240 0.049 Uiso calc R 1 2 . .
C C3 0.28465(9) 0.17335(9) 0.63296(13) 0.0389(3) Uani d . 1 2 . .
H H3 0.2834 0.2222 0.7020 0.047 Uiso calc R 1 2 . .
C C4 0.22585(8) 0.09028(8) 0.63192(12) 0.0335(2) Uani d . 1 2 . .
C C5 0.23419(8) 0.02078(8) 0.52553(12) 0.0330(2) Uani d . 1 2 . .
C C6 0.12671(8) -0.02604(8) 0.66320(12) 0.0332(2) Uani d . 1 2 . .
C C7 0.16889(10) -0.14643(8) 0.46766(13) 0.0403(3) Uani d . 1 2 . .
H H7A 0.1356 -0.1952 0.5182 0.048 Uiso calc R 1 2 . .
H H7B 0.2363 -0.1683 0.4670 0.048 Uiso calc R 1 2 . .
C C8 0.11655(12) -0.13785(11) 0.31346(15) 0.0547(4) Uani d . 1 2 . .
H H8A 0.0490 -0.1186 0.3137 0.082 Uiso calc R 1 2 . .
H H8B 0.1181 -0.1997 0.2655 0.082 Uiso calc R 1 2 . .
H H8C 0.1493 -0.0897 0.2629 0.082 Uiso calc R 1 2 . .
C C9 0.05197(8) -0.08407(8) 0.72257(12) 0.0341(2) Uani d . 1 2 . .
C C10 0.05089(10) -0.08248(9) 0.87147(13) 0.0427(3) Uani d . 1 2 . .
H H10 0.0986 -0.0476 0.9329 0.051 Uiso calc R 1 2 . .
C C11 -0.02193(11) -0.13343(10) 0.92665(15) 0.0500(3) Uani d . 1 2 . .
H H11 -0.0225 -0.1305 1.0262 0.060 Uiso calc R 1 2 . .
C C12 -0.08936(10) -0.18810(10) 0.70402(15) 0.0459(3) Uani d . 1 2 . .
H H12 -0.1370 -0.2251 0.6457 0.055 Uiso calc R 1 2 . .
C C13 -0.02073(9) -0.13820(9) 0.63755(13) 0.0386(3) Uani d . 1 2 . .
H H13 -0.0233 -0.1409 0.5373 0.046 Uiso calc R 1 2 . .
C C14 0.40351(9) 0.04175(9) 0.22118(14) 0.0425(3) Uani d . 1 2 . .
C C15 0.33767(10) 0.04307(10) 0.09494(15) 0.0488(3) Uani d . 1 2 . .
H H15 0.2913 0.0930 0.0769 0.059 Uiso calc R 1 2 . .
C C16 0.34062(10) -0.03057(11) -0.00606(15) 0.0508(3) Uani d . 1 2 . .
H H16 0.2964 -0.0299 -0.0927 0.061 Uiso calc R 1 2 . .
C C17 0.40900(10) -0.10480(10) 0.02181(15) 0.0479(3) Uani d . 1 2 . .
C C18 0.47462(11) -0.10467(11) 0.14910(16) 0.0546(4) Uani d . 1 2 . .
H H18 0.5211 -0.1544 0.1679 0.066 Uiso calc R 1 2 . .
C C19 0.47204(10) -0.03162(11) 0.24862(16) 0.0512(3) Uani d . 1 2 . .
H H19 0.5167 -0.0318 0.3348 0.061 Uiso calc R 1 2 . .
C C20 0.35584(16) -0.18189(16) -0.2055(2) 0.0799(5) Uani d . 1 2 . .
H H20A 0.2878 -0.1767 -0.1920 0.120 Uiso calc R 1 2 . .
H H20B 0.3653 -0.2416 -0.2555 0.120 Uiso calc R 1 2 . .
H H20C 0.3727 -0.1276 -0.2621 0.120 Uiso calc R 1 2 . .
N N1 0.29165(7) 0.02406(7) 0.42238(11) 0.0374(2) Uani d . 1 2 . .
N N2 0.17080(7) -0.05379(7) 0.54614(10) 0.0340(2) Uani d . 1 2 . .
N N3 0.15774(7) 0.05932(7) 0.71772(10) 0.0357(2) Uani d . 1 2 . .
N N4 -0.09155(9) -0.18655(9) 0.84645(13) 0.0512(3) Uani d . 1 2 . .
O O1 0.40353(7) 0.11775(7) 0.32231(11) 0.0511(2) Uani d . 1 2 . .
O O2 0.41700(9) -0.18162(9) -0.06945(12) 0.0716(3) Uani d . 1 2 . .
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
N1 C1 O1 . . 118.16(10) ?
N1 C1 C2 . . 125.63(11) ?
O1 C1 C2 . . 116.21(10) ?
C3 C2 C1 . . 119.44(11) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 117.22(11) ?
C2 C3 H3 . . 121.4 ?
C4 C3 H3 . . 121.4 ?
N3 C4 C5 . . 109.76(10) ?
N3 C4 C3 . . 133.26(10) ?
C5 C4 C3 . . 116.98(10) ?
N1 C5 N2 . . 125.53(10) ?
N1 C5 C4 . . 127.79(10) ?
N2 C5 C4 . . 106.68(9) ?
N3 C6 N2 . . 113.32(9) ?
N3 C6 C9 . . 122.41(10) ?
N2 C6 C9 . . 124.27(10) ?
N2 C7 C8 . . 112.19(10) ?
N2 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
N2 C7 H7B . . 109.2 ?
C8 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C13 C9 C10 . . 117.46(11) ?
C13 C9 C6 . . 123.59(10) ?
C10 C9 C6 . . 118.91(11) ?
C11 C10 C9 . . 118.99(12) ?
C11 C10 H10 . . 120.5 ?
C9 C10 H10 . . 120.5 ?
N4 C11 C10 . . 124.17(12) ?
N4 C11 H11 . . 117.9 ?
C10 C11 H11 . . 117.9 ?
N4 C12 C13 . . 124.07(13) ?
N4 C12 H12 . . 118.0 ?
C13 C12 H12 . . 118.0 ?
C12 C13 C9 . . 118.98(11) ?
C12 C13 H13 . . 120.5 ?
C9 C13 H13 . . 120.5 ?
C15 C14 C19 . . 120.64(13) ?
C15 C14 O1 . . 119.97(12) ?
C19 C14 O1 . . 119.35(13) ?
C14 C15 C16 . . 119.40(13) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C17 C16 C15 . . 120.04(13) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
O2 C17 C18 . . 115.72(12) ?
O2 C17 C16 . . 124.63(13) ?
C18 C17 C16 . . 119.66(13) ?
C19 C18 C17 . . 120.31(13) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C18 C19 C14 . . 119.94(13) ?
C18 C19 H19 . . 120.0 ?
C14 C19 H19 . . 120.0 ?
O2 C20 H20A . . 109.5 ?
O2 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O2 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C1 N1 C5 . . 112.91(10) ?
C5 N2 C6 . . 105.53(9) ?
C5 N2 C7 . . 122.62(9) ?
C6 N2 C7 . . 131.19(9) ?
C6 N3 C4 . . 104.72(9) ?
C11 N4 C12 . . 116.31(11) ?
C1 O1 C14 . . 116.08(9) ?
C17 O2 C20 . . 117.96(13) ?
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
C1 N1 . 1.3161(15) ?
C1 O1 . 1.3667(14) ?
C1 C2 . 1.4020(17) ?
C2 C3 . 1.3744(17) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.3928(16) ?
C3 H3 . 0.9300 ?
C4 N3 . 1.3842(14) ?
C4 C5 . 1.3924(15) ?
C5 N1 . 1.3328(14) ?
C5 N2 . 1.3724(14) ?
C6 N3 . 1.3192(14) ?
C6 N2 . 1.3788(13) ?
C6 C9 . 1.4686(15) ?
C7 N2 . 1.4638(14) ?
C7 C8 . 1.5066(19) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C13 . 1.3857(17) ?
C9 C10 . 1.3899(16) ?
C10 C11 . 1.3786(18) ?
C10 H10 . 0.9300 ?
C11 N4 . 1.3312(18) ?
C11 H11 . 0.9300 ?
C12 N4 . 1.3322(17) ?
C12 C13 . 1.3823(17) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.365(2) ?
C14 C19 . 1.3708(19) ?
C14 O1 . 1.4048(16) ?
C15 C16 . 1.385(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.3784(19) ?
C16 H16 . 0.9300 ?
C17 O2 . 1.3687(17) ?
C17 C18 . 1.371(2) ?
C18 C19 . 1.369(2) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 O2 . 1.406(2) ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 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
N1 C1 C2 C3 . . . . -1.3(2) ?
O1 C1 C2 C3 . . . . 178.21(11) ?
C1 C2 C3 C4 . . . . -0.17(18) ?
C2 C3 C4 N3 . . . . -179.45(12) ?
C2 C3 C4 C5 . . . . 0.96(16) ?
N3 C4 C5 N1 . . . . 179.77(11) ?
C3 C4 C5 N1 . . . . -0.54(18) ?
N3 C4 C5 N2 . . . . -0.12(13) ?
C3 C4 C5 N2 . . . . 179.56(10) ?
N3 C6 C9 C13 . . . . 142.45(12) ?
N2 C6 C9 C13 . . . . -37.09(17) ?
N3 C6 C9 C10 . . . . -35.08(17) ?
N2 C6 C9 C10 . . . . 145.39(12) ?
C13 C9 C10 C11 . . . . -0.54(19) ?
C6 C9 C10 C11 . . . . 177.14(12) ?
C9 C10 C11 N4 . . . . 1.3(2) ?
N4 C12 C13 C9 . . . . 1.1(2) ?
C10 C9 C13 C12 . . . . -0.60(17) ?
C6 C9 C13 C12 . . . . -178.16(11) ?
C19 C14 C15 C16 . . . . -0.1(2) ?
O1 C14 C15 C16 . . . . 177.83(11) ?
C14 C15 C16 C17 . . . . 0.6(2) ?
C15 C16 C17 O2 . . . . 178.89(13) ?
C15 C16 C17 C18 . . . . -0.7(2) ?
O2 C17 C18 C19 . . . . -179.25(14) ?
C16 C17 C18 C19 . . . . 0.4(2) ?
C17 C18 C19 C14 . . . . 0.1(2) ?
C15 C14 C19 C18 . . . . -0.2(2) ?
O1 C14 C19 C18 . . . . -178.17(12) ?
O1 C1 N1 C5 . . . . -177.83(11) ?
C2 C1 N1 C5 . . . . 1.63(18) ?
N2 C5 N1 C1 . . . . 179.15(11) ?
C4 C5 N1 C1 . . . . -0.73(17) ?
N1 C5 N2 C6 . . . . -179.62(11) ?
C4 C5 N2 C6 . . . . 0.28(12) ?
N1 C5 N2 C7 . . . . 8.72(18) ?
C4 C5 N2 C7 . . . . -171.38(10) ?
N3 C6 N2 C5 . . . . -0.36(13) ?
C9 C6 N2 C5 . . . . 179.21(10) ?
N3 C6 N2 C7 . . . . 170.30(11) ?
C9 C6 N2 C7 . . . . -10.13(19) ?
C8 C7 N2 C5 . . . . -76.72(15) ?
C8 C7 N2 C6 . . . . 113.98(14) ?
N2 C6 N3 C4 . . . . 0.28(13) ?
C9 C6 N3 C4 . . . . -179.30(10) ?
C5 C4 N3 C6 . . . . -0.09(13) ?
C3 C4 N3 C6 . . . . -179.70(13) ?
C10 C11 N4 C12 . . . . -0.8(2) ?
C13 C12 N4 C11 . . . . -0.4(2) ?
N1 C1 O1 C14 . . . . -0.86(17) ?
C2 C1 O1 C14 . . . . 179.63(11) ?
C15 C14 O1 C1 . . . . 90.64(14) ?
C19 C14 O1 C1 . . . . -91.40(14) ?
C18 C17 O2 C20 . . . . -175.90(15) ?
C16 C17 O2 C20 . . . . 4.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656788
