##############################################################################
###                                                                        ###
###        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
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-02-22
_journal_date_accepted     2010-03-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o755
_journal_page_last     o755
_journal_paper_category     QO
_journal_coeditor_code     HG2649
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;\
6-Bromo-1-(1,2-propadienyl)-3-(2-propynyl)-1H-imidazo[4,5-b]\
pyridin-2(3H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Dahmani, S.'
;
Laboratoire de Chimie Organique Appliquée
Faculté des Sciences et Techniques
Université Sidi Mohamed Ben Abdallah
Fés
Morocco
;
    'Haoudi, A.'
;
Laboratoire de Chimie Organique Appliquée
Faculté des Sciences et Techniques
Université Sidi Mohamed Ben Abdallah
Fés
Morocco
;
    'Capet, F.'
;
Unité de Catalyse et de Chimie du Solide
Ecole Nationale Supérieure de Chimie de Lille
Lille
France
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique Hétérocyclique
Pôle de Compétences Pharmacochimie
Université Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6-Bromo-1-(1,2-propadienyl)-3-(2-propynyl)-1H-
imidazo[4,5-b]pyridin-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H8 Br N3 O'
_chemical_formula_sum     'C12 H8 Br N3 O'
_chemical_formula_iupac     'C12 H8 Br N3 O'
_chemical_formula_weight     290.12
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     9.6369(4)
_cell_length_b     9.3086(4)
_cell_length_c     13.5481(5)
_cell_angle_alpha     90.00
_cell_angle_beta     99.123(2)
_cell_angle_gamma     90.00
_cell_volume     1199.97(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9975
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     25.6
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Irregular
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.606
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     3.412
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.2555
_exptl_absorpt_correction_T_max     0.4276
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker X8 APEXII'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     51411
_diffrn_reflns_av_R_equivalents     0.0403
_diffrn_reflns_av_sigmaI/netI     0.0173
_diffrn_reflns_theta_min     2.67
_diffrn_reflns_theta_max     29.71
_diffrn_reflns_theta_full     29.71
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3393
_reflns_number_gt     2577
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0487
_refine_ls_R_factor_gt     0.0314
_refine_ls_wR_factor_gt     0.0774
_refine_ls_wR_factor_ref     0.0874
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3393
_refine_ls_number_parameters     166
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0413P)²+0.4635P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.487
_refine_diff_density_min     -0.633
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    Br Br1 0.40648(3) 0.39876(3) 0.231050(17) 0.06785(11) Uani d . 1 . .
    O O1 0.49655(17) 0.95432(17) 0.64205(11) 0.0577(4) Uani d . 1 . .
    N N1 0.21863(16) 0.64109(19) 0.42594(13) 0.0453(4) Uani d . 1 . .
    N N2 0.54742(15) 0.78896(16) 0.52363(11) 0.0395(3) Uani d . 1 . .
    N N3 0.32605(16) 0.81244(17) 0.54674(11) 0.0417(3) Uani d . 1 . .
    C C1 0.2477(2) 0.5495(2) 0.35479(15) 0.0490(4) Uani d . 1 . .
    H H1 0.1744 0.4972 0.3188 0.059 Uiso calc R 1 . .
    C C2 0.3815(2) 0.53039(19) 0.33326(13) 0.0435(4) Uani d . 1 . .
    C C3 0.4981(2) 0.60309(19) 0.38454(13) 0.0399(4) Uani d . 1 . .
    H H3 0.5887 0.5895 0.3708 0.048 Uiso calc R 1 . .
    C C4 0.46792(17) 0.69616(18) 0.45684(12) 0.0346(3) Uani d . 1 . .
    C C5 0.32815(18) 0.71031(18) 0.47294(12) 0.0365(3) Uani d . 1 . .
    C C6 0.6938(2) 0.8150(2) 0.53701(16) 0.0503(5) Uani d . 1 . .
    H H6 0.7302 0.8828 0.5845 0.060 Uiso calc R 1 . .
    C C7 0.7806(2) 0.7510(2) 0.48776(17) 0.0529(5) Uani d . 1 . .
    C C8 0.8709(3) 0.6872(4) 0.4413(2) 0.0750(8) Uani d D 1 . .
    H H81 0.916(3) 0.602(2) 0.467(3) 0.106(12) Uiso d D 1 . .
    H H82 0.890(3) 0.722(3) 0.3788(13) 0.089(10) Uiso d D 1 . .
    C C9 0.4605(2) 0.8628(2) 0.57909(14) 0.0416(4) Uani d . 1 . .
    C C10 0.2020(2) 0.8584(2) 0.58740(16) 0.0509(5) Uani d . 1 . .
    H H10A 0.1252 0.8736 0.5328 0.061 Uiso calc R 1 . .
    H H10B 0.2218 0.9494 0.6217 0.061 Uiso calc R 1 . .
    C C11 0.1586(2) 0.7538(2) 0.65707(15) 0.0521(5) Uani d . 1 . .
    C C12 0.1208(3) 0.6715(3) 0.71186(19) 0.0694(7) Uani d D 1 . .
    H H12 0.093(3) 0.601(2) 0.7550(18) 0.088(11) Uiso d 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
    Br1 0.0918(2) 0.05653(15) 0.05116(14) 0.01376(12) -0.00107(12) -0.01710(9)
    O1 0.0645(9) 0.0499(8) 0.0563(9) 0.0031(7) 0.0024(7) -0.0158(7)
    N1 0.0357(8) 0.0481(9) 0.0513(9) -0.0027(7) 0.0046(7) 0.0022(7)
    N2 0.0367(7) 0.0396(8) 0.0417(7) -0.0023(6) 0.0050(6) -0.0021(6)
    N3 0.0417(8) 0.0425(8) 0.0431(8) 0.0011(6) 0.0133(6) -0.0014(6)
    C1 0.0469(10) 0.0461(10) 0.0504(10) -0.0050(8) -0.0035(8) -0.0017(8)
    C2 0.0555(11) 0.0369(9) 0.0362(8) 0.0034(8) 0.0016(7) -0.0014(7)
    C3 0.0408(9) 0.0411(9) 0.0385(8) 0.0031(7) 0.0085(7) 0.0024(7)
    C4 0.0351(8) 0.0350(8) 0.0334(7) -0.0008(6) 0.0051(6) 0.0060(6)
    C5 0.0386(8) 0.0350(8) 0.0364(8) 0.0006(7) 0.0079(6) 0.0057(6)
    C6 0.0381(9) 0.0515(11) 0.0592(12) -0.0078(8) 0.0015(8) -0.0032(9)
    C7 0.0343(9) 0.0597(12) 0.0628(12) -0.0064(9) 0.0017(9) 0.0098(10)
    C8 0.0396(11) 0.101(2) 0.0867(19) 0.0039(13) 0.0176(12) 0.0060(17)
    C9 0.0474(10) 0.0370(9) 0.0402(9) 0.0029(7) 0.0061(7) 0.0014(7)
    C10 0.0512(11) 0.0491(11) 0.0570(12) 0.0097(9) 0.0224(9) 0.0029(9)
    C11 0.0510(11) 0.0614(12) 0.0461(10) 0.0007(9) 0.0149(8) -0.0033(9)
    C12 0.0748(16) 0.0808(18) 0.0555(13) -0.0120(14) 0.0197(12) 0.0087(12)
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
    Br1 C2 . 1.8928(18) ?
    O1 C9 . 1.216(2) ?
    N1 C5 . 1.312(2) ?
    N1 C1 . 1.349(3) ?
    N2 C4 . 1.390(2) ?
    N2 C9 . 1.393(2) ?
    N2 C6 . 1.414(2) ?
    N3 C5 . 1.382(2) ?
    N3 C9 . 1.382(2) ?
    N3 C10 . 1.458(2) ?
    C1 C2 . 1.378(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.398(3) ?
    C3 C4 . 1.373(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.404(2) ?
    C6 C7 . 1.295(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.296(4) ?
    C8 H81 . 0.950(10)
                     ?
    C8 H82 . 0.950(10)
                     ?
    C10 C11 . 1.463(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.164(3) ?
    C12 H12 . 0.940(10)
                      ?
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
    C5 N1 C1 . . 114.50(16) ?
    C4 N2 C9 . . 109.96(14) ?
    C4 N2 C6 . . 128.72(16) ?
    C9 N2 C6 . . 121.29(16) ?
    C5 N3 C9 . . 110.03(15) ?
    C5 N3 C10 . . 125.63(16) ?
    C9 N3 C10 . . 124.33(16) ?
    N1 C1 C2 . . 122.72(18) ?
    N1 C1 H1 . . 118.6 ?
    C2 C1 H1 . . 118.6 ?
    C1 C2 C3 . . 122.49(17) ?
    C1 C2 Br1 . . 118.07(14) ?
    C3 C2 Br1 . . 119.43(14) ?
    C4 C3 C2 . . 114.56(16) ?
    C4 C3 H3 . . 122.7 ?
    C2 C3 H3 . . 122.7 ?
    C3 C4 N2 . . 134.39(16) ?
    C3 C4 C5 . . 119.12(16) ?
    N2 C4 C5 . . 106.49(15) ?
    N1 C5 N3 . . 125.87(16) ?
    N1 C5 C4 . . 126.59(17) ?
    N3 C5 C4 . . 107.53(15) ?
    C7 C6 N2 . . 124.62(19) ?
    C7 C6 H6 . . 117.7 ?
    N2 C6 H6 . . 117.7 ?
    C8 C7 C6 . . 178.0(3) ?
    C7 C8 H81 . . 121(2) ?
    C7 C8 H82 . . 120.7(19) ?
    H81 C8 H82 . . 118(3) ?
    O1 C9 N3 . . 127.55(18) ?
    O1 C9 N2 . . 126.48(18) ?
    N3 C9 N2 . . 105.97(15) ?
    N3 C10 C11 . . 112.56(17) ?
    N3 C10 H10A . . 109.1 ?
    C11 C10 H10A . . 109.1 ?
    N3 C10 H10B . . 109.1 ?
    C11 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.8 ?
    C12 C11 C10 . . 178.4(3) ?
    C11 C12 H12 . . 177.2(19) ?
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
    C5 N1 C1 C2 . . . . 0.0(3) ?
    N1 C1 C2 C3 . . . . 0.9(3) ?
    N1 C1 C2 Br1 . . . . -179.76(15) ?
    C1 C2 C3 C4 . . . . -0.8(3) ?
    Br1 C2 C3 C4 . . . . 179.81(12) ?
    C2 C3 C4 N2 . . . . -179.36(18) ?
    C2 C3 C4 C5 . . . . 0.0(2) ?
    C9 N2 C4 C3 . . . . 178.04(18) ?
    C6 N2 C4 C3 . . . . -0.3(3) ?
    C9 N2 C4 C5 . . . . -1.41(19) ?
    C6 N2 C4 C5 . . . . -179.75(17) ?
    C1 N1 C5 N3 . . . . 178.16(17) ?
    C1 N1 C5 C4 . . . . -0.9(3) ?
    C9 N3 C5 N1 . . . . -179.84(17) ?
    C10 N3 C5 N1 . . . . 1.8(3) ?
    C9 N3 C5 C4 . . . . -0.67(19) ?
    C10 N3 C5 C4 . . . . -179.00(16) ?
    C3 C4 C5 N1 . . . . 0.9(3) ?
    N2 C4 C5 N1 . . . . -179.58(17) ?
    C3 C4 C5 N3 . . . . -178.29(15) ?
    N2 C4 C5 N3 . . . . 1.26(18) ?
    C4 N2 C6 C7 . . . . -1.4(3) ?
    C9 N2 C6 C7 . . . . -179.6(2) ?
    C5 N3 C9 O1 . . . . 178.90(19) ?
    C10 N3 C9 O1 . . . . -2.7(3) ?
    C5 N3 C9 N2 . . . . -0.2(2) ?
    C10 N3 C9 N2 . . . . 178.17(16) ?
    C4 N2 C9 O1 . . . . -178.10(19) ?
    C6 N2 C9 O1 . . . . 0.4(3) ?
    C4 N2 C9 N3 . . . . 1.00(19) ?
    C6 N2 C9 N3 . . . . 179.49(16) ?
    C5 N3 C10 C11 . . . . 76.4(2) ?
    C9 N3 C10 C11 . . . . -101.7(2) ?
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
    C12 H12 O1 2_546 0.940(10)
                             2.220(10)
                                     3.161(3) 173(2) yes
