Expedient synthesis of 3-hydroxypyrroles via Bu3SnH-triggered ionic 5-exo-trig-cyclization of 5-chloro-3-azamuconoate derivatives
Agafonova, Anastasiya V.; Smetanin, Ilia A.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; Organic Chemistry Frontiers 5 (2018) 3396–; doi:10.1039/C8QO00982A

data_1554482
_publ_section_title
;
 Expedient synthesis of 3-hydroxypyrroles via Bu3SnH-triggered ionic
 5-exo-trig-cyclization of 5-chloro-3-azamuconoate derivatives
;
_journal_issue                   23
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3396
_journal_paper_doi               10.1039/C8QO00982A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C26 H22 Br N O9'
_chemical_formula_sum            'C26 H22 Br N O9'
_chemical_formula_weight         572.35
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-15 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.426(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2685(6)
_cell_length_b                   18.6581(7)
_cell_length_c                   12.8795(8)
_cell_measurement_reflns_used    2472
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0130
_cell_measurement_theta_min      3.0040
_cell_volume                     2520.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -90.00    4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -30.0000 94

  2 omega  -52.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000   90.0000 97

  3 omega  -26.00   -1.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   19.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0375685000
_diffrn_orient_matrix_UB_12      -0.0245418000
_diffrn_orient_matrix_UB_13      -0.0409788000
_diffrn_orient_matrix_UB_21      0.0224324000
_diffrn_orient_matrix_UB_22      -0.0285163000
_diffrn_orient_matrix_UB_23      0.0385551000
_diffrn_orient_matrix_UB_31      -0.0515901000
_diffrn_orient_matrix_UB_32      0.0053550000
_diffrn_orient_matrix_UB_33      0.0182695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10736
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.766
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0284P)^2^+1.1288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4439
_reflns_number_total             5709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00982a2.cif
_cod_data_source_block           smi1new
_cod_original_cell_volume        2520.8(2)
_cod_database_code               1554482
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C24 h20 n1 o6 br1'
_reflns_odcompleteness_completeness 98.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C6(H6), C22(H22), C9(H9), C23(H23), C24(H24), C26(H26),
 C8(H8), C25(H25)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_shelx_res_checksum              34743
_shelx_hkl_checksum              46475
_olex2_submission_special_instructions 'No special instructions were received'