#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/27/7112704.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7112704
loop_
_publ_author_name
'Sucunza, David'
'Samadi, Abdelouahid'
'Chioua, Mourad'
'Silva, Daniel B.'
'Yunta, Cristina'
'Infantes, Lourdes'
'Carmo Carreiras, M.'
'Soriano, Elena'
'Marco-Contelles, José'
_publ_section_title
;
 A practical two-step synthesis of imidazo[1,2-a]pyridines from
 N-(prop-2-yn-1-yl)pyridin-2-amines.
;
_journal_issue                   17
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5043
_journal_page_last               5045
_journal_paper_doi               10.1039/c1cc10641d
_journal_volume                  47
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H7 Cl1 N4 O1'
_chemical_formula_sum            'C11 H7 Cl N4 O'
_chemical_formula_weight         246.66
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-07-22T18:35:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                82.408(2)
_cell_angle_beta                 81.742(2)
_cell_angle_gamma                82.153(2)
_cell_formula_units_Z            2
_cell_length_a                   5.9010(4)
_cell_length_b                   8.9910(7)
_cell_length_c                   10.1390(8)
_cell_measurement_reflns_used    4784
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      64.89
_cell_measurement_theta_min      4.44
_cell_volume                     523.89(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_radiation_monochromator  'Mirrors, multilayer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5676
_diffrn_reflns_theta_full        65.97
_diffrn_reflns_theta_max         65.97
_diffrn_reflns_theta_min         4.44
_exptl_absorpt_coefficient_mu    3.142
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.5440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.734
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.734
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1281P)²+0.7995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                1543
_reflns_number_total             1683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10641d.txt
_cod_data_source_block           dsb48
_cod_original_formula_sum        'C11 H7 Cl1 N4 O1'
_cod_database_code               7112704
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
C2 C 0.0004(5) -0.1629(3) 0.3706(3) 0.0271(6) Uani 1 1 d
C3 C 0.1381(4) -0.1219(2) 0.2373(2) 0.0217(5) Uani 1 1 d
C5 C 0.1208(4) -0.1820(3) 0.0042(2) 0.0234(6) Uani 1 1 d
C6 C -0.0002(4) -0.2671(3) -0.0690(2) 0.0241(6) Uani 1 1 d
C7 C -0.1824(4) -0.3406(3) -0.0065(3) 0.0251(6) Uani 1 1 d
C8 C -0.2546(4) -0.3448(3) 0.1316(2) 0.0233(5) Uani 1 1 d
C9 C -0.1320(4) -0.2710(3) 0.2074(2) 0.0221(5) Uani 1 1 d
C11 C -0.2942(5) -0.3488(3) 0.4443(3) 0.0303(6) Uani 1 1 d
C31 C 0.3129(4) -0.0399(3) 0.2124(2) 0.0237(6) Uani 1 1 d
C61 C 0.0759(4) -0.2682(3) -0.2092(3) 0.0268(6) Uani 1 1 d
C81 C -0.4546(4) -0.4144(3) 0.1884(2) 0.0252(6) Uani 1 1 d
N1 N -0.1527(3) -0.2633(2) 0.3383(2) 0.0241(5) Uani 1 1 d
N4 N 0.0413(3) -0.1895(2) 0.14199(19) 0.0217(5) Uani 1 1 d
N61 N 0.1397(4) -0.2728(3) -0.3217(2) 0.0332(6) Uani 1 1 d
N81 N -0.6206(4) -0.4692(2) 0.2278(2) 0.0310(5) Uani 1 1 d
O51 O 0.2773(3) -0.1080(2) -0.04401(17) 0.0303(5) Uani 1 1 d
Cl31 Cl 0.40086(10) 0.02877(6) 0.34609(5) 0.0287(3) Uani 1 1 d
H11A H -0.294(5) -0.447(4) 0.420(3) 0.030(7) Uiso 1 1 d
H2A H 0.095(4) -0.213(3) 0.435(3) 0.018(6) Uiso 1 1 d
H11B H -0.224(5) -0.356(3) 0.525(3) 0.029(7) Uiso 1 1 d
H2B H -0.088(5) -0.074(3) 0.401(3) 0.023(6) Uiso 1 1 d
H7 H -0.263(4) -0.390(3) -0.057(3) 0.016(6) Uiso 1 1 d
H31 H 0.398(5) -0.015(3) 0.125(3) 0.038(8) Uiso 1 1 d
H11C H -0.452(7) -0.301(4) 0.458(3) 0.053(10) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
N1 C2 C3 102.81(19)
N1 C2 H2A 110.7(15)
C3 C2 H2A 112.2(15)
N1 C2 H2B 110.1(16)
C3 C2 H2B 109.3(16)
H2A C2 H2B 111(2)
C31 C3 N4 126.8(2)
C31 C3 C2 127.4(2)
N4 C3 C2 105.76(19)
O51 C5 N4 120.4(2)
O51 C5 C6 125.7(2)
N4 C5 C6 113.9(2)
C7 C6 C61 121.8(2)
C7 C6 C5 121.2(2)
C61 C6 C5 117.0(2)
C6 C7 C8 122.5(2)
C6 C7 H7 119.6(16)
C8 C7 H7 117.9(16)
C9 C8 C7 117.8(2)
C9 C8 C81 122.6(2)
C7 C8 C81 119.5(2)
N1 C9 N4 110.1(2)
N1 C9 C8 130.9(2)
N4 C9 C8 119.0(2)
N1 C11 H11A 108.4(17)
N1 C11 H11B 107.4(17)
H11A C11 H11B 110(2)
N1 C11 H11C 112(2)
H11A C11 H11C 109(3)
H11B C11 H11C 110(3)
C3 C31 Cl31 118.13(19)
C3 C31 H31 125.3(19)
Cl31 C31 H31 116.5(19)
N61 C61 C6 178.3(3)
N81 C81 C8 176.3(3)
C9 N1 C11 127.3(2)
C9 N1 C2 111.52(19)
C11 N1 C2 121.0(2)
C9 N4 C5 125.4(2)
C9 N4 C3 109.52(19)
C5 N4 C3 124.99(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N1 1.458(3)
C2 C3 1.503(3)
C2 H2A 0.95(3)
C2 H2B 0.96(3)
C3 C31 1.325(4)
C3 N4 1.427(3)
C5 O51 1.219(3)
C5 N4 1.404(3)
C5 C6 1.449(3)
C6 C7 1.372(4)
C6 C61 1.429(3)
C7 C8 1.402(4)
C7 H7 0.94(3)
C8 C9 1.406(3)
C8 C81 1.424(3)
C9 N1 1.325(3)
C9 N4 1.380(3)
C11 N1 1.464(3)
C11 H11A 0.95(3)
C11 H11B 0.96(3)
C11 H11C 0.97(4)
C31 Cl31 1.731(2)
C31 H31 0.97(3)
C61 N61 1.153(3)
C81 N81 1.153(3)
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
N1 C2 C3 C31 -175.4(2)
N1 C2 C3 N4 4.8(2)
O51 C5 C6 C7 -176.6(2)
N4 C5 C6 C7 3.0(3)
O51 C5 C6 C61 2.2(4)
N4 C5 C6 C61 -178.24(19)
C61 C6 C7 C8 177.9(2)
C5 C6 C7 C8 -3.4(4)
C6 C7 C8 C9 -0.5(3)
C6 C7 C8 C81 175.8(2)
C7 C8 C9 N1 -175.9(2)
C81 C8 C9 N1 8.0(4)
C7 C8 C9 N4 4.5(3)
C81 C8 C9 N4 -171.6(2)
N4 C3 C31 Cl31 -179.44(17)
C2 C3 C31 Cl31 0.8(3)
C7 C6 C61 N61 -74(9)
C5 C6 C61 N61 107(9)
C9 C8 C81 N81 151(4)
C7 C8 C81 N81 -25(4)
N4 C9 N1 C11 -171.5(2)
C8 C9 N1 C11 8.9(4)
N4 C9 N1 C2 4.3(3)
C8 C9 N1 C2 -175.3(2)
C3 C2 N1 C9 -5.6(3)
C3 C2 N1 C11 170.5(2)
N1 C9 N4 C5 175.2(2)
C8 C9 N4 C5 -5.1(3)
N1 C9 N4 C3 -0.9(3)
C8 C9 N4 C3 178.7(2)
O51 C5 N4 C9 -179.1(2)
C6 C5 N4 C9 1.3(3)
O51 C5 N4 C3 -3.5(3)
C6 C5 N4 C3 176.9(2)
C31 C3 N4 C9 177.6(2)
C2 C3 N4 C9 -2.6(2)
C31 C3 N4 C5 1.4(4)
C2 C3 N4 C5 -178.8(2)
