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_7159120
_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         'C18 H15 F N2 O3 S'
_chemical_formula_sum            'C18 H15 F N2 O3 S'
_chemical_formula_weight         358.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-12-28 deposited with the CCDC.	2023-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.17910(10)
_cell_length_b                   19.9839(3)
_cell_length_c                   20.2957(3)
_cell_measurement_reflns_used    8521
_cell_measurement_temperature    298.98(10)
_cell_measurement_theta_max      77.0520
_cell_measurement_theta_min      4.3720
_cell_volume                     3317.34(8)
_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      298.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_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     37.00  62.00   0.50    0.46    --  108.86 -57.00 150.00   50
  2  \w     40.00  65.00   0.50    0.46    --  108.86 -57.00 120.00   50
  3  \w     39.00  64.00   0.50    0.46    --  108.86 -57.00  60.00   50
  4  \w     37.00  62.00   0.50    0.46    --  108.86 -57.00 -60.00   50
  5  \w     38.00  63.00   0.50    0.46    --  108.86 -57.00 -90.00   50
  6  \w     41.00  66.00   0.50    0.46    --  108.86 -57.00-120.00   50
  7  \w    109.00 178.00   0.50    0.46    --  108.86  88.00  -9.00  138
  8  \w    -71.00  -3.00   0.50    0.12    --  -48.55  82.00-112.00  136
  9  \w    -66.00 -32.00   0.50    0.46    --  -91.75  57.00 -60.00   68
 10  \w    -61.00 -19.00   0.50    0.46    --  -91.75  57.00  60.00   84
 11  \w   -157.00 -79.00   0.50    0.46    --  -91.75 -55.00 -15.00  156
 12  \w   -138.00 -90.00   0.50    0.46    --  -91.75 -82.00 126.00   96
 13  \w   -114.00 -87.00   0.50    0.12    --  -48.55-125.00  30.00   54
 14  \w   -119.00 -74.00   0.50    0.12    --  -48.55-125.00 -90.00   90
 15  \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      -0.0686793000
_diffrn_orient_matrix_UB_12      -0.0666478000
_diffrn_orient_matrix_UB_13      0.0262076000
_diffrn_orient_matrix_UB_21      -0.1033737000
_diffrn_orient_matrix_UB_22      -0.0077380000
_diffrn_orient_matrix_UB_23      -0.0630323000
_diffrn_orient_matrix_UB_31      0.1416964000
_diffrn_orient_matrix_UB_32      -0.0379510000
_diffrn_orient_matrix_UB_33      -0.0331964000
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.372
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.015
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69836
_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    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00106(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0467P)^2^+0.7843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2917
_reflns_number_total             3297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02334b2.cif
_cod_data_source_block           exp_3718_auto
_cod_depositor_comments
'Adding full bibliography for 7159119--7159120.cif.'
_cod_database_code               7159120
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.88
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00J(H00J), C00K(H00K), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P)
2.d Idealised Me refined as rotating group:
 C00L(H00E,H00H,H00I)
;
_shelx_res_checksum              77359
_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 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.781