Intramolecular H-bonding interaction in angular 3-pi-EWG substituted imidazo[1,2-a]pyridines contributes to conformational preference
Manuel Velazquez-Ponce; Hector Salgado-Zamora; Hugo A Jimenez-Vazquez; Maria Elena Campos-Aldrete; Rogelio Jimenez; Humberto Cervantes; Taibi Ben Hadda; Chemistry Central Journal 7 (2013) 20–; doi:10.1186/1752-153X-7-20

data_1547260
_publ_section_title
;
 Intramolecular H-bonding interaction in angular 3-pi-EWG substituted
 imidazo[1,2-a]pyridines contributes to conformational preference
;
_journal_name_full               'Chemistry Central Journal'
_journal_page_first              20
_journal_paper_doi               10.1186/1752-153X-7-20
_journal_volume                  7
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H9 N3 O1'
_chemical_formula_sum            'C13 H9 N3 O'
_chemical_formula_weight         223.23
_chemical_name_systematic
;
 3-nitroso-2-phenylimidazo[1,2-a]pyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-09-11T12:55:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.433(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8388(3)
_cell_length_b                   8.8885(3)
_cell_length_c                   22.1827(7)
_cell_measurement_reflns_used    6974
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      32.3166
_cell_measurement_theta_min      2.4701
_cell_measurement_wavelength     0.71073
_cell_volume                     2101.76(12)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.2257
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.019058656
_diffrn_orient_matrix_UB_12      -0.0039820177
_diffrn_orient_matrix_UB_13      -0.0322599203
_diffrn_orient_matrix_UB_21      0.0039596999
_diffrn_orient_matrix_UB_22      -0.0796071429
_diffrn_orient_matrix_UB_23      0.001449501
_diffrn_orient_matrix_UB_31      -0.0636228578
_diffrn_orient_matrix_UB_32      -0.0036937555
_diffrn_orient_matrix_UB_33      0.0035973288
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16558
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         32.39
_diffrn_reflns_theta_min         2.47
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_correction_T_min  0.9359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0754
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.8360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.134
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                4149
_reflns_number_total             6450
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            13065_2012_625_MOESM1_ESM.cif
_cod_data_source_block           0003-hjsza
_cod_original_cell_volume        2101.76(11)
_cod_database_code               1547260