#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/59/7225950.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_7225950
loop_
_publ_author_name
'Chapman, Michael R.'
'Kwan, Maria H. T.'
'King, Georgina E.'
'Kyffin, Benjamin A.'
'Blacker, A. John'
'Willans, Charlotte E.'
'Nguyen, Bao N.'
_publ_section_title
;
 Rapid, metal-free and aqueous synthesis of imidazo[1,2-a]pyridine under
 ambient conditions
;
_journal_issue                   17
_journal_name_full               'Green Chem.'
_journal_page_first              4623
_journal_paper_doi               10.1039/C6GC01601D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C8 H7 N3 O2'
_chemical_formula_sum            'C8 H7 N3 O2'
_chemical_formula_weight         177.17
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   24.304(2)
_cell_length_b                   24.304(2)
_cell_length_c                   6.8579(5)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    119.99(14)
_cell_measurement_theta_max      30.4590
_cell_measurement_theta_min      3.9140
_cell_volume                     3508.1(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_details
;
  1 omega  -16.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   19.0000   90.0000 62

  2 omega    3.00   57.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   19.0000   30.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0105511000
_diffrn_orient_matrix_UB_12      -0.0251292000
_diffrn_orient_matrix_UB_13      0.0685678000
_diffrn_orient_matrix_UB_21      0.0312945000
_diffrn_orient_matrix_UB_22      0.0135108000
_diffrn_orient_matrix_UB_23      0.0375710000
_diffrn_orient_matrix_UB_31      -0.0066919000
_diffrn_orient_matrix_UB_32      0.0179315000
_diffrn_orient_matrix_UB_33      0.0677552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4155
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.24
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.0982
_exptl_crystal_size_min          0.0286
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0520
_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/[\s^2^(Fo^2^)+(0.0522P)^2^+2.5247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                1655
_reflns_number_total             2170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01601d5.cif
_cod_data_source_block           mrc218
_cod_depositor_comments
'Adding full bibliography for 7225942--7225950.cif.'
_cod_database_code               7225950
_chemical_oxdiff_formula         'C10 H10 N3 O2'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_date_sample_data_collection 2016-01-25
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'
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
_atom_site_refinement_flags_posn
O2 O 0.25580(6) 0.28922(6) 0.62654(18) 0.0304(3) Uani 1 d .
O1 O 0.15656(6) 0.22171(6) 0.6808(2) 0.0338(3) Uani 1 d .
N1 N 0.21550(6) 0.42759(6) 0.50884(18) 0.0175(3) Uani 1 d .
N2 N 0.15166(6) 0.46958(6) 0.48463(19) 0.0206(3) Uani 1 d .
N3 N 0.19960(7) 0.27483(7) 0.63475(19) 0.0223(3) Uani 1 d .
C1 C 0.15296(7) 0.41680(7) 0.5231(2) 0.0175(3) Uani 1 d .
C5 C 0.23076(7) 0.38184(7) 0.5435(2) 0.0187(3) Uani 1 d .
H5 H 0.2734 0.3905 0.5341 0.022 Uiso 1 calc R
C7 C 0.21371(7) 0.51488(7) 0.4444(2) 0.0197(3) Uani 1 d .
C4 C 0.18265(8) 0.32315(7) 0.5922(2) 0.0190(3) Uani 1 d .
C3 C 0.11834(7) 0.30817(7) 0.6085(2) 0.0199(3) Uani 1 d .
H3 H 0.0860 0.2665 0.6430 0.024 Uiso 1 calc R
C2 C 0.10413(7) 0.35494(8) 0.5735(2) 0.0203(3) Uani 1 d .
H2 H 0.0614 0.3460 0.5829 0.024 Uiso 1 calc R
C6 C 0.25361(7) 0.49068(7) 0.4584(2) 0.0200(3) Uani 1 d .
H6 H 0.2982 0.5126 0.4379 0.024 Uiso 1 calc R
C8 C 0.23129(8) 0.58147(8) 0.3942(3) 0.0261(4) Uani 1 d .
H8A H 0.2066 0.5812 0.2809 0.039 Uiso 1 calc GR
H8B H 0.2767 0.6060 0.3634 0.039 Uiso 1 calc GR
H8C H 0.2221 0.6009 0.5054 0.039 Uiso 1 calc GR
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
O2 0.0301(7) 0.0327(7) 0.0371(7) 0.0037(5) 0.0031(5) 0.0222(6)
O1 0.0333(7) 0.0188(6) 0.0459(8) 0.0050(5) 0.0000(6) 0.0104(6)
N1 0.0156(6) 0.0185(6) 0.0180(6) -0.0008(5) -0.0004(5) 0.0084(5)
N2 0.0188(7) 0.0221(7) 0.0216(7) 0.0004(5) 0.0000(5) 0.0107(6)
N3 0.0270(8) 0.0216(7) 0.0206(7) -0.0018(5) -0.0016(6) 0.0140(6)
C1 0.0148(7) 0.0229(8) 0.0155(7) -0.0026(6) -0.0022(5) 0.0100(6)
C5 0.0183(7) 0.0227(8) 0.0183(7) -0.0015(6) -0.0010(6) 0.0126(6)
C7 0.0202(8) 0.0201(8) 0.0188(7) 0.0001(6) -0.0004(6) 0.0101(7)
C4 0.0233(8) 0.0198(8) 0.0161(7) -0.0012(6) -0.0008(6) 0.0124(7)
C3 0.0194(8) 0.0182(8) 0.0179(7) -0.0010(6) 0.0007(6) 0.0061(6)
C2 0.0155(7) 0.0233(8) 0.0194(7) -0.0021(6) 0.0003(6) 0.0077(6)
C6 0.0162(7) 0.0178(8) 0.0240(8) 0.0014(6) 0.0018(6) 0.0070(6)
C8 0.0244(9) 0.0222(8) 0.0327(9) 0.0046(7) 0.0028(7) 0.0125(7)
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 N1 C1 123.09(13)
C5 N1 C6 130.30(13)
C6 N1 C1 106.60(12)
C1 N2 C7 105.49(13)
O2 N3 C4 118.92(14)
O1 N3 O2 123.45(14)
O1 N3 C4 117.61(14)
N1 C1 C2 117.86(13)
N2 C1 N1 110.56(13)
N2 C1 C2 131.58(14)
N1 C5 H5 121.3
N1 C5 C4 117.30(14)
C4 C5 H5 121.3
N2 C7 C8 121.18(14)
C6 C7 N2 111.73(14)
C6 C7 C8 127.09(14)
C5 C4 N3 117.00(14)
C5 C4 C3 123.19(14)
C3 C4 N3 119.77(14)
C4 C3 H3 120.8
C2 C3 C4 118.49(14)
C2 C3 H3 120.8
C1 C2 H2 120.0
C3 C2 C1 120.06(14)
C3 C2 H2 120.0
N1 C6 H6 127.2
C7 C6 N1 105.62(13)
C7 C6 H6 127.2
C7 C8 H8A 109.5
C7 C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8B 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 N3 1.2301(18)
O1 N3 1.2291(18)
N1 C1 1.4107(19)
N1 C5 1.3576(19)
N1 C6 1.381(2)
N2 C1 1.325(2)
N2 C7 1.379(2)
N3 C4 1.455(2)
C1 C2 1.416(2)
C5 H5 0.9500
C5 C4 1.358(2)
C7 C6 1.366(2)
C7 C8 1.493(2)
C4 C3 1.421(2)
C3 H3 0.9500
C3 C2 1.364(2)
C2 H2 0.9500
C6 H6 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
O2 N3 C4 C5 0.6(2)
O2 N3 C4 C3 -177.50(13)
O1 N3 C4 C5 179.31(14)
O1 N3 C4 C3 1.2(2)
N1 C1 C2 C3 0.7(2)
N1 C5 C4 N3 -178.26(12)
N1 C5 C4 C3 -0.2(2)
N2 C1 C2 C3 -179.26(15)
N2 C7 C6 N1 0.21(18)
N3 C4 C3 C2 178.05(13)
C1 N1 C5 C4 0.6(2)
C1 N1 C6 C7 -0.06(16)
C1 N2 C7 C6 -0.27(17)
C1 N2 C7 C8 -179.83(14)
C5 N1 C1 N2 179.07(13)
C5 N1 C1 C2 -0.9(2)
C5 N1 C6 C7 -179.16(14)
C5 C4 C3 C2 0.0(2)
C7 N2 C1 N1 0.23(16)
C7 N2 C1 C2 -179.83(16)
C4 C3 C2 C1 -0.3(2)
C6 N1 C1 N2 -0.11(17)
C6 N1 C1 C2 179.94(13)
C6 N1 C5 C4 179.60(15)
C8 C7 C6 N1 179.73(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 821069
