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#$Date: 2023-06-06 08:34:53 +0300 (Tue, 06 Jun 2023) $
#$Revision: 284386 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022737.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_2022737
loop_
_publ_author_name
'Ahmed, Basil M.'
'Zeller, Matthias'
'Mezei, Gellert'
_publ_section_title
;
 Crystal and mol-ecular structure of 4-fluoro-1H-pyrazole at
 150 K.
;
_journal_coeditor_code           VM2280
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              428
_journal_page_last               431
_journal_paper_doi               10.1107/S2056989023003055
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C3 H3 F N2'
_chemical_formula_moiety         'C3 H3 F N2'
_chemical_formula_sum            'C3 H3 F N2'
_chemical_formula_weight         86.07
_chemical_name_systematic
;
4-Fluoro-1H-pyrazole
;
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                71.689(2)
_cell_angle_beta                 87.731(2)
_cell_angle_gamma                84.968(2)
_cell_formula_units_Z            4
_cell_length_a                   5.6045(2)
_cell_length_b                   7.4315(3)
_cell_length_c                   9.5396(4)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1425
_cell_measurement_theta_min      2.2489
_cell_volume                     375.72(3)
_computing_cell_refinement
;
SAINT V8.40B (Bruker, 2022)
;
_computing_data_collection
;
APEX4 v2022.1-1 (Bruker, 2022)
;
_computing_data_reduction
;
SAINT V8.40B (Bruker, 2022)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b),
ShelXle Rev1460 (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15049
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.160
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           30
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.257
_refine_ls_extinction_coef       0.040(10)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0356
_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)+(0.0579P)²+0.0788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                2635
_reflns_number_total             2875
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2280sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022737.cif.'
_cod_database_code               2022737
_cod_database_fobs_code          2022737
_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   0.942
_shelx_estimated_absorpt_t_max   0.950
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 F1_1 0.51610(12) 0.62514(11) 0.13759(7) 0.03931(17) Uani d 1 . .
N N1_1 0.64380(12) 0.73038(10) 0.45438(7) 0.02162(13) Uani d 1 . .
H H1N_1 0.721(3) 0.7343(19) 0.5331(15) 0.032 Uiso d 1 . .
N N2_1 0.42422(12) 0.82300(10) 0.42828(7) 0.02262(14) Uani d 1 . .
C C1_1 0.71303(14) 0.64372(11) 0.35314(9) 0.02302(15) Uani d 1 . .
H H1_1 0.859931 0.571209 0.349074 0.028 Uiso calc 1 . .
C C2_1 0.52537(14) 0.68285(11) 0.25714(8) 0.02251(15) Uani d 1 . .
C C3_1 0.34891(13) 0.79346(11) 0.30642(8) 0.02192(15) Uani d 1 . .
H H3_1 0.198692 0.840571 0.260776 0.026 Uiso calc 1 . .
F F1_2 0.00161(11) 0.77865(9) 1.05091(6) 0.03386(15) Uani d 1 . .
N N1_2 0.13614(12) 0.82593(10) 0.68400(7) 0.02239(14) Uani d 1 . .
H H1N_2 0.217(3) 0.845(2) 0.6004(16) 0.034 Uiso d 1 . .
N N2_2 -0.06438(12) 0.73275(10) 0.69835(7) 0.02286(14) Uani d 1 . .
C C1_2 0.19488(14) 0.85549(11) 0.81020(8) 0.02229(15) Uani d 1 . .
H H1_2 0.328762 0.916175 0.826384 0.027 Uiso calc 1 . .
C C2_2 0.01926(14) 0.77888(11) 0.91040(8) 0.02065(14) Uani d 1 . .
C C3_2 -0.13824(14) 0.70401(11) 0.83817(8) 0.02168(14) Uani d 1 . .
H H3_2 -0.276718 0.642113 0.881490 0.026 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 0.0033 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1_1 N1_1 N2_1 . . 112.75(6) ?
C1_1 N1_1 H1N_1 . . 129.5(9) ?
N2_1 N1_1 H1N_1 . . 117.7(9) ?
C3_1 N2_1 N1_1 . . 105.50(6) ?
N1_1 C1_1 C2_1 . . 105.09(7) ?
N1_1 C1_1 H1_1 . . 127.5 ?
C2_1 C1_1 H1_1 . . 127.5 ?
F1_1 C2_1 C1_1 . . 125.91(7) ?
F1_1 C2_1 C3_1 . . 126.73(7) ?
C1_1 C2_1 C3_1 . . 107.36(7) ?
N2_1 C3_1 C2_1 . . 109.29(7) ?
N2_1 C3_1 H3_1 . . 125.4 ?
C2_1 C3_1 H3_1 . . 125.4 ?
C1_2 N1_2 N2_2 . . 112.72(6) ?
C1_2 N1_2 H1N_2 . . 129.9(9) ?
N2_2 N1_2 H1N_2 . . 116.9(9) ?
C3_2 N2_2 N1_2 . . 105.43(6) ?
N1_2 C1_2 C2_2 . . 105.10(7) ?
N1_2 C1_2 H1_2 . . 127.5 ?
C2_2 C1_2 H1_2 . . 127.5 ?
F1_2 C2_2 C1_2 . . 126.25(7) ?
F1_2 C2_2 C3_2 . . 126.46(7) ?
C1_2 C2_2 C3_2 . . 107.29(6) ?
N2_2 C3_2 C2_2 . . 109.46(7) ?
N2_2 C3_2 H3_2 . . 125.3 ?
C2_2 C3_2 H3_2 . . 125.3 ?
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
F1_1 C2_1 . 1.3428(8) ?
N1_1 C1_1 . 1.3473(10) ?
N1_1 N2_1 . 1.3484(9) ?
N1_1 H1N_1 . 0.892(14) ?
N2_1 C3_1 . 1.3391(10) ?
C1_1 C2_1 . 1.3729(11) ?
C1_1 H1_1 . 0.9500 ?
C2_1 C3_1 . 1.3922(11) ?
C3_1 H3_1 . 0.9500 ?
F1_2 C2_2 . 1.3396(8) ?
N1_2 C1_2 . 1.3476(10) ?
N1_2 N2_2 . 1.3513(10) ?
N1_2 H1N_2 . 0.878(14) ?
N2_2 C3_2 . 1.3375(10) ?
C1_2 C2_2 . 1.3742(10) ?
C1_2 H1_2 . 0.9500 ?
C2_2 C3_2 . 1.3924(10) ?
C3_2 H3_2 . 0.9500 ?
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
C1_1 N1_1 N2_1 C3_1 . . . . 0.49(9) ?
N2_1 N1_1 C1_1 C2_1 . . . . -0.31(9) ?
N1_1 C1_1 C2_1 F1_1 . . . . 179.71(7) ?
N1_1 C1_1 C2_1 C3_1 . . . . 0.01(9) ?
N1_1 N2_1 C3_1 C2_1 . . . . -0.46(9) ?
F1_1 C2_1 C3_1 N2_1 . . . . -179.41(7) ?
C1_1 C2_1 C3_1 N2_1 . . . . 0.29(9) ?
C1_2 N1_2 N2_2 C3_2 . . . . 0.85(9) ?
N2_2 N1_2 C1_2 C2_2 . . . . -0.88(9) ?
N1_2 C1_2 C2_2 F1_2 . . . . -178.67(7) ?
N1_2 C1_2 C2_2 C3_2 . . . . 0.55(9) ?
N1_2 N2_2 C3_2 C2_2 . . . . -0.46(9) ?
F1_2 C2_2 C3_2 N2_2 . . . . 179.16(7) ?
C1_2 C2_2 C3_2 N2_2 . . . . -0.06(9) ?
