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_4518591
_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         'C10 H13 N O4'
_chemical_formula_sum            'C10 H13 N O4'
_chemical_formula_weight         211.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 90.577(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3507(5)
_cell_length_b                   13.6579(6)
_cell_length_c                   12.1808(5)
_cell_measurement_reflns_used    9819
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.24
_cell_volume                     2054.61(15)
_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 0.995
_diffrn_measured_fraction_theta_max 0.996
_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  0.0277
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49545
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.054
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         6002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0594P)^2^+1.2668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5474
_reflns_number_total             6002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c00331_si_003.cif
_cod_data_source_block           flik190208
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518591
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              92638
_shelx_hkl_checksum              7063