Visible light-promoted synthesis of 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-diones via [3+2] cycloaddition reaction of 2H-azirines with maleimides
Guo, Hao; Wang, Huahao; Zhao, Hongyi; Zhang, Dongfeng; New Journal of Chemistry 47 (2023) 5634–5638; doi:10.1039/D2NJ06257G

data_7062383
_publ_section_title
;
 Visible light-promoted synthesis of
 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-diones via [3+2]
 cycloaddition reaction of 2H-azirines with maleimides
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5634
_journal_page_last               5638
_journal_paper_doi               10.1039/D2NJ06257G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-30 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                109.529(3)
_cell_angle_beta                 106.432(2)
_cell_angle_gamma                96.016(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9663(2)
_cell_length_b                   9.2196(3)
_cell_length_c                   10.1384(3)
_cell_measurement_reflns_used    10071
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      31.1820
_cell_measurement_theta_min      2.2190
_cell_volume                     738.97(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     27.00  55.00   0.50    3.00    --    5.00  45.00  60.00   56
  2  \w    -30.00  -4.00   0.50    3.00    --    5.00  45.00  60.00   52
  3  \w    -79.00  93.00   0.50    3.00    --    5.00  45.00 150.00  344
  4  \w     -3.00  56.00   0.50    3.00    --   -8.00  45.00   0.00  118
  5  \w    -82.00 -32.00   0.50    3.00    --   -8.00  45.00   0.00  100
  6  \w    -97.00  80.00   0.50    3.00    --   -8.00  45.00  90.00  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088026000
_diffrn_orient_matrix_UB_12      -0.0438819000
_diffrn_orient_matrix_UB_13      -0.0685875000
_diffrn_orient_matrix_UB_21      -0.0074278000
_diffrn_orient_matrix_UB_22      0.0650896000
_diffrn_orient_matrix_UB_23      -0.0219191000
_diffrn_orient_matrix_UB_31      0.0837699000
_diffrn_orient_matrix_UB_32      0.0290139000
_diffrn_orient_matrix_UB_33      0.0322803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13059
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.331
_diffrn_reflns_theta_min         2.266
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0643P)^2^+0.2238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3692
_reflns_number_total             3958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj06257g2.cif
_cod_data_source_block           mx8663
_cod_database_code               7062383
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              37976
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.830