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#$Date: 2022-06-15 09:43:17 +0300 (Wed, 15 Jun 2022) $
#$Revision: 276037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105417.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_8105417
loop_
_publ_author_name
'Jaćimović, Željko. K.'
'Novaković, Sladjana B.'
'Bogdanović, Goran A.'
'Kosović, Milica'
'Libowitzky, Eugen'
'Giester, Gerald'
_publ_section_title
;
 Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate,
 C7H7F3N2O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1189
_journal_page_last               1190
_journal_paper_doi               10.1515/ncrs-2020-0242
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C7 H7 F3 N2 O2'
_chemical_formula_sum            'C7 H7 F3 N2 O2'
_chemical_formula_weight         208.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 105.416(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8088(8)
_cell_length_b                   6.7699(9)
_cell_length_c                   9.9351(12)
_cell_measurement_reflns_used    1686
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.12
_cell_volume                     441.48(9)
_computing_cell_refinement       'APEX2 (Bruker, 2008)'
_computing_data_collection       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Mercury (Macrae, 2020)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker ApexII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17052
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.240
_diffrn_reflns_theta_min         2.126
_diffrn_source                   'Incoatec ImS'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  1.008
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       prism
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.045(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0398
_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)+(0.0547P)²+0.0979P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1466
_reflns_number_total             1819
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0242_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               8105417
_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.
;
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'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
F1 F 0.43896(17) 0.2500 0.08691(10) 0.0588(4) Uani 1 2 d S T P . .
F2 F 0.67754(12) 0.40673(15) 0.23115(9) 0.0573(3) Uani 1 1 d . . . . .
O1 O 0.85926(15) 0.2500 0.52269(12) 0.0416(3) Uani 1 2 d S T P . .
O2 O 0.70241(15) 0.2500 0.69374(10) 0.0336(2) Uani 1 2 d S T P . .
N1 N 0.16706(17) 0.2500 0.39173(13) 0.0314(3) Uani 1 2 d S T P . .
N2 N 0.23079(17) 0.2500 0.27439(13) 0.0319(3) Uani 1 2 d S T P . .
C3 C 0.43220(19) 0.2500 0.32107(13) 0.0263(2) Uani 1 2 d S T P . .
C4 C 0.49813(18) 0.2500 0.46784(13) 0.0235(2) Uani 1 2 d S T P . .
C5 C 0.31902(19) 0.2500 0.50850(14) 0.0272(3) Uani 1 2 d S T P . .
H5 H 0.3066 0.2500 0.6015 0.033 Uiso 1 2 calc R U P . .
C6 C 0.70491(19) 0.2500 0.56073(14) 0.0265(3) Uani 1 2 d S T P . .
C7 C 0.8989(2) 0.2500 0.79805(16) 0.0369(3) Uani 1 2 d S T P . .
H7A H 0.9783 0.3688 0.7875 0.044 Uiso 1 1 d R U . . .
C8 C 0.8546(3) 0.2500 0.93749(18) 0.0520(5) Uani 1 2 d S T P . .
H8A H 0.9829 0.2500 1.0112 0.078 Uiso 1 2 d R U P . .
H8B H 0.7758 0.1318 0.9463 0.078 Uiso 1 1 d R U . . .
C9 C 0.5551(2) 0.2500 0.21712(15) 0.0363(3) Uani 1 2 d S T P . .
H1N H 0.041(3) 0.2500 0.387(2) 0.042(5) Uiso 1 2 d S . 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'
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'
F F 0.0171 0.0103 '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
C6 O2 C7 117.11(11) . .
C5 N1 N2 113.50(11) . .
C5 N1 H1N 126.2(15) . .
N2 N1 H1N 120.3(15) . .
C3 N2 N1 103.79(11) . .
N2 C3 C4 112.20(11) . .
N2 C3 C9 118.44(12) . .
C4 C3 C9 129.35(12) . .
C5 C4 C3 103.86(11) . .
C5 C4 C6 126.21(12) . .
C3 C4 C6 129.93(11) . .
N1 C5 C4 106.64(11) . .
N1 C5 H5 126.7 . .
C4 C5 H5 126.7 . .
O1 C6 O2 123.69(12) . .
O1 C6 C4 125.01(12) . .
O2 C6 C4 111.30(11) . .
O2 C7 C8 106.59(13) . .
O2 C7 H7A 110.4 . .
C8 C7 H7A 110.4 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
F1 C9 F2 107.24(9) . .
F1 C9 F2 107.24(9) . 4_565
F2 C9 F2 105.43(13) . 4_565
F1 C9 C3 112.13(12) . .
F2 C9 C3 112.19(8) . .
F2 C9 C3 112.19(8) 4_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C9 1.3249(18) .
F2 C9 1.3336(12) .
O1 C6 1.2077(15) .
O2 C6 1.3261(16) .
O2 C7 1.4583(17) .
N1 C5 1.3335(17) .
N1 N2 1.3477(17) .
N1 H1N 0.85(2) .
N2 C3 1.3257(17) .
C3 C4 1.4070(18) .
C3 C9 1.4921(19) .
C4 C5 1.3829(16) .
C4 C6 1.4640(17) .
C5 H5 0.9500 .
C7 C8 1.494(2) .
C7 H7A 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C9 F2 1.3336(12) 4_565
