Practical Synthesis and Application of Halogen-Doped Pyrrole Building Blocks
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; ACS Omega  (2021) –; doi:10.1021/acsomega.1c00331

data_4518590
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0793P)^2^+1.8527P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              60824
_shelx_hkl_checksum              58767