#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/11/7221141.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_7221141
loop_
_publ_author_name
'Khan, Abu Taleb'
'Ray Bagdi, Prasanta'
'Basha R, Sidick'
_publ_section_title
;
 Synthesis of 2-triazolyl-imidazo[1,2-a]pyridine through one-pot
 three-component reaction using nano copper oxide assisted click-catalyst
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA09671E
_journal_year                    2015
_chemical_formula_moiety         'C7 H11 N3 O3'
_chemical_formula_sum            'C7 H11 N3 O3'
_chemical_formula_weight         185.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_audit_update_record
;
2014-01-06 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.296(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9591(4)
_cell_length_b                   4.8417(3)
_cell_length_c                   23.7648(14)
_cell_measurement_temperature    296(2)
_cell_volume                     913.22(9)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3611
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0481
_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)+(0.0376P)²+0.1006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                1385
_reflns_number_total             1648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra09671e2.cif
_cod_data_source_block           exp_931
_cod_original_cell_volume        913.21(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7221141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.22362(18) 0.6611(4) 0.55673(6) 0.0612(5) Uani 1 1 d
H1 H 0.124(3) 0.611(6) 0.5608(11) 0.093(9) Uiso 1 1 d
O2 O 0.35580(19) 0.5976(3) 0.28824(6) 0.0613(5) Uani 1 1 d
O3 O 0.52899(16) 0.2688(3) 0.25931(5) 0.0487(4) Uani 1 1 d
N1 N 0.12550(18) 0.4479(4) 0.43439(6) 0.0519(5) Uani 1 1 d
N2 N 0.1790(2) 0.2899(4) 0.39441(7) 0.0551(5) Uani 1 1 d
N3 N 0.34305(17) 0.3470(3) 0.39160(6) 0.0420(4) Uani 1 1 d
C1 C 0.2341(3) 0.7985(5) 0.50465(9) 0.0562(6) Uani 1 1 d
H1A H 0.135(3) 0.910(5) 0.4954(8) 0.064(6) Uiso 1 1 d
H1B H 0.339(3) 0.933(5) 0.5068(9) 0.077(7) Uiso 1 1 d
C2 C 0.2546(2) 0.6047(4) 0.45684(7) 0.0407(5) Uani 1 1 d
C3 C 0.3940(2) 0.5414(4) 0.42958(7) 0.0419(5) Uani 1 1 d
H3 H 0.512(2) 0.607(4) 0.4344(7) 0.048(5) Uiso 1 1 d
C4 C 0.4378(3) 0.2165(5) 0.34903(8) 0.0451(5) Uani 1 1 d
H4A H 0.549(3) 0.204(4) 0.3633(8) 0.059(6) Uiso 1 1 d
H4B H 0.389(2) 0.042(5) 0.3404(8) 0.057(6) Uiso 1 1 d
C5 C 0.4336(2) 0.3863(4) 0.29573(8) 0.0413(5) Uani 1 1 d
C6 C 0.5304(4) 0.4016(7) 0.20414(10) 0.0624(7) Uani 1 1 d
H6A H 0.418(4) 0.355(6) 0.1854(11) 0.114(10) Uiso 1 1 d
H6B H 0.560(3) 0.596(6) 0.2100(10) 0.089(9) Uiso 1 1 d
C7 C 0.6643(4) 0.2726(7) 0.17347(11) 0.0695(7) Uani 1 1 d
H7A H 0.667(3) 0.358(5) 0.1361(11) 0.083(8) Uiso 1 1 d
H7B H 0.774(4) 0.311(6) 0.1952(12) 0.117(11) Uiso 1 1 d
H7C H 0.642(4) 0.071(7) 0.1701(12) 0.114(11) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0379(7) 0.1061(14) 0.0403(8) -0.0069(8) 0.0077(6) -0.0016(9)
O2 0.0744(10) 0.0493(9) 0.0616(9) 0.0049(8) 0.0136(8) 0.0187(8)
O3 0.0549(8) 0.0545(9) 0.0386(7) 0.0058(7) 0.0160(6) 0.0119(7)
N1 0.0364(8) 0.0747(13) 0.0454(9) -0.0068(9) 0.0090(7) -0.0004(9)
N2 0.0423(9) 0.0738(13) 0.0505(10) -0.0100(10) 0.0108(7) -0.0112(9)
N3 0.0360(8) 0.0518(10) 0.0394(8) -0.0019(8) 0.0100(6) 0.0032(8)
C1 0.0519(12) 0.0640(15) 0.0546(13) -0.0070(12) 0.0174(10) 0.0083(12)
C2 0.0349(9) 0.0478(11) 0.0396(9) 0.0023(9) 0.0054(7) 0.0047(9)
C3 0.0357(9) 0.0505(12) 0.0401(10) -0.0033(9) 0.0062(8) 0.0017(9)
C4 0.0485(11) 0.0482(13) 0.0401(11) -0.0036(10) 0.0130(9) 0.0058(11)
C5 0.0395(9) 0.0414(11) 0.0432(10) -0.0017(9) 0.0043(8) 0.0017(9)
C6 0.0723(16) 0.0721(18) 0.0446(12) 0.0158(13) 0.0158(11) 0.0063(15)
C7 0.0731(17) 0.090(2) 0.0482(14) 0.0025(15) 0.0221(12) -0.0053(17)
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
C5 O3 C6 116.18(17)
N2 N1 C2 109.48(15)
N1 N2 N3 106.57(15)
N2 N3 C3 110.88(15)
N2 N3 C4 120.24(17)
C3 N3 C4 128.76(16)
O1 C1 C2 112.8(2)
N1 C2 C3 107.92(17)
N1 C2 C1 121.98(17)
C3 C2 C1 130.06(18)
N3 C3 C2 105.14(16)
N3 C4 C5 111.61(17)
O2 C5 O3 125.74(18)
O2 C5 C4 124.55(18)
O3 C5 C4 109.71(17)
O3 C6 C7 108.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.413(3)
O2 C5 1.202(2)
O3 C5 1.322(2)
O3 C6 1.461(2)
N1 N2 1.315(2)
N1 C2 1.354(2)
N2 N3 1.341(2)
N3 C3 1.346(2)
N3 C4 1.451(2)
C1 C2 1.492(3)
C2 C3 1.361(2)
C4 C5 1.508(3)
C6 C7 1.475(4)
