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#$Date: 2022-12-15 11:43:04 +0200 (Thu, 15 Dec 2022) $
#$Revision: 279910 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106407.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_8106407
loop_
_publ_author_name
'You, Gui-Rong'
'Rao, Guo-Wu'
_publ_section_title
;
 Crystal structure of
 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1081
_journal_page_last               1082
_journal_paper_doi               10.1515/ncrs-2018-0199
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C9 H5 F3 N2 O'
_chemical_formula_sum            'C9 H5 F3 N2 O'
_chemical_formula_weight         214.15
_chemical_name_systematic
;
8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.276(2)
_cell_length_b                   6.7773(19)
_cell_length_c                   17.613(5)
_cell_measurement_reflns_used    3435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.31
_cell_volume                     868.5(4)
_computing_cell_refinement       'Bruker SAINT [1] '
_computing_data_collection       'Bruker SMART [1] '
_computing_data_reduction        'Bruker SAINT [1] '
_computing_molecular_graphics    'ORTEP [4]'
_computing_publication_material  'WINGX [4]'
_computing_structure_refinement  SHELXL-2018/3[3]
_computing_structure_solution    'SHELXS-97 [2] '
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3447
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.012
_diffrn_reflns_theta_max         25.012
_diffrn_reflns_theta_min         2.313
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0587P)²+0.2014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                729
_reflns_number_total             839
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0199_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8106407
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.3077(3) 0.250000 0.72589(9) 0.1097(8) Uani 1 2 d S T P . .
O1 O 0.5672(4) 0.250000 0.30615(12) 0.1035(9) Uani 1 2 d S T P . .
N2 N 0.4273(2) 0.250000 0.46238(10) 0.0462(5) Uani 1 2 d S T P . .
C1 C 0.2995(3) 0.250000 0.52023(13) 0.0470(5) Uani 1 2 d S T P . .
C5 C 0.6134(3) 0.250000 0.47587(14) 0.0522(6) Uani 1 2 d S T P . .
H5 H 0.696268 0.250000 0.435652 0.063 Uiso 1 2 calc R U P . .
C7 C 0.5492(3) 0.250000 0.60820(14) 0.0565(6) Uani 1 2 d S T P . .
H7 H 0.593426 0.250000 0.657737 0.068 Uiso 1 2 calc R U P . .
C8 C 0.3642(3) 0.250000 0.59566(13) 0.0508(6) Uani 1 2 d S T P . .
N1 N 0.1282(2) 0.250000 0.49314(13) 0.0622(6) Uani 1 2 d S T P . .
C3 C 0.3284(3) 0.250000 0.39507(13) 0.0576(6) Uani 1 2 d S T P . .
C6 C 0.6736(3) 0.250000 0.54729(14) 0.0575(6) Uani 1 2 d S T P . .
H6 H 0.799254 0.250000 0.556898 0.069 Uiso 1 2 calc R U P . .
C9 C 0.2287(4) 0.250000 0.65861(14) 0.0689(7) Uani 1 2 d S T P . .
F1 F 0.11835(17) 0.0932(2) 0.65681(7) 0.0995(6) Uani 1 1 d . . . . .
C4 C 0.4055(5) 0.250000 0.32040(16) 0.0797(9) Uani 1 2 d S T P . .
H4 H 0.324295 0.250000 0.279642 0.096 Uiso 1 2 calc R U P . .
C2 C 0.1488(4) 0.250000 0.41754(17) 0.0688(8) Uani 1 2 d S T P . .
H2 H 0.050531 0.250000 0.383756 0.083 Uiso 1 2 calc R U P . .
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'
F F 0.0171 0.0103 '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
C5 N2 C1 122.43(19) . .
C5 N2 C3 131.2(2) . .
C1 N2 C3 106.35(19) . .
N1 C1 N2 111.4(2) . .
N1 C1 C8 130.5(2) . .
N2 C1 C8 118.10(18) . .
C6 C5 N2 119.1(2) . .
C6 C5 H5 120.4 . .
N2 C5 H5 120.4 . .
C8 C7 C6 120.8(2) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C7 C8 C1 118.8(2) . .
C7 C8 C9 122.3(2) . .
C1 C8 C9 118.8(2) . .
C1 N1 C2 104.5(2) . .
C2 C3 N2 104.4(2) . .
C2 C3 C4 130.0(3) . .
N2 C3 C4 125.6(2) . .
C5 C6 C7 120.7(2) . .
C5 C6 H6 119.7 . .
C7 C6 H6 119.7 . .
F2 C9 F1 106.52(15) . 8_565
F2 C9 F1 106.52(15) . .
F1 C9 F1 105.8(2) 8_565 .
F2 C9 C8 112.5(2) . .
F1 C9 C8 112.50(14) 8_565 .
F1 C9 C8 112.50(14) . .
O1 C4 C3 125.2(3) . .
O1 C4 H4 117.4 . .
C3 C4 H4 117.4 . .
N1 C2 C3 113.3(2) . .
N1 C2 H2 123.4 . .
C3 C2 H2 123.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F2 C9 1.317(3) .
O1 C4 1.202(4) .
N2 C5 1.375(3) .
N2 C1 1.380(3) .
N2 C3 1.387(3) .
C1 N1 1.334(3) .
C1 C8 1.410(3) .
C5 C6 1.332(3) .
C5 H5 0.9300 .
C7 C8 1.364(3) .
C7 C6 1.404(3) .
C7 H7 0.9300 .
C8 C9 1.483(3) .
N1 C2 1.340(4) .
C3 C2 1.365(4) .
C3 C4 1.430(4) .
C6 H6 0.9300 .
C9 F1 1.332(2) 8_565
C9 F1 1.332(2) .
C4 H4 0.9300 .
C2 H2 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O1 0.93 2.47 3.008(3) 117.2 . yes
C4 H4 O1 0.93 2.40 3.321(4) 168.4 3_455 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N2 C1 N1 180.000(1) . . . .
C3 N2 C1 N1 0.000(1) . . . .
C5 N2 C1 C8 0.000(1) . . . .
C3 N2 C1 C8 180.000(1) . . . .
C1 N2 C5 C6 0.000(1) . . . .
C3 N2 C5 C6 180.000(1) . . . .
C6 C7 C8 C1 0.000(1) . . . .
C6 C7 C8 C9 180.000(1) . . . .
N1 C1 C8 C7 180.000(1) . . . .
N2 C1 C8 C7 0.000(1) . . . .
N1 C1 C8 C9 0.000(1) . . . .
N2 C1 C8 C9 180.000(1) . . . .
N2 C1 N1 C2 0.000(1) . . . .
C8 C1 N1 C2 180.000(1) . . . .
C5 N2 C3 C2 180.000(1) . . . .
C1 N2 C3 C2 0.000(1) . . . .
C5 N2 C3 C4 0.000(1) . . . .
C1 N2 C3 C4 180.000(1) . . . .
N2 C5 C6 C7 0.000(1) . . . .
C8 C7 C6 C5 0.000(1) . . . .
C7 C8 C9 F2 0.000(1) . . . .
C1 C8 C9 F2 180.000(1) . . . .
C7 C8 C9 F1 120.31(17) . . . 8_565
C1 C8 C9 F1 -59.69(17) . . . 8_565
C7 C8 C9 F1 -120.31(17) . . . .
C1 C8 C9 F1 59.69(17) . . . .
C2 C3 C4 O1 180.000(1) . . . .
N2 C3 C4 O1 0.000(1) . . . .
C1 N1 C2 C3 0.000(1) . . . .
N2 C3 C2 N1 0.000(1) . . . .
C4 C3 C2 N1 180.000(1) . . . .
