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#$Date: 2022-01-01 06:52:08 +0200 (Sat, 01 Jan 2022) $
#$Revision: 271670 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243965.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243965
loop_
_publ_author_name
'Guseinov, Firudin I.'
'Kobrakov, Konstantin I.'
'Ugrak, Bogdan I.'
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 2,2,2-trifluoro-1-(7-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one
;
_journal_coeditor_code           YK2161
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              12
_journal_page_last               17
_journal_paper_doi               10.1107/S2056989021012676
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C10 H7 F3 N2 O'
_chemical_formula_moiety         'C10 H7 F3 N2 O'
_chemical_formula_sum            'C10 H7 F3 N2 O'
_chemical_formula_weight         228.18
_chemical_name_systematic
;
2,2,2-Trifluoro-1-(7-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                102.501(2)
_cell_angle_beta                 96.764(2)
_cell_angle_gamma                91.415(2)
_cell_formula_units_Z            2
_cell_length_a                   5.43840(10)
_cell_length_b                   8.8298(2)
_cell_length_c                   10.0744(2)
_cell_measurement_reflns_used    11472
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.1370
_cell_measurement_theta_min      4.4910
_cell_volume                     468.387(17)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14165
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.451
_diffrn_reflns_theta_min         4.532
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2021)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.263
_refine_ls_extinction_coef       0.0061(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0617P)²+0.1479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                1927
_reflns_number_total             2006
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2161sup1.cif
_cod_data_source_block           I
_cod_database_code               2243965
_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.
;
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F3 0.83669(15) 0.51338(8) 0.12281(8) 0.0298(2) Uani d 1 . .
F F1 1.03655(15) 0.72062(9) 0.10632(8) 0.0306(2) Uani d 1 . .
F F2 0.63947(16) 0.69737(10) 0.05569(8) 0.0352(2) Uani d 1 . .
O O1 0.94235(16) 0.85798(10) 0.34833(9) 0.0231(2) Uani d 1 . .
N N2 0.53525(17) 0.75163(11) 0.47862(10) 0.0178(2) Uani d 1 . .
N N1 0.25848(19) 0.55184(12) 0.38082(11) 0.0224(2) Uani d 1 . .
C C3 0.3285(2) 0.66590(13) 0.49404(12) 0.0195(3) Uani d 1 . .
C C7 0.6410(2) 0.87311(13) 0.57981(12) 0.0199(3) Uani d 1 . .
H H7 0.783693 0.930322 0.567582 0.024 Uiso calc 1 . .
C C6 0.5364(2) 0.90977(14) 0.69840(12) 0.0214(3) Uani d 1 . .
H H6 0.608051 0.993640 0.769395 0.026 Uiso calc 1 . .
C C4 0.2206(2) 0.70392(14) 0.61568(13) 0.0214(3) Uani d 1 . .
H H4 0.077951 0.646052 0.626999 0.026 Uiso calc 1 . .
C C5 0.3224(2) 0.82541(14) 0.71850(13) 0.0211(3) Uani d 1 . .
C C2 0.4210(2) 0.56623(14) 0.29402(12) 0.0210(3) Uani d 1 . .
H H2 0.416403 0.500889 0.205342 0.025 Uiso calc 1 . .
C C1 0.5986(2) 0.68799(13) 0.34799(12) 0.0191(3) Uani d 1 . .
C C9 0.8297(2) 0.66755(14) 0.14284(13) 0.0231(3) Uani d 1 . .
C C8 0.7991(2) 0.74800(13) 0.29223(12) 0.0190(3) Uani d 1 . .
C C10 0.2118(2) 0.87010(16) 0.85047(13) 0.0267(3) Uani d 1 . .
H H10A 0.336148 0.863035 0.927312 0.040 Uiso calc 1 . .
H H10B 0.068569 0.799545 0.848113 0.040 Uiso calc 1 . .
H H10C 0.158430 0.976875 0.862058 0.040 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N2 C1 . . 106.60(10) ?
C7 N2 C3 . . 122.01(10) ?
C7 N2 C1 . . 131.39(10) ?
C2 N1 C3 . . 105.23(10) ?
N2 C3 C4 . . 119.63(11) ?
N1 C3 N2 . . 111.28(10) ?
N1 C3 C4 . . 129.10(11) ?
N2 C7 H7 . . 120.8 ?
C6 C7 N2 . . 118.35(11) ?
C6 C7 H7 . . 120.8 ?
C7 C6 H6 . . 119.2 ?
C7 C6 C5 . . 121.61(11) ?
C5 C6 H6 . . 119.2 ?
C3 C4 H4 . . 120.2 ?
C5 C4 C3 . . 119.55(11) ?
C5 C4 H4 . . 120.2 ?
C6 C5 C10 . . 119.98(11) ?
C4 C5 C6 . . 118.86(11) ?
C4 C5 C10 . . 121.17(11) ?
N1 C2 H2 . . 123.7 ?
N1 C2 C1 . . 112.65(11) ?
C1 C2 H2 . . 123.7 ?
N2 C1 C8 . . 123.53(11) ?
C2 C1 N2 . . 104.25(10) ?
C2 C1 C8 . . 132.19(11) ?
F3 C9 F2 . . 106.95(10) ?
F3 C9 C8 . . 113.36(9) ?
F1 C9 F3 . . 107.82(10) ?
F1 C9 F2 . . 107.29(10) ?
F1 C9 C8 . . 110.72(10) ?
F2 C9 C8 . . 110.45(10) ?
O1 C8 C1 . . 126.81(11) ?
O1 C8 C9 . . 117.43(10) ?
C1 C8 C9 . . 115.72(10) ?
C5 C10 H10A . . 109.5 ?
C5 C10 H10B . . 109.5 ?
C5 C10 H10C . . 109.5 ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F3 C9 . 1.3345(14) ?
F1 C9 . 1.3292(14) ?
F2 C9 . 1.3453(14) ?
O1 C8 . 1.2208(15) ?
N2 C3 . 1.3827(14) ?
N2 C7 . 1.3706(15) ?
N2 C1 . 1.4011(15) ?
N1 C3 . 1.3571(16) ?
N1 C2 . 1.3367(16) ?
C3 C4 . 1.3997(17) ?
C7 H7 . 0.9500 ?
C7 C6 . 1.3629(17) ?
C6 H6 . 0.9500 ?
C6 C5 . 1.4245(17) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.3728(18) ?
C5 C10 . 1.5028(17) ?
C2 H2 . 0.9500 ?
C2 C1 . 1.3987(16) ?
C1 C8 . 1.4247(16) ?
C9 C8 . 1.5489(17) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 F3 . 0.95 2.53 2.9876(14) 110 no
C4 H4 N1 2_566 0.95 2.48 3.4139(16) 167 yes
C7 H7 O1 . 0.95 2.43 2.9864(14) 117 no
C7 H7 O1 2_776 0.95 2.30 3.1464(14) 147 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F3 C9 C8 O1 . . . . 130.29(11) ?
F3 C9 C8 C1 . . . . -51.85(14) ?
F1 C9 C8 O1 . . . . 8.98(15) ?
F1 C9 C8 C1 . . . . -173.16(10) ?
F2 C9 C8 O1 . . . . -109.71(12) ?
F2 C9 C8 C1 . . . . 68.15(13) ?
N2 C3 C4 C5 . . . . -0.35(17) ?
N2 C7 C6 C5 . . . . -0.07(17) ?
N2 C1 C8 O1 . . . . 1.14(19) ?
N2 C1 C8 C9 . . . . -176.48(9) ?
N1 C3 C4 C5 . . . . -179.91(11) ?
N1 C2 C1 N2 . . . . -0.09(13) ?
N1 C2 C1 C8 . . . . -177.96(12) ?
C3 N2 C7 C6 . . . . -0.37(16) ?
C3 N2 C1 C2 . . . . -0.03(12) ?
C3 N2 C1 C8 . . . . 178.08(10) ?
C3 N1 C2 C1 . . . . 0.16(13) ?
C3 C4 C5 C6 . . . . -0.07(16) ?
C3 C4 C5 C10 . . . . 179.86(10) ?
C7 N2 C3 N1 . . . . -179.78(10) ?
C7 N2 C3 C4 . . . . 0.59(16) ?
C7 N2 C1 C2 . . . . 179.87(11) ?
C7 N2 C1 C8 . . . . -2.02(19) ?
C7 C6 C5 C4 . . . . 0.29(17) ?
C7 C6 C5 C10 . . . . -179.65(10) ?
C2 N1 C3 N2 . . . . -0.18(13) ?
C2 N1 C3 C4 . . . . 179.41(11) ?
C2 C1 C8 O1 . . . . 178.67(12) ?
C2 C1 C8 C9 . . . . 1.04(18) ?
C1 N2 C3 N1 . . . . 0.13(13) ?
C1 N2 C3 C4 . . . . -179.50(9) ?
C1 N2 C7 C6 . . . . 179.75(11) ?

_cod_database_fobs_code 2243965
