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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_journal_date_recd_electronic     2008-04-08
_journal_date_accepted     2008-04-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      5
_journal_page_first     o927
_journal_page_last     o927
_journal_paper_category     QO
_journal_coeditor_code     BG2180
_publ_contact_author_name     'Fejfarova, Karla'
_publ_contact_author_address
;
Institute of Physics
Na Slovance 2
182 21 Praha 8
Czech Republic
;
_publ_contact_author_email     fejfarov@fzu.cz
_publ_contact_author_fax     '+420 233 343 184'
_publ_contact_author_phone     '+420 220 318 594'
_publ_section_title
;
2-Phenylimidazo[1,2-<i>a</i>]pyridine-3-carbaldehyde
;
loop_
    _publ_author_name
    _publ_author_address
    'Anaflous, Abderrahman'
;
D\'epartement de Chimie
Facult\'e des Sciences
BP 717, 60000 Oujda
Morocco
;
    'Albay, Hanane'
;
D\'epartement de Chimie
Facult\'e des Sciences
BP 717, 60000 Oujda
Morocco
;
    'Benchat, Nour-eddine'
;
D\'epartement de Chimie
Facult\'e des Sciences
BP 717, 60000 Oujda
Morocco
;
    'El Bali, Brahim'
;
Laboratory of Mineral Solid and Analytical Chemistry
`LMSAC'
Department of Chemistry
Faculty of Sciences
University Mohamed I
PO Box 717
60000 Oujda
Morocco
;
    'Du\<sek, Michal'
;
Institute of Physics
Na Slovance 2
182 21 Praha 8
Czech Republic
;
    'Fejfarov\'a, Karla'
;
Institute of Physics
Na Slovance 2
182 21 Praha 8
Czech Republic
;
data_I
_chemical_name_systematic
;
2-Phenylimidazo[1,2-<i>a</i>]pyridine-3-carbaldehyde
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H10 N2 O'
_chemical_formula_sum     'C14 H10 N2 O1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C14 H10 N2 O'
_chemical_formula_weight     222.2
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2+x,y,1/2-z
    3 1/2-x,1/2+y,z
    4 -x,1/2+y,1/2-z
    5 -x,-y,-z
    6 1/2-x,-y,1/2+z
    7 1/2+x,1/2-y,-z
    8 x,1/2-y,1/2+z
_cell_length_a     13.0640(3)
_cell_length_b     7.4162(2)
_cell_length_c     21.6698(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2099.48(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8746
_cell_measurement_theta_min     2.7407
_cell_measurement_theta_max     26.4995
_cell_measurement_temperature     120
_cell_special_details
; ?
;
_exptl_crystal_description     'prism'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.5733
_exptl_crystal_size_mid     0.4037
_exptl_crystal_size_min     0.2410
_exptl_crystal_density_diffrn     1.40579
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     928
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     120
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
      'Oxford Diffraction Xcalibur2 diffractometer with  Sapphire2 CCD detector'
_diffrn_measurement_method     'Rotation method data acquisition using \w'
_diffrn_detector_area_resol_mean     8.3438
_diffrn_reflns_number     25795
_diffrn_reflns_av_R_equivalents     0.0490
_diffrn_reflns_av_sigmaI/netI     0.0568
_diffrn_reflns_theta_min     3.12
_diffrn_reflns_theta_max     26.56
_diffrn_reflns_theta_full     26.56
_diffrn_measured_fraction_theta_max     1.00
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_reflns_reduction_process
;
Integration of the CCD images was done by program Crysalis RED
(Oxford diffraction, 2006).
;
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
The refinement was carried out against all reflections. The conventional
<i>R</i>-factor is always based on <i>F</i>. The goodness of fit as well as
the weighted <i>R</i>-factor are based on <i>F</i> and <i>F</i>^2^ for
refinement carried out on <i>F</i> and <i>F</i>^2^, respectively. The
threshold expression is used only for calculating <i>R</i>-factors <i>etc</i>.
and it is not relevant to the choice of reflections for refinement.
All the H atoms were discernible in difference Fourier maps and could be
refined to reasonable geometry. According to standard procedures for organic
compounds the H atoms bonded to C atoms were constrained to ideal positions.
The isotropic atomic displacement parameters of hydrogen atoms were evaluated
as 1.2*<i>U</i>~eq~ of the parent atom.
The program used for refinement, Jana2006, uses the weighting scheme based on
the experimental expectations, see _refine_ls_weighting_details, that does not
force <i>S</i> to be one. Therefore the values of <i>S</i> are usually larger
than the ones from the <i>SHELX</i> program.
;
_reflns_number_total     2196
_reflns_number_gt     1305
_reflns_threshold_expression     I>3\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.0561
_refine_ls_R_factor_gt     0.0314
_refine_ls_wR_factor_gt     0.0742
_refine_ls_wR_factor_ref     0.0773
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     ?
_refine_ls_number_reflns     2196
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_number_constraints     36
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w=1/[\s^2^(I)+0.0016I^2^]'
_refine_ls_shift/su_max     0.0067
_refine_ls_shift/su_mean     0.0002
_refine_diff_density_max     0.15
_refine_diff_density_min     -0.16
_refine_ls_extinction_method     'none'
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.003 0.002 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.4'
    H 0.000 0.000 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.4'
    O 0.011 0.006 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.4'
    N 0.006 0.003 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution     'SIR2002 (Burla <i>et al.</i>,  2003)'
_computing_structure_refinement
                                'JANA2000 (Pet\<r\'i\<cek <i>et al.</i>,  2000)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
                                'JANA2000 (Pet\<r\'i\<cek <i>et al.</i>,  2000)'
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 N1 0.38579(8) 0.13099(13) 0.06669(5) 0.0227(3) Uani d . 1 . .
    N N2 0.22707(8) 0.09004(13) 0.02784(5) 0.0204(3) Uani d . 1 . .
    O O1 0.03531(7) 0.19646(11) 0.08623(4) 0.0297(3) Uani d . 1 . .
    C C1 0.31590(10) 0.18666(16) 0.10870(6) 0.0208(4) Uani d . 1 . .
    C C2 0.33161(10) 0.07295(16) 0.01765(6) 0.0207(4) Uani d . 1 . .
    C C3 0.21543(10) 0.16659(16) 0.08658(6) 0.0204(4) Uani d . 1 . .
    C C4 0.36597(11) -0.00163(16) -0.03801(6) 0.0235(4) Uani d . 1 . .
    C C5 0.29491(10) -0.05736(17) -0.08037(7) 0.0243(4) Uani d . 1 . .
    C C6 0.18958(10) -0.03859(17) -0.06861(6) 0.0247(4) Uani d . 1 . .
    C C7 0.15617(10) 0.03543(16) -0.01503(6) 0.0236(4) Uani d . 1 . .
    C C8 0.35054(10) 0.25310(16) 0.16940(6) 0.0214(4) Uani d . 1 . .
    C C9 0.29235(10) 0.23521(17) 0.22302(7) 0.0238(4) Uani d . 1 . .
    C C10 0.32855(11) 0.30105(17) 0.27874(7) 0.0274(5) Uani d . 1 . .
    C C11 0.42372(11) 0.38290(17) 0.28223(6) 0.0283(5) Uani d . 1 . .
    C C12 0.48307(11) 0.39863(17) 0.22959(6) 0.0282(4) Uani d . 1 . .
    C C13 0.44708(10) 0.33402(16) 0.17344(6) 0.0242(4) Uani d . 1 . .
    C C14 0.11885(10) 0.22273(16) 0.11073(7) 0.0245(4) Uani d . 1 . .
    H H4 0.437543 -0.014444 -0.047038 0.0282 Uiso d . 1 . .
    H H5 0.318903 -0.109503 -0.118246 0.0292 Uiso d . 1 . .
    H H6 0.139117 -0.077351 -0.097954 0.0296 Uiso d . 1 . .
    H H7 0.084111 0.048834 -0.007645 0.0283 Uiso d . 1 . .
    H H9 0.226757 0.177012 0.221555 0.0286 Uiso d . 1 . .
    H H10 0.287357 0.289867 0.315233 0.0329 Uiso d . 1 . .
    H H11 0.448433 0.4285 0.320918 0.0339 Uiso d . 1 . .
    H H12 0.549259 0.454408 0.232038 0.0339 Uiso d . 1 . .
    H H13 0.489068 0.345338 0.137292 0.0291 Uiso d . 1 . .
    H H14 0.108688 0.287015 0.148695 0.0294 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
    _atom_site_aniso_type_symbol
    N1 0.0207(6) 0.0225(5) 0.0249(6) 0.0004(5) 0.0004(5) 0.0017(5) N
    N2 0.0196(6) 0.0177(5) 0.0239(6) -0.0005(5) -0.0001(5) 0.0031(5) N
    O1 0.0200(6) 0.0315(5) 0.0376(6) 0.0000(4) -0.0002(5) 0.0024(5) O
    C1 0.0221(7) 0.0149(7) 0.0255(8) 0.0007(6) 0.0019(6) 0.0052(6) C
    C2 0.0192(7) 0.0170(6) 0.0259(8) -0.0002(6) 0.0015(6) 0.0051(6) C
    C3 0.0211(7) 0.0179(6) 0.0223(7) -0.0008(6) 0.0022(6) 0.0026(6) C
    C4 0.0219(8) 0.0224(7) 0.0263(8) -0.0005(6) 0.0024(6) 0.0027(6) C
    C5 0.0281(8) 0.0201(7) 0.0248(8) -0.0015(6) 0.0020(6) 0.0031(6) C
    C6 0.0245(8) 0.0220(7) 0.0275(8) -0.0044(6) -0.0037(6) 0.0023(6) C
    C7 0.0194(8) 0.0225(7) 0.0289(8) -0.0025(6) -0.0031(6) 0.0043(6) C
    C8 0.0228(8) 0.0155(6) 0.0260(8) 0.0027(6) -0.0010(6) 0.0032(5) C
    C9 0.0216(8) 0.0212(7) 0.0288(8) -0.0003(6) -0.0001(7) 0.0034(6) C
    C10 0.0313(8) 0.0267(7) 0.0242(8) 0.0049(7) 0.0017(7) 0.0034(6) C
    C11 0.0330(8) 0.0255(7) 0.0263(8) 0.0053(7) -0.0057(7) -0.0006(6) C
    C12 0.0266(8) 0.0242(7) 0.0339(8) -0.0021(6) -0.0043(7) 0.0013(7) C
    C13 0.0243(8) 0.0222(7) 0.0263(8) 0.0009(6) 0.0007(6) 0.0032(6) C
    C14 0.0262(8) 0.0201(7) 0.0271(8) 0.0008(7) 0.0032(7) 0.0041(6) C
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C1 . . 1.3537(16) ?
    N1 C2 . . 1.3475(16) ?
    N2 C2 . . 1.3893(16) ?
    N2 C3 . . 1.4020(17) ?
    N2 C7 . . 1.3731(17) ?
    O1 C14 . . 1.2293(16) ?
    C1 C3 . . 1.4052(18) ?
    C1 C8 . . 1.4758(18) ?
    C2 C4 . . 1.4008(18) ?
    C3 C14 . . 1.4279(18) ?
    C4 C5 . . 1.3693(19) ?
    C4 H4 . . 0.9600 ?
    C5 C6 . . 1.4063(18) ?
    C5 H5 . . 0.9600 ?
    C6 C7 . . 1.3564(19) ?
    C6 H6 . . 0.9600 ?
    C7 H7 . . 0.9600 ?
    C8 C9 . . 1.3949(19) ?
    C8 C13 . . 1.3994(18) ?
    C9 C10 . . 1.386(2) ?
    C9 H9 . . 0.9600 ?
    C10 C11 . . 1.3857(19) ?
    C10 H10 . . 0.9600 ?
    C11 C12 . . 1.3840(19) ?
    C11 H11 . . 0.9600 ?
    C12 C13 . . 1.3897(19) ?
    C12 H12 . . 0.9600 ?
    C13 H13 . . 0.9600 ?
    C14 H14 . . 0.9600 ?
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C2 . . . 105.87(10) ?
    C2 N2 C3 . . . 106.74(10) ?
    C2 N2 C7 . . . 121.92(11) ?
    C3 N2 C7 . . . 131.34(11) ?
    N1 C1 C3 . . . 111.62(11) ?
    N1 C1 C8 . . . 119.62(11) ?
    C3 C1 C8 . . . 128.74(12) ?
    N1 C2 N2 . . . 111.21(11) ?
    N1 C2 C4 . . . 129.56(12) ?
    N2 C2 C4 . . . 119.21(11) ?
    N2 C3 C1 . . . 104.54(11) ?
    N2 C3 C14 . . . 123.14(12) ?
    C1 C3 C14 . . . 132.02(12) ?
    C2 C4 C5 . . . 118.63(12) ?
    C2 C4 H4 . . . 121.78 ?
    C5 C4 H4 . . . 119.59 ?
    C4 C5 C6 . . . 120.80(13) ?
    C4 C5 H5 . . . 118.26 ?
    C6 C5 H5 . . . 120.94 ?
    C5 C6 C7 . . . 120.66(12) ?
    C5 C6 H6 . . . 121.49 ?
    C7 C6 H6 . . . 117.85 ?
    N2 C7 C6 . . . 118.78(12) ?
    N2 C7 H7 . . . 121.20 ?
    C6 C7 H7 . . . 120.02 ?
    C1 C8 C9 . . . 122.93(12) ?
    C1 C8 C13 . . . 118.38(12) ?
    C9 C8 C13 . . . 118.67(12) ?
    C8 C9 C10 . . . 120.43(12) ?
    C8 C9 H9 . . . 120.11 ?
    C10 C9 H9 . . . 119.46 ?
    C9 C10 C11 . . . 120.53(13) ?
    C9 C10 H10 . . . 119.74 ?
    C11 C10 H10 . . . 119.73 ?
    C10 C11 C12 . . . 119.65(13) ?
    C10 C11 H11 . . . 120.24 ?
    C12 C11 H11 . . . 120.11 ?
    C11 C12 C13 . . . 120.19(12) ?
    C11 C12 H12 . . . 119.70 ?
    C13 C12 H12 . . . 120.11 ?
    C8 C13 C12 . . . 120.50(12) ?
    C8 C13 H13 . . . 120.09 ?
    C12 C13 H13 . . . 119.40 ?
    O1 C14 C3 . . . 125.44(13) ?
    O1 C14 H14 . . . 109.03 ?
    C3 C14 H14 . . . 125.53 ?
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
    C4 H4 N1 5_655 0.96 2.50 3.4386(18) 165 y
    C6 H6 O1 5_555 0.96 2.46 3.1856(16) 133 y