#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/79/4027925.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_4027925
loop_
_publ_author_name
'Darapaneni Chandra Mohan'
'Sadu Nageswara Rao'
'Subbarayappa Adimurthy'
_publ_section_title
;
 Synthesis of Imidazo[1,2-a]pyridines: "Water-Mediated" Hydroamination and
 Silver-Catalyzed Aminooxygenation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1266
_journal_page_last               1272
_journal_paper_doi               10.1021/jo3025303
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H12 N2 O2'
_chemical_formula_weight         252.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.666(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.742(6)
_cell_length_b                   6.730(4)
_cell_length_c                   18.736(11)
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.34
_cell_volume                     1217.4(13)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.902
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5173
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       plates
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1343P)²+0.0454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1913
_refine_ls_wR_factor_ref         0.1997
_reflns_number_gt                1734
_reflns_number_total             2113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3025303_si_001.cif
_cod_data_source_block           711cmm
_cod_database_code               4027925
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'
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_calc_flag
O1 O 0.70871(16) 0.8244(2) 0.04831(9) 0.0327(5) Uani 1 d
O2 O 1.02673(18) 0.3194(3) -0.18042(10) 0.0421(5) Uani 1 d
N1 N 0.87809(16) 0.5341(3) -0.07505(9) 0.0258(5) Uani 1 d
N2 N 0.86468(19) 0.8684(3) -0.06834(11) 0.0326(5) Uani 1 d
C1 C 0.4951(2) 1.1050(4) 0.12180(12) 0.0338(6) Uani 1 d
C2 C 0.4766(3) 1.2814(4) 0.15739(14) 0.0376(6) Uani 1 d
C3 C 0.5722(2) 1.3410(4) 0.21408(14) 0.0363(6) Uani 1 d
C4 C 0.6867(2) 1.2246(4) 0.23464(14) 0.0380(6) Uani 1 d
C5 C 0.7060(2) 1.0491(4) 0.19930(13) 0.0358(6) Uani 1 d
C6 C 0.6099(2) 0.9867(3) 0.14231(12) 0.0292(6) Uani 1 d
C7 C 0.6284(3) 0.7923(4) 0.10682(15) 0.0357(6) Uani 1 d
C8 C 0.7500(2) 0.6581(3) 0.01626(11) 0.0273(5) Uani 1 d
C9 C 0.7229(2) 0.4660(4) 0.03316(13) 0.0330(6) Uani 1 d
C10 C 0.7769(2) 0.3078(4) -0.00385(14) 0.0331(6) Uani 1 d
C11 C 0.8544(2) 0.3406(3) -0.05690(13) 0.0297(6) Uani 1 d
C12 C 0.8298(2) 0.6946(3) -0.04069(12) 0.0267(5) Uani 1 d
C13 C 0.9371(2) 0.8166(4) -0.12168(14) 0.0359(6) Uani 1 d
C14 C 0.9490(2) 0.6128(4) -0.12853(12) 0.0308(6) Uani 1 d
C15 C 1.0192(2) 0.5010(4) -0.17735(13) 0.0346(6) Uani 1 d
H1 H 0.425(3) 1.062(4) 0.0796(16) 0.049(7) Uiso 1 d
H2 H 0.389(3) 1.354(4) 0.1407(15) 0.047(7) Uiso 1 d
H3 H 0.561(3) 1.457(4) 0.2396(14) 0.038(7) Uiso 1 d
H4 H 0.755(3) 1.265(4) 0.2748(16) 0.039(7) Uiso 1 d
H5 H 0.789(3) 0.971(4) 0.2129(14) 0.039(7) Uiso 1 d
H7B H 0.541(3) 0.738(3) 0.0852(15) 0.034(6) Uiso 1 d
H7A H 0.681(3) 0.694(4) 0.1436(17) 0.052(8) Uiso 1 d
H9 H 0.672(3) 0.433(4) 0.0726(15) 0.047(7) Uiso 1 d
H10 H 0.760(3) 0.180(4) 0.0072(15) 0.037(7) Uiso 1 d
H11 H 0.894(3) 0.245(4) -0.0811(13) 0.026(6) Uiso 1 d
H13 H 0.979(3) 0.921(4) -0.1510(15) 0.047(7) Uiso 1 d
H15 H 1.060(3) 0.585(5) -0.2124(18) 0.059(9) Uiso 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O1 C7 115.75(17)
C12 N1 C11 123.42(19)
C12 N1 C14 105.74(19)
C11 N1 C14 130.83(19)
C12 N2 C13 104.27(19)
C6 C1 C2 120.7(2)
C6 C1 H1 119.0(15)
C2 C1 H1 120.3(15)
C3 C2 C1 120.2(2)
C3 C2 H2 124.2(16)
C1 C2 H2 115.5(17)
C4 C3 C2 119.4(2)
C4 C3 H3 118.8(15)
C2 C3 H3 121.9(15)
C3 C4 C5 120.7(2)
C3 C4 H4 120.3(15)
C5 C4 H4 119.0(15)
C4 C5 C6 120.5(2)
C4 C5 H5 120.0(15)
C6 C5 H5 119.5(15)
C1 C6 C5 118.5(2)
C1 C6 C7 121.5(2)
C5 C6 C7 120.0(2)
O1 C7 C6 108.47(18)
O1 C7 H7B 106.0(16)
C6 C7 H7B 111.6(15)
O1 C7 H7A 109.2(17)
C6 C7 H7A 110.0(16)
H7B C7 H7A 112(2)
O1 C8 C9 126.9(2)
O1 C8 C12 114.43(19)
C9 C8 C12 118.63(19)
C8 C9 C10 120.3(2)
C8 C9 H9 121.7(17)
C10 C9 H9 117.9(17)
C11 C10 C9 121.5(2)
C11 C10 H10 117.4(18)
C9 C10 H10 121.1(18)
C10 C11 N1 118.0(2)
C10 C11 H11 125.1(16)
N1 C11 H11 116.9(16)
N2 C12 N1 112.6(2)
N2 C12 C8 129.2(2)
N1 C12 C8 118.14(19)
N2 C13 C14 112.6(2)
N2 C13 H13 121.0(16)
C14 C13 H13 126.4(16)
C13 C14 N1 104.74(19)
C13 C14 C15 129.4(2)
N1 C14 C15 125.9(2)
O2 C15 C14 126.3(2)
O2 C15 H15 120.3(18)
C14 C15 H15 113.3(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.356(3)
O1 C7 1.445(3)
O2 C15 1.227(3)
N1 C12 1.372(3)
N1 C11 1.373(3)
N1 C14 1.395(3)
N2 C12 1.341(3)
N2 C13 1.344(3)
C1 C6 1.385(3)
C1 C2 1.385(3)
C1 H1 1.01(3)
C2 C3 1.376(4)
C2 H2 0.99(3)
C3 C4 1.375(4)
C3 H3 0.93(3)
C4 C5 1.379(3)
C4 H4 0.98(3)
C5 C6 1.388(3)
C5 H5 0.97(3)
C6 C7 1.490(3)
C7 H7B 0.96(3)
C7 H7A 1.04(3)
C8 C9 1.365(3)
C8 C12 1.423(3)
C9 C10 1.410(3)
C9 H9 0.97(3)
C10 C11 1.344(3)
C10 H10 0.90(3)
C11 H11 0.90(3)
C13 C14 1.384(4)
C13 H13 1.01(3)
C14 C15 1.427(3)
C15 H15 0.99(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13680202
