Sequential multicomponent site-selective synthesis of 4-iodo and 5-iodopyrrole-3-carboxaldehydes from a common set of starting materials by tuning the conditions.
Choudhary, Sachin; Yadav, Jyothi; Mamta, ?; Pawar, Amol Prakash; Vanaparthi, Satheeshvarma; Mir, Nisar A.; Iype, Eldhose; Sharma, Ratika; Kant, Rajni; Kumar, Indresh; Organic & biomolecular chemistry 18 (2020) 1155–1164; doi:10.1039/c9ob02501d

data_7157316
_publ_section_title
;
 Sequential multicomponent site-selective synthesis of 4-iodo and
 5-iodopyrrole-3-carboxaldehydes from a common set of starting materials
 by tuning the conditions.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1155
_journal_page_last               1164
_journal_paper_doi               10.1039/c9ob02501d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C17 H10 Cl2 I N O'
_chemical_formula_sum            'C17 H10 Cl2 I N O'
_chemical_formula_weight         442.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-09-07 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.291(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6656(7)
_cell_length_b                   19.4376(15)
_cell_length_c                   13.2403(13)
_cell_measurement_reflns_used    1559
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0600
_cell_measurement_theta_min      3.9860
_cell_volume                     1662.4(3)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.1049
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4614
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         3.788
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66391
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.3021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2288
_reflns_number_total             3039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02501d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7157315--7157316.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157316
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              90816