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_7133165
_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            'C19 H22 N O4'
_chemical_formula_weight         328.37
_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
_audit_creation_date             2023-11-08
_audit_creation_method
;
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                90
_cell_angle_beta                 93.934(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1005(18)
_cell_length_b                   9.9090(10)
_cell_length_c                   11.5159(15)
_cell_measurement_reflns_used    10627
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4550
_cell_measurement_theta_min      5.3050
_cell_volume                     1719.1(4)
_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_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23697
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.835
_diffrn_reflns_theta_min         5.343
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.724
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0021(3)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0394P)^2^+0.5015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2890
_reflns_number_total             3496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01437e2.cif
_cod_data_source_block           20221122a_auto
_cod_depositor_comments
'Adding full bibliography for 7133162--7133165.cif.'
_cod_database_code               7133165
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
1.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C8(H8), C10(H10), C11(H11), C12(H12)
1.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              38103
_shelx_hkl_checksum              99757
_olex2_submission_special_instructions 'No special instructions were received'