#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:52:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178448 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/69/4026979.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_4026979
loop_
_publ_author_name
'Ru-Long Yan'
'Hao Yan'
'Chao Ma'
'Zhi-Yong Ren'
'Xi-Ai Gao'
'Guo-Sheng Huang'
'Yong-Min Liang'
_publ_section_title
;
 Cu(I)-Catalyzed Synthesis of Imidazo[1,2-a]pyridines from Aminopyridines
 and Nitroolefins Using Air as the Oxidant
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2024
_journal_page_last               2028
_journal_paper_doi               10.1021/jo202447p
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C14 H11 N3 O2'
_chemical_formula_weight         253.26
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 120.519(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.247(7)
_cell_length_b                   7.550(3)
_cell_length_c                   18.304(10)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      2.34
_cell_volume                     2410.4(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8363
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0505
_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)+(0.0689P)²+0.5697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                1617
_reflns_number_total             2233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202447p_si_002.cif
_cod_data_source_block           c2c
_cod_original_cell_volume        2410.4(17)
_cod_database_code               4026979
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
N3 N 0.08274(8) 0.3831(2) 0.02444(10) 0.0374(4) Uani 1 1 d .
N2 N 0.13888(9) 0.6447(2) 0.08273(10) 0.0395(4) Uani 1 1 d .
C13 C 0.10822(10) 0.5443(3) 0.01230(12) 0.0369(5) Uani 1 1 d .
C6 C 0.16709(10) 0.6199(3) 0.22850(12) 0.0381(5) Uani 1 1 d .
O2 O 0.04160(10) 0.1238(2) 0.09842(11) 0.0674(5) Uani 1 1 d .
C7 C 0.13467(11) 0.5486(3) 0.14228(12) 0.0375(5) Uani 1 1 d .
N1 N 0.07542(10) 0.2529(2) 0.14220(12) 0.0472(5) Uani 1 1 d .
C8 C 0.09941(11) 0.3871(3) 0.10823(12) 0.0389(5) Uani 1 1 d .
C5 C 0.15252(12) 0.7952(3) 0.23844(14) 0.0445(5) Uani 1 1 d .
H5 H 0.1203 0.8627 0.1909 0.053 Uiso 1 1 calc R
O1 O 0.08771(11) 0.2711(2) 0.21467(11) 0.0712(5) Uani 1 1 d .
C12 C 0.10221(11) 0.5829(3) -0.06614(12) 0.0434(5) Uani 1 1 d .
C9 C 0.05240(12) 0.2564(3) -0.03784(14) 0.0480(5) Uani 1 1 d .
H9 H 0.0355 0.1484 -0.0289 0.058 Uiso 1 1 calc R
C1 C 0.21672(11) 0.5231(3) 0.30005(13) 0.0498(6) Uani 1 1 d .
H1 H 0.2276 0.4058 0.2946 0.060 Uiso 1 1 calc R
C2 C 0.25005(13) 0.6002(4) 0.37934(14) 0.0613(7) Uani 1 1 d .
H2 H 0.2836 0.5349 0.4271 0.074 Uiso 1 1 calc R
C11 C 0.07230(11) 0.4551(3) -0.12702(13) 0.0508(6) Uani 1 1 d .
H11 H 0.0681 0.4763 -0.1792 0.061 Uiso 1 1 calc R
C14 C 0.12925(15) 0.7585(3) -0.07818(15) 0.0628(7) Uani 1 1 d .
H14A H 0.1841 0.7643 -0.0439 0.094 Uiso 1 1 calc R
H14B H 0.1070 0.8510 -0.0616 0.094 Uiso 1 1 calc R
H14C H 0.1140 0.7731 -0.1368 0.094 Uiso 1 1 calc R
C10 C 0.04779(12) 0.2932(3) -0.11270(14) 0.0538(6) Uani 1 1 d .
H10 H 0.0278 0.2086 -0.1555 0.065 Uiso 1 1 calc R
C3 C 0.23377(14) 0.7729(4) 0.38790(16) 0.0621(7) Uani 1 1 d .
H3 H 0.2558 0.8238 0.4415 0.075 Uiso 1 1 calc R
C4 C 0.18517(13) 0.8701(3) 0.31772(15) 0.0563(6) Uani 1 1 d .
H4 H 0.1742 0.9871 0.3237 0.068 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
C9 N3 C13 121.77(18)
C9 N3 C8 133.31(17)
C13 N3 C8 104.84(15)
C13 N2 C7 106.49(17)
N2 C13 N3 111.72(16)
N2 C13 C12 128.28(18)
N3 C13 C12 119.97(17)
C1 C6 C5 118.64(19)
C1 C6 C7 122.37(19)
C5 C6 C7 118.79(17)
N2 C7 C8 109.79(17)
N2 C7 C6 119.60(18)
C8 C7 C6 130.59(18)
O2 N1 O1 122.32(18)
O2 N1 C8 119.34(19)
O1 N1 C8 118.32(18)
C7 C8 N3 107.15(16)
C7 C8 N1 130.63(19)
N3 C8 N1 121.94(18)
C4 C5 C6 120.7(2)
C4 C5 H5 119.6
C6 C5 H5 119.6
C11 C12 C13 117.4(2)
C11 C12 C14 123.53(19)
C13 C12 C14 119.06(18)
C10 C9 N3 118.0(2)
C10 C9 H9 121.0
N3 C9 H9 121.0
C2 C1 C6 120.2(2)
C2 C1 H1 119.9
C6 C1 H1 119.9
C3 C2 C1 120.2(2)
C3 C2 H2 119.9
C1 C2 H2 119.9
C12 C11 C10 121.4(2)
C12 C11 H11 119.3
C10 C11 H11 119.3
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C9 C10 C11 121.5(2)
C9 C10 H10 119.2
C11 C10 H10 119.2
C4 C3 C2 120.1(2)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.1(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C9 1.371(3)
N3 C13 1.383(2)
N3 C8 1.393(2)
N2 C13 1.345(2)
N2 C7 1.348(2)
C13 C12 1.408(3)
C6 C1 1.387(3)
C6 C5 1.388(3)
C6 C7 1.470(3)
O2 N1 1.227(2)
C7 C8 1.390(3)
N1 O1 1.227(2)
N1 C8 1.399(3)
C5 C4 1.374(3)
C5 H5 0.9300
C12 C11 1.361(3)
C12 C14 1.493(3)
C9 C10 1.354(3)
C9 H9 0.9300
C1 C2 1.380(3)
C1 H1 0.9300
C2 C3 1.373(4)
C2 H2 0.9300
C11 C10 1.393(3)
C11 H11 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C10 H10 0.9300
C3 C4 1.369(3)
C3 H3 0.9300
C4 H4 0.9300
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
C7 N2 C13 N3 0.8(2)
C7 N2 C13 C12 -177.16(18)
C9 N3 C13 N2 -177.15(16)
C8 N3 C13 N2 -0.07(19)
C9 N3 C13 C12 1.0(3)
C8 N3 C13 C12 178.10(16)
C13 N2 C7 C8 -1.3(2)
C13 N2 C7 C6 177.24(15)
C1 C6 C7 N2 -129.8(2)
C5 C6 C7 N2 44.8(2)
C1 C6 C7 C8 48.3(3)
C5 C6 C7 C8 -137.0(2)
N2 C7 C8 N3 1.2(2)
C6 C7 C8 N3 -177.05(18)
N2 C7 C8 N1 -172.57(19)
C6 C7 C8 N1 9.1(3)
C9 N3 C8 C7 175.89(19)
C13 N3 C8 C7 -0.70(19)
C9 N3 C8 N1 -9.6(3)
C13 N3 C8 N1 173.77(17)
O2 N1 C8 C7 176.29(19)
O1 N1 C8 C7 -2.2(3)
O2 N1 C8 N3 3.3(3)
O1 N1 C8 N3 -175.20(17)
C1 C6 C5 C4 -1.5(3)
C7 C6 C5 C4 -176.36(18)
N2 C13 C12 C11 176.53(18)
N3 C13 C12 C11 -1.3(3)
N2 C13 C12 C14 -2.9(3)
N3 C13 C12 C14 179.31(18)
C13 N3 C9 C10 -0.1(3)
C8 N3 C9 C10 -176.19(19)
C5 C6 C1 C2 0.6(3)
C7 C6 C1 C2 175.31(18)
C6 C1 C2 C3 0.5(3)
C13 C12 C11 C10 0.7(3)
C14 C12 C11 C10 -180.0(2)
N3 C9 C10 C11 -0.6(3)
C12 C11 C10 C9 0.2(3)
C1 C2 C3 C4 -0.9(3)
C2 C3 C4 C5 0.0(3)
C6 C5 C4 C3 1.2(3)
