#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/73/7117313.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_7117313
loop_
_publ_author_name
'Ahmed Kamal'
'Chada Narsimha Reddy'
'Malasala Satyaveni'
'D. Chandrasekhar'
'Jagadeesh Babu Nanubolu'
'Kiran Kumar Singarapud'
'Ram Awatar Maurya'
_publ_section_title
;
 Cu(OAc)2-Et3N mediated oxidative coupling of alpha-azido ketones with
 pyridinium ylides: utilizing in situ generated imines for regioselective
 synthesis of imidazo[1,2-a]pyridines
;
_journal_name_full               Chem.Commun.
_journal_page_first              10475
_journal_paper_doi               10.1039/C5cc00815H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C23 H16 N2 O3'
_chemical_formula_sum            'C23 H16 N2 O3'
_chemical_formula_weight         368.38
_chemical_name_systematic
; 
 6-acetylimidazo[1,2-a]pyridine-2,3-diyl)bis(phenylmethanone)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-16 deposited with the CCDC.
2015-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.035(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.382(3)
_cell_length_b                   8.7432(9)
_cell_length_c                   15.9370(16)
_cell_measurement_reflns_used    7483
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.46
_cell_volume                     3648.4(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16935
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0341
_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)+(0.0540P)²+1.1122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                2751
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00815h2.cif
_cod_data_source_block           ay05m
_cod_original_cell_volume        3648.4(6)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               7117313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.37173(4) 0.51950(13) 0.22665(6) 0.0680(3) Uani 1 1 d . . .
N1 N 0.46838(4) 0.84659(12) 0.12637(7) 0.0488(3) Uani 1 1 d . . .
C17 C 0.38796(5) 0.90572(15) 0.18830(8) 0.0484(3) Uani 1 1 d . . .
O2 O 0.40479(4) 1.02507(12) 0.22061(7) 0.0648(3) Uani 1 1 d . . .
C19 C 0.30592(5) 0.78782(15) 0.11932(8) 0.0520(3) Uani 1 1 d . . .
H19 H 0.3230 0.7483 0.0765 0.062 Uiso 1 1 calc R . .
C10 C 0.38131(5) 0.52841(15) 0.15393(9) 0.0522(3) Uani 1 1 d . . .
C4 C 0.49226(5) 0.98617(16) 0.12947(8) 0.0514(3) Uani 1 1 d . . .
H4 H 0.4774 1.0703 0.1525 0.062 Uiso 1 1 calc R . .
N2 N 0.45969(4) 0.59652(13) 0.09475(8) 0.0595(3) Uani 1 1 d . . .
C11 C 0.35852(5) 0.42421(15) 0.08651(9) 0.0497(3) Uani 1 1 d . . .
C7 C 0.48957(5) 0.71893(15) 0.09192(9) 0.0551(3) Uani 1 1 d . . .
C18 C 0.33259(5) 0.86992(15) 0.18506(8) 0.0477(3) Uani 1 1 d . . .
C3 C 0.53792(5) 1.00055(16) 0.09860(9) 0.0542(3) Uani 1 1 d . . .
C9 C 0.41889(5) 0.64541(15) 0.13147(9) 0.0507(3) Uani 1 1 d . . .
C8 C 0.42169(5) 0.80005(15) 0.15107(8) 0.0480(3) Uani 1 1 d . . .
O1 O 0.60477(5) 1.15940(14) 0.06830(9) 0.0865(4) Uani 1 1 d . . .
C16 C 0.33732(5) 0.28686(16) 0.10915(10) 0.0592(4) Uani 1 1 d . . .
H16 H 0.3391 0.2596 0.1658 0.071 Uiso 1 1 calc R . .
C12 C 0.35573(5) 0.46252(16) 0.00137(9) 0.0556(3) Uani 1 1 d . . .
H12 H 0.3700 0.5537 -0.0145 0.067 Uiso 1 1 calc R . .
C6 C 0.53639(5) 0.73395(18) 0.05978(11) 0.0664(4) Uani 1 1 d . . .
H6 H 0.5513 0.6501 0.0365 0.080 Uiso 1 1 calc R . .
C23 C 0.30598(6) 0.93204(17) 0.24694(9) 0.0578(4) Uani 1 1 d . . .
H23 H 0.3233 0.9891 0.2907 0.069 Uiso 1 1 calc R . .
C20 C 0.25401(5) 0.76472(17) 0.11747(10) 0.0596(4) Uani 1 1 d . . .
H20 H 0.2364 0.7081 0.0739 0.072 Uiso 1 1 calc R . .
C22 C 0.25425(6) 0.9098(2) 0.24396(10) 0.0664(4) Uani 1 1 d . . .
H22 H 0.2367 0.9521 0.2855 0.080 Uiso 1 1 calc R . .
C21 C 0.22826(6) 0.82513(18) 0.17982(10) 0.0633(4) Uani 1 1 d . . .
H21 H 0.1933 0.8088 0.1786 0.076 Uiso 1 1 calc R . .
C13 C 0.33183(6) 0.36603(19) -0.05975(10) 0.0653(4) Uani 1 1 d . . .
H13 H 0.3298 0.3921 -0.1166 0.078 Uiso 1 1 calc R . .
C1 C 0.56588(6) 1.14979(17) 0.10165(10) 0.0618(4) Uani 1 1 d . . .
C5 C 0.55976(5) 0.87201(17) 0.06296(10) 0.0640(4) Uani 1 1 d . . .
H5 H 0.5907 0.8825 0.0413 0.077 Uiso 1 1 calc R . .
C2 C 0.54610(7) 1.28332(18) 0.14564(11) 0.0746(5) Uani 1 1 d . . .
H2A H 0.5698 1.3666 0.1462 0.112 Uiso 1 1 calc R . .
H2B H 0.5420 1.2554 0.2027 0.112 Uiso 1 1 calc R . .
H2C H 0.5137 1.3141 0.1164 0.112 Uiso 1 1 calc R . .
C15 C 0.31378(6) 0.19155(18) 0.04800(11) 0.0689(4) Uani 1 1 d . . .
H15 H 0.2997 0.0998 0.0635 0.083 Uiso 1 1 calc R . .
C14 C 0.31092(6) 0.23059(19) -0.03567(11) 0.0690(4) Uani 1 1 d . . .
H14 H 0.2948 0.1653 -0.0766 0.083 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N1 C7 121.55(11) . .
C4 N1 C8 131.70(11) . .
C7 N1 C8 106.73(11) . .
O2 C17 C8 120.26(12) . .
O2 C17 C18 119.87(11) . .
C8 C17 C18 119.85(12) . .
C20 C19 C18 120.08(13) . .
O3 C10 C11 122.57(13) . .
O3 C10 C9 119.43(13) . .
C11 C10 C9 117.97(12) . .
C3 C4 N1 119.47(13) . .
C7 N2 C9 105.39(11) . .
C12 C11 C16 119.09(14) . .
C12 C11 C10 121.91(12) . .
C16 C11 C10 118.94(12) . .
N2 C7 N1 111.29(11) . .
N2 C7 C6 129.74(13) . .
N1 C7 C6 118.97(13) . .
C19 C18 C23 118.98(13) . .
C19 C18 C17 122.63(11) . .
C23 C18 C17 118.18(12) . .
C4 C3 C5 119.60(13) . .
C4 C3 C1 121.53(13) . .
C5 C3 C1 118.87(13) . .
N2 C9 C8 112.41(12) . .
N2 C9 C10 118.13(11) . .
C8 C9 C10 129.05(12) . .
C9 C8 N1 104.15(11) . .
C9 C8 C17 133.68(12) . .
N1 C8 C17 122.17(12) . .
C15 C16 C11 120.11(14) . .
C13 C12 C11 120.39(14) . .
C5 C6 C7 119.22(14) . .
C22 C23 C18 120.41(14) . .
C21 C20 C19 120.29(14) . .
C23 C22 C21 120.32(14) . .
C22 C21 C20 119.89(14) . .
C14 C13 C12 119.42(15) . .
O1 C1 C2 121.02(15) . .
O1 C1 C3 119.03(15) . .
C2 C1 C3 119.95(13) . .
C6 C5 C3 121.19(13) . .
C14 C15 C16 120.43(15) . .
C15 C14 C13 120.55(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C10 1.2185(16) .
N1 C4 1.3715(17) .
N1 C7 1.3910(16) .
N1 C8 1.3988(16) .
C17 O2 1.2228(16) .
C17 C8 1.4583(18) .
C17 C18 1.4888(18) .
C19 C20 1.3811(19) .
C19 C18 1.3884(19) .
C10 C11 1.479(2) .
C10 C9 1.4983(19) .
C4 C3 1.3616(19) .
N2 C7 1.3332(18) .
N2 C9 1.3557(17) .
C11 C12 1.3907(19) .
C11 C16 1.3908(19) .
C7 C6 1.4001(19) .
C18 C23 1.3891(18) .
C3 C5 1.413(2) .
C3 C1 1.497(2) .
C9 C8 1.3875(19) .
O1 C1 1.2150(18) .
C16 C15 1.372(2) .
C12 C13 1.381(2) .
C6 C5 1.354(2) .
C23 C22 1.374(2) .
C20 C21 1.376(2) .
C22 C21 1.375(2) .
C13 C14 1.380(2) .
C1 C2 1.489(2) .
C15 C14 1.369(2) .
