##############################################################################
###                                                                        ###
###        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.                                        #
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# 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     o756
_journal_page_last     o756
_journal_paper_category     QO
_journal_coeditor_code     HG2650
_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-1,3-di-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-1,3-di-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/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     9.0725(3)
_cell_length_b     18.6212(5)
_cell_length_c     7.0684(2)
_cell_angle_alpha     90.00
_cell_angle_beta     102.9950(10)
_cell_angle_gamma     90.00
_cell_volume     1163.56(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9924
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     31.8
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.656
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     3.518
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.3723
_exptl_absorpt_correction_T_max     0.6204
_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     27315
_diffrn_reflns_av_R_equivalents     0.0318
_diffrn_reflns_av_sigmaI/netI     0.0175
_diffrn_reflns_theta_min     2.55
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3383
_reflns_number_gt     2810
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0379
_refine_ls_R_factor_gt     0.0291
_refine_ls_wR_factor_gt     0.0803
_refine_ls_wR_factor_ref     0.0854
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     3383
_refine_ls_number_parameters     162
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0475P)²+0.4099P] 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     0.870
_refine_diff_density_min     -0.803
_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 0.40313(3) 0.071904(9) 0.35455(3) 0.05174(9) Uani d . 1 . .
    O O1 0.32318(15) 0.47483(7) 0.3528(2) 0.0435(3) Uani d . 1 . .
    N N1 0.12161(15) 0.24467(8) 0.3731(2) 0.0354(3) Uani d . 1 . .
    N N2 0.18505(15) 0.37028(8) 0.3651(2) 0.0326(3) Uani d . 1 . .
    N N3 0.42693(14) 0.35966(7) 0.35770(18) 0.0289(3) Uani d . 1 . .
    C C1 0.1822(2) 0.17839(9) 0.3720(2) 0.0368(4) Uani d . 1 . .
    H H1 0.1213 0.1387 0.3786 0.044 Uiso calc R 1 . .
    C C2 0.3302(2) 0.16693(8) 0.3614(2) 0.0322(3) Uani d . 1 . .
    C C3 0.43018(17) 0.22350(8) 0.3550(2) 0.0289(3) Uani d . 1 . .
    H H3 0.5302 0.2161 0.3481 0.035 Uiso calc R 1 . .
    C C4 0.21635(17) 0.29782(8) 0.3662(2) 0.0279(3) Uani d . 1 . .
    C C5 0.36927(16) 0.29091(8) 0.3596(2) 0.0251(3) Uani d . 1 . .
    C C6 0.0418(2) 0.40256(12) 0.3799(3) 0.0457(4) Uani d . 1 . .
    H H6A 0.0621 0.4471 0.4522 0.055 Uiso calc R 1 . .
    H H6B -0.0093 0.3705 0.4524 0.055 Uiso calc R 1 . .
    C C7 -0.0586(2) 0.41743(12) 0.1911(3) 0.0484(5) Uani d . 1 . .
    C C8 -0.1389(3) 0.43130(16) 0.0410(4) 0.0699(8) Uani d D 1 . .
    H H8 -0.212(3) 0.442(2) -0.073(3) 0.108(13) Uiso d D 1 . .
    C C9 0.31325(18) 0.40998(9) 0.3577(2) 0.0307(3) Uani d . 1 . .
    C C10 0.58352(18) 0.38016(10) 0.3664(3) 0.0380(4) Uani d . 1 . .
    H H10A 0.5957 0.4311 0.3946 0.046 Uiso calc R 1 . .
    H H10B 0.6068 0.3718 0.2408 0.046 Uiso calc R 1 . .
    C C11 0.68988(18) 0.33965(10) 0.5150(3) 0.0397(4) Uani d . 1 . .
    C C12 0.7772(2) 0.30575(14) 0.6294(4) 0.0559(6) Uani d D 1 . .
    H H12 0.849(2) 0.2804(13) 0.721(3) 0.070(8) 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 0.07831(18) 0.02651(10) 0.04492(13) 0.00475(8) 0.00231(10) -0.00343(6)
    O1 0.0484(7) 0.0281(6) 0.0488(7) 0.0041(5) -0.0001(6) 0.0039(5)
    N1 0.0277(6) 0.0436(8) 0.0344(7) -0.0079(6) 0.0059(5) -0.0006(6)
    N2 0.0261(6) 0.0344(7) 0.0357(7) 0.0063(5) 0.0039(5) 0.0004(5)
    N3 0.0234(6) 0.0261(6) 0.0353(6) -0.0012(4) 0.0023(5) 0.0030(5)
    C1 0.0402(9) 0.0356(8) 0.0330(8) -0.0124(7) 0.0050(7) -0.0002(6)
    C2 0.0437(9) 0.0262(7) 0.0246(7) -0.0018(6) 0.0036(6) -0.0010(5)
    C3 0.0291(7) 0.0294(7) 0.0276(7) 0.0028(5) 0.0051(6) 0.0003(5)
    C4 0.0248(7) 0.0332(7) 0.0240(6) 0.0005(5) 0.0022(5) -0.0001(5)
    C5 0.0237(6) 0.0269(7) 0.0236(6) -0.0015(5) 0.0034(5) 0.0005(5)
    C6 0.0346(9) 0.0554(11) 0.0481(10) 0.0163(8) 0.0114(8) -0.0029(9)
    C7 0.0306(9) 0.0535(11) 0.0610(12) 0.0143(8) 0.0101(8) 0.0079(9)
    C8 0.0452(13) 0.093(2) 0.0672(16) 0.0256(12) 0.0040(11) 0.0159(13)
    C9 0.0304(7) 0.0294(7) 0.0286(7) 0.0028(6) -0.0014(6) 0.0018(6)
    C10 0.0274(7) 0.0392(9) 0.0457(9) -0.0064(6) 0.0047(7) 0.0103(7)
    C11 0.0236(7) 0.0455(9) 0.0482(10) -0.0043(6) 0.0042(7) 0.0049(8)
    C12 0.0307(9) 0.0659(14) 0.0661(14) 0.0016(9) 0.0002(9) 0.0171(11)
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 . 1.8935(16) ?
    O1 C9 . 1.212(2) ?
    N1 C4 . 1.319(2) ?
    N1 C1 . 1.352(2) ?
    N2 C4 . 1.378(2) ?
    N2 C9 . 1.389(2) ?
    N2 C6 . 1.457(2) ?
    N3 C5 . 1.3842(19) ?
    N3 C9 . 1.394(2) ?
    N3 C10 . 1.459(2) ?
    C1 C2 . 1.379(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.397(2) ?
    C3 C5 . 1.375(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.405(2) ?
    C6 C7 . 1.463(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.173(3) ?
    C8 H8 . 0.948(10) ?
    C10 C11 . 1.466(2) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.179(3) ?
    C12 H12 . 0.939(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
    C4 N1 C1 . . 114.56(14) ?
    C4 N2 C9 . . 110.37(13) ?
    C4 N2 C6 . . 126.11(16) ?
    C9 N2 C6 . . 123.44(15) ?
    C5 N3 C9 . . 109.91(13) ?
    C5 N3 C10 . . 127.46(14) ?
    C9 N3 C10 . . 122.53(14) ?
    N1 C1 C2 . . 122.96(15) ?
    N1 C1 H1 . . 118.5 ?
    C2 C1 H1 . . 118.5 ?
    C1 C2 C3 . . 122.16(15) ?
    C1 C2 Br1 . . 119.74(12) ?
    C3 C2 Br1 . . 118.10(13) ?
    C5 C3 C2 . . 114.86(14) ?
    C5 C3 H3 . . 122.6 ?
    C2 C3 H3 . . 122.6 ?
    N1 C4 N2 . . 126.85(15) ?
    N1 C4 C5 . . 126.10(15) ?
    N2 C4 C5 . . 107.05(13) ?
    C3 C5 N3 . . 133.58(14) ?
    C3 C5 C4 . . 119.33(14) ?
    N3 C5 C4 . . 107.09(13) ?
    N2 C6 C7 . . 113.27(16) ?
    N2 C6 H6A . . 108.9 ?
    C7 C6 H6A . . 108.9 ?
    N2 C6 H6B . . 108.9 ?
    C7 C6 H6B . . 108.9 ?
    H6A C6 H6B . . 107.7 ?
    C8 C7 C6 . . 178.2(3) ?
    C7 C8 H8 . . 174(2) ?
    O1 C9 N2 . . 126.84(15) ?
    O1 C9 N3 . . 127.61(16) ?
    N2 C9 N3 . . 105.55(13) ?
    N3 C10 C11 . . 111.93(14) ?
    N3 C10 H10A . . 109.2 ?
    C11 C10 H10A . . 109.2 ?
    N3 C10 H10B . . 109.2 ?
    C11 C10 H10B . . 109.2 ?
    H10A C10 H10B . . 107.9 ?
    C12 C11 C10 . . 177.6(2) ?
    C11 C12 H12 . . 177.7(17) ?
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
    C4 N1 C1 C2 . . . . -1.0(2) ?
    N1 C1 C2 C3 . . . . 1.4(3) ?
    N1 C1 C2 Br1 . . . . -178.53(12) ?
    C1 C2 C3 C5 . . . . -0.2(2) ?
    Br1 C2 C3 C5 . . . . 179.73(10) ?
    C1 N1 C4 N2 . . . . 179.82(15) ?
    C1 N1 C4 C5 . . . . -0.5(2) ?
    C9 N2 C4 N1 . . . . 179.78(15) ?
    C6 N2 C4 N1 . . . . 2.9(3) ?
    C9 N2 C4 C5 . . . . 0.05(17) ?
    C6 N2 C4 C5 . . . . -176.84(15) ?
    C2 C3 C5 N3 . . . . 179.41(15) ?
    C2 C3 C5 C4 . . . . -1.2(2) ?
    C9 N3 C5 C3 . . . . 177.86(16) ?
    C10 N3 C5 C3 . . . . -5.7(3) ?
    C9 N3 C5 C4 . . . . -1.58(16) ?
    C10 N3 C5 C4 . . . . 174.83(15) ?
    N1 C4 C5 C3 . . . . 1.7(2) ?
    N2 C4 C5 C3 . . . . -178.61(13) ?
    N1 C4 C5 N3 . . . . -178.81(14) ?
    N2 C4 C5 N3 . . . . 0.92(16) ?
    C4 N2 C6 C7 . . . . -93.3(2) ?
    C9 N2 C6 C7 . . . . 90.2(2) ?
    C4 N2 C9 O1 . . . . 179.15(16) ?
    C6 N2 C9 O1 . . . . -3.9(3) ?
    C4 N2 C9 N3 . . . . -0.99(17) ?
    C6 N2 C9 N3 . . . . 175.99(15) ?
    C5 N3 C9 O1 . . . . -178.56(16) ?
    C10 N3 C9 O1 . . . . 4.8(3) ?
    C5 N3 C9 N2 . . . . 1.58(17) ?
    C10 N3 C9 N2 . . . . -175.03(14) ?
    C5 N3 C10 C11 . . . . -45.0(2) ?
    C9 N3 C10 C11 . . . . 131.00(17) ?
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
    C8 H8 O1 3_565 0.950(10)
                           2.53(2) 3.392(3) 151(3) yes
    C12 H12 N1 4_666 0.940(10)
                             2.51(2) 3.346(2) 149(2) yes
