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#$Date: 2021-03-31 00:34:33 +0300 (Wed, 31 Mar 2021) $
#$Revision: 263453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518590.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_4518590
loop_
_publ_author_name
'Cotman, Andrej Emanuel'
'Guérin, Thomas'
'Kovačević, Ivana'
'Benedetto Tiz, Davide'
'Durcik, Martina'
'Fulgheri, Federica'
'Možina, Štefan'
'Secci, Daniela'
'Sterle, Maša'
'Ilaš, Janez'
'Zega, Anamarija'
'Zidar, Nace'
'Mašič, Lucija Peterlin'
'Tomašič, Tihomir'
'Leroux, Frédéric R.'
'Hanquet, Gilles'
'Kikelj, Danijel'
_publ_section_title
;
 Practical Synthesis and Application of Halogen-Doped Pyrrole Building
 Blocks
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c00331
_journal_year                    2021
_chemical_formula_moiety         'C8 H10 F N O2'
_chemical_formula_sum            'C8 H10 F N O2'
_chemical_formula_weight         171.17
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                69.282(5)
_cell_angle_beta                 78.205(5)
_cell_angle_gamma                74.208(5)
_cell_formula_units_Z            4
_cell_length_a                   7.9582(11)
_cell_length_b                   9.7232(13)
_cell_length_c                   11.9573(15)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.68
_cell_volume                     826.72(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            48844
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.163
_diffrn_reflns_theta_min         2.295
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0733
_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)+(0.0793P)²+1.8527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3936
_reflns_number_total             4742
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c00331_si_002.cif
_cod_data_source_block           flik190207
_cod_database_code               4518590
_shelx_shelxl_version_number     2014/7
_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   0.967
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.3145(3) 0.4085(3) 0.5233(2) 0.0197(4) Uani 1 1 d . . . . .
C2 C 0.2677(3) 0.3232(3) 0.6403(2) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.3795(3) 0.1799(3) 0.6689(2) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.3754 0.0997 0.7428 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4976(3) 0.1805(2) 0.5659(2) 0.0185(4) Uani 1 1 d . . . . .
C5 C 0.2336(3) 0.5642(3) 0.4509(2) 0.0252(5) Uani 1 1 d . . . . .
H5A H 0.3219 0.6063 0.3871 0.038 Uiso 1 1 calc R U . . .
H5B H 0.1904 0.6276 0.5033 0.038 Uiso 1 1 calc R U . . .
H5C H 0.1353 0.5610 0.4147 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6496(3) 0.0684(2) 0.5405(2) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.8223(3) -0.1772(3) 0.6118(2) 0.0205(4) Uani 1 1 d . . . . .
H7A H 0.9317 -0.1408 0.5983 0.025 Uiso 1 1 calc R U . . .
H7B H 0.8149 -0.2033 0.5403 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8217(3) -0.3131(3) 0.7234(2) 0.0237(5) Uani 1 1 d . . . . .
H8A H 0.8244 -0.2848 0.7938 0.036 Uiso 1 1 calc R U . . .
H8B H 0.9254 -0.3924 0.7150 0.036 Uiso 1 1 calc R U . . .
H8C H 0.7150 -0.3503 0.7339 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9843(3) 0.1062(3) 0.1514(2) 0.0211(4) Uani 1 1 d . . . . .
C10 C 1.0251(3) 0.1875(3) 0.0326(2) 0.0212(5) Uani 1 1 d . . . . .
C11 C 0.9209(3) 0.3333(3) 0.0048(2) 0.0217(5) Uani 1 1 d . . . . .
H11 H 0.9228 0.4114 -0.0704 0.026 Uiso 1 1 calc R U . . .
C12 C 0.8141(3) 0.3390(3) 0.1109(2) 0.0199(4) Uani 1 1 d . . . . .
C13 C 1.0615(4) -0.0513(3) 0.2234(2) 0.0263(5) Uani 1 1 d . . . . .
H13A H 0.9918 -0.0780 0.3025 0.039 Uiso 1 1 calc R U . . .
H13B H 1.1829 -0.0583 0.2338 0.039 Uiso 1 1 calc R U . . .
H13C H 1.0604 -0.1208 0.1811 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6754(3) 0.4581(3) 0.1398(2) 0.0205(4) Uani 1 1 d . . . . .
C15 C 0.5074(3) 0.7055(3) 0.0678(2) 0.0246(5) Uani 1 1 d . . . . .
H15A H 0.5364 0.7396 0.1290 0.030 Uiso 1 1 calc R U . . .
H15B H 0.3951 0.6718 0.0980 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4914(4) 0.8321(3) -0.0499(2) 0.0272(5) Uani 1 1 d . . . . .
H16A H 0.6026 0.8655 -0.0781 0.041 Uiso 1 1 calc R U . . .
H16B H 0.3969 0.9164 -0.0381 0.041 Uiso 1 1 calc R U . . .
H16C H 0.4642 0.7965 -0.1099 0.041 Uiso 1 1 calc R U . . .
N1 N 0.4557(3) 0.3185(2) 0.48006(18) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.8541(3) 0.2019(2) 0.19779(19) 0.0201(4) Uani 1 1 d . . . . .
O1 O 0.7501(2) 0.0901(2) 0.44727(16) 0.0253(4) Uani 1 1 d . . . . .
O2 O 0.6693(2) -0.06107(18) 0.63135(15) 0.0197(3) Uani 1 1 d . . . . .
O3 O 0.5919(2) 0.4465(2) 0.23933(16) 0.0281(4) Uani 1 1 d . . . . .
O4 O 0.6474(2) 0.58266(19) 0.04506(15) 0.0230(4) Uani 1 1 d . . . . .
F1 F 0.1322(2) 0.37330(18) 0.71480(14) 0.0323(4) Uani 1 1 d . . . . .
F2 F 1.1503(2) 0.13094(18) -0.04464(14) 0.0303(4) Uani 1 1 d . . . . .
H1N H 0.507(4) 0.348(4) 0.410(3) 0.027(8) Uiso 1 1 d . . . . .
H2N H 0.805(5) 0.181(4) 0.271(4) 0.037(9) Uiso 1 1 d . . . . .
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
_geom_angle_publ_flag
N1 C1 C2 105.5(2) . . ?
N1 C1 C5 123.7(2) . . ?
C2 C1 C5 130.8(2) . . ?
F1 C2 C1 123.9(2) . . ?
F1 C2 C3 125.6(2) . . ?
C1 C2 C3 110.6(2) . . ?
C4 C3 C2 104.9(2) . . ?
C4 C3 H3 127.5 . . ?
C2 C3 H3 127.5 . . ?
N1 C4 C3 108.4(2) . . ?
N1 C4 C6 119.9(2) . . ?
C3 C4 C6 131.6(2) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 O2 123.4(2) . . ?
O1 C6 C4 124.0(2) . . ?
O2 C6 C4 112.61(19) . . ?
O2 C7 C8 107.03(19) . . ?
O2 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O2 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 105.6(2) . . ?
N2 C9 C13 123.6(2) . . ?
C10 C9 C13 130.8(2) . . ?
F2 C10 C9 123.6(2) . . ?
F2 C10 C11 125.6(2) . . ?
C9 C10 C11 110.8(2) . . ?
C12 C11 C10 104.8(2) . . ?
C12 C11 H11 127.6 . . ?
C10 C11 H11 127.6 . . ?
N2 C12 C11 108.7(2) . . ?
N2 C12 C14 119.6(2) . . ?
C11 C12 C14 131.7(2) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 123.2(2) . . ?
O3 C14 C12 124.2(2) . . ?
O4 C14 C12 112.6(2) . . ?
O4 C15 C16 107.2(2) . . ?
O4 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O4 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C4 110.6(2) . . ?
C1 N1 H1N 122(2) . . ?
C4 N1 H1N 127(2) . . ?
C9 N2 C12 110.1(2) . . ?
C9 N2 H2N 125(3) . . ?
C12 N2 H2N 125(3) . . ?
C6 O2 C7 115.01(18) . . ?
C14 O4 C15 115.23(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.357(3) . ?
C1 C2 1.385(3) . ?
C1 C5 1.492(3) . ?
C2 F1 1.350(3) . ?
C2 C3 1.401(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 N1 1.373(3) . ?
C4 C6 1.453(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O1 1.220(3) . ?
C6 O2 1.336(3) . ?
C7 O2 1.461(3) . ?
C7 C8 1.510(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.361(3) . ?
C9 C10 1.380(3) . ?
C9 C13 1.495(3) . ?
C10 F2 1.354(3) . ?
C10 C11 1.396(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 N2 1.372(3) . ?
C12 C14 1.452(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O3 1.222(3) . ?
C14 O4 1.336(3) . ?
C15 O4 1.457(3) . ?
C15 C16 1.508(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 H1N 0.84(4) . ?
N2 H2N 0.86(4) . ?
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
N1 H1N O3 0.84(4) 1.99(4) 2.817(3) 170(3) .
N2 H2N O1 0.86(4) 1.98(4) 2.820(3) 165(4) .
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
_geom_torsion_publ_flag
N1 C1 C2 F1 179.8(2) . . . . ?
C5 C1 C2 F1 -1.8(4) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
C5 C1 C2 C3 177.9(2) . . . . ?
F1 C2 C3 C4 -179.7(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 N1 -0.4(3) . . . . ?
C2 C3 C4 C6 176.8(2) . . . . ?
N1 C4 C6 O1 2.9(3) . . . . ?
C3 C4 C6 O1 -173.9(2) . . . . ?
N1 C4 C6 O2 -178.04(19) . . . . ?
C3 C4 C6 O2 5.1(3) . . . . ?
N2 C9 C10 F2 179.8(2) . . . . ?
C13 C9 C10 F2 1.6(4) . . . . ?
N2 C9 C10 C11 -0.1(3) . . . . ?
C13 C9 C10 C11 -178.3(2) . . . . ?
F2 C10 C11 C12 -179.9(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 N2 0.0(3) . . . . ?
C10 C11 C12 C14 -178.5(2) . . . . ?
N2 C12 C14 O3 1.9(4) . . . . ?
C11 C12 C14 O3 -179.7(3) . . . . ?
N2 C12 C14 O4 -177.7(2) . . . . ?
C11 C12 C14 O4 0.7(4) . . . . ?
C2 C1 N1 C4 0.2(3) . . . . ?
C5 C1 N1 C4 -178.3(2) . . . . ?
C3 C4 N1 C1 0.1(3) . . . . ?
C6 C4 N1 C1 -177.44(19) . . . . ?
C10 C9 N2 C12 0.1(3) . . . . ?
C13 C9 N2 C12 178.5(2) . . . . ?
C11 C12 N2 C9 -0.1(3) . . . . ?
C14 C12 N2 C9 178.7(2) . . . . ?
O1 C6 O2 C7 0.2(3) . . . . ?
C4 C6 O2 C7 -178.83(18) . . . . ?
C8 C7 O2 C6 179.87(19) . . . . ?
O3 C14 O4 C15 -0.7(3) . . . . ?
C12 C14 O4 C15 178.95(19) . . . . ?
C16 C15 O4 C14 -177.7(2) . . . . ?
