Iron-Mediated Annulation between Methylene Ketones and Diethanolamines: A Sustainable and Scalable Procedure toward N-(2-Hydroxyethyl) Pyrroles.
Hu, Weiming; Yu, Jin-Tao; Ye, Dengman; Zhou, Zhou; Sun, Song; Cheng, Jiang; The Journal of organic chemistry 81 (2016) 9389–9395; doi:10.1021/acs.joc.6b01195

data_4032054
_publ_section_title
;
 Iron-Mediated Annulation between Methylene Ketones and Diethanolamines: A
 Sustainable and Scalable Procedure toward N-(2-Hydroxyethyl) Pyrroles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9389
_journal_page_last               9395
_journal_paper_doi               10.1021/acs.joc.6b01195
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                98.559(13)
_cell_angle_beta                 101.929(13)
_cell_angle_gamma                90.335(12)
_cell_formula_units_Z            4
_cell_length_a                   9.022(4)
_cell_length_b                   11.781(6)
_cell_length_c                   15.387(8)
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.023
_cell_measurement_theta_min      2.309
_cell_volume                     1581.2(14)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1625
_diffrn_reflns_av_unetI/netI     0.1568
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9298
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.749
_exptl_absorpt_coefficient_mu    2.598
_exptl_absorpt_correction_T_max  0.626
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         1.436
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.211
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0921
_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^)+(0.1740P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2435
_refine_ls_wR_factor_ref         0.2918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3018
_reflns_number_total             5851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01195_si_001.cif
_cod_data_source_block           P-Br
_cod_depositor_comments
;
          Adding full bibliography for 4032054.cif.

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H32 Br2 N2 O2'
_cod_original_formula_weight         684.45
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1581.1(13)
_cod_database_code               4032054
_shelx_estimated_absorpt_t_min   0.599
_shelx_estimated_absorpt_t_max   0.652