#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/37/2223714.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_2223714
loop_
_publ_author_name
'Doumbia, Mohamadou Lamine'
'Bouhfid, Rachid'
'Essassi, El Mokhtar'
'El Ammari, Lahcen'
_publ_section_title
;
 5-Methyl-3-[1-(2-pyridylmethyl)-1H-benzimidazol-2-ylmethyl]isoxazole
;
_journal_coeditor_code           DN2494
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2714
_journal_page_last               o2715
_journal_paper_doi               10.1107/S1600536809040100
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H16 N4 O'
_chemical_formula_moiety         'C18 H16 N4 O'
_chemical_formula_sum            'C18 H16 N4 O'
_chemical_formula_weight         304.35
_chemical_name_systematic
;
5-Methyl-3-[1-(2-pyridylmethyl)-1H-benzimidazol-2-ylmethyl]isoxazole
;
_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                90.0
_cell_angle_beta                 103.1360(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   11.0761(2)
_cell_length_b                   8.65350(10)
_cell_length_c                   16.5920(3)
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.52
_cell_volume                     1548.68(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (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 X8 APEX Diffractometer'
_diffrn_measurement_method       'φ and ω'
_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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29777
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.137
_refine_ls_extinction_coef       0.0099(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0396
_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)+(0.0445P)²+0.2578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2460
_reflns_number_total             3567
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2494.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223714
_cod_database_fobs_code          2223714
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
O O1 0.35108(10) -0.03671(13) 0.02360(6) 0.0584(3) Uani d . 1 . .
N N1 0.28238(12) 0.07631(17) 0.05503(8) 0.0587(4) Uani d . 1 . .
N N2 0.14275(11) 0.00694(14) 0.28340(7) 0.0462(3) Uani d . 1 . .
N N3 0.02122(11) 0.07134(13) 0.16088(7) 0.0421(3) Uani d . 1 . .
N N4 -0.03858(11) 0.38647(14) 0.14258(7) 0.0472(3) Uani d . 1 . .
C C1 0.41164(13) -0.12534(17) 0.08719(9) 0.0461(4) Uani d . 1 . .
C C2 0.38459(14) -0.07581(17) 0.15741(9) 0.0467(4) Uani d . 1 . .
H H2 0.4130 -0.1163 0.2102 0.056 Uiso calc R 1 . .
C C3 0.30411(13) 0.05044(16) 0.13448(9) 0.0438(3) Uani d . 1 . .
C C4 0.24511(14) 0.15139(17) 0.18861(9) 0.0519(4) Uani d . 1 . .
H H4B 0.3067 0.1774 0.2384 0.061(5) Uiso calc R 1 . .
H H4A 0.2178 0.2469 0.1595 0.067(5) Uiso calc R 1 . .
C C5 0.13705(13) 0.07608(15) 0.21254(8) 0.0414(3) Uani d . 1 . .
C C6 0.02351(13) -0.04756(15) 0.27876(8) 0.0428(3) Uani d . 1 . .
C C7 -0.02328(16) -0.13135(18) 0.33632(10) 0.0559(4) Uani d . 1 . .
H H7 0.0275 -0.1608 0.3866 0.067 Uiso calc R 1 . .
C C8 -0.14703(17) -0.1693(2) 0.31653(11) 0.0655(5) Uani d . 1 . .
H H8 -0.1803 -0.2249 0.3543 0.079 Uiso calc R 1 . .
C C9 -0.22337(16) -0.1265(2) 0.24140(11) 0.0657(5) Uani d . 1 . .
H H9 -0.3067 -0.1538 0.2302 0.079 Uiso calc R 1 . .
C C10 -0.17938(14) -0.04485(19) 0.18304(10) 0.0553(4) Uani d . 1 . .
H H10 -0.2307 -0.0165 0.1327 0.066 Uiso calc R 1 . .
C C11 -0.05416(13) -0.00683(15) 0.20323(8) 0.0416(3) Uani d . 1 . .
C C12 -0.01820(15) 0.13746(17) 0.07846(8) 0.0469(4) Uani d . 1 . .
H H12A -0.0812 0.0708 0.0458 0.052(4) Uiso calc R 1 . .
H H12B 0.0521 0.1375 0.0526 0.056(4) Uiso calc R 1 . .
C C13 -0.06934(12) 0.29955(15) 0.07513(7) 0.0380(3) Uani d . 1 . .
C C14 -0.08168(16) 0.53187(18) 0.13659(10) 0.0568(4) Uani d . 1 . .
H H14 -0.0619 0.5940 0.1835 0.068 Uiso calc R 1 . .
C C15 -0.15277(16) 0.5944(2) 0.06597(11) 0.0610(4) Uani d . 1 . .
H H15 -0.1801 0.6961 0.0650 0.073 Uiso calc R 1 . .
C C16 -0.18271(15) 0.5037(2) -0.00321(10) 0.0600(4) Uani d . 1 . .
H H16 -0.2305 0.5428 -0.0524 0.072 Uiso calc R 1 . .
C C17 -0.14106(13) 0.35385(18) 0.00120(9) 0.0496(4) Uani d . 1 . .
H H17 -0.1608 0.2897 -0.0449 0.060 Uiso calc R 1 . .
C C18 0.48944(16) -0.2503(2) 0.06534(11) 0.0633(4) Uani d . 1 . .
H H18A 0.4381 -0.3218 0.0286 0.095 Uiso calc R 1 . .
H H18B 0.5309 -0.3033 0.1147 0.095 Uiso calc R 1 . .
H H18C 0.5499 -0.2068 0.0386 0.095 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'
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
C1 O1 N1 . . 108.57(11) ?
C3 N1 O1 . . 105.28(11) ?
C5 N2 C6 . . 104.75(11) ?
C5 N3 C11 . . 106.49(11) ?
C5 N3 C12 . . 127.86(12) ?
C11 N3 C12 . . 125.63(12) ?
C13 N4 C14 . . 116.77(12) ?
C2 C1 O1 . . 109.15(13) ?
C2 C1 C18 . . 134.95(14) ?
O1 C1 C18 . . 115.90(13) ?
C1 C2 C3 . . 105.48(12) ?
C1 C2 H2 . . 127.3 ?
C3 C2 H2 . . 127.3 ?
N1 C3 C2 . . 111.51(13) ?
N1 C3 C4 . . 119.88(13) ?
C2 C3 C4 . . 128.61(13) ?
C5 C4 C3 . . 112.85(12) ?
C5 C4 H4B . . 109.0 ?
C3 C4 H4B . . 109.0 ?
C5 C4 H4A . . 109.0 ?
C3 C4 H4A . . 109.0 ?
H4B C4 H4A . . 107.8 ?
N2 C5 N3 . . 113.28(12) ?
N2 C5 C4 . . 124.10(13) ?
N3 C5 C4 . . 122.62(12) ?
N2 C6 C7 . . 129.63(13) ?
N2 C6 C11 . . 110.42(12) ?
C7 C6 C11 . . 119.95(14) ?
C8 C7 C6 . . 117.89(15) ?
C8 C7 H7 . . 121.1 ?
C6 C7 H7 . . 121.1 ?
C7 C8 C9 . . 121.43(16) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C10 C9 C8 . . 121.93(16) ?
C10 C9 H9 . . 119.0 ?
C8 C9 H9 . . 119.0 ?
C9 C10 C11 . . 116.48(15) ?
C9 C10 H10 . . 121.8 ?
C11 C10 H10 . . 121.8 ?
N3 C11 C10 . . 132.63(13) ?
N3 C11 C6 . . 105.05(12) ?
C10 C11 C6 . . 122.32(14) ?
N3 C12 C13 . . 115.46(11) ?
N3 C12 H12A . . 108.4 ?
C13 C12 H12A . . 108.4 ?
N3 C12 H12B . . 108.4 ?
C13 C12 H12B . . 108.4 ?
H12A C12 H12B . . 107.5 ?
N4 C13 C17 . . 122.74(13) ?
N4 C13 C12 . . 118.28(11) ?
C17 C13 C12 . . 118.90(12) ?
N4 C14 C15 . . 124.12(15) ?
N4 C14 H14 . . 117.9 ?
C15 C14 H14 . . 117.9 ?
C14 C15 C16 . . 118.38(15) ?
C14 C15 H15 . . 120.8 ?
C16 C15 H15 . . 120.8 ?
C15 C16 C17 . . 118.87(14) ?
C15 C16 H16 . . 120.6 ?
C17 C16 H16 . . 120.6 ?
C16 C17 C13 . . 119.12(14) ?
C16 C17 H17 . . 120.4 ?
C13 C17 H17 . . 120.4 ?
C1 C18 H18A . . 109.5 ?
C1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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
O1 C1 . 1.3526(17) ?
O1 N1 . 1.4100(17) ?
N1 C3 . 1.3044(17) ?
N2 C5 . 1.3079(17) ?
N2 C6 . 1.3880(18) ?
N3 C5 . 1.3720(17) ?
N3 C11 . 1.3840(18) ?
N3 C12 . 1.4548(16) ?
N4 C13 . 1.3270(16) ?
N4 C14 . 1.3414(19) ?
C1 C2 . 1.338(2) ?
C1 C18 . 1.478(2) ?
C2 C3 . 1.407(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.504(2) ?
C4 C5 . 1.494(2) ?
C4 H4B . 0.9700 ?
C4 H4A . 0.9700 ?
C6 C7 . 1.390(2) ?
C6 C11 . 1.3945(19) ?
C7 C8 . 1.375(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.388(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.374(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.390(2) ?
C10 H10 . 0.9300 ?
C12 C13 . 1.5090(19) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C17 . 1.3833(18) ?
C14 C15 . 1.366(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.368(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.372(2) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 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
C2 H2 N4 2_545 0.93 2.52 3.385(2) 155 yes
C12 H12B N1 . 0.97 2.60 3.479(2) 151 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743457
