Synthesis of β-Nitro Ketone from Geminal Bromonitroalkane and Silyl Enol Ether by Visible Light Photoredox Catalysis
Cao, Haoying; Ma, Shanshan; Feng, Yanhong; Guo, Yawen; Jiao, Peng; Chemical Communications  (2022) –; doi:10.1039/D1CC06529G

data_7129526
_publ_section_title
;
 Synthesis of \b-Nitro Ketone from Geminal Bromonitroalkane and Silyl Enol
 Ether by Visible Light Photoredox Catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06529G
_journal_year                    2022
_chemical_formula_moiety         'C9 H13 N O3'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-09-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.274(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.94438(17)
_cell_length_b                   15.3656(5)
_cell_length_c                   9.9491(4)
_cell_measurement_reflns_used    7781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6740
_cell_measurement_theta_min      5.3130
_cell_volume                     903.30(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.983
_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     34.00 120.00   0.50    0.05    --   46.70  37.00  30.00  172
  2  \w     32.00  69.00   0.50    0.05    --   46.70  57.00 150.00   74
  3  \w     92.00 178.00   0.50    0.16    --  104.75  30.00  30.00  172
  4  \w     92.00 178.00   0.50    0.16    --  104.75  30.00 -90.00  172
  5  \w     32.00 109.00   0.50    0.16    --  104.75 -94.00-120.00  154
  6  \w     35.00 121.00   0.50    0.05    --   46.70-165.00-128.00  172
  7  \w     35.00 145.00   0.50    0.16    --  104.75-165.00-128.00  220
  8  \w     32.00 117.00   0.50    0.16    --  104.75-125.00 -60.00  170
  9  \w     32.00 109.00   0.50    0.16    --  104.75 -94.00-150.00  154
 10  \w      9.00  90.00   0.50    0.05    --   46.70-116.00  18.00  162
 11  \w     32.00 112.00   0.50    0.16    --  104.75-116.00  18.00  160
 12  \w     32.00 108.00   0.50    0.16    --  104.75 -77.00   0.00  152
 13  \w     32.00  73.00   0.50    0.16    --  104.75 -61.00  60.00   82
 14  \w     32.00  73.00   0.50    0.16    --  104.75 -61.00 150.00   82
 15  \w     81.00 178.00   0.50    0.16    --  104.75 116.00 107.00  194
 16  \w     76.00 178.00   0.50    0.16    --  104.75 125.00  60.00  204
 17  \w     50.00 119.00   0.50    0.05    --   46.70 165.00-105.00  138
 18  \w     50.00 159.00   0.50    0.16    --  104.75 165.00-105.00  218
 19  \w     76.00 178.00   0.50    0.16    --  104.75 125.00-180.00  204
 20  \w   -121.00 -31.00   0.50    0.05    --  -46.70 165.00-105.00  180
 21  \w   -144.00 -31.00   0.50    0.16    -- -102.00 165.00-105.00  226
 22  \w    -90.00  -4.00   0.50    0.05    --  -46.70 116.00 107.00  172
 23  \w   -112.00 -29.00   0.50    0.16    -- -102.00 116.00 107.00  166
 24  \w    -69.00 -29.00   0.50    0.16    -- -102.00  61.00  60.00   80
 25  \w    -24.00  29.00   0.50    0.05    --  -46.70  19.00-180.00  106
 26  \w    -24.00  29.00   0.50    0.05    --  -46.70  19.00 120.00  106
 27  \w    -69.00 -29.00   0.50    0.16    -- -102.00  61.00 150.00   80
 28  \w    -69.00 -29.00   0.50    0.16    -- -102.00  61.00 120.00   80
 29  \w    -69.00 -29.00   0.50    0.16    -- -102.00  61.00  90.00   80
 30  \w   -175.00 -88.00   0.50    0.16    -- -102.00 -15.00  90.00  174
 31  \w   -174.00 -89.00   0.50    0.16    -- -102.00 -45.00  60.00  170
 32  \w   -175.00 -89.00   0.50    0.16    -- -102.00 -30.00-150.00  172
 33  \w   -175.00 -85.00   0.50    0.16    -- -102.00 -61.00 -60.00  180
 34  \w   -175.00 -77.00   0.50    0.16    -- -102.00-116.00  18.00  196
 35  \w   -118.00 -71.00   0.50    0.05    --  -46.70-125.00  90.00   94
 36  \w   -118.00 -71.00   0.50    0.05    --  -46.70-125.00  60.00   94
 37  \w   -118.00 -71.00   0.50    0.05    --  -46.70-125.00 -90.00   94
 38  \w   -118.00 -45.00   0.50    0.05    --  -46.70-165.00-128.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1256122000
_diffrn_orient_matrix_UB_12      0.0454845000
_diffrn_orient_matrix_UB_13      -0.1243558000
_diffrn_orient_matrix_UB_21      0.1020241000
_diffrn_orient_matrix_UB_22      0.0879533000
_diffrn_orient_matrix_UB_23      0.0497269000
_diffrn_orient_matrix_UB_31      0.2042406000
_diffrn_orient_matrix_UB_32      -0.0159222000
_diffrn_orient_matrix_UB_33      -0.0796306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.990
_diffrn_reflns_theta_min         5.319
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0032(10)
_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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0738P)^2^+0.2199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1685
_reflns_number_total             1860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210716f
_cod_database_code               7129526
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1
_diffrn_oxdiff_digest_frames
;
0104b6f008d6c2b3862f21288451aaea0000103556b
;
_diffrn_oxdiff_digest_hkl
;
01e9779195c9e8bffaccc8525cd868af8995ce
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
1.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              30018
_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 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.620