NHC-catalyzed [3 + 3] cycloaddition of α-bromoenals with nitroketene aminals or nitroketene <i>N</i>,<i>S</i>-acetals: synthesis of nitro-containing dihydropyridin-2-ones.
Li, Yarui; Huang, Xiaoxia; Peng, Shiyong; Wang, Jian; Lang, Ming; Organic & biomolecular chemistry 21 (2023) 1399–1403; doi:10.1039/d2ob02334b

data_7159119
_publ_section_title
;
 NHC-catalyzed [3 + 3] cycloaddition of &#x3b1;-bromoenals with
 nitroketene aminals or nitroketene <i>N</i>,<i>S</i>-acetals: synthesis
 of nitro-containing dihydropyridin-2-ones.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1399
_journal_page_last               1403
_journal_paper_doi               10.1039/d2ob02334b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         '0.994(C14.086 H15.092 N3.018 O3.012)'
_chemical_formula_sum            'C14 H15 N3 O3'
_chemical_formula_weight         273.29
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-12-28 deposited with the CCDC.	2023-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.995(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2441(3)
_cell_length_b                   25.3839(8)
_cell_length_c                   8.4223(3)
_cell_measurement_reflns_used    4973
_cell_measurement_temperature    298.37(10)
_cell_measurement_theta_max      76.4910
_cell_measurement_theta_min      5.6220
_cell_volume                     1305.78(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.37(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.949
_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     55.00  80.00   0.50    0.12    --   48.55  13.00 -12.00   50
  2  \w     99.00 133.00   0.50    0.50    --  108.86  13.00 -12.00   68
  3  \w     -2.00  23.00   0.50    0.12    --   48.55 -13.00 175.00   50
  4  \w     37.00  67.00   0.50    0.50    --  108.86 -77.00  90.00   60
  5  \w     69.00  96.00   0.50    0.50    --  108.86 -77.00  90.00   54
  6  \w     38.00  65.00   0.50    0.50    --  108.86 -57.00 -30.00   54
  7  \w     37.00  62.00   0.50    0.50    --  108.86 -57.00 -60.00   50
  8  \w     38.00  63.00   0.50    0.50    --  108.86 -57.00 -90.00   50
  9  \w     40.00  65.00   0.50    0.50    --  108.86 -57.00-150.00   50
 10  \w     37.00  62.00   0.50    0.50    --  108.86 -57.00-180.00   50
 11  \w     37.00  63.00   0.50    0.50    --  108.86 -57.00-120.00   52
 12  \w     38.00  64.00   0.50    0.50    --  108.86 -57.00 120.00   52
 13  \w     39.00  64.00   0.50    0.50    --  108.86 -57.00  90.00   50
 14  \w     81.00 106.00   0.50    0.50    --  108.86 -99.00 -60.00   50
 15  \w     37.00  67.00   0.50    0.50    --  108.86 -99.00 -60.00   60
 16  \w     39.00 106.00   0.50    0.50    --  108.86 -99.00  30.00  134
 17  \w     36.00  75.00   0.50    0.50    --  108.86 -99.00  60.00   78
 18  \w     52.00 106.00   0.50    0.50    --  108.86 -99.00  90.00  108
 19  \w    -16.00  10.00   0.50    0.12    --  -48.55  13.00 -12.00   52
 20  \w    -85.00 -15.00   0.50    0.12    --  -48.55 125.00 120.00  140
 21  \w    -63.00 -37.00   0.50    0.50    --  -91.75 125.00  30.00   52
 22  \w    -66.00 -32.00   0.50    0.50    --  -91.75  57.00 -90.00   68
 23  \w   -113.00 -75.00   0.50    0.12    --  -48.55-125.00  90.00   76
 24  \w   -120.00 -85.00   0.50    0.12    --  -48.55 -13.00 175.00   70
 25  \w    -72.00 -41.00   0.50    0.12    --  -48.55 -13.00 175.00   62
 26  \w   -160.00 -78.00   0.50    0.50    --  -91.75 -13.00 175.00  164
 27  \w   -163.00 -94.00   0.50    0.50    --  -91.75 -19.00  90.00  138
 28  \w   -121.00 -81.00   0.50    0.12    --  -48.55-125.00-120.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356750000
_diffrn_orient_matrix_UB_12      -0.0017017000
_diffrn_orient_matrix_UB_13      0.1755057000
_diffrn_orient_matrix_UB_21      -0.2461122000
_diffrn_orient_matrix_UB_22      -0.0101503000
_diffrn_orient_matrix_UB_23      -0.0643651000
_diffrn_orient_matrix_UB_31      0.0426814000
_diffrn_orient_matrix_UB_32      -0.0597861000
_diffrn_orient_matrix_UB_33      0.0060742000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8613
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.262
_diffrn_reflns_theta_min         3.482
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0610
_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^)+(0.1017P)^2^+0.2867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2163
_reflns_number_total             2622
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02334b2.cif
_cod_data_source_block           exp_3722_auto
_cod_depositor_comments
'Adding full bibliography for 7159119--7159120.cif.'
_cod_database_code               7159119
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00C), C00E(H00D,H00E), C00F(H00F,H00G), C00G(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00H(H00J), C00I(H00K), C00J(H00L), C00K(H00M)
;
_shelx_res_checksum              5560
_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.789