#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226813.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_2226813
loop_
_publ_author_name
'Ouzidan, Younès'
'Rodi, Youssef Kandri'
'Zouihri, Hafid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine
 monohydrate
;
_journal_coeditor_code           CI5117
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1903
_journal_paper_doi               10.1107/S1600536810025122
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H12 Br N3, H2 O'
_chemical_formula_moiety         'C15 H12 Br N3, H2 O'
_chemical_formula_sum            'C15 H14 Br N3 O'
_chemical_formula_weight         332.20
_chemical_name_systematic
;
4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.0760(10)
_cell_angle_beta                 74.6370(10)
_cell_angle_gamma                79.7360(10)
_cell_formula_units_Z            2
_cell_length_a                   7.43630(10)
_cell_length_b                   9.42380(10)
_cell_length_c                   11.0829(2)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.3
_cell_volume                     692.022(18)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker X8 APEXII area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14314
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.969
_exptl_absorpt_correction_T_max  0.6644
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.1091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                2791
_reflns_number_total             3158
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5117.cif
_cod_data_source_block           I
_cod_database_code               2226813
_cod_database_fobs_code          2226813
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.78351(3) 0.73753(2) 0.425170(19) 0.05007(9) Uani d . 1 . .
O O1 1.1389(9) 0.1942(6) 0.8855(4) 0.0635(16) Uani d PD 0.582(14) A 1
H H11 1.028(3) 0.229(7) 0.903(7) 0.095 Uiso d PD 0.582(14) A 1
H H12 1.208(6) 0.237(6) 0.908(6) 0.095 Uiso d PD 0.582(14) A 1
O O1' 1.0501(14) 0.1260(12) 0.8987(6) 0.081(3) Uani d PD 0.418(14) A 2
H H13 1.089(17) 0.191(10) 0.917(11) 0.122 Uiso d PD 0.418(14) A 2
H H14 1.001(16) 0.059(9) 0.969(6) 0.122 Uiso d PD 0.418(14) A 2
N N1 0.61186(19) 0.78390(15) 0.79149(15) 0.0323(3) Uani d . 1 . .
N N2 0.66816(19) 0.61173(15) 1.00435(15) 0.0347(3) Uani d . 1 . .
N N3 0.82874(19) 0.41411(16) 0.93153(16) 0.0358(3) Uani d . 1 . .
C C1 0.6432(2) 0.80592(19) 0.66074(18) 0.0350(3) Uani d . 1 . .
H H1 0.5976 0.8977 0.6035 0.042 Uiso calc R 1 . .
C C2 0.7415(2) 0.6947(2) 0.61055(19) 0.0368(4) Uani d . 1 . .
C C3 0.8123(2) 0.55420(19) 0.69201(19) 0.0371(4) Uani d . 1 . .
H H3 0.8780 0.4791 0.6576 0.044 Uiso calc R 1 . .
C C4 0.7798(2) 0.53257(18) 0.82533(18) 0.0331(3) Uani d . 1 . .
C C5 0.6797(2) 0.65118(18) 0.87503(17) 0.0313(3) Uani d . 1 . .
C C6 0.5091(2) 0.90590(19) 0.84527(19) 0.0381(4) Uani d . 1 . .
H H6A 0.4210 0.9672 0.7908 0.046 Uiso calc R 1 . .
H H6B 0.4386 0.8587 0.9352 0.046 Uiso calc R 1 . .
C C7 0.6408(3) 1.0068(2) 0.8464(2) 0.0481(5) Uani d . 1 . .
H H7 0.7367 0.9607 0.8917 0.058 Uiso calc R 1 . .
C C8 0.6310(5) 1.1541(3) 0.7888(3) 0.0711(7) Uani d . 1 . .
H H8A 0.5368 1.2037 0.7427 0.085 Uiso calc R 1 . .
H H8B 0.7180 1.2105 0.7933 0.085 Uiso calc R 1 . .
C C9 0.7604(2) 0.46733(18) 1.03315(18) 0.0339(3) Uani d . 1 . .
C C10 0.7799(2) 0.37743(19) 1.17031(18) 0.0354(4) Uani d . 1 . .
C C11 0.7034(3) 0.4364(2) 1.2724(2) 0.0422(4) Uani d . 1 . .
H H11A 0.6407 0.5342 1.2535 0.051 Uiso calc R 1 . .
C C12 0.7194(3) 0.3511(3) 1.4024(2) 0.0498(5) Uani d . 1 . .
H H12A 0.6678 0.3919 1.4699 0.060 Uiso calc R 1 . .
C C13 0.8118(3) 0.2058(3) 1.4313(2) 0.0522(5) Uani d . 1 . .
H H13A 0.8219 0.1481 1.5184 0.063 Uiso calc R 1 . .
C C14 0.8890(3) 0.1467(2) 1.3309(2) 0.0509(5) Uani d . 1 . .
H H14A 0.9520 0.0490 1.3505 0.061 Uiso calc R 1 . .
C C15 0.8741(3) 0.2306(2) 1.2012(2) 0.0436(4) Uani d . 1 . .
H H15 0.9269 0.1892 1.1342 0.052 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'
Br Br -0.2901 2.4595 '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
H11 O1 H12 . . 110.6(18) ?
H12 O1 H13 . . 101(6) ?
H11 O1' H14 . . 114(9) ?
H13 O1' H14 . . 110.2(19) ?
C1 N1 C5 . . 119.78(14) ?
C1 N1 C6 . . 120.89(14) ?
C5 N1 C6 . . 119.29(14) ?
C5 N2 C9 . . 101.46(14) ?
C9 N3 C4 . . 103.09(13) ?
N1 C1 C2 . . 120.95(16) ?
N1 C1 H1 . . 119.5 ?
C2 C1 H1 . . 119.5 ?
C1 C2 C3 . . 122.00(17) ?
C1 C2 Br1 . . 117.99(14) ?
C3 C2 Br1 . . 120.01(13) ?
C4 C3 C2 . . 116.73(15) ?
C4 C3 H3 . . 121.6 ?
C2 C3 H3 . . 121.6 ?
N3 C4 C3 . . 132.84(15) ?
N3 C4 C5 . . 106.85(15) ?
C3 C4 C5 . . 120.29(15) ?
N2 C5 N1 . . 128.19(15) ?
N2 C5 C4 . . 111.57(14) ?
N1 C5 C4 . . 120.24(16) ?
C7 C6 N1 . . 110.95(14) ?
C7 C6 H6A . . 109.4 ?
N1 C6 H6A . . 109.4 ?
C7 C6 H6B . . 109.4 ?
N1 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C8 C7 C6 . . 124.3(2) ?
C8 C7 H7 . . 117.8 ?
C6 C7 H7 . . 117.8 ?
C7 C8 H8A . . 120.0 ?
C7 C8 H8B . . 120.0 ?
H8A C8 H8B . . 120.0 ?
N3 C9 N2 . . 117.02(16) ?
N3 C9 C10 . . 122.81(15) ?
N2 C9 C10 . . 120.17(16) ?
C11 C10 C15 . . 118.49(18) ?
C11 C10 C9 . . 120.61(16) ?
C15 C10 C9 . . 120.90(17) ?
C12 C11 C10 . . 120.79(18) ?
C12 C11 H11A . . 119.6 ?
C10 C11 H11A . . 119.6 ?
C13 C12 C11 . . 120.0(2) ?
C13 C12 H12A . . 120.0 ?
C11 C12 H12A . . 120.0 ?
C14 C13 C12 . . 119.7(2) ?
C14 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
C13 C14 C15 . . 120.79(19) ?
C13 C14 H14A . . 119.6 ?
C15 C14 H14A . . 119.6 ?
C14 C15 C10 . . 120.2(2) ?
C14 C15 H15 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
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 . 1.8887(19) ?
O1 H11 . 0.834(10) ?
O1 H12 . 0.838(10) ?
O1 H13 . 0.43(12) ?
O1' H11 . 0.97(5) ?
O1' H13 . 0.836(10) ?
O1' H14 . 0.838(10) ?
N1 C1 . 1.346(2) ?
N1 C5 . 1.354(2) ?
N1 C6 . 1.489(2) ?
N2 C5 . 1.322(2) ?
N2 C9 . 1.372(2) ?
N3 C9 . 1.344(2) ?
N3 C4 . 1.365(2) ?
C1 C2 . 1.375(2) ?
C1 H1 . 0.93 ?
C2 C3 . 1.398(2) ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.433(2) ?
C6 C7 . 1.487(3) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.291(3) ?
C7 H7 . 0.93 ?
C8 H8A . 0.93 ?
C8 H8B . 0.93 ?
C9 C10 . 1.470(3) ?
C10 C11 . 1.389(3) ?
C10 C15 . 1.396(2) ?
C11 C12 . 1.388(3) ?
C11 H11A . 0.93 ?
C12 C13 . 1.379(3) ?
C12 H12A . 0.93 ?
C13 C14 . 1.374(3) ?
C13 H13A . 0.93 ?
C14 C15 . 1.381(3) ?
C14 H14A . 0.93 ?
C15 H15 . 0.93 ?
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
O1 H11 N3 . 0.830(10) 2.14(3) 2.887(4) 149(5) yes
O1 H12 N2 2_767 0.840(10) 2.41(2) 3.229(7) 165(5) no
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 . . . . 0.8(2) ?
C6 N1 C1 C2 . . . . 178.59(16) ?
N1 C1 C2 C3 . . . . 0.4(3) ?
N1 C1 C2 Br1 . . . . -178.60(12) ?
C1 C2 C3 C4 . . . . -0.4(3) ?
Br1 C2 C3 C4 . . . . 178.57(12) ?
C9 N3 C4 C3 . . . . 177.66(18) ?
C9 N3 C4 C5 . . . . -0.79(17) ?
C2 C3 C4 N3 . . . . -178.94(17) ?
C2 C3 C4 C5 . . . . -0.7(2) ?
C9 N2 C5 N1 . . . . 179.89(16) ?
C9 N2 C5 C4 . . . . -0.63(17) ?
C1 N1 C5 N2 . . . . 177.63(16) ?
C6 N1 C5 N2 . . . . -0.2(3) ?
C1 N1 C5 C4 . . . . -1.8(2) ?
C6 N1 C5 C4 . . . . -179.69(15) ?
N3 C4 C5 N2 . . . . 0.95(19) ?
C3 C4 C5 N2 . . . . -177.74(14) ?
N3 C4 C5 N1 . . . . -179.52(14) ?
C3 C4 C5 N1 . . . . 1.8(2) ?
C1 N1 C6 C7 . . . . -91.40(19) ?
C5 N1 C6 C7 . . . . 86.45(19) ?
N1 C6 C7 C8 . . . . 124.1(2) ?
C4 N3 C9 N2 . . . . 0.46(19) ?
C4 N3 C9 C10 . . . . 179.96(15) ?
C5 N2 C9 N3 . . . . 0.11(19) ?
C5 N2 C9 C10 . . . . -179.41(14) ?
N3 C9 C10 C11 . . . . -178.67(16) ?
N2 C9 C10 C11 . . . . 0.8(2) ?
N3 C9 C10 C15 . . . . 0.8(2) ?
N2 C9 C10 C15 . . . . -179.71(15) ?
C15 C10 C11 C12 . . . . -0.3(3) ?
C9 C10 C11 C12 . . . . 179.18(17) ?
C10 C11 C12 C13 . . . . -0.1(3) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C12 C13 C14 C15 . . . . -0.4(3) ?
C13 C14 C15 C10 . . . . 0.0(3) ?
C11 C10 C15 C14 . . . . 0.4(3) ?
C9 C10 C15 C14 . . . . -179.12(16) ?
