Dearomative pyrrole (3+2) reaction with geminal bromonitroalkane: synthesis of 2,3-dihydropyrroles.
Shi, Lin; Liu, Lidong; Lei, Xingyu; Wang, Yihan; Fang, Yeguang; Jiao, Peng; Chemical communications (Cambridge, England) 60 (2024) 6953–6956; doi:10.1039/d4cc01437e

data_7133163
_publ_section_title
;
 Dearomative pyrrole (3+2) reaction with geminal bromonitroalkane:
 synthesis of 2,3-dihydropyrroles.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6953
_journal_page_last               6956
_journal_paper_doi               10.1039/d4cc01437e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H22 N2 O4'
_chemical_formula_sum            'C18 H22 N2 O4'
_chemical_formula_weight         330.37
_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   geom
_audit_creation_date             2023-05-16
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Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-09 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                77.914(6)
_cell_angle_beta                 71.586(8)
_cell_angle_gamma                89.936(6)
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_cell_length_c                   10.0293(9)
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_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      4.6670
_cell_volume                     853.33(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22766
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.947
_diffrn_reflns_theta_min         4.686
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77464
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0485P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2698
_reflns_number_total             3413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01437e2.cif
_cod_data_source_block           20230101a_auto
_cod_depositor_comments
'Adding full bibliography for 7133162--7133165.cif.'
_cod_database_code               7133163
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
1.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C10(H10), C14(H14), C12(H12), C11(H11)
1.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              68957
_shelx_hkl_checksum              98628
_olex2_submission_special_instructions 'No special instructions were received'